Dicyclohexylamine

Nitrogen Compounds -> Amines, Cyclic

Corrosives

FAINT FISHY ODOR

Amine odor.

0.913 to 0.919 at 59 °F (NTP, 1992)

0.9104 at 25 °C/25 °C

Relative density (water = 1): 0.9

Slightly soluble (NTP, 1992)

SPARINGLY SOL IN WATER; SOL IN USUAL ORGANIC SOLVENTS; MISCIBLE WITH CYCLOHEXYLAMINE

Soluble in ethanol, ether, benzene.

Soluble in oxygenated solvents.

Solubility in water, g/100ml at 25 °C: 0.08

greater than 210 °F (NTP, 1992)

105 °C

105 °C o.c.

492.4 °F at 760 mmHg (NTP, 1992)

255.8 °C @ 760 MM HG

256 °C

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P270, P273, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P363, P391, P405, and P501 (click each P-code to see the statement)

Danger

H302 (91.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P264+P265, P270, P273, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P391, P405, and P501 (click each P-code to see the statement)

Chemical: Cyclohexanamine, N-cyclohexyl-

Cyclohexanamine, N-cyclohexyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclohexanamine, N-cyclohexyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 06-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13263

Dicyclohexylamine: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· Combustible material: may burn but does not ignite readily.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; May cause pulmonary edema; [ICSC] Possible skin sensitizer; [Merck Index] Toxic by ingestion, inhalation, and skin contact; [CAMEO] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; No sensitizing effects known; [MSDSonline] Danger of cutaneous absorption; [MAK]

DICYCLOHEXYLAMINE reacts with oxidizing agents. Forms crystalline salts with many N-protected amino acids (NTP, 1992). Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Cautiously neutralize remainder. Then wash away with plenty of water.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Immediate precautionary measure

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 260(SRC), determined from a structure estimation method(2), indicates that dicyclohexylamine is expected to have moderate mobility in soil(SRC). Volatilization of dicyclohexylamine from moist soil surfaces is expected given an estimated Henry's Law constant of 5.5X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Dicyclohexylamine is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 3.4X10-2 mm Hg(4).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 260(SRC), determined from a structure estimation method(2), indicates that dicyclohexylamine is expected to adsorb to suspended solids and sediment in water(SRC). Dicyclohexylamine is expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 5.5X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated volatilization half-lives for a model river and model lake are 1.1 and 12 days, respectively(3,SRC). According to a classification scheme(5), an estimated BCF value of 1200(3,SRC), from an estimated log Kow of 4.37(6,SRC), suggests that bioconcentration in aquatic organisms is very high(SRC). A biodegradation study based on BOD measurements, using an activated sludge seed, and an initial concentration of 100 mg/l, indicated 76.9% degradation of dicyclohexylamine after 2 weeks(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dicyclohexylamine, which has an experimental vapor pressure of 3.4X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dicyclohexylamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 2.9 hours(3,SRC).

Sore throat. Cough. Burning sensation. Shortness of breath. Laboured breathing. Symptoms may be delayed.

Pain. Redness. Blisters. Skin burns.

Pain. Redness. Severe deep burns.

Burning sensation. Abdominal pain. Shock or collapse.

Dicyclohexylamine was detected in 2 of 9 biologically treated effluent samples from a bleached Kraft mill, at a mean concentration of 60 ug/l(1). Trench leachates from Maxey Flats, Kentucky and West Valley, NY low-level radioactive waste disposal sites, contained unspecified levels of dicyclohexylamine(2).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for dicyclohexylamine can be estimated to be about 260(SRC). According to a recommended classification scheme(2), this estimated Koc value suggests that dicyclohexylamine is expected to have moderate mobility in soil(SRC).

Dicyclohexylamine (CAS # 101-83-7) was evaluated for acute oral toxicity in male and female Sprague-Dawley albino rats (alternately 2 and 3/sex/treatment level) administered single undiluted doses of 158, 200, 251 and 316 mg/kg. Treatment-related mortality was consistent with an Oral LD50 (with 95% confidence limits) of 240 (205-285) mg/kg as follows: 158 mg/kg (0/2M; 0/3F), 200 mg/kg (0/3M; 1/2F), 251 mg/kg (1/2M; 2/3F), and 316 mg/kg (3/3M; 1/2F). Death occurred from several hours to 24 hours after dosing. Pharmacotoxic signs included reduction in food consumption and activity (1 day in survivors), progressive weakness, prostration and death. Upon gross necropsy of the study lethalities, treatment-related changes of visceral organs included focal hemorrhaging of the lungs, discolored liver and acute inflammation of the gastrointestinal tract. Study survivors of 14-day post-treatment observation were free of any gross treatment-related pathology at terminal sacrifice. This study was briefly summarized. No further information was reported.

Dicyclohexylamine (CAS # 101-83-7) was evaluated for acute dermal toxicity in solitary male or female New Zealand albino rabbits administered single undiluted dermal applications of 126, 316 and 501 mg/kg for 24 hours. Two male and 3 female rabbits each were administered doses of 200 mg/kg. Treatment-related mortality was consistent with a Dermal LD50 in rabbits of 200-316 mg/kg as follows: 200 mg/kg (1/2M; 0/3F), 316 mg/kg (1/1F), and 501 mg/kg (1/1M). Death occurred prior to 16th hour post-treatment observation in all cases. A solitary male of the 126 mg/kg dose and a male and 3 females of 200 mg/kg doses survived to the 14th day end of post-treatment observation and terminal sacrifice. Pharmacotoxic signs associated with treatment included reduced appetite and activity (2-3 days in survivors), progressive weakness, prostration and death. Upon terminal necropsy of study lethalities, focal hemorrhage of the lungs, discoloration of liver, enlarged gall bladder and inflammation of the gastrointestinal tract were identified. Terminal sacrifice of the study survivors found them with normal-appearing viscera and no gross treatment-related pathology. This study was briefly summarized. No further information was reported.

Dicyclohexylamine (CAS # 101-83-7) was evaluated for acute inhalation toxicity in 6 male New Zealand albino rabbits administered whole-body exposures to 1.4 mg/L for 6 hours. A 2.1 g sample was vaporized and supplied to the 35L exposure chamber via an air flow rate of 4.0 L/min. There was no mortality associated with treatment. Treated rabbits exhibited slight lethargy only, which resolved immediately after termination of the exposure and no further untoward effects of toxicity were noted throughout 14-day post-exposure observation. Upon terminal necropsy, all viscera appeared normal. This study was briefly summarized. No further information was reported.

Dicyclohexylamine (CAS # 101-83-7) was evaluated for primary dermal irritation in 6 New Zealand albino rabbits each administered 0.5 ml undiluted dermal applications to both intact and abraded skin for 24 hours. The unanimous response and a 24-72 hour average primary irritation score was assigned a classification of corrosive. Continued observation found loosening at the edges of the resultant scab showing injury in depth within 17 to 21 days after treatment. This study was briefly summarized. No further information was reported.

Dicyclohexylamine (CAS # 101-83-7) was evaluated for acute eye irritation in 6 New Zealand albino rabbits administered single 0.1 ml undiluted ocular instillations for 24 hours. A 24-72 hour average irritation score of 32.6/110 reflected an overall response assigned a classification of moderately irritating. Treatment initially caused severe discomfort and rabbits pawed and tightly closed the treated eyes. At 1 hour post-treatment, severe erythema was apparent that was unresolved at 24th hour examination. The 24th hour post-instillation examination also found treated rabbits with slight corneal cloudiness and a sluggish iridic reaction to light. Gradual improvement was seen over the ensuing 48-168 hours and, at 14th day examination, all treated eyes were clear of any signs of irritation. This study was briefly summarized. No further information was reported.

SKIN IRRITANT & POSSIBLE SENSITIZER.

SYSTEMIC EFFECTS IN MAN INCL NAUSEA & VOMITING, ANXIETY, RESTLESSNESS & DROWSINESS. /CYCLOHEXYLAMINE/

HUMAN LYMPHOCYTE CULTURES EXPOSED TO 4 COMPD @ 3 CONCN (10-3, 10-4 & 10-5 MOLAR) DURING FINAL 5 & 25 HR OF CULTURE. RESULTS CONFIRM THAT CYCLAMATE & CYCLOHEXYLAMINE @ HIGH CONCN CAN INDUCE CHROMOSOME ABERRATIONS. N-HYDROXYCYCLOHEXYLAMINE & DICYCLOHEXYLAMINE HAVE SIMILAR EFFECTS.

ENHANCED FREQUENCIES OF GAPS & BREAKS FOLLOWING TREATMENT OF HUMAN LEUKOCYTE CULTURES WITH DICYCLOHEXYLAMINE SULFATE. ABERRATION FREQUENCIES IN CONTROLS ABOUT 6% & 2-FOLD & 3-FOLD INCR IN CHROMATID DAMAGE WITH INT & HIGHER DOSES OF ALL TEST COMPD. EXPOSURE TIMES AS SHORT AS 5 HR.

STRONG IRRITANT TO SKIN & MUCOUS MEMBRANES.

Dicyclohexylamine's production and use as a chemical intermediate; in insecticides and plasticizers; as a corrosion inhibitor; as an antioxidant in rubber, lubricating oils, and fuels; as a catalyst for paint, varnishes, and inks; as a detergent and as an extractant(1) will result in its release to the environment(SRC).

Used to make drugs, soaps, detergents, vapor-phase corrosion inhibitors , dyestuffs, emulsifying agents, and acid gas absorbents; Also used in insecticides and as a plasticizer, antioxidant (rubber, lubricating oils, and fuels), catalyst (paints, varnishes, and inks), and extractant (natural products); [HSDB]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

INTERMEDIATE; INSECTICIDES; PLASTICIZER; CORROSION INHIBITORS; ANTIOXIDANTS IN RUBBER, LUBRICATING OILS, FUELS; CATALYSTS FOR PAINT, VARNISHES & INKS; DETERGENTS; EXTRACTANT

CHEM INT FOR MEDICINALS, SOAPS AND DETERGENTS, CATALYSTS IN PAINT, VARNISH, & INK MFR; EXTRACTANT FOR NATURAL PRODUCTS; CHEM INT FOR VAPOR-PHASE CORROSION INHIBITORS, RUBBER PROCESSING CHEMICALS

Manuf dyestuff, emulsifying agents, dry-cleaning soaps, acid gas absorbents

Dicyclohexylamine can be commercially important in manufacturing sulfenamides

(1976) 3.84X10+5 GRAMS (PRINCPL CUSTMS DISTS)

(1977) 4.32X10+7 GRAMS (PRINCPL CUSTMS DISTS)

2023: 1,000,000 - <2,500,000 lb

(1975) PROBABLY GREATER THAN 1.36X10+6 GRAMS

(1977) PROBABLY GREATER THAN 4.54X10+6 GRAMS

MFR PROCESS BY HYDROGENATION OF EQUIMOLAR AMT OF CYCLOHEXANONE & CYCLOHEXYLAMINE.

Cyclohexanone + ammonia (reductive ammoniation; coproduced with cyclohexylamine)

Aniline is hydrogenated in the vapor phase over a nickel-on-pumice catalyst.

All Other Chemical Product and Preparation Manufacturing

Cyclohexanamine, N-cyclohexyl-: ACTIVE

PREPD BY CATALYTIC HYDROGENATION OF ANILINE @ ELEVATED TEMP & PRESSURES. FRACTIONATION OF CRUDE REACTION PRODUCT YIELDS CYCLOHEXYLAMINE, UNCHANGED ANILINE, & HIGH-BOILING RESIDUE CONTAINING N-PHENYLCYCLOHEXYLAMINE...& DICYCLOHEXYLAMINE. /CYCLOHEXYLAMINE/

INTEREST IN THIS COMPD DERIVES FROM INTEREST IN CYCLAMATES AND ARTIFICIAL SWEETENERS.

DICYCLOHEXYLAMINE WAS NOT DETECTED IN SODIUM N-CYCLOHEXYSULFAMATE POWD & FOUND IN ONLY ONE MFR PRODUCT IN AMT OF 1.6 MG/KG.