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시클로헥센

시클로헥센
시클로헥센 구조식 이미지
카스 번호:
110-83-8
한글명:
시클로헥센
동의어(한글):
시클로헥센;사이클로헥산
상품명:
Cyclohexene
동의어(영문):
HX;ohexene;Cyclohexen;CYCLOHEXENE;Cykloheksen;1-Cyclohexene;JACS-110-83-8;Cyclohex-1-ene;Hexanaphthylene;cyclohexenering
CBNumber:
CB2852823
분자식:
C6H10
포뮬러 무게:
82.14
MOL 파일:
110-83-8.mol

시클로헥센 속성

녹는점
?104 °C (lit.)
끓는 점
83 °C (lit.)
밀도
0.811 g/mL at 25 °C (lit.)
증기 밀도
2.8 (vs air)
증기압
160 mm Hg ( 20 °C)
굴절률
n20/D 1.446(lit.)
인화점
10 °F
저장 조건
Store below +30°C.
용해도
water: insoluble
물리적 상태
Liquid
색상
Clear colorless
Specific Gravity
0.811
수소이온지수(pH)
7-8 (0.2g/l, H2O, 20℃)
폭발한계
1.2-7.7%(V)
수용성
insoluble
Merck
14,2727
BRN
906737
Henry's Law Constant
3.85 x 10-2 atm?m3/mol at 25 °C (Nielsen et al., 1994)
노출 한도
TLV-TWA 300 ppm (~1015 mg/m3) (ACGIH, OSHA, and NIOSH); IDLH 10,000 ppm (NIOSH).
안정성
Stable in the absence of air - may form peroxides in storage. Incompatible with oxidizing agents. Highly flammable.
InChIKey
HGCIXCUEYOPUTN-UHFFFAOYSA-N
CAS 데이터베이스
110-83-8(CAS DataBase Reference)
NIST
Cyclohexene(110-83-8)
EPA
Cyclohexene (110-83-8)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 F,Xn
위험 카페고리 넘버 11-21/22-65
안전지침서 16-29-33-36/37-62
유엔번호(UN No.) UN 2256 3/PG 2
WGK 독일 1
RTECS 번호 GW2500000
자연 발화 온도 590 °F
TSCA Yes
위험 등급 3
포장분류 II
HS 번호 29021990
유해 물질 데이터 110-83-8(Hazardous Substances Data)
독성 LD50 orally in Rabbit: 1300 mg/kg
기존화학 물질 KE-33445
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H225 고인화성 액체 및 증기 인화성 액체 구분 2 위험 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 P264, P270, P301+P312, P330, P501
H304 삼켜서 기도로 유입되면 치명적일 수 있음 흡인 유해성물질 구분 1 위험
H311 피부와 접촉하면 유독함 급성 독성 물질 - 경피 구분 3 위험 P280, P302+P352, P312, P322, P361,P363, P405, P501
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
H336 졸음 또는 현기증을 일으킬 수 있음 특정표적장기 독성 물질(1회 노출);마취작용 구분 3 경고 P261, P271, P304+P340, P312,P403+P233, P405, P501
H411 장기적 영향에 의해 수생생물에 유독함 수생 환경유해성 물질 - 만성 구분 2
예방조치문구:
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.
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
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.
P312 불편함을 느끼면 의료기관(의사)의 진찰을 받으시오.
P331 토하게 하지 마시오.
P391 누출물을 모으시오.
P301+P310 삼켰다면 즉시 의료기관(의사)의 진찰을 받으시오.
P303+P361+P353 피부(또는 머리카락)에 묻으면 오염된 모든 의복은 벗거나 제거하시오 피부를 물로 씻으시오/샤워하시오.
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.
P501 ...에 내용물 / 용기를 폐기 하시오.
NFPA 704
3
1 0

시클로헥센 C화학적 특성, 용도, 생산

개요

Cyclohexene is a hydrocarbon, mostly obtained from the hydrogenation of benzene.

화학적 성질

Cyclohexene is a colorless liquid (cyclic alkene) with a sweetish odor.

물리적 성질

Clear, colorless liquid with a sweet odor. Odor threshold concentration is 0.18 ppm (quoted, Amoore and Hautala, 1983).

용도

It occurs in coal tar and is obtained by catalyticdehydration of cyclohexanol and dehydrogenationof cyclohexane. Cyclohexene isused in making adipic acid, maleic acid,and butadiene; in oil extraction; as a stabilizerfor high-octane gasoline; and in organicsynthesis.

용도

Alkylation component. In the manufacture of adipic acid, maleic acid, hexahydrobenzoic acid and aldehyde. To prepare butadiene in the laboratory. Has been suggested for the synthesis of maleic acid and as stabilizer for high octane gasoline.

용도

Manufacture of adipic acid, maleic acid, hexahydrobenzoic acid, and aldehyde; stabilizer for high-octane gasoline

생산 방법

Cyclohexene is prepared by dehydration of cyclohexanol by thermal reaction of an ethylene–propylene–butadiene mixture (1).

정의

ChEBI: A cycloalkene that is cylohexane with a single double bond.

일반 설명

A colorless liquid. Insoluble in water and less dense than water. Flash point 20°F. Vapors heavier than air. Inhalation of high concentrations may have a narcotic effect. Used to make other chemicals.

공기와 물의 반응

Highly flammable. Insoluble in water.

반응 프로필

Cyclohexene may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions. Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154].

건강위험

There are very few toxicological data availableon cyclohexene. Inhalation producesirritation of the eyes and respiratory tract. Itis also an irritant to skin. Its acute toxicityis low; the toxic effects are similar to thoseof cyclohexane. Exposure to high concentrationsor ingestion may cause drowsiness.Single exposures to 15,000 ppm of cyclohexenecould be lethal to rats.

화재위험

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety Profile

Moderately toxic by inhalation and ingestion. A very dangerous fire hazard when exposed to flame; can react with oxidizers. Dangerous; keep away fromheat and open flame. To fight fire, use foam, CO2, dry chemical.

잠재적 노출

May be used as an intermediate in making other chemicals (e.g., adipic acid, maleic acid, hex- ahydro benzoic acid), oil extraction and as a catalyst solvent.

Carcinogenicity

Cyclohexene was not mutagenic in Salmonella typhimurium with or without metabolic activation.

환경귀착

Biological. Cyclohexene biodegrades to cyclohexanone (Dugan, 1972; Verschueren, 1983).
Photolytic. The following rate constants were reported for the reaction of cyclohexene with OH radicals in the atmosphere: 6.80 x 10-11 cm3/molecule?sec (Atkinson et al., 1979), 6.75 x 10-11 cm3/molecule?sec at 298 K (Sablji? and Güsten, 1990), 5.40 x 10-11 cm3/molecule?sec at 298 K (Rogers, 1989), 1.0 x 10-10 cm3/molecule?sec at 298 K (Atkinson, 1990); with ozone in the gasphase: 1.69 x 10-16 cm3/molecule?sec at 298 K (Japar et al., 1974), 2.0 x 10-16 at 294 K (Adeniji et al., 1981), 1.04 x 10-16 cm3/molecule?sec (Atkinson et al., 1983), 1.04 x 10-16 at 298 K (Atkinson and Carter, 1984); with NO3 in the atmosphere: 5.26 x 10-13 cm3/molecule?sec (Sablji? and Güsten, 1990); 5.3 x 10-13 cm3/molecule?sec at 298 K (Atkinson, 1990), and 5.28 x 10-13 cm3/molecule?sec at 295 K (Atkinson, 1991). Cox et al. (1980) reported a rate constant of 6.2 x 10-11 cm3/molecule?sec for the reaction of gaseous cyclohexene with OH radicals based on a value of 8 x 10-12 cm3/molecule?sec for the reaction of ethylene with OH radicals.
Chemical/Physical. Gaseous products formed from the reaction of cyclohexene with ozone were (% yield): formic acid , carbon monoxide , carbon dioxide, ethylene, and valeraldehyde (Hatakeyama et al., 1987). In a smog chamber experiment conducted in the dark at 25 °C, cyclohexane reacted with ozone. The following products and their respective molar yields were: oxalic acid (6.16%), malonic acid (6.88%), succinic acid (0.63%), glutaric acid (5.89%), adipic acid (2.20%), 4-hydroxybutanal (2.60%), hydroxypentanoic acid (1.02%), hydroxyglutaric acid (2.33%), hydroxyadipic acid (1.19%), 4-oxobutanoic acid (6.90%), 4- oxopentanoic acid (4.52%), 6-oxohexanoic acid (4.16%), 1,4-butandial (0.53%), 1,5-pentanedial (0.44%), 1,6-hexanedial (1.64%), and pentanal (17.05%).
Grosjean et al. (1996) investigated the atmospheric chemistry of cyclohexene with ozone and an ozone-nitrogen oxide mixture under ambient conditions. The reaction of cyclohexene and ozone in the dark yielded pentanal and cyclohexanone. The sunlight irradiation of cyclohexene with ozonenitrogen oxide yielded the following carbonyls: formaldehyde, acetaldehyde, acetone, propanal, butanal, pentanal, and a C4 carbonyl.
Cyclohexene reacts with chlorine dioxide in water forming 2-cyclohexen-1-one (Rav-Acha et al., 1987).

운송 방법

UN2256 Cyclohexene, Hazard Class: 3; Labels: 3-Flammable liquid.

Purification Methods

Free cyclohexene from peroxides by washing with successive portions of dilute acidified ferrous sulfate, or with NaHSO3 solution, then with distilled water, drying with CaCl2 or CaSO4, and distilling under N2. Alternative methods for removing peroxides include passage through a column of alumina, refluxing with sodium wire or cupric stearate (then distilling from sodium). The diene is removed by refluxing with maleic anhydride before distilling under vacuum. Treatment with 0.1moles of MeMgI in 40mL of diethyl ether removes traces of oxygenated impurities. Other purification procedures include washing with aqueous NaOH, drying and distilling under N2 through a spinning band column, redistilling from CaH2, storing under sodium wire, and passing through a column of alumina, under N2, immediately before use. Store it at <0o under argon. [Coleman & Johnstone Org Synth Coll Vol I 83 1955, Carson & Ipatieff Org Synth Coll Vol II 152 1943, Woon et al. J Am Chem Soc 108 7990 1986, Wong et al. J Am Chem Soc 109 3428 1987.] [Beilstein 5 IV 218.]

Toxicity evaluation

The release of cyclohexene into the air occurs in the form of waste streams from manufacturing units. Cyclohexene has a vapor pressure of 89mm Hg at 25°C, indicating that it exists as a vapor form in the environment and is degraded by reactions with photochemically induced hydroxyl radicals, ozone, and nitrate radicals. The half-life for these reactions in the air is 6, 2, and 4 h, respectively.
Estimated Koc of 850 indicates that cyclohexene has low mobility in the soil. Cyclohexene has Henry’s law constant of 4.55×10-2atm-m3 mol-1. Based on this Henry’s law constant, volatilization is expected to be the major process of removal of cyclohexene from moist soil and water, if released into it.

비 호환성

Vapor may form explosive mixture with air. The substance can form explosive peroxides. The sub- stance may polymerize under certain conditions. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoa- cids, epoxides.

폐기물 처리

Dissolve or mix the material with a combustible solvent and burn in a chemical incinera- tor equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

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