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What is cyclohexylamine used for?

2021-01-13

What is cyclohexylamine used for?

Cyclohexylamine is a transparent, colorless liquid with a strong fishy and ammonia smell. Flammable, relative molecular mass is 99.18, relative density is 0.8191, melting point is -17.7℃, boiling point is 134.5, 118.9(6.67×104Pa), 102.5(4.00×104Pa), 72.0(1.33×104Pa), 56.0(6.67×103Pa), 45.1( 4.00×103Pa), 41.3°C (3.333×103Pa), 36.4°C (2.67×103Pa), 303.5°C (6.5°C), 303.5°C (103Pa), 3.99°C (103.5°C), 2.5°C), 2.95°C (1035°C), 2.35°C (15 ), 2.35(1.3.3.5), 2.3.3.5), 2.5.

It is soluble in water and can be mixed and dissolved with ethanol, ether, acetone, ethyl acetate, chloroform, heptane, benzene, and other common organic solvents. Cyclohexylamine can evaporate with steam and absorb carbon dioxide in the air to form white crystalline carbonate.

It can form an azeotropic substance with water, and the azeotropic point is 96.4℃, the water content is 55.8%, its aqueous solution is alkaline. pH value of 0.01% aqueous solution is 10.5.

Its steam can form an explosive mixture with air. The product is toxic, irritating to the skin and mucous membranes. Inhalation of the vapor that may cause undesirable maggots has an anesthetic effect but does not cause blood poisoning. Oral dose for rats:LD50:710 mg/kg. The maximum allowable concentration in the workplace is 10×10-6.

 

Heating cyclohexylamine and hydrogen iodide together in a sealed tube at 200°C produces methyl cyclopentane. Cyclohexylamine and dimethyl sulfate can be heated together in ether to produce methane and also a small amount of dimethyl cyclohexylamine. Its hydrochloride can be reacted with sodium nitrite salt to form cyclohexanol. The reaction of excess ammonia and zinc chloride produces 2-methylpyridine.

 

Preparation: Finished cyclohexylamine can be made by catalytic reduction of aniline at high temperature and pressure (with nickel or cobalt as a catalyst) to produce cyclohexanol cyclohexanone from the catalytic reduction of phenol as raw material or by amination with ammonia. In industry, cyclohexylamine is mainly used as an azole vulcanization accelerator for rubber and a tank detergent, dyeing auxiliary, and surfactant.

Dai Xiongfeng Chemistry Book edits the above information.

 

Cyclohexylamine


Main purpose.

Cyclohexylamine can be used as raw material for surfactants, production of alkylbenzene sulfonate, used as an emulsifier and foaming agent.

It can be used as a raw material for the production of perfume, producing allyl cyclohexyl propionate.

It can be used as raw materials for dye production, such as acid blue 62, disperse fluorescent yellow, fluorescent yellow dispersion H5GL, weak acid blue BRN, disperse blue 6, and dye additives.

As a raw material for food additive sweeteners, cyclohexylamine can also produce cyclohexylamine sulfonate and sodium cyclamate, the latter sweetener being 30 times sweeter than sucrose. The Ministry of Health of China has approved the application in sauces, dressings, prepared wines, cakes, cookies, bread, frozen drinks, and beverages at a maximum allowable amount of 0.65g/kg.

It can be used to produce insecticide "Propargite," herbicide "Wilbur," fungicide, and other pesticide materials for fruit trees.

It can prepare additives for petroleum products, boiler feed water treatment agents, rust removers, etc.

As a raw material for rubber CZazole vulcanization accelerator production, this vulcanization accelerator has a good effect and is especially suitable for SBR and FDA rubber.

It can be used as an antirust agent for the production of antirust paper.

It can be used as a tank cleaning agent.

It can be used as an antifreeze agent. It can be used as a tank cleaner for the production of antirust paper.

It can be used as an antistatic agent (textile auxiliary), latex coagulant, and additive of petroleum products.

Due to the alkaline nature of cyclohexylamine aqueous solution, it can be used as an absorbent to remove carbon dioxide and sulfur dioxide.

Chemical properties.

This product is a colorless liquid with odor. The product is mixed and dissolved with various organic solvents.

Uses.

It can be used as a vulcanization accelerator of rubber, as the raw material of synthetic fiber, dyestuff, vapor phase corrosion inhibitor. It can be used to make dyestuff, softener VS, and drugs, such as Antiradon, Thio-TEPA, solaziquone, etc. It can also be used in medicine and pesticide.

It can be used to manufacture dyes, softener VS, Antiradon, Thio-TEPA, solaziquone, and other drugs of medicine and pesticide.

 

Cyclohexylamine is the intermediate of herbicide "hexazinone" and the intermediate of rubber accelerator, oil additive, and corrosion inhibitor.

It can be used to produce cyclohexanol, cyclohexanone and caprolactam, cellulose acetate, and nylon 6. Cyclohexylamine itself is a solvent and can be used in resin, paint, grease, and paraffin oil. It can also be used to manufacture desulfurization agents, rubber antioxidants, vulcanization accelerators, plastic and textile chemical auxiliaries, boiler feedwater treatment agents, and metal corrosion inhibitors emulsifiers, preservatives, antistatic agents, latex coagulants, oil additives, fungicides, pesticides, and dye intermediates. Cyclohexylamine sulfonate can be used as an artificial sweetener in food, beverage, and medicine.

 

It can be used in organic synthesis, plastic synthesis, and preservative and acid gas absorber.

It can be used as an intermediate in producing water treatment chemicals, artificial sweeteners, rubber processing chemicals, and agrochemicals, and as an acid gas absorber for organic synthesis.

It can be used as an acid gas absorbent for organic synthesis.

 

Production method.

It is derived from the catalytic hydrogenation of aniline. The process can be divided into the atmospheric pressure method and reduced pressure method. Other methods such as catalytic ammonolysis of cyclohexane or cyclohexanol, recovery of nitrocyclohexane, and catalytic ammonolysis of cyclohexanone can also be used to produce cyclohexylamine.

It is made by catalytic hydrogenation of aniline as raw material. Mixing aniline vapor and hydrogen, pouring into the catalytic reactor under the action of cobalt catalyst, the hydrogenation reaction is carried out at 130~170℃, and the product obtained after cooling is further distilled.

 

Category.

Flammable liquid.

Toxicity classification.

Highly toxic.

Acute toxicity.

Oral-rat LD50:156 mg/kg Oral-rat LD50:224 mg/kg.

Irritation data.

Skin-Rabbit 2mg/24h, mild; Eyes-Rabbit 0.05mg/24h, severe.

Hazardous properties of explosive material.

The explosion will occur when mixed with air.

Flammability and hazard.

Flammable in the presence of fire, heat, and oxidizing agents produce toxic nitrogen oxide fumes on combustion.

Storage properties.

Storage: Store separately from ventilated, low temperature, dry oxidizers, and acids.

Fire extinguishing agent.

Dry powder, dry sand, carbon dioxide, foam, 1211 fire extinguishing agent.

Professional standard.

TWA40mg/m3.

Chemical properties.

Cleaning fluid.

Chemical properties.

Cyclohexylamine is a liquid from colorless to yellow (amine, primary aromatic). Has an unpleasant fishy odor.

Chemical properties.

Cyclohexylamine is a derivative of ammonia with hydrogen atoms replacing the six-carbon saturated ring. It is a strong base and forms salts with all acids, including carbon dioxide, which is rapidly absorbed from the air. It reacts with carbon disulfide to produce the usual reaction of aliphatic amines to form carbamate disulfide. Cyclohexylamine reacts with long-chain fatty acids to form soap. Reaction with nitric acid releases nitrogen to form cyclohexanol (Schweizer 1978). Cyclohexylamine reacts with organic compounds containing reactive halogen atoms, acid anhydrides, and alkyl oxides, replacing one or two hydrogens on the nitrogen atom.

Cyclohexylamine can attack all copper alloys and lead. When hot, aluminum attacks very slowly (Carswell et al., 1937).

 

Uses.

In organic synthesis, plasticizers, corrosion inhibitors, rubber chemicals, dyes, emulsifiers, dry-cleaning soaps, and acid gas absorbers make insecticides.

Uses.

Cyclohexylamine is used to manufacture a variety of products, including plasticizers, dry-cleaning soaps, insecticides, and emulsifiers. Cyclohexylamine is also used as a corrosion inhibitor and in organic synthesis.

Uses.

Used in the manufacture of plasticizers, dry cleaning soap, insecticides, emulsifiers, and many other products.

Production of rubber processing chemicals boiler water supply in the production of corrosion inhibitors production of insecticides, plasticizers, dry cleaning soap sweetener cyclamate metabolites.

Definition.

ChEBI. Primary aliphatic amine consisting of cyclic self alkane with amino substitution.

Production method.

Cyclohexylamine is the reaction of ammonia and cyclohexanol at high temperature and pressure in the presence of a silica-alumina catalyst (SRI, 1985). Cyclohexylamine can also be prepared by a similar process of catalytic hydrogenation of aniline at high temperature and pressure. The reaction products are fractionated to give CHA, aniline, and a high boiling point residue containing ortho-phenylcyclohexylamine and dicyclohexylamine.In 1982, U.S. production was 4.54 metric tons, and U.S. imports were 739.3 metric tons (SRI, 1985).

 

General Description.

Colorless to yellow transparent liquid with an ammonia odor. Flashpoint is 90° F. Irritating to eyes and respiratory system. May burn on skin contact. Density is less than water. Vapor is heavier than air. Produces toxic nitrogen oxides on combustion.

The reaction of air and water.

Highly flammable. Sensitive to air and light. Easily soluble in water.

Reactivity Introduction.

Cyclohexylamine is neutralized with acid in an exothermic reaction to form a salt plus water. Isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, acid anhydrides, and acid halides may be incompatible. Combination with strong reducing agents (hydrides, etc.) may produce flammable gaseous hydrogen.

Health hazard.

The substance is classified as a highly toxic-70 kg (150 lb) person who may die orally at doses of 50-500 mg/kg or 1 teaspoon to 1 oz. It is considered to be neurotoxic. It is a weak substance that forms methemoglobin.

Health hazard.

Severe irritation and mild sensitization have been reported in humans exposed to a 25% aqueous cyclohexylamine solution in skin paste tests (Malette and vonHaam, 1952). Exposure to high concentrations of cyclohexylamine may cause nausea and anesthesia (Windholz et al., 1983). Three cases of transient systemic toxic effects caused by acute accidental industrial exposure have been reported. Victims reported dizziness, drowsiness, anxiety, worry, and nausea. Some had unclear speech, vomiting, and dilated pupils. However, workers exposed from 4 to 10 p.m. did not experience adverse effects.

Oral administration of cycloheximide (5 and 10 mg/kg) to adult males resulted in headaches, blurred vision, and tremors in the subjects.

Dependent increases in arterial blood pressure were observed in humans with oral administration of cycloheximide (2.5, 5.0, 10 mg/kg) (Eichelbaum et al., 1974). Researchers calculated that plasma levels of cycloheximide must reach 0.7-0.8 μg/ml to cause a significant increase in blood pressure. Only the highest dose (11 mg/ml) significantly increased the cumulative excretion of plasma free fatty acids and catecholamines. These data suggest that cycloheximide is an indirectly acting sympathomimetic substance that, despite its relatively low potency, correlates well with animal studies' results (Classen and Marquardt1969; Rosenblum and Rosenblum1968a, 1968b; Wechsler et al. 1969; Yamamura et al. 1968 ).

Health hazards.

Cyclohexylamine is a severe irritant to the eyes, skin, and respiratory tract. Skin contact can cause burns and sensitization Pure or concentrated liquids can cause blindness in contact with the eyes.

In test substrates, cyclohexylamine has moderate acute oral and dermal toxicity. Toxic effects include nausea, vomiting, and degenerative changes in the brain, liver, and kidneys. Inhalation of high concentrations of cyclohexylamine vapor causes narcotic effects.

LD50 value, oral (rat):156 mg/kg.

LD50 value, dermal (rabbit):277 mg/g.

Cyclohexylamine may be mutagenic, and tests in this area have been inconclusive so far. Administration of this compound to animals affects the reproductive system, including embryotoxicity and decreased male fertility. Roberts and coworkers (1989) studied the metabolism and testicular toxicity of cyclohexylamine in rats and mice. After 13 weeks of chronic dietary administration at 400 mg/kg/day, Wistar and dark agoutiDA rats showed decreased organ weights, histological changes, and testicular atrophy. Still, the degree varied greatly, and the rats showed no evidence of testicular damage.

There is no evidence that cycloheximide is carcinogenic to animals or humans.

Fire is dangerous.

When heated to decomposition, cyclohexylamine releases highly toxic fumes. Vapors may travel considerable distances to reach the ignition source and flash. Combustion produces toxic nitrogen oxides. Nitric acid; reacts violently with oxidizing substances. Good stability, avoid physical damage, store with oxidizing substances.

Industrial use.

The primary use of cyclohexylamine is as a corrosion inhibitor in boiler water treatment and oilfield applications (HSDB, 1989). It is also a chemical intermediate for rubber processing chemicals, dyes (Acid Blue 62, previous use), carbamate artificial sweeteners and herbicides, and a process agent for nylon fiber production (SRI, 1985). According to Windholz et al. (1983), used in the manufacture of insecticides, plasticizers, emulsifiers, dry cleaning soaps, and acid gas absorbers.

Safety profile.

Toxic by ingestion, dermal contact, and intraperitoneal channels. Experimental deformities and reproductive effects. Severe irritation to human skin. Can cause dermatitis and cramps. Human mutation data have been reported. Suspected carcinogen. Flammable liquid. Fire hazard when exposed to heat, flame, or oxidizing agents. Use alcohol foam, carbon dioxide, and dry chemicals when extinguishing fires. When heated to decomposition, releases fumes of toxic nitrogen oxides.

Potential Exposure.

CHA is used in the manufacture of dyes, chemical reagents, insecticides for dry cleaning chemicals, plasticizers, rubbers, and as a chemical intermediate for cyclic glycine sweetener production. It is used in water treatment and boiler water supply additives. Also used in rubber production to retard degradation.

Carcinogenicity.

According to the International Agency for Research on Cancer (IARC) Task Force report, there is no evidence that cyclohexylamine is teratogenic or carcinogenic.

Price et al. reported the development of bladder tumors in Charles River rats fed cyclohexylamine sulfate for 2 years at doses of 0, 0.15, 1.5, and 15 mg/kg/day per group, with 25 males and 25 females per group. In the first year, only slight control of body weight gain was observed in males of the high-dose group, and no other signs of toxicity were observed. At the end of 2 years (104 weeks), 13-16 animals remained alive in the 0.15- and 1.5-mg/kg groups, and 8 males and 9 females in the 15-mg/kg group. Invasive transitional cell carcinoma of the bladder was observed in one of the eight male survivors in the high-dose group. The authors noted that spontaneous bladder tumors were sporadic in the rat line used. No other relevant findings were noted. Gaunt conducted a 2-year dietary feeding study with the same doses in Wistar rats. They observed no evidence of carcinogenesis, slight anemia, inability to produce normally concentrated urine, and an increased number of animals with foamy macrophages in the alveoli at the highest dose level. Food intake was reduced, body weight was increased, and organ weights were reduced compared to controls. Animals ingesting 2000 or 6000 ppm had testicular atrophy or less tubular spermatozoa. In both studies, the level without side effects was 600 ppm, which corresponds to an intake of about 30 mg/kg per day.

Metabolism.

Cyclopamine is metabolized to cyclohexylamine by rat intestinal flora (Renwick and Williams, 1969 Bickel et al., 1974 Tesoriero and Roxon, 1975) and is excreted in the urine after ingestion by rats, rabbits, dogs, monkeys, and humans (Asahina et al., 1971 Coulston et al. 1977 Kojima and Ichibagase, 1968 Leahy et al. 1967 Individual differences exist in the ability to biotransform cyclamic acid to cyclohexylamine, possibly due to the presence or absence of the necessary bacteria. Bacteria exposed to cyclamate appear to have acquired the ability to convert cyclamate. Individuals that did produce cycloheximide were classified as converters by the researchers. Rhesus monkeys kept for 8 years converted 0.5% of their dose to cyclohexylamine, which metabolizes cyclohexanone and cyclohexanol at a 1-2% (Coulston et al. 1977).

In general, cyclohexylamine is readily absorbed and rapidly excreted from the body. After feeding to rats, cyclohexylamine appeared in body tissues with the highest concentrations in the lungs, spleen, liver, adrenals, heart, stomach, intestines, and kidneys (reported by Estep and Wiegand, 1967, Bopp et al. 1986).

Following oral administration (0.2 g/kg) to rabbits, cyclohexylamine produced unchanged cyclohexylamine and 7V-hydroxycyclohexylamine in the urine (Elliott et al. 1968). When [14C]-labeled cyclohexylamine was administered, 68% of the radioactivity was recovered in the urine after 60 hours, a small amount (0.5%) was eliminated in the breath, and 45% of the administered amount was excreted in the urine as unbound cyclohexylamine, 0.2% as bound JV-hydroxycyclohexylamine, and 2.5% as cyclohexanone oxime. The authors speculate that the post-metabolites are unrealistically imagined to be formed during hydrolysis of TV-hydroxycyclohexylamine glucuronide.

 

In contrast to rabbits, more than 90% of the [14C] dose-labeled cyclohexylamine excreted by humans and rats and guinea pigs- was unchanged in the urine. Small amounts of radioactivity were found in the feces, more than 1% in humans, rats and rabbits, and 4-7% in guinea pigs. Rats and guinea pigs metabolized only 4-5% of the dose in 24 hours, and humans metabolized 1-2% of the dose. Explicit metabolites suggest that cyclohexylamine is metabolized primarily by cyclohexane cyclohydroxylation in rats, by deamination in humans, and by cyclohydroxylation and deamination in guinea pigs and rabbits. The metabolites of cyclohexylamine are excreted in both free and conjugated forms.

 

When cyclohexylamine was administered orally to healthy adults at 2.5, 5, and 10 mg/kg, 86-95% of the weight was excreted in the urine as unchanged cyclohexylamine within 48 hours (Eichelbaum et al., 1974). studies by Roberts and Renwick (1985) showed that cyclohexylamine's metabolism differs in other species and varieties, with dose dependence at a plasma half-life of 3.5 to 4.8 hours. After administering [14C]-cyclohexylamine (35-500 mg/kg) to male rats and mice, 80% of the urine was excreted 24 hours after dosing. In Wistar rats, 14-19% of 14C was present in 3- and 4-aminocyclohexanols, and in rats of the DA strain, aminocyclohexanols accounted for only 1-2% of activity, with <1% in rats. There was no significant effect on metabolism by the amount or channel of administration.

 

When [14C]-cyclohexylamine hydrochloride was infused into pregnant rhesus monkeys via the antecubital vein, maternal and fetal radioactivity levels were essentially identical over 6 hours (Pitkin et al. 1969), indicating that cyclohexylamine can freely pass through the bloodstream placenta.

Cyclohexylamine can be deaminated to cyclohexanone in the presence of NADPH and molecular oxygen in rabbit liver microsomes (Kurebayashi et al. 1979). Cyclohexanone is then reduced to an alcohol (~75% of the deamination product). Carbon monoxide, SKF 525A, methyl ethyl ketone, potassium cyanide, and mercuric chloride controlled the deamination. These results suggest that the microsomal pigment P-450 monooxygenase system catalyzes deamination.

Transport.

UN2357 Cyclohexylamine, Hazard Class. 8; Label:8-Corrosive substance, 3-Flammable liquid. 8-Corrosive substance, 3-Flammable liquid.

Purification Method.

Dry amine with CaCl2 or LiAlH4, then distill with BaO, KOH or Na under N2. It can also be converted to hydrochloride (crystallized from water several times) and then purified by releasing the amine with alkali and fractional distillation under N2. The m of the hydrochloride is 205-207o (dioxane/EtOH). Lycan et al. OrgSynthCollVolII3191943, Beilstein 12II10, 12IV8.

Incompatibility.

May form explosive mixtures with air. Cyclohexylamine is a strong base: Reacts strongly with acids. Contact with strong oxidizing agents may lead to fire and explosion. Incompatible with organic anhydrides, isocyanates, ethyl acetate, acrylates, substituted propylene, alkyl oxides, epichlorohydrin, ketones, aldehydes, alcohols, glycols, phenols, cresols, self-caprolactam solutions, lead, etc. Corrosive to copper alloys, zinc or galvanized steel.

Waste disposal.

Incineration; incinerators equipped with scrubbers or heat units to reduce NOx emissions.

 

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