P-CHLOROANILINE
HAZARDTEXT ®
Information to help in the initial response for evaluating chemical incidents
-IDENTIFICATION
SYNONYMS
1-AMINO-4-CHLOROBENZENE 4-AMINO-1-CHLOROBENZENE 4-AMINOCHLOROBENZENE 4-CHLORANILIN (CZECH) 4-CHLOROANILINE 4-CHLORO-1-AMINOBENZENE 4-CHLOROBENZAMINE 4-CHLOROBENZENAMINE 4-CHLOROBENZENEAMINE 4-CHLOROPHENYLAMINE ANILINE, 4-CHLORO- ANILINE, P-CHLORO- BENZENAMINE, 4-CHLORO- P-AMINOCHLOROBENZENE P-CA P-CHLORANILINE P-CHLOROANILINE P-CHLOROANILINE, LIQUID P-CHLOROANILINE, SOLID P-CHLOROPHENYLAMINE para-AMINOCHLOROBENZENE para-CHLOROPHENYLAMINE PCA
IDENTIFIERS
IMO CLASSIFICATION:6.1 - Chloroanilines, liquid or solid STANDARD INDUSTRIAL TRADE CLASSIFICATION NUMBER:51453
SYNONYM REFERENCE
- (Ashford, 2001; Bingham et al, 2001; HSDB , 2002; IARC , 1993; RTECS , 2002)
USES/FORMS/SOURCES
p-Chloroaniline is primarily used as a chemical intermediate in the manufacture of dyes and pigments and in the production pharmaceuticals and agricultural chemicals (urea herbicides) (Bingham et al, 2001; Harbison, 1998a; ILO, 1998; Lewis, 2001a). Aromatic amines, such as p-chloroaniline, are used in the manufacture of polymers, rubber, agricultural chemicals, dyes, pigments, pharmaceuticals, and photographic chemicals. Worldwide production of these chemicals is mostly for the production of monomeric and polymeric isocyanates as crosslinking agents for the manufacture of rigid polyurethanes and reaction-injection-molded parts for the construction, automotive, and durable goods industries. Rubber chemicals such as antioxidants, stabilizers, and antiozonants are the second largest demand for aromatic amines. The aromatic amines and their derivatives are also important components of hair dye and colorant products (Bingham et al, 2001). p-Chloroaniline reacts with anhydrous hydrogen chloride and phosgene at 70-75 degrees C in dioxane to produce p-chlorophenyl isocyanate, an intermediate used for the production of urea herbicides (HSDB , 2002).
The para-isomer of the chloroanilines is a white or pale-yellow crystalline solid. It is also described as colorless to light amber rhombic crystals. The solid material may be dissolved in a liquid carrier substance. It has a slightly sweet characteristic amine odor. There are two grades of purity available: 99.0% and technical grade (AAR, 2000; Bingham et al, 2001; CHRIS, 2002; HSDB , 2002; ITI, 1995; Lewis, 2001a; Pohanish, 2002). p-Chloroaniline occurs as orthorhombic crystals from alcohol or petroleum ether or as needles from toluene (Budavari, 2001; Lewis, 2000a).
p-Chloroaniline is produced from nitro reduction of p-chloronitrobenzene (Ashford, 2001). It is manufactured by catalytic hydrogenation of chloronitrobenzene; by reduction of chloronitrobenzene with NaHS. It is also reported that ozonization of p-aminoazobenzene in water at room temperature in the presence of HCl produced phenol, p-chloroaniline, and p-nitroazobenzene (HSDB , 2002). p-Chloroaniline is a persistent environmental degradation product of some herbicides and fungicides (HSDB , 2002; IARC , 1993).
-CLINICAL EFFECTS
GENERAL CLINICAL EFFECTS
p-Chloroaniline is highly toxic by inhalation. Short-term inhalation exposure of vapors will irritate the respiratory tract and may affect red blood cells resulting in methemoglobin formation and hemolysis. Chloroanilines, in general, cause methemoglobinemia with cyanosis signified by a bluish tint to the lips, fingernails, skin or ears. Other symptoms from inhalation exposure may include headache, dizziness, drowsiness, weakness, difficulty breathing, unconsciousness and possibly death.
It is a skin and eye irritant. The liquid can be absorbed through the skin. It causes redness to the skin and eyes on contact and may burn the eyes. Skin burns and blisters can result from contact with molten material. When dermally absorbed, p-chloroaniline may cause similar symptoms as inhalation or ingestion exposure. Dichloraniline derivatives, such as p-chloroaniline, have been associated with chloracne in occupational exposure scenarios.
p-Chloroaniline is a confirmed carcinogen. Chronic toxicity can occur from the ingestion, inhalation, skin contact, subcutaneous, and intravenous routes of exposure. It is a microsomal cytochrome P-450 enzyme inhibitor. It has been linked to oxidative hemolytic anemia in humans. Long term exposure may damage the spleen, liver, and kidneys. Methemoglobinemia can occur gradually from chronic exposure. Repeated or prolonged contact can cause skin sensitization. In vitro effects on leukocytes have been observed from a variety of species. The effects associated with p-chloroaniline occurred at concentrations tenfold lower than other aniline derivative compounds. p-Chloroaniine induced DNA damage in bacteria. However, conflicting results were obtained for gene mutation. Gene mutation was induced in fungi, but mitotic recombination was not evident. Gene mutation, sister chromatid exchange and chromosomal aberrations were induced in cultured mammalian cells, and conflicting data was shown for cell transformation. CARCINOGENICITY RATINGS
- POTENTIAL HEALTH HAZARDS - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 152 (ERG, 2004)
Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
-MEDICAL TREATMENT
LIFE SUPPORT
- Support respiratory and cardiovascular function.
SUMMARY
- FIRST AID - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 152 (ERG, 2004)
Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves.
INHALATION EXPOSURE - INHALATION: Move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with an inhaled beta2-adrenergic agonist. Consider systemic corticosteroids in patients with significant bronchospasm. If bronchospasm and wheezing occur, consider treatment with inhaled sympathomimetic agents. METHEMOGLOBINEMIA: Determine the methemoglobin concentration and evaluate the patient for clinical effects of methemoglobinemia (ie, dyspnea, headache, fatigue, CNS depression, tachycardia, metabolic acidosis). Treat patients with symptomatic methemoglobinemia with methylene blue (this usually occurs at methemoglobin concentrations above 20% to 30%, but may occur at lower methemoglobin concentrations in patients with anemia, or underlying pulmonary or cardiovascular disorders). Administer oxygen while preparing for methylene blue therapy. METHYLENE BLUE: INITIAL DOSE/ADULT OR CHILD: 1 mg/kg IV over 5 to 30 minutes; a repeat dose of up to 1 mg/kg may be given 1 hour after the first dose if methemoglobin levels remain greater than 30% or if signs and symptoms persist. NOTE: Methylene blue is available as follows: 50 mg/10 mL (5 mg/mL or 0.5% solution) single-dose ampules and 10 mg/1 mL (1% solution) vials. Additional doses may sometimes be required. Improvement is usually noted shortly after administration if diagnosis is correct. Consider other diagnoses or treatment options if no improvement has been observed after several doses. If intravenous access cannot be established, methylene blue may also be given by intraosseous infusion. Methylene blue should not be given by subcutaneous or intrathecal injection. NEONATES: DOSE: 0.3 to 1 mg/kg. Concomitant use of methylene blue with serotonergic drugs, including serotonin reuptake inhibitors (SRIs), selective serotonin reuptake inhibitors (SSRIs), serotonin and norepinephrine reuptake inhibitors (SNRIs), tricyclic antidepressants (TCAs), norepinephrine-dopamine reuptake inhibitors (NDRIs), triptans, and ergot alkaloids may increase the risk of potentially fatal serotonin syndrome.
DERMAL EXPOSURE - DECONTAMINATION: Remove contaminated clothing and jewelry and place them in plastic bags. Wash exposed areas with soap and water for 10 to 15 minutes with gentle sponging to avoid skin breakdown. A physician may need to examine the area if irritation or pain persists (Burgess et al, 1999). Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines. METHEMOGLOBINEMIA: Determine the methemoglobin concentration and evaluate the patient for clinical effects of methemoglobinemia (ie, dyspnea, headache, fatigue, CNS depression, tachycardia, metabolic acidosis). Treat patients with symptomatic methemoglobinemia with methylene blue (this usually occurs at methemoglobin concentrations above 20% to 30%, but may occur at lower methemoglobin concentrations in patients with anemia, or underlying pulmonary or cardiovascular disorders). Administer oxygen while preparing for methylene blue therapy. METHYLENE BLUE: INITIAL DOSE/ADULT OR CHILD: 1 mg/kg IV over 5 to 30 minutes; a repeat dose of up to 1 mg/kg may be given 1 hour after the first dose if methemoglobin levels remain greater than 30% or if signs and symptoms persist. NOTE: Methylene blue is available as follows: 50 mg/10 mL (5 mg/mL or 0.5% solution) single-dose ampules and 10 mg/1 mL (1% solution) vials. Additional doses may sometimes be required. Improvement is usually noted shortly after administration if diagnosis is correct. Consider other diagnoses or treatment options if no improvement has been observed after several doses. If intravenous access cannot be established, methylene blue may also be given by intraosseous infusion. Methylene blue should not be given by subcutaneous or intrathecal injection. NEONATES: DOSE: 0.3 to 1 mg/kg. Concomitant use of methylene blue with serotonergic drugs, including serotonin reuptake inhibitors (SRIs), selective serotonin reuptake inhibitors (SSRIs), serotonin and norepinephrine reuptake inhibitors (SNRIs), tricyclic antidepressants (TCAs), norepinephrine-dopamine reuptake inhibitors (NDRIs), triptans, and ergot alkaloids may increase the risk of potentially fatal serotonin syndrome.
EYE EXPOSURE - DECONTAMINATION: Remove contact lenses and irrigate exposed eyes with copious amounts of room temperature 0.9% saline or water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist after 15 minutes of irrigation, the patient should be seen in a healthcare facility.
ORAL EXPOSURE - Because of the potential for gastrointestinal tract irritation, DO NOT induce emesis. PREHOSPITAL ACTIVATED CHARCOAL ADMINISTRATION Consider prehospital administration of activated charcoal as an aqueous slurry in patients with a potentially toxic ingestion who are awake and able to protect their airway. Activated charcoal is most effective when administered within one hour of ingestion. Administration in the prehospital setting has the potential to significantly decrease the time from toxin ingestion to activated charcoal administration, although it has not been shown to affect outcome (Alaspaa et al, 2005; Thakore & Murphy, 2002; Spiller & Rogers, 2002). In patients who are at risk for the abrupt onset of seizures or mental status depression, activated charcoal should not be administered in the prehospital setting, due to the risk of aspiration in the event of spontaneous emesis. The addition of flavoring agents (cola drinks, chocolate milk, cherry syrup) to activated charcoal improves the palatability for children and may facilitate successful administration (Guenther Skokan et al, 2001; Dagnone et al, 2002).
ACTIVATED CHARCOAL: Administer charcoal as a slurry (240 mL water/30 g charcoal). Usual dose: 25 to 100 g in adults/adolescents, 25 to 50 g in children (1 to 12 years), and 1 g/kg in infants less than 1 year old. METHEMOGLOBINEMIA: Determine the methemoglobin concentration and evaluate the patient for clinical effects of methemoglobinemia (ie, dyspnea, headache, fatigue, CNS depression, tachycardia, metabolic acidosis). Treat patients with symptomatic methemoglobinemia with methylene blue (this usually occurs at methemoglobin concentrations above 20% to 30%, but may occur at lower methemoglobin concentrations in patients with anemia, or underlying pulmonary or cardiovascular disorders). Administer oxygen while preparing for methylene blue therapy. METHYLENE BLUE: INITIAL DOSE/ADULT OR CHILD: 1 mg/kg IV over 5 to 30 minutes; a repeat dose of up to 1 mg/kg may be given 1 hour after the first dose if methemoglobin levels remain greater than 30% or if signs and symptoms persist. NOTE: Methylene blue is available as follows: 50 mg/10 mL (5 mg/mL or 0.5% solution) single-dose ampules and 10 mg/1 mL (1% solution) vials. Additional doses may sometimes be required. Improvement is usually noted shortly after administration if diagnosis is correct. Consider other diagnoses or treatment options if no improvement has been observed after several doses. If intravenous access cannot be established, methylene blue may also be given by intraosseous infusion. Methylene blue should not be given by subcutaneous or intrathecal injection. NEONATES: DOSE: 0.3 to 1 mg/kg. Concomitant use of methylene blue with serotonergic drugs, including serotonin reuptake inhibitors (SRIs), selective serotonin reuptake inhibitors (SSRIs), serotonin and norepinephrine reuptake inhibitors (SNRIs), tricyclic antidepressants (TCAs), norepinephrine-dopamine reuptake inhibitors (NDRIs), triptans, and ergot alkaloids may increase the risk of potentially fatal serotonin syndrome.
-RANGE OF TOXICITY
MINIMUM LETHAL EXPOSURE
MAXIMUM TOLERATED EXPOSURE
EPA has published an oral reference dose (RfD) for chronic oral exposure of 4 x 10(-3) mg/kg/day for p-chloroaniline. This value is based on a critical effect of nonneoplastic lesions of the splenic capsule recorded in a chronic oral bioassay study of rats. The 250 ppm dose level (12.5 mg/kg/day) is considered to be the LOAEL. This value was divided by an uncertainty factor (UF) of 3000 to obtain the RfD. The UF included a value of 10 to extrapolate from a LOAEL to a NOEL, 10 to extrapolate from rats to humans, 10 to protect sensitive humans, and an additional UF of 3 for lack of supporting reproductive and other toxicity data (EPA , 1995).
CARCINOGENICITY IARC: 2B, Possibly Carcinogenic to Humans (ACGIH, 2002b; (Bingham et al, 2001; IARC , 1993) MAK - 2, Carcinogenic for Man (ACGIH, 2002b)
- Carcinogenicity Ratings for CAS106-47-8 :
ACGIH (American Conference of Governmental Industrial Hygienists, 2010): Not Listed EPA (U.S. Environmental Protection Agency, 2011): Not Assessed under the IRIS program. ; Listed as: p-Chloroaniline IARC (International Agency for Research on Cancer (IARC), 2016; International Agency for Research on Cancer, 2015; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010a; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2008; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2007; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2006; IARC, 2004): 2B ; Listed as: para-Chloroaniline 2B : The agent (mixture) is possibly carcinogenic to humans. The exposure circumstance entails exposures that are possibly carcinogenic to humans. This category is used for agents, mixtures and exposure circumstances for which there is limited evidence of carcinogenicity in humans and less than sufficient evidence of carcinogenicity in experimental animals. It may also be used when there is inadequate evidence of carcinogenicity in humans but there is sufficient evidence of carcinogenicity in experimental animals. In some instances, an agent, mixture or exposure circumstance for which there is inadequate evidence of carcinogenicity in humans but limited evidence of carcinogenicity in experimental animals together with supporting evidence from other relevant data may be placed in this group.
NIOSH (National Institute for Occupational Safety and Health, 2007): Not Listed MAK (DFG, 2002): Category 2 ; Listed as: p-Chloroaniline NTP (U.S. Department of Health and Human Services, Public Health Service, National Toxicology Project ): Not Listed
TOXICITY AND RISK ASSESSMENT VALUES
- EPA Risk Assessment Values for CAS106-47-8 (U.S. Environmental Protection Agency, 2011):
Oral: Slope Factor: RfD: 4x10(-3) mg/kg-day
Inhalation: Drinking Water:
-STANDARDS AND LABELS
WORKPLACE STANDARDS
- ACGIH TLV Values for CAS106-47-8 (American Conference of Governmental Industrial Hygienists, 2010):
- AIHA WEEL Values for CAS106-47-8 (AIHA, 2006):
- NIOSH REL and IDLH Values for CAS106-47-8 (National Institute for Occupational Safety and Health, 2007):
- OSHA PEL Values for CAS106-47-8 (U.S. Occupational Safety, and Health Administration (OSHA), 2010):
- OSHA List of Highly Hazardous Chemicals, Toxics, and Reactives for CAS106-47-8 (U.S. Occupational Safety and Health Administration, 2010):
ENVIRONMENTAL STANDARDS
- EPA CERCLA, Hazardous Substances and Reportable Quantities for CAS106-47-8 (U.S. Environmental Protection Agency, 2010):
Listed as: Benzenamine, 4-chloro- Final Reportable Quantity, in pounds (kilograms): Additional Information: Listed as: p-Chloroaniline Final Reportable Quantity, in pounds (kilograms): Additional Information:
- EPA CERCLA, Hazardous Substances and Reportable Quantities, Radionuclides for CAS106-47-8 (U.S. Environmental Protection Agency, 2010):
- EPA RCRA Hazardous Waste Number for CAS106-47-8 (U.S. Environmental Protection Agency, 2010b):
Listed as: Benzenamine, 4-chloro- P or U series number: P024 Footnote: Listed as: p-Chloroaniline P or U series number: P024 Footnote: Editor's Note: The D, F, and K series waste numbers and Appendix VIII to Part 261 -- Hazardous Constituents were not included. Please refer to 40 CFR Part 261.
- EPA SARA Title III, Extremely Hazardous Substance List for CAS106-47-8 (U.S. Environmental Protection Agency, 2010):
- EPA SARA Title III, Community Right-to-Know for CAS106-47-8 (40 CFR 372.65, 2006; 40 CFR 372.28, 2006):
Listed as: p-Chloroaniline Effective Date for Reporting Under 40 CFR 372.30: 1/1/95 Lower Thresholds for Chemicals of Special Concern under 40 CFR 372.28:
- DOT List of Marine Pollutants for CAS106-47-8 (49 CFR 172.101 - App. B, 2005):
- EPA TSCA Inventory for CAS106-47-8 (EPA, 2005):
SHIPPING REGULATIONS
- DOT -- Table of Hazardous Materials and Special Provisions for UN/NA Number 2018 (49 CFR 172.101, 2005):
- ICAO International Shipping Name for UN2018 (ICAO, 2002):
LABELS
- NFPA Hazard Ratings for CAS106-47-8 (NFPA, 2002):
-HANDLING AND STORAGE
SUMMARY
Only trained personnel should handle this chemical. p-Chloroaniline presents flammability and explosion hazards. It is a combustible solid. Violent reactions occur upon contact with oxidizers, such as perchlorates, peroxides, permanganates, chlorates, and nitrates. It is also incompatible with a number of other compounds, including strong acids, organic anhydrides, isocyanates, aldehydes, chlorosulfonic acid, and ozone. Personal protective equipment should be used to prevent chemical exposure to p-chloroaniline as it is a skin and eye irritant and a systemic toxin. Vapors are highly toxic, as are the liquid and solid forms. Containers should be kept tightly closed and stored in a well-ventilated, cool environment away from incompatibles. Work and storage areas where it is used, handled, or stored should be marked according to OSHA regulations (Harbison, 1998; ILO , 1998; Pohanish, 2002; Pohanish & Greene, 1997).
HANDLING
- Persons that handle or use p-chloroaniline, or any of the chloroanilines, should be properly trained on storage and handling. Workplace hazards associated with p-chloroaniline are related to the toxicity, reactivity, and flammability of this chemical. Skin and eye contact should be avoided. Chemical exposure should be prevented through the use of personal protective equipment, due to the high toxicity of this material and because it can be dermally absorbed (Harbison, 1998; Pohanish, 2002).
- Caution should be used during use and handling of p-chloroaniline because it is incompatible with a number of substances, including, but not limited to, strong oxidizers. Reaction with oxidizers can present a serious fire and explosion hazard. Storage containers for p-chloroaniline should be tightly closed, and the material should be kept away from incompatible materials (Pohanish, 2002).
- Stability during transport: stable (CHRIS , 2002).
STORAGE
This material should be stored in a tightly closed container. Open venting using a flame arrester is recommended during shipping (CHRIS , 2002; Pohanish, 2002). DOT requires that shipments of chloroanilines be labeled as poison (Pohanish, 2002).
- ROOM/CABINET RECOMMENDATIONS
Containers of p-chloroaniline should be stored in a cool, well-ventilated area away from oxidizers due to the risk of violent reactions or explosion. A regulated, marked area should be established where the material is stored, handled, or used in order to maintain compliance with applicable OSHA regulations (CHRIS , 2002; Pohanish, 2002). Ambient temperature is acceptable for storage during shipping (CHRIS , 2002). HSDB provides precautions for carcinogens, and recommends that carcinogens, such as p-chloroaniline, be stored close to the area of use as is practicable. A designated and labeled storage area for carcinogens should be maintained within the storage cabinet or segregation and posting can be accomplished within the storage area (HSDB , 2002).
Fire and explosion may result due to violent reactions when p-chloroaniline comes into contact with strong oxidizers such as perchlorates, permanganates, peroxides, chlorates, and nitrates. It is also incompatible with strong acids, organic anhydrides, isocyanates, aldehydes, chlorosulfonic acid, and ozone. It does not react with water (CHRIS , 2002; Pohanish, 2002; Pohanish & Greene, 1997).
-PERSONAL PROTECTION
SUMMARY
- RECOMMENDED PROTECTIVE CLOTHING - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 152 (ERG, 2004)
Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.
- p-Chloroaniline is a confirmed carcinogen, and is poisonous by the ingestion, inhalation, skin contact, subcutaneous, and intravenous routes of exposure. It is an irritant to the skin and a severe eye irritant. Skin and eye contact should be avoided. Eye protection and solvent-resistant gloves and clothing should be worn when handling p-chloroaniline. Protective gloves and clothing materials should be selected that are appropriate for the operation. Respiratory protection should also be used (Lewis, 2000; Pohanish, 2002).
EYE/FACE PROTECTION
- Unless a full-face respirator is worn, eye and face protection should be used. When working with liquid, splash-proof chemical goggles and face shield should be worn. Dust-proof goggles and face shield should be worn when working with the solid material (Pohanish, 2002).
RESPIRATORY PROTECTION
- To avoid inhalation exposure, respiratory protection should be used work handling p-chloroaniline. In addition, highly toxic fumes are emitted when p-chloroaniline is heated to decomposition. Precautions should be taken to avoid inhalation of dusts, fumes, or vapors. In some cases, a dust respirator can be used as part of personal protective equipment. Otherwise, a MSHA/NIOSH approved supplied-air respirator with a full facepiece operated in positive pressure mode or with a full facepiece, hood, or helmet in the continuous flow mode should be used. A MSHA/NIOSH approved self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive pressure mode can also be used if deemed appropriate (CHRIS , 2002; HSDB , 2002; Pohanish, 2002; ITI, 1995).
PROTECTIVE CLOTHING
- CHEMICAL PROTECTIVE CLOTHING. Search results for CAS 106-47-8.
ENGINEERING CONTROLS
- HSDB, 2002 identifies a number of precautions for carcinogens that may be considered when working with p-chloroaniline (HSDB , 2002).
Operations associated with synthesis and purification should be conducted under a well- ventilated hood. In addition, analytical and laboratory procedures that involve p-chloroaniline should be completed where vapor removal can be accomplished, such as in a fume cupboard or glovebox or under a hood. Work with the powder form of p-chloroaniline will require decreased air extraction to avoid being blown around the hood. Gloveboxes should be kept under negative pressure, and air changes should be sufficient to prevent concentration of vapors during work activities (HSDB , 2002). A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to remove the contaminant from exhaust emissions released from ventilated safety cabinets, lab hoods, gloveboxes, or rooms (HSDB , 2002).
-PHYSICAL HAZARDS
FIRE HAZARD
POTENTIAL FIRE OR EXPLOSION HAZARDS - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 152 (ERG, 2004) Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
p-Chloroaniline is a combustible solid. It may be dissolved in a liquid carrier substance. Regardless of form, it is a fire hazard. The material also presents a reactivity and explosion hazard due to its incompatibility with strong oxidizers, strong acids, organic anhydrides, isocyanates, aldehydes, chlorosulfonic acid, and ozone. Contact with strong oxidizers may lead to fire and explosion. p-Chloroaniline will decompose above 160 degrees C, and will emit toxic and corrosive fumes of chlorine, nitrogen oxides, and hydrogen chloride when heated to decomposition. Containers may explode in a fire (CHRIS , 2002; ILO , 1998; Lewis, 2000; Pohanish, 2002; Pohanish & Greene, 1997). An extinguishing agent should be used that is suitable for the surrounding type of fire and for p-chloroaniline. Dry chemical, carbon dioxide, water spray, or alcohol foam extinguishers can be used (AAR, 2000). Containers may explode in a fire. A water spray should be used from a secure, explosion-proof location to cool any exposed containers. However, if cooling streams are ineffective as evidenced by increased volume and pitch of container venting sound, discoloration of container or tank, or signs of deformation, personnel should withdraw immediately to a secure position (Pohanish, 2002).
- FLAMMABILITY CLASSIFICATION
- NFPA Flammability Rating for CAS106-47-8 (NFPA, 2002):
- INITIATING OR CONTRIBUTING PROPERTIES
- FIRE CONTROL/EXTINGUISHING AGENTS
- SMALL FIRE PRECAUTIONS - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 152 (ERG, 2004)
- LARGE FIRE PRECAUTIONS - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 152 (ERG, 2004)
Water spray, fog or regular foam. Move containers from fire area if you can do it without risk. Dike fire control water for later disposal; do not scatter the material. Use water spray or fog; do not use straight streams.
- TANK OR CAR/TRAILER LOAD FIRE PRECAUTIONS - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 152 (ERG, 2004)
Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn.
- NFPA Extinguishing Methods for CAS106-47-8 (NFPA, 2002):
- Dry chemical, carbon dioxide, water spray, or alcohol foam extinguishers should be used. In addition, an extinguishing agent should be used that is suitable for the surrounding type of fire (AAR, 2000; (CHRIS , 2002; Pohanish, 2002).
p-Chloroaniline will decompose when heated above 160 degrees C. Toxic and corrosive fumes of nitrogen oxides, chlorine, and hydrogen chloride will be generated when p-chloroaniline burns (ILO , 1998; Lewis, 2000).
EXPLOSION HAZARD
- Fire and explosion may result when p-chloroaniline comes into contact with strong oxidizers (Pohanish, 2002).
DUST/VAPOR HAZARD
- Dusts of p-chloroaniline can be absorbed through the skin. Personal protective equipment should be utilized to avoid exposure to this material (Bingham et al, 2001; Pohanish, 2002).
REACTIVITY HAZARD
- This substance will react violently with oxidants. The material presents a reactivity and explosion hazard due to its incompatibility with oxidizers, strong acids, acetic anhydride, organic anhydrides, isocyanates, aldehydes, chlorosufonic acid, and ozone (ILO , 1998; Lewis, 2000; Pohanish, 2002; Pohanish & Greene, 1997).
EVACUATION PROCEDURES
- Editor's Note: This material is not listed in the Table of Initial Isolation and Protective Action Distances.
- SPILL - PUBLIC SAFETY EVACUATION DISTANCES - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 152 (ERG, 2004)
Increase, in the downwind direction, as necessary, the isolation distance of at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids in all directions.
- FIRE - PUBLIC SAFETY EVACUATION DISTANCES - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 152 (ERG, 2004)
If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.
- PUBLIC SAFETY MEASURES - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 152 (ERG, 2004)
CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number: MEXICO: SETIQ: 01-800-00-214-00 in the Mexican Republic; For calls originating in Mexico City and the Metropolitan Area: 5559-1588; For calls originating elsewhere, call: 011-52-555-559-1588.
CENACOM: 01-800-00-413-00 in the Mexican Republic; For calls originating in Mexico City and the Metropolitan Area: 5550-1496, 5550-1552, 5550-1485, or 5550-4885; For calls originating elsewhere, call: 011-52-555-550-1496, or 011-52-555-550-1552; 011-52-555-550-1485, or 011-52-555-550-4885.
ARGENTINA: CIQUIME: 0-800-222-2933 in the Republic of Argentina; For calls originating elsewhere, call: +54-11-4613-1100.
BRAZIL: PRÓ-QUÍMICA: 0-800-118270 (Toll-free in Brazil); For calls originating elsewhere, call: +55-11-232-1144 (Collect calls are accepted).
COLUMBIA: CISPROQUIM: 01-800-091-6012 in Colombia; For calls originating in Bogotá, Colombia, call: 288-6012; For calls originating elsewhere, call: 011-57-1-288-6012.
CANADA: UNITED STATES:
For additional details see the section entitled "WHO TO CALL FOR ASSISTANCE" under the ERG Instructions. As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas.
- Persons not wearing personal protective equipment should be evacuated from the area of a spill or leak until cleanup is complete. Evacuees should keep upwind. Breathing of vapors should be avoided (AAR, 2000; (Pohanish, 2002).
- AIHA ERPG Values for CAS106-47-8 (AIHA, 2006):
- DOE TEEL Values for CAS106-47-8 (U.S. Department of Energy, Office of Emergency Management, 2010):
Listed as Chloroaniline, p- TEEL-0 (units = mg/m3): 0.0025 TEEL-1 (units = mg/m3): 0.0075 TEEL-2 (units = mg/m3): 0.05 TEEL-3 (units = mg/m3): 250 Definitions: TEEL-0: The threshold concentration below which most people will experience no adverse health effects. TEEL-1: The airborne concentration (expressed as ppm [parts per million] or mg/m(3) [milligrams per cubic meter]) of a substance above which it is predicted that the general population, including susceptible individuals, could experience notable discomfort, irritation, or certain asymptomatic, nonsensory effects. However, these effects are not disabling and are transient and reversible upon cessation of exposure. TEEL-2: The airborne concentration (expressed as ppm or mg/m(3)) of a substance above which it is predicted that the general population, including susceptible individuals, could experience irreversible or other serious, long-lasting, adverse health effects or an impaired ability to escape. TEEL-3: The airborne concentration (expressed as ppm or mg/m(3)) of a substance above which it is predicted that the general population, including susceptible individuals, could experience life-threatening adverse health effects or death.
- AEGL Values for CAS106-47-8 (National Research Council, 2010; National Research Council, 2009; National Research Council, 2008; National Research Council, 2007; NRC, 2001; NRC, 2002; NRC, 2003; NRC, 2004; NRC, 2004; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; United States Environmental Protection Agency Office of Pollution Prevention and Toxics, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2009; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2008; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2007; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2005; National Advisory Committee for Acute Exposure Guideline Levels for Hazardous Substances, 2006; 62 FR 58840, 1997; 65 FR 14186, 2000; 65 FR 39264, 2000; 65 FR 77866, 2000; 66 FR 21940, 2001; 67 FR 7164, 2002; 68 FR 42710, 2003; 69 FR 54144, 2004):
- NIOSH IDLH Values for CAS106-47-8 (National Institute for Occupational Safety and Health, 2007):
CONTAINMENT/WASTE TREATMENT OPTIONS
SPILL OR LEAK PRECAUTIONS - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 152 (ERG, 2004) ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Cover with plastic sheet to prevent spreading. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS.
RECOMMENDED PROTECTIVE CLOTHING - EMERGENCY RESPONSE GUIDEBOOK, GUIDE 152 (ERG, 2004) Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.
In the event of a spill to land, a pit, pond, lagoon, or holding area should be excavated to contain liquid or solid material. If safe and personnel hazard can be avoided, an attempt to stop the leak should be undertaken. Personal protective equipment should be used, such as gloves, boots, and goggles. Surface flow can be controlled or diverted using soil, sandbags, foamed polyurethane, or foamed concrete as a dike. Bulk liquid can be absorbed using fly ash, cement powder, or commercial sorbents. A water spray or mist can be used to prevent vaporization to the atmosphere. Material and run-off should be kept out of water sources and sewers (AAR, 2000). All ignition sources should be eliminated during spill response activities. Powdered material should be collected in a safe manner and placed in sealed containers for disposition. The area should continue to be ventilated after spill cleanup. If material enters waterways, downstream users should be notified. Regional EPA and local environmental regulatory offices should be contacted for specific recommendations for spill handling (Pohanish, 2002). Employees participating as spill response personnel must be properly trained and equipped according to OSHA requirements. OSHA 1910.120(q) may be applicable (Pohanish, 2002).
Electrochemical treatment may be used to remove chloroaniline from wastewate (HSDB , 2002). Editor's Note: Waste contaminated with p-chloroaniline may be regulated under RCRA. Waste storage, handling, treatment, transportation, and disposal should be in accordance with 40 CFR 240-280, 300-306, or 702-799. Quantities greater than or equal to 100 kg/month are subject to EPA requirements for hazardous waste (RCRA Number P024). Waste management activities associated with material disposition are unique to individual situations. Proper waste characterization and decisions regarding waste management should be coordinated with the appropriate local, state, or federal authorities to ensure compliance with all applicable rules and regulations.
p-Chloroaniline may be incinerated by rotary kiln incineration. HSDB provides a number of precautions for carcinogens that should be considered when incineration is used (HSDB , 2002). Incinerability: On a thermal stability ranking of hazardous organic compounds, p-chloroaniline ranks 37 on a scale of 1 (highest stability) to 320 (lowest stability) (Verschueren, 2001).
-ENVIRONMENTAL HAZARD MANAGEMENT
POLLUTION HAZARD
- Releases to the environment may occur as fugitive emissions or wastewater effluent from production or manufacturing facilities where p-chloroaniline is produced or used. p-Chloroaniline is also a widespread soil contaminant resulting from its persistence as an environmental degradation product of some herbicides and fungicides. It has specifically been identified as a degradation product of 4-chlorophenylurea herbicide and a photooxidation product of monuron. Binding to soil reportedly extends its life in soil. However, soil concentrations of p-chloroaniline can undergo degradation by chemical and biological transformation processes (HSDB , 2002; Howard, 1989; IARC , 1993).
- It is a degradation product of the hospital disinfectant, chlorhexidine digluconate, based on results of acclimated activated sludge experiments (HSDB , 2002).
- p-Chloroaniline can enter the environment through the use of chlorhexide, a soft contact lense product, because it is a contaminant of this material (HSDB , 2002).
ENVIRONMENTAL FATE AND KINETICS
In the atmosphere, p-chloroaniline will most likely exist in the vapor phase, based on its vapor pressure of 0.027 mmHg at 26 degrees C. Rain washout can occur due to the solubility of p-chloroaniline. It will degrade in air by reaction with photochemically produced hydroxyl radicals. Vapor phase p-chloroaniline or chemical concentrations adsorbed to airborne particulate matter may also undergo photolysis (Howard, 1989; HSDB , 2002).
SURFACE WATER When p-chloroaniline is released to water, it will primarily be lost through volatilization. Photooxidation of the chemical will also occur in the surface layer of a water source. Biodegradation occurs to a certain extent, and rates have been shown to decrease and are shorter in acclimated waters. In addition, p-chloroaniline tends to chemically react and bind to particulate matter, clay particles, or humic material in water and in sediment. These reactions can occur rapidly and contribute to its degradation in water (Howard, 1989; HSDB , 2002).
TERRESTRIAL When released to soil, p-chloroaniline will initially volatilize to a very small extent. It will primarily adsorb to soil with adsorption highly dependent on soil organic content, increasing with the organic carbon content. Under certain conditions, it may bind with clay. Binding of p-chloroaniline to soil may extend its life in soil to 10 years. Its formation of covalent bonds and polymers with soil components reportedly makes it highly resistant to mineralization. Although, there are conflicting results regarding the biodegradation of p-chloroaniline. Adsorption processes will also limit migration, and transport to surrounding soils, deeper soil layers, or to groundwater is not expected (Howard, 1989; HSDB , 2002). Concentrations of p-chloroaniline will be partially mineralized through chemical and biological transformation processes in soil, with most of the chemical transforming into inextractable residues that are bound tightly to soil (Howard, 1989; HSDB , 2002). Studies of the degradation of p-chloroaniline in soil have shown that soil concentrations will decline rapidly in the first few weeks due to mineralization. Releases to the atmosphere occur primarily as CO2 from mineralization, and not as volatilized p-chloroaniline or its conversion products (Howard, 1989; HSDB , 2002).
Field testing where C-14 labeled p-chloroaniline was applied to cultivated soil under outdoor conditions showed 30% retention of the applied radioactivity and 67% atmospheric loss after the first year. Plant uptake and contaminant leaching were low. Results were not different after two or three years, and the contaminant was not present as free unchanged product in the soil or plants. Additional findings were (HSDB , 2002): After 20 weeks, there was 32.8% radiocarbon recovery, with 32.4% in soil, 0.3% in plants, and 0.1% in leachate. The soil radioactivity from the applied C-14 was made up of 30.8% unextractable residues and 1.6% soluble conversion products, while that in plants was 0.24% unextractable residues and 0.03% soluble conversion products. Conversion products found in the soluble radioactive fractions in soil and plants of the first two years were: 4-chloroformanilide, 4-chloroacetanilide, 4-chloronitrobenzene, 4-chloronitrosobenzene, and the condensation products 4,4'-dichloroazoxybenzene and 4,4'-dichloroazobenzene. Phenolic and hydroxylamine metabolites were not identified, possibly due to their chemical instability. However, these compounds were found in laboratory experiments. Radioactive substances which were unextractable in soil and in leachate were partially hydrolyzable and indicated p-chloroaniline. The study concluded that free p-chloroaniline is not persistent in soil. Rather, it is subject to various acylation and oxidation reactions and then total biodegradation and incorporation into soil and plant constituents.
Degradability of p-chloroaniline and binding sites among different soil fractions were evaluated using C-14 labeled p-chloroaniline incubated under outdoor conditions for 20 to 25 weeks. Total recovery was 32.4%, of which 95.1% was bound residues. Concentrations of bound C-14 in the soil fractions, given as microgram equivalents to parent compound per gram dry soil fraction, were (HSDB , 2002):
OTHER The half-life associated with degradation by reaction with hydroxyl radicals in air is 4.6 hours, assuming a concentration of 5 x 10(5) radicals/cm(3). It reacts with a rate constant of 8.3 x 10(-11) cm(3)/molecule-sec (Howard, 1989; HSDB , 2002). The half-life of p-chloroaniline was decreased by a factor of 2 with the presence of the photosensitizer riboflavin. This study used a photoreactor and light greater than 290 nm (HSDB , 2002). p-Chloroaniline has a volatilization half-life of 6.4 hours in a model river (Howard, 1989). Based on the Henry's Law constant of 1.16 x 10 (-5) atm-m(3)/mol, calculated from its water solubility of 3,900 mg/l and its vapor pressure of 0.027 mmHg at 26 degrees C, a half-life of 35.7 days was estimated for a model river 1 m deep with a 1 m/sec current and 3 m/sec wind (HSDB , 2002). In the surface layers of water bodies, photooxidation occurs at a half-life of 0.4 hours. Conditions evaluated were typical for surface water in the U.S. during summer. Rates were not influenced by the presence of algae (Howard, 1989; HSDB , 2002). The biodegradation half-life in water is several days in well-acclimated water; otherwise it is on the order of several months (Howard, 1989; HSDB , 2002) A two-stage loss mechanism was observed when C-14 labeled p-chloroaniline was evaluated in an experimental pond. Half-lives of 3 and 11 days were recorded. The reduced loss rate after the first few days may have been a result of the lower volatility of decomposition products (Howard, 1989). The half-life for p-chloroaniline in a river was estimated to be 0.3 to 3 days from examination of sampling at points along the Rhine River in the Netherlands (Howard, 1989). C-14 labeled p-chloroaniline applied to Guelph loam soil was degraded by mineralization approximately 7.5% in the first 6 weeks of incubation and 17% in 16 weeks (HSDB , 2002).
ABIOTIC DEGRADATION
- p-Chloroaniline will undergo photodecomposition by photomineralization or photolysis. It absorbs light at wavelengths greater than 290 nm. Photosensitizers will increase the rate photodecomposition (Howard, 1989; HSDB , 2002).
Experimental data showed formation of 4-chloronitrobenzene and 4-chloronitrosobenzene and complete disappearance of p-chloroaniline within six hours when irradiated at greater than 290 nm in water saturated with air (Howard, 1989; HSDB , 2002). Photomineralization to CO2 occurred in 17 hours for 28% of p-chloroaniline adsorbed on silica gel (Howard, 1989; HSDB , 2002).
- Chemical reactions will take place after p-chloroaniline adsorbs to clay surfaces or humus. These reactions are irreversible and can contribute to chemical losses in environmental media (Howard, 1989; HSDB , 2002).
- p-Chloroaniline reacts with manganese dioxide present in natural water or soil forming azo compounds (HSDB , 2002).
BIODEGRADATION
- Biodegradation studies have presented conflicting results. p-Chloroaniline is most often reported to degrade slowly with acclimation increasing the degradation rates over time. Conflicting results may be associated with metabolic intermediate toxicity, concentration and inocula differences, chemical oxidation of p-chloroaniline, and acclimation period needs. Biotransformation of p-chloroaniline will frequently involve acylation and oxidation to phenols (Howard, 1989; HSDB , 2002).
- C-14 labeled p-chloroaniline has been used in a number of soil incubation studies evaluating biological mineralization (Howard, 1989; HSDB , 2002):
One study showed 7.5% mineralization in six weeks, with residues being 72% unextractable and 7% extractable. Part of the extractable fraction was also biologically mineralized, and biological transformation of the unextractable residue was reported. Another study noted 12-17% mineralization in 16 weeks. Maximum degradation occurred between weeks 1 and 3. 86% of the residue was bound to the soil as unextractable material and 1-4% was extractable.
- Anaerobic conditions are not favorable for biodegradation of p-chloroaniline. This was evidenced in a few studies:
Biotransformation did not occur under anaerobic conditions of incubation for 8 months where separate methanogenic and sulfate-reducing samples were used within a shallow unconfined aquifer polluted by municipal landfill leachate (HSDB , 2002). Mineralization did not take place under anaerobic incubation of p-chloroaniline with digester sludge for one month (Howard, 1989).
- Aerobic conditions have been shown to contribute to biodegradation of p-chloroaniline, as reported in the following results (HSDB , 2002):
One case involved a pilot-scale study of the removal of p-chloroaniline and other pollutants by a continuous-flow conventional activated sludge treatment plant. Results showed 87.6% removal of p-chloroaniline during treatment, with 78% attributed to biodegradation (HSDB , 2002). Aerobic biomineralization in the soil was examined over a period of 28 days and ranged from 1.21% for the humic acid organic material of soil to 4.98% for the fulvic acid. While overall, it was reported to be 2.18%. This was compared to 9.04% for the free chemical. Similar results were noted in a standard photomineralization test. C-14 labeled CO2 formation ranged from 0.08% for humic acid to 1.43% for fulvic acid, and 1.39% overall, compared to 26.06% for the free chemical (HSDB , 2002).
- Biodegradation in a soil-water suspension at 35 degrees C at an initial concentration of 0.1 mg/l have been reported as follows (Verschueren, 2001):
Aerobic conditions - 1.5% mineralization to CO2 after 5 days; 3% mineralization to CO2 after 56 days; 15% of the initial concentration remaining in the water after 56 days. Anaerobic conditions - 2% mineralization to CO2 after 56 days; 22% of the initial concentration remaining in the water after 56 days.
- Isolated soil fungus cultures of Fusarium oxysporum schlect were used to study the metabolism of p-chloroaniline. The metabolite, 2-amino-5-chlorophenol was positively identified (HSDB , 2002).
- A Pseudomonas species isolated from soil was grown under aerobic conditions using only p-chloroaniline as its carbon and nitrogen source. A generation time of 15 hours was reported. Use of C-14 labeled chemical showed that 64% of the carbon from p-chloroaniline was released as CO2 and 14% was associated with the biomass (HSDB , 2002).
BIOACCUMULATION
AQUATIC Uptake of p-chloroaniline by tomatoes increased with increased concentrations in soil (HSDB , 2002). Carrots accumulated p-chloroaniline slightly more in roots than in green portions of the plant. Translocation increased with increasing soil concentrations (HSDB , 2002). Wheat and barley were shown to take up p-chloroaniline (HSDB , 2002). Soil treated with 1 ppm C14-labelled p-chloroaniline was taken up and translocated by oats at 1.4% of the soil-bound concentration within six weeks, while uptake from solution was from 1.7% to 2.3%. Results were only slightly different in the two soil types studied, humus-rich gley and parabrown (HSDB , 2002).
Carp: Average BCFs of 0.8 at high exposure levels and 1.7 at low exposure levels (whole body; exposed in flow-through experiments for 24 to 336 hours) (HSDB , 2002). Carp: BCF less than 10 for Leuciscus idus melanotus (using a formulation of 52 mcg/L; 3D; freshwater) ((EPA, 2002f)) Green Algae: 24-hour log BCF = 3.08 (dry weight basis); 24-hour log BCF = 2.42 (wet weight basis) (Howard, 1989; HSDB , 2002). Green Algae: BCF = 260 for Chlorella fusca (using a formulation of approximately 50 mcg/L; 24H; freshwater) ((EPA, 2002f)) Green Algae: BCF = 260 for Chlorella fusca vacuolata (using a formulation of 50 mcg/L; 24H-static; freshwater) ((EPA, 2002f)) Green Algae: BCF = greater than or equal to 60 for Chlorella fusca vacuolata (using a formulation of 50 mcg/L; 24H-static; freshwater) ((EPA, 2002f)) GUPPY (Poecilia reticulata): BCF = 1.12 (using a formulation of 198 mcmol/L; 39H-flow-through; freshwater) ((EPA, 2002f)) IDE, SILVER OR GOLDEN ORFE (Leuciscus idus): log BCF <1.30 (3-day exposure) (Howard, 1989; HSDB , 2002) IDE, SILVER OR GOLDEN ORFE (Leuciscus idus): BCF = 13 (using a formulation of approximately 50 mcg/L; 3D; freshwater) ((EPA, 2002f)) IDE, SILVER OR GOLDEN ORFE (Leuciscus idus): BCF less than 20 (whole organism; using a formulation of 52 mcg/L; 3D-static; freshwater) ((EPA, 2002f)) BCF MEDAKA, HIGH-EYES (Oryzias latipes): approximately 4 (using a formulation of 7.61 ng/ml; 10M-flow-through; freshwater) ((EPA, 2002f)) BCF MEDAKA, HIGH-EYES (Oryzias latipes): greater than 8 and less than 12 (using a formulation of 7.61 ng/ml; 80M-flow-through; freshwater) ((EPA, 2002f)) Zebrafish: BCF = 8.1 (24H) (HSDB , 2002)
ENVIRONMENTAL TOXICITY
- AQUATIC LIFE TOXICITY DATA
EC40 - (FRESHWATER) DIATOM (Nitzschia palea): 1 mcmol/L formulation for 16D-static -- general population changes (EPA, 2002f) EC40 - (FRESHWATER) GREEN ALGAE (Scenedesmus quadricauda): 2 mcmol/L formulation for 16D- static -- general population changes (EPA, 2002f) EC50 - (WATER) CILIATE (Tetrahymena pyriformis): 10,000 mcg/L formulation for 24H-static -- general effects on growth (EPA, 2002f) EC50 - (FRESHWATER) GREEN ALGAE (Chlorella zofingiensis): 0.717 mmol/L formulation for 48H-static -- physiological effects related to assimilation efficiency (EPA, 2002f) EC50 - (FRESHWATER) GREEN ALGAE (Chlorella zofingiensis): greater than 200 mcM formulation for 48H-static -- biochemical effects on chlorophyll (EPA, 2002f) EC50 - (FRESHWATER) GREEN ALGAE (Scenedesmus abundans): 2,400 mcg/L formulation for 96H- static -- general effects on growth (EPA, 2002f) EC50 - (FRESHWATER) GREEN ALGAE (Scenedesmus quadricauda): 2.2 mg/L formulation for 96H -- histological effects, proliferation (EPA, 2002f) EC50 - (FRESHWATER) GREEN ALGAE (Scenedesmus subspicatus): 8,000 mcg/L formulation for 48H- static -- population effects related to biomass (EPA, 2002f) EC50 - (FRESHWATER) WATER FLEA (Daphnia magna): 13 mg/L formulation for 24H-renewal -- behavioral effects associated with equilibrium (EPA, 2002f) EC50 - (FRESHWATER) WATER FLEA (Daphnia magna): 3.2 mg/L formulation for 24H - behavioral effects associated with equilibrium (EPA, 2002f) EC100 - (FRESHWATER) GREEN ALGAE (Chlorococcum): 1 mcmol/L formulation for 16 D-static -- general population changes (EPA, 2002f) LC0 - (FRESHWATER) WATER FLEA (Daphnia magna): 0.483 mcg/L formulation for 21D (EPA, 2002f) LC50 - (SALTWATER) BAY SHRIMP, SAND SHRIMP (Crangon septemspinosa): 12,500 mcg/L formulation for 10H- renewal (EPA, 2002f) LC50 - (FRESHWATER) BLUEGILL (Lepomis macrochirus): mean value of 2,400 mcg/L formulation for 96H- static (EPA, 2002f; Verschueren, 2001) LC50 - (FRESHWATER) CHANNEL CATFISH (Ictalurus punctatus): mean value of 23,000 mcg/L formulation for 96H-static (EPA, 2002f; Verschueren, 2001) LC50 - (FRESHWATER) FATHEAD MINNOW (Pimephales promelas): 30,600 mcg/L formulation for 96H- flow-through (EPA, 2002f) LC50 - (FRESHWATER) FATHEAD MINNOW (Pimephales promelas): 12,000 mcg/L formulation for 96H- static (EPA, 2002f; Verschueren, 2001) LC50 - (WATER) FATHEAD MINNOW (Pimephalus promelas): 29 mg/l for 96H (Verschueren, 2001) LC50 - (FRESHWATER) GUPPY (Poecilia reticulata): 26,000 mcg/L formulation for 14D-static (EPA, 2002f; Verschueren, 2001) LC50 - (FRESHWATER) IDE, SILVER OR GOLDEN ORFE (Leuciscus idus): 23,000 mcg/L formulation (EPA, 2002f) LC50 - (FRESHWATER) MEDAKA, HIGH-EYES (Oryzias latipes): 28,000 mcg/L formulation for 48H-static (EPA, 2002f) LC50 - (FRESHWATER) RAINBOW TROUT,DONALDSON TROUT (Oncorhynchus mykiss): 11,000 mcg/L formulation for 96H-flow-through (EPA, 2002f) LC50 - (FRESHWATER) RAINBOW TROUT,DONALDSON TROUT (Oncorhynchus mykiss): 14,000 mcg/L formulation for 96H-static (EPA, 2002f; Verschueren, 2001) LC50 - (FRESHWATER) RAINBOW TROUT,DONALDSON TROUT (Oncorhynchus mykiss): 0.128 mmol/L formulation for 96H-static (EPA, 2002f) LC50 - (WATER) RAINBOW TROUT,DONALDSON TROUT (Salmo gairdneri): 14 mg/l for 96H (Verschueren, 2001) LC50 - (FRESHWATER) ROTIFER (Brachionus rubens): 100,000 mcg/L formulation for 24 H-static (EPA, 2002f) LC50 - (SALTWATER) SAND GAPER, SOFT SHELL CLAM (Mya arenaria): 15,100 mcg/L formulation for 29 H- renewal (EPA, 2002f) LC50 - (FRESHWATER) ZEBRA DANIO (Danio rerio): 270 mcmol/L formulation for 96H-renewal (EPA, 2002f) LOEC - (FRESHWATER) GREEN ALGAE (Chlorella zofingiensis): 0.1 mmol/L formulation for 48H- static -- physiological effects related to assimilation efficiency (EPA, 2002f) NOEC - (FRESHWATER) WATER FLEA (Daphnia magna): 0.01 mg/L formulation for 21D-renewal -- behavioral effects associated with equilibrium (EPA, 2002f) NOEC - (FRESHWATER) WATER FLEA (Daphnia magna): 10 mcg/L formulation for 21D-renewal -- general reproductive effects (EPA, 2002f) NR-LETH - (FRESHWATER) CLAWED TOAD (Xenopus laevis): 100,000 mcg/L formulation for 3W- renewal -- 100% mortality or 0% survival of organisms (EPA, 2002f) NR-ZERO - (FRESHWATER) MEDAKA, HIGH-EYES (Oryzias latipes): 29,000 mcg/L formulation for 96H- flow-through -- 0% mortality or 100% survival of organisms (EPA, 2002f)
- TERRESTRIAL PLANTS AND WILDLIFE TOXICITY DATA
EC50 - (UNKNOWN SOIL) BREAD WHEAT (Triticum aestivum): 1000 mg/kg; 14 D; soil pH 6 -- general effects on growth (EPA, 2002f) EC50 - (UNKNOWN SOIL) COMMON OAT (Avena sativa): 1000 mg/kg; 14 D; soil pH 6 -- general effects on growth (EPA, 2002f) EC50 - (UNKNOWN SOIL) GARDEN CRESS (Lepidium sativum): 1000 mg/kg; 14 D; soil pH 6 -- general effects on growth (EPA, 2002f) EC50 - (UNKNOWN SOIL) GRAIN SORGHUM (Sorghum bicolor bicolor): 100 mg/kg; 14 D; soil pH 6 -- general effects on growth (EPA, 2002f) EC50 - (UNKNOWN SOIL) LETTUCE (Lactuca sativa): 1000 mg/kg; 14D; soil pH 6 -- general effects on growth (EPA, 2002f) EC50 - (UNKNOWN SOIL) PAK-CHOI (Brassica chinensis): 1000 mg/kg; 14D; soil pH 6 -- general effects on growth (EPA, 2002f) EC50 - (UNKNOWN SOIL) RADISH (Raphanus sativus): 1000 mg/kg; 14D; soil pH 6 -- general effects on growth (EPA, 2002f) EC50 - (UNKNOWN SOIL) RAPE (Brassica napus): 1000 mg/kg; 14 D; pH 6 -- general effects on growth (EPA, 2002f) EC50 - (UNKNOWN SOIL) RED CLOVER (Trifolium pratense): 1000 mg/kg; 14D; soil pH 6 -- general effects on growth (EPA, 2002f) EC50 - (UNKNOWN SOIL) TURNIP (Brassica rapa): 1000 mg/kg; 14D; soil pH 6 - general effects on growth (EPA, 2002f) EC50 - (UNKNOWN SOIL) PERENNIAL RYEGRASS (Lolium perenn): 1000 mg/kg; 14D; soil pH 6 -- general effects on growth (EPA, 2002f) EC50 - (UNKNOWN SOIL) WHITE MUSTARD (Sinapis alba): 1000 mg/kg; 14D; soil pH 6 -- general effects on growth (EPA, 2002f) LC50 - (UNKNOWN SOIL) BIRD RAPE (Brassica rapa): 66.5 mg/kg; 14D; soil pH 0 (EPA, 2002f) LC50 - (UNKNOWN SOIL) BIRD RAPE (Brassica rapa): 200 mg/kg; 14D; soil pH 0 (EPA, 2002f) LC50 - (UNKNOWN SOIL) COMMON OAT (Avena sativa): 140 mg/kg; 14D; soil pH 0 (EPA, 2002f) LC50 - (ARTIFICIAL SOIL MEDIA) EARTHWORM (Eisenia fetida): 180 mg/kg; 14D; soil pH 0 (EPA, 2002f) LC50 - (ARTIFICIAL SOIL MEDIA) EARTHWORM (Eisenia fetida): 540 mg/kg; 28D; soil pH 0 (EPA, 2002f)
- Effect of low concentrations on aquatic life is unknown (CHRIS , 2002).
- A study of p-chloroaniline as a degradation product of dibenzofuran reported a 96-hour median lethal dose of 2.4 mg/l for bluegill fish (HSDB , 2002).
- Lethal effects were observed in Xenopus Laevis embryos at 100 ppm (HSDB , 2002).
-PHYSICAL/CHEMICAL PROPERTIES
MOLECULAR WEIGHT
DESCRIPTION/PHYSICAL STATE
- p-Chloroanilines is a white or pale-yellow crystalline solid. The solid material may be dissolved in a liquid carrier substance. It has a slightly sweet characteristic amine odor. There are two grades of purity, 99.0% and technical grade. In water it sinks and mixes slowly into solution. Its physical state at 15 degrees C and 1 atm is a solid (AAR, 2000; (Bingham et al, 2001; CHRIS , 2002; HSDB , 2002; ITI, 1995; Lewis, 2001; Pohanish, 2002).
VAPOR PRESSURE
- 0.025 mmHg (at 25 degrees C) (Howard, 1989)
- 0.027 mm Hg (at 26 degrees C) (HSDB , 2002)
- 0.015 mmHg (at 20 degrees C) (Verschueren, 2001)
- 0.05 mmHg (at 30 degrees C) (Verschueren, 2001)
- 10 mmHg (at 102.1 degrees C) (HSDB , 2002)
- 40 mmHg (at 135 degrees C) (HSDB , 2002)
- 100 mmHg (at 159.9 degrees C) (HSDB , 2002)
SPECIFIC GRAVITY
- OTHER TEMPERATURE AND/OR PRESSURE
SOLID: 1.43 at 19/4 degrees C (CHRIS , 2002; Verschueren, 2001) 1.169 at 77/4 degrees C (Budavari, 2001; ITI, 1995) 1.427 at 19/4 degrees C (Bingham et al, 2001)
- TEMPERATURE AND/OR PRESSURE NOT LISTED
1.169 (Lewis, 2000) 1.4 (ILO , 1998)
DENSITY
- OTHER TEMPERATURE AND/OR PRESSURE
- TEMPERATURE AND/OR PRESSURE NOT LISTED
FREEZING/MELTING POINT
68-71 degrees C (Ashford, 2001) 72.5 degrees C (Bingham et al, 2001; Budavari, 2001; Howard, 1989) 70 degrees C (Pohanish, 2002) 70-71 degrees C (ITI, 1995; Lewis, 2000) 69.5 degrees C (Lewis, 2001)
BOILING POINT
- 230-232 degrees C (Ashford, 2001)
- 232 degrees C (Budavari, 2001; ILO , 1998; ITI, 1995; Pohanish, 2002)
- 232 degrees C (at 760 mmHg) (Howard, 1989)
- 230 degrees C = 446 degrees F = 503 K (at 1 atm) (CHRIS , 2002)
- 231-232 degrees C (Bingham et al, 2001)
FLASH POINT
- 120-123 degrees C (ILO , 1998; Pohanish, 2002)
- > 220 degrees F (open cup; combustible solid) (CHRIS , 2002)
AUTOIGNITION TEMPERATURE
- 685 degrees C (ILO , 1998; Pohanish, 2002)
SOLUBILITY
Soluble in hot water (Ashford, 2001; Budavari, 2001; Lewis, 2001; Lewis, 2000; Lewis, 1998; Pohanish, 2002) Soluble in warm water (ITI, 1995) 3.9 g/l = 3900 mg/l (Howard, 1989; HSDB , 2002) Insoluble in water (Bingham et al, 2001)
Soluble in oxygenated solvents (Ashford, 2001) Freely soluble in alcohol, ether, acetone, and carbon disulfide (Budavari, 2002; (Lewis, 1998; Lewis, 2000) Soluble in most organic solvents (ITI, 1995; Lewis, 2001). Soluble in ether and miscible with ethanol (Bingham et al, 2001)
OCTANOL/WATER PARTITION COEFFICIENT
- Log Kow = 1.83 (Howard, 1989; HSDB , 2002; Verschueren, 2001)
HENRY'S CONSTANT
- 1.07 x 10(-5) atm-m(3)/mol (calculated from vapor pressure and water solubility) (Howard, 1989)
SPECTRAL CONSTANTS
OTHER/PHYSICAL
- NUCLEAR MAGNETIC RESONANCE
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