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벤조니트릴

벤조니트릴
벤조니트릴 구조식 이미지
카스 번호:
100-47-0
한글명:
벤조니트릴
동의어(한글):
벤조나이트라일;벤조나이트릴;벤조니트릴;벤조산니트릴;시아노벤젠;페닐시아나이드;벤젠, 사이아노-;벤젠나이트릴;벤젠카보나이트릴;벤조 산 나이트릴;벤조산 나이트릴;사이아노벤젠;페닐 사이아나이드;페닐 시아나이드
상품명:
Benzonitrile
동의어(영문):
BN;FB;3BN;BRR;BRN;2BNC;AKOS 91614;Benzoitrile;Benzontrile;Fenylkyanid
CBNumber:
CB7852585
분자식:
C7H5N
포뮬러 무게:
103.12
MOL 파일:
100-47-0.mol

벤조니트릴 속성

녹는점
-13 °C (lit.)
끓는 점
191 °C (lit.)
밀도
1.01
증기 밀도
3.6 (vs air)
증기압
1 hPa at 20 °C
굴절률
n20/D 1.528(lit.)
인화점
161 °F
저장 조건
Store below +30°C.
용해도
10g/l
물리적 상태
Liquid
색상
Clear colorless to slightly yellow
상대극성
0.333
냄새
Almond-like.
폭발한계
1.4-7.2%(V)
수용성
10 g/L (100 ºC)
최대 파장(λmax)
λ: 300 nm Amax: 1.0
λ: 310 nm Amax: 0.40
λ: 335 nm Amax: 0.03
λ: 360-400 nm Amax: 0.01
Merck
14,1097
BRN
506893
안정성
Stable. Incompatible with strong bases, strong acids, strong oxidizing agents, strong reducing agents. Air-sensitive. Combustible.
InChIKey
JFDZBHWFFUWGJE-UHFFFAOYSA-N
CAS 데이터베이스
100-47-0(CAS DataBase Reference)
NIST
Benzonitrile(100-47-0)
EPA
Benzonitrile (100-47-0)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn
위험 카페고리 넘버 21/22-38
안전지침서 23
유엔번호(UN No.) UN 2224 6.1/PG 2
WGK 독일 2
RTECS 번호 DI2450000
자연 발화 온도 550 °C
TSCA Yes
위험 등급 6.1
포장분류 II
HS 번호 29269090
유해 물질 데이터 100-47-0(Hazardous Substances Data)
독성 LDLo orl-rat: 720 mg/kg AMRL** TR-74-78,74
기존화학 물질 KE-02715
그림문자(GHS):
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H227 가연성 액체 인화성 액체 구분 4 경고 P210, P280, P370+P378, P403+P235,P501
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
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H331 흡입하면 유독함 급성 독성 물질 흡입 구분 3 위험 P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
H371 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킬 수 있음(노출되어도 특정 표적장기 독성을 일으키지 않는다는 결정적인 노출경로가 있다면 노출경로를 기재) 특정 표적장기 독성 - 2회 노출 구분 2 경고 P260, P264, P270, P309+P311, P405,P501
H373 장기간 또는 반복 노출되면 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킬 수 있음 특정 표적장기 독성 - 반복 노출 구분 2 경고 P260, P314, P501
H402 수생생물에 유해함 수생 환경유해성 물질 - 급성 구분 3
예방조치문구:
P210 열·스파크·화염·고열로부터 멀리하시오 - 금연 하시오.
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.
P321 (…) 처치를 하시오.
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.
P403+P235 환기가 잘 되는 곳에 보관하고 저온으로 유지하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.
NFPA 704
2
2 0

벤조니트릴 C화학적 특성, 용도, 생산

개요

벤젠의 수소 한 개를 시아노기로 치환한 무색, 방향성 액체. 분자량 103.1, 녹는점 -13.2℃, 끓는점 191.1℃, 비중 1.0051(20℃)이다. 에틸알코올 · 벤젠 · 에테르에 녹고 물에는 약간 녹는다.

용도

용제로 쓰이며 플라스틱 원료로도 이용된다.

일반 설명

Benzonitrile is a clear colorless liquid with an almond-like odor. Flash point 161°F. Denser (at 8.4 lb / gal) than water and slightly soluble in water. Used as a specialty solvent and to make other chemicals.

화학적 성질

Bezonitrile is a colorless, oily liquid. It has an almond odor.

화학적 성질

When heated to decomposition, benzonitrile emits toxic hydrogen cyanide and oxides of nitrogen (HSDB 1988).

출처

Benzonitrile is reported to be found in natural cocoa aroma), in milk products, roasted filberts and peanuts and cooked trassi . Benzonitrile also has been detected in the thermal decomposition products of flexible polyurethane foam.

용도

The most important commercial use for benzonitrile is the synthesis of benzoguanamine, which is a derivative of melamine and is used in protective coatings and molding resins.

용도

Benzonitrile is a widely utilized as a solvent and an intermediate in industries making drugs, perfumes, dyes, rubber, textiles, resins and specialty lacquers. It finds application as a versatile precursor for many derivatives. It coordinates with transition metal to form complexes which act as synthetic intermediates.

용도

Manufacture of benzoguanamine; intermediate for rubber chemicals; solvent for nitrile rubber, spe- cialty lacquers, and many resins and polymers, and for many anhydrous metallic salts.

생산 방법

Benzonitrile can be prepared by one of the following methods: 1) on a small scale by the dehydration in an inert solvent with phosphorus oxychloride or benzenesulfonyl chloride and an organic amine; 2) from benzoic acid by heating with lead thiocyanate; 3) by heating sodium benzenesulfonate with sodium cyanide or by adding benzenediazonium chloride solution to a hot aq sodium cyanide solution containing cupric sulfate and distilling by ammoxidation of toluene.

정의

ChEBI: A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a phenyl group.

생산 방법

Benzonitrile can be produced in high yield by the vapor-phase catalytic ammoxidation of toluene.

Synthesis Reference(s)

Chemistry Letters, 13, p. 1913, 1984
Journal of the American Chemical Society, 111, p. 4903, 1989 DOI: 10.1021/ja00195a050
Tetrahedron Letters, 11, p. 2085, 1970

공기와 물의 반응

Slightly soluble in water.

반응 프로필

The cyano group can be readily hydrolyzed in the presence of mineral acids to produce stable, moderately toxic benzoic acid . When heated to decomposition, Benzonitrile emits highly toxic fumes of nitrogen oxides and hydrogen cyanide [Sax, 9th ed., 1996, p. 353].

위험도

High toxicity; absorbed by skin.

건강위험

Benzonitrile may enter the human body by ingestion, absorption through the skin, or inhalation. The earliest symptoms of cyano compound intoxication may be weakness, headaches, confusion, and occasionally nausea and vomiting. The respiratory rate and depth will usually be increased at the beginning and at later stages become slow and gasping. Blood pressure is usually normal, especially in the mild or moderately severe cases, although the pulse rate is usually more rapid than normal.

건강위험

Following an occupational accident in which a worker's head and clothing were drenched with benzonitrile (Zeller et al 1969), the worker suffered severe respiratory distress and tonic convulsions between periods of unconsciousness which lasted for 75 min. Thereafter he gradually recovered, but several years later he experienced episodes of unconsciousness which might have been related to the benzonitrile exposure.
Extensive reddening and blister formation resulted from accidental exposure of human skin to benzonitrile (Zeller et al 1969). A maximization test (Kligman 1966; Kligman and Epstein 1975) was also carried out on 35 volunteers. Benzonitrile was tested at a concentration of 2% in petrolatum on 27 volunteers in a mixed panel, and was found to produce no sensitization reactions after a 48 h closed-patch test (Opdyke 1979).

화재위험

Special Hazards of Combustion Products: Toxic hydrogen cyanide and oxides of nitrogen may form in fire.

화학 반응

Reactivity with Water No reaction; Reactivity with Common Materials: Will attack some plastics; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

공업 용도

Benzonitrile is used as an intermediate for rubber chemicals and as a solvent for nitrile rubber, specialty lacquers, many resins, polymers and for many anhydrous metallic salts (HSDB 1988; Hawley 1981). It is principally used as an intermediate for benzoguanamine (HSDB 1988). It is also used as an additive in nickel-plating baths, separating naphthalene and alkylnaphthalenes from non-aromatics by azetropic distillation; as jet-fuel additive; in cotton bleaching baths; as a drying additive for acrylic fibers; and in the removal of titanium tetrachloride and vanadium oxychloride from silicon tetrachloride (HSDB 1988; Smiley 1981). Benzonitrile is also used in perfumes at a maximum level of 0.2% in the final product (Opdyke 1979).

Safety Profile

Poison by intraperitoneal andsubcutaneous routes. Moderately toxic by ingestion,inhalation, and skin contact. A skinirritant. Combustible liquid. When heated todecomposition it emits toxic fumes of CN- and NOx.

잠재적 노출

Bezonitrile is used as an electroplating agent; in organic synthesis of pharmaceuticals; dyestuffs; rubber chemicals; as a solvent and chemical intermediate.

신진 대사

Benzonitrile is mainly hydroxylated in vivo to cyanophenols, a small amount being hydrolysed to benzoic acid (Williams 1959). Benzonitrile also forms 6>-hydroxybenzonitrile, m-hydroxybenzonitrile, and /p-hydroxybenzonitrile in rabbits (HSDB 1988). In rabbit, 50% of a dose of 150 mg/kg was converted to conjugated cyanophenols and 10% of the benzonitrile fed was excreted as benzoic acid. Hydrogen cyanide is not a metabolite of benzonitrile (Williams 1959) and cyanide was not found to be formed by benzonitrile either in vivo or in vitro (Tanii and Hashimoto 1984). The in vivo microsomal hydroxylation of specifically deuterated benzonitrile in the rat yielded mainly 4-hydroxybenzonitrile with 41% retention of deuterium (Daly et al 1968).

운송 방법

UN2224 Benzonitrile, Hazard Class: 6.1; Labels: 6.1—Poisonous materials.

Purification Methods

Dry benzonitrile with CaSO4, CaCl2, MgSO4 or K2CO3, and distil it from P2O5 in an all-glass apparatus, under reduced pressure (b 69o/10mm), collecting the middle fraction. Distillation from CaH2 causes some decomposition of benzonitrile. Isonitriles can be removed by preliminary treatment with conc HCl until the odour of isonitrile (carbylamine) has gone, followed by preliminary drying with K2CO3. (This treatment also removes amines.) Steam distil (to remove small quantities of carbylamine). The distillate is extracted into ether, washed with dilute Na2CO3, dried overnight with CaCl2, and the ether is removed by evaporation. The residue is distilled at 40mm (b 96o) [Kice et al. J Am Chem Soc 82 834 1960]. Conductivity grade benzonitrile (specific conductance 2 x 10-8 mho) is obtained by treatment with anhydrous AlCl3, followed by rapid distillation at 40-50o under vacuum. After washing with alkali and drying with CaCl2, the distillate is redistilled in a vacuum several times at 35o before fractionally crystallising several times by partial freezing. It is dried over finely divided activated alumina from which it is withdrawn when required [Van Dyke & Harrison J Am Chem Soc 73 402 1951]. [Beilstein 9 IV 892.]

비 호환성

May form explosive mixture with air. Strong acids which can release hydrogen cyanide. 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, oxoacids, epoxides. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible Benzonitrile 403 with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

폐기물 처리

(1) Mix with calcium hypochlorite and flush to sewer with water or (2) incinerate.

벤조니트릴 준비 용품 및 원자재

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