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시클로헥실아민

시클로헥실아민
시클로헥실아민 구조식 이미지
카스 번호:
108-91-8
한글명:
시클로헥실아민
동의어(한글):
시클로헥실아민;사이클로헥실아민(시클로헥실아민);시클로헥산아민;아미노시클로헥산;헥사하이드로벤젠아민;1-시클로헥실아민
상품명:
Cyclohexylamine
동의어(영문):
CHA;CHA-60;cha[qr];AURORA KA-7609;Cyclohexylamin;CYCLOHEXYLAMINE;hexahydro-anilin;cyclohexaneamine;AMINOCYCLOHEXANE;HEXAHYDROANILINE
CBNumber:
CB8139274
분자식:
C6H13N
포뮬러 무게:
99.17412
MOL 파일:
108-91-8.mol

시클로헥실아민 속성

녹는점
-17 °C
끓는 점
134 °C(lit.)
밀도
0.867 g/mL at 25 °C(lit.)
증기 밀도
3.42 (vs air)
증기압
10 mm Hg ( 22 °C)
굴절률
n20/D 1.459(lit.)
인화점
90 °F
저장 조건
Flammables area
용해도
organic solvents: miscible
물리적 상태
Liquid
산도 계수 (pKa)
10.66(at 24℃)
색상
Clear
수소이온지수(pH)
11.5 (100g/l, H2O, 20℃)
폭발한계
1.6-9.4%(V)
수용성
MISCIBLE
어는점
-17.7℃
감도
Air Sensitive
Merck
14,2729
BRN
471175
노출 한도
TLV-TWA 10 ppm (~40 mg/m3) (ACGIH).
CAS 데이터베이스
108-91-8(CAS DataBase Reference)
NIST
Cyclohexanamine(108-91-8)
EPA
Cyclohexanamine(108-91-8)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 C,T
위험 카페고리 넘버 10-21/22-34-62-24-22
안전지침서 36/37/39-45-1/2-26
유엔번호(UN No.) UN 2357 8/PG 2
WGK 독일 1
RTECS 번호 GX0700000
F 고인화성물질 10-34
자연 발화 온도 559 °F
TSCA Yes
HS 번호 2921 30 10
위험 등급 8
포장분류 II
유해 물질 데이터 108-91-8(Hazardous Substances Data)
독성 LD50 orally in rats: 0.71 ml/kg (Smyth)
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H226 인화성 액체 및 증기 인화성 액체 구분 3 경고
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 P264, P270, P301+P312, P330, P501
H312 피부와 접촉하면 유해함 급성 독성 물질 - 경피 구분 4 경고 P280,P302+P352, P312, P322, P363,P501
H314 피부에 심한 화상과 눈에 손상을 일으킴 피부부식성 또는 자극성물질 구분 1A, B, C 위험 P260,P264, P280, P301+P330+ P331,P303+P361+P353, P363, P304+P340,P310, P321, P305+ P351+P338, P405,P501
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
H340 유전적인 결함을 일으킬 수 있음 (노출되어도 생식세포 유전독성을 일으키지 않는다는 결정적인 증거가 있는 노출경로가 있다면 노출경로 기재) 생식세포 변이원성 물질 구분 1A, 1B 위험
H361 태아 또는 생식능력에 손상을 일으킬 것으로 의심됨 생식독성 물질 구분 2 경고 P201, P202, P281, P308+P313, P405,P501
H370 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킴(노출되어도 특정 표적장기 독성을 일으키지 않는다는 결정적인 노출경로가 있다면 노출경로를 기재) 특정 표적장기 독성 - 1회 노출 구분 1 위험 P260, P264, P270, P307+P311, P321,P405, P501
H402 수생생물에 유해함 수생 환경유해성 물질 - 급성 구분 3
예방조치문구:
P201 사용 전 취급 설명서를 확보하시오.
P202 모든 안전 조치 문구를 읽고 이해하기 전에는 취급하지 마시오.
P210 열·스파크·화염·고열로부터 멀리하시오 - 금연 하시오.
P233 용기를 단단히 밀폐하시오. 용기는 환기가 잘 되는 곳에 단단히 밀폐하여 보관하시오.
P240 용기와 수용설비를 접지 및 접합시키시오.
P260 분진·흄·가스·미스트·증기·...·스프레이를 흡입하지 마시오.
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P270 이 제품을 사용할 때에는 먹거나, 마시거나 흡연하지 마시오.
P271 옥외 또는 환기가 잘 되는 곳에서만 취급하시오.
P273 환경으로 배출하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P303+P361+P353 피부(또는 머리카락)에 묻으면 오염된 모든 의복은 벗거나 제거하시오 피부를 물로 씻으시오/샤워하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P307+P311 노출된 경우,독성 물질 센터 또는 의사에게 전화하기
P370+P378 화재 시 불을 끄기 위해 (Section 5. 폭발, 화재시 대처방법의 적절한 소화제)을(를) 사용하시오.
P405 밀봉하여 저장하시오.
P403+P233 용기는 환기가 잘 되는 곳에 단단히 밀폐하여 저장하시오.

시클로헥실아민 C화학적 특성, 용도, 생산

용도

유기 합성의 중간체, 특히 제초제, 산화 방지제 및 가황 촉진제, 부식 방지제, 인공 감미료 등에 사용됩니다.

포장, 보관 및 운송

용기는 건조하고 통풍이 잘되는 곳에 단단히 밀폐시켜야합니다. 개봉 한 용기는 조심스럽게 다시 봉한 다음 누출을 방지하기 위해 똑바로 세워야합니다. 서늘한 곳에 보관하십시오. 불활성 가스하에 보관하십시오. 이산화탄소에 민감 함 불활성 가스 처리. 습기로부터 보호하십시오. 공기에 민감합니다.

화학적 성질

clear liquid

화학적 성질

Cyclohexylamine is a colorless to yellow liq- uid (amines, primary aromatic). It has an unpleasant fishy odor.

화학적 성질

Cyclohexylamine is a derivative of ammonia in which one of the hydrogen atoms has been replaced with a six-carbon, saturated ring. It is a very strong base and forms salts with all acids, including carbon dioxide which it rapidly absorbs from the air. It undergoes the usual reaction of aliphatic amines with carbon disulfide to form dithiocarbamates. Cyclohexylamine reacts with long-chain fatty acids to form soaps (Carswell and Morrill 1937). With nitrous acid, it forms cyclohexanol with the release of nitrogen (Schweizer 1978). Cyclohexylamine reacts with organic compounds containing an active halogen atom, acid anhydrides, and alkylene oxides to replace one or both hydrogens on the nitrogen atom.
Cyclohexylamine attacks all copper alloys and lead. When hot, it attacks aluminum very slowly (Carswell et al 1937).

용도

In organic synthesis, manufacture of insecticides, plasticizers, corrosion inhibitors, rubber chemicals, dyestuffs, emulsifying agents, dry-cleaning soaps, acid gas absorbents.

용도

Cyclohexylamine is used in the manufactureof a number of products, including plasticizers, drycleaning soaps, insecticides, andemulsifying agents. It is also used as a cor rosion inhibitor and in organic synthesis.

정의

ChEBI: A primary aliphatic amine consisting of cyclohexane carrying an amino substituent.

생산 방법

Cyclohexylamine is produced by the reaction of ammonia and cyclohexanol at elevated temperature and pressure in the presence of a silica-alumina catalyst (SRI 1985). It is also prepared by a similar process of catalytic hydrogenation of aniline at elevated temperature and pressure. Fractionation of the product of this reaction yields CHA, aniline, and a high-boiling residue containing n-phenylcyclohexylamine and dicyclohexylamine (Carswell and Morrill 1937). In 1982, U.S. production was 4.54 metric tons and 739.3 metric tons were imported into the U.S. (SRI 1985).

일반 설명

A clear colorless to yellow liquid with an odor of ammonia. Flash point 90°F. Irritates the eyes and respiratory system. Skin contact may cause burns. Less dense than water. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion.

공기와 물의 반응

Highly flammable. Sensitive to air and light. Soluble in water.

반응 프로필

Cyclohexylamine 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.

건강위험

This is classified as very toxic -- probable oral lethal dose is 50-500 mg/kg or between 1 teaspoon and 1 ounce for a 70 kg (150 lb.) person. It is considered a nerve poison. This is a weak methemoglobin-forming substance.

건강위험

When humans were exposed to a 25% solution of aqueous cyclohexylamine in skin patch tests, irritation was reported as severe and sensitization as slight (Malette and von Haam 1952). Exposure to high concentrations may cause nausea and narcotic effects (Windholz et al 1983). Three cases of transitory systemic toxic effects due to acute accidental industrial exposure have been reported (Watrous and Schultz 1950). Victims reported lightheadedness, drowsiness, anxiety, apprehension and nausea. One person suffered from slurred speech, vomiting and pupillary dilation. Workers exposed to 4 to 10 p.p.m. however, had no negative effects.
Oral administration of cyclohexylamine (5 and 10 mg/kg) to adult male humans caused headache, blurring of vision and shivering in the exposed subjects (Eichelbaum et al 1974).
When cyclohexylamine was administered orally to humans (2.5, 5.0 and 10 mg/kg), a dose-dependent rise in arterial blood pressure was observed (Eichelbaum et al 1974). The investigators calculated that plasma levels of cyclohexylamine of 0.7 to 0.8 μg/ml were required to cause a significant increase. Only the highest dose (11 mg/ml) produced a significant increase in plasma free fatty acids and cumulative excretion of catecholamines. These data suggest that cyclohexylamine is an indirect acting sympathomimetic substance, although of relatively low potency and are in good correlation with results obtained from animal studies (Classen and Marquardt 1969; Rosenblum and Rosenblum 1968a, 1968b; Wechsler et al 1969; Yamamura et al 1968).

건강위험

Cyclohexylamine is a severe irritant to theeyes, skin, and respiratory passage. Skincontact can produce burns and sensitization;contact of the pure liquid or its concentratedsolutions with the eyes may cause loss ofvision.
The acute oral and dermal toxicity ofcyclohexylamine was moderate in test sub jects. The toxic effects include nausea, vom iting, and degenerative changes in the brain,liver, and kidney. Inhalation of its vaporsat high concentrations may cause a narcoticeffect.
LD50 value, oral (rats): 156 mg/kg
LD50 value, skin (rabbits): 277 mg/klg
Cyclohexylamine may be mutagenic, thetest for which has so far given inconclusiveresults. Administration of this compoundin animals produced a reproductive effect,including embryotoxicity and a reductionin male fertility. Intraperitoneal injectionof the amine in rats caused a dose dependent increase in chromosomal breaks.Roberts and coworkers (1989) studied themetabolism and testicular toxicity of cyclohexylamine (a metabolite of cyclamate)in rats and mice. Chronic dietary administration of 400 mg/kg/day for 13 weeksshowed decrease in organ weigh, histological changes, and testicular atrophy in boththe Wistar and dark agouti DA rats, but to awidely varying extent, while mice exhibitedno evidence of testicular damage.
There is no evidence of carcinogenicityin animals or humans caused by cyclohexy lamine.

화재위험

When heated to decomposition, Cyclohexylamine emits highly toxic fumes. Vapor may travel a considerable distance to source of ignition and flash back. Toxic oxides of nitrogen are produced during combustion. Nitric acid; reacts vigorously with oxiding materials. Stable, avoid physical damage, storage with oxidizing material.

공업 용도

The primary use of cyclohexylamine is as a corrosion inhibitor in boiler water treatment and in oil field applications (HSDB 1989). It is also a chemical intermediate for rubber processing chemicals, dyes (acid blue 62, former use), cyclamate artificial sweeteners and herbicides and a processing agent for nylon fiber production (SRI 1985). Windholz et al (1983) reports its use in the manufacture of insecticides, plasticizers, emulsifying agents, dry-cleaning soaps, and acid gas absorbents.

Safety Profile

A poison by ingestion, skin contact, and intraperitoneal routes. Experimental teratogenic and reproductive effects. A severe human skin irritant. Can cause dermatitis and convulsions. Human mutation data reported. Questionable carcinogen. Flammable liquid. Dangerous fire hazard when exposed to heat, flame, or oxidizers. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of NOx.

잠재적 노출

CHA is used in making dyes, chemi- cals, dry cleaning chemicals; insecticides, plasticizers, rub- ber chemicals; and as a chemical intermediate in the production of cyclamate sweeteners. Used in water treat- ment and as a boiler feedwater additive. It is also used in rubber production to retard degradation.

신진 대사

Cyclamate is metabolized to cyclohexylamine by the gut flora in the rat (Renwick and Williams 1969; Bickel et al 1974; Tesoriero and Roxon 1975) and is excreted in the urine after cyclamate ingestion by rats, rabbits, dogs, monkeys, and humans (Asahina et al 1971; Coulston et al 1977; Kojima and Ichibagase 1968; Leahy et al 1967; Oser et al 1968). There is individual variation in the ability to biotransform cyclamate to cyclohexylamine, probably due to the presence or absence of the necessary bacteria. Bacteria exposed to cyclamate seem to acquire the ability to convert cyclamate. Those individuals that do produce cyclohexylamine have been categorized by researchers as convertors. Rhesus monkeys fed cyclamate for eight years converted 0.5% of the dose to cyclohexylamine which in turn was metabolized to cyclohexanone and cyclohexanol to the extent of 1-2% (Coulston et al 1977).
Generally, cyclohexylamine is readily absorbed and rapidly excreted from the body. After administration to rats, cyclohexylamine appears in body tissues with the highest concentrations in the lungs, spleen, liver, adrenals, heart, gastrointes- tinal tract and kidneys (Estep and Wiegand 1967 as reported by Bopp et al 1986).
After oral administration (0.2 g/kg) to rabbits, cyclohexylamine gave rise to unchanged cyclohexylamine and 7V-hydroxycyclohexylamine in the urine (Elliott et al 1968). When [14C]-labelled cyclohexylamine was administered, 68% of the radioactivity was recovered in the urine after 60 h. A small amount (0.5%) was eliminated in the breath and 45% of the administered dose was shown to be excreted in the urine as unconjugated cyclohexylamine, 0.2% as JV-hydroxycyclohexylamine in conjugated form, and 2.5% as cyclohexanone oxime. The authors postulated the latter metabolite to be an artifact formed from the glucuronide of TV-hydroxy cyclohexylamine during the hydrolysis procedure.
In contrast to rabbits, man, as well as rats and guinea pigs, excrete 90% or more of a dose of [14C]-labelled cyclohexylamine unchanged in the urine (Renwick and Williams 1972). Small amounts of radioactivity were found in the feces, 1% or less in man, rat and rabbit, and 4-7% in the guinea pig. Only 4-5% of the dose was metabolized in 24 h in the rat and guinea pig and 1-2% in man. The metabolites identified indicated that in rats, the metabolism of cyclohexylamine was mainly through hydroxylation of the cyclohexane ring, in man by deamination and in guinea pigs and rabbits by ring hydroxylation and deamination. The metabolites to cyclohexylamine were excreted in both free and conjugated forms.
When cyclohexylamine was administered orally to healthy adult humans at doses of 2.5, 5, and 10 mg/kg body weight, 86-95% of the dose was excreted in the urine in 48 h as unchanged cyclohexylamine (Eichelbaum et al 1974). Dose dependency was shown by the plasma half-lives which ranged from 3.5 to 4.8 h. A study by Roberts and Renwick (1985) showed other species and strain differences in metabolism of cyclohexylamine. After administration of [14C]- cyclohexylamine (35-500 mg/kg) to male mice and rats, 80% of the dose was excreted in the urine 24 h after dosing. In Wistar rats, 14-19% of the 14C was present as 3- and 4-aminocyclohexanols, while in the DA strain rat, aminocyclohexanols accounted for only 1-2% of the activity, and in mouse, <1%. Dose or route of administration did not significantly affect metabolism.
When [14C]-cyclohexylamine hydrochloride was administered to pregnant rhesus monkeys by infusion into the antecubital vein, maternal and fetal levels of radioactivity were virtually identical over a period of 6 h (Pitkin et al 1969) indicating that cyclohexylamine freely crosses the hemochorial placenta.
Rabbit liver microsomes have been shown to deaminate cyclohexylamine to cyclohexanone in the presence of NADPH and molecular oxygen (Kurebayashi et al 1979). The hexanone was then reduced to the alcohol (approximately 75% of the deaminated product). Carbon monoxide, SKF 525A, metyrapone, potassium cyanide and mercuric chloride inhibited the deamination. These results suggest that the deamination is catalyzed by a microsomal cytochrome P-450 monooxygenase system.

운송 방법

UN2357 Cyclohexylamine, Hazard class: 8; Labels: 8-Corrosive material, 3-Flammable liquid.

Purification Methods

Dry the amine with CaCl2 or LiAlH4, then distil it from BaO, KOH or Na, under N2. Also purify it by conversion to the hydrochloride (which is crystallised several times from water), then liberation of the amine with alkali and fractional distillation under N2. The hydrochloride has m 205-207o (dioxane/EtOH). [Lycan et al. Org Synth Coll Vol II 319 1943, Beilstein 12 III 10, 12 IV 8.]

비 호환성

May form explosive mixture with air. Cyclohexylamine is a strong base: it reacts violently with acid. Contact with strong oxidizers may cause fire and explosion hazard. Incompatible with organic anhydrides; isocyanates, vinyl acetate; acrylates, substituted allyls; alkylene oxides; epichlorohydrin, ketones, aldehydes, alco- hols, glycols, phenols, cresols, caprolactum solution; lead. Corrosive to copper alloys, zinc, or galvanized steel.

폐기물 처리

Incineration; incinerator equipped with a scrubber or thermal unit to reduce nitrogen oxides emissions.

시클로헥실아민 준비 용품 및 원자재

원자재

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