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벤질 알코올

벤질 알코올
벤질 알코올 구조식 이미지
카스 번호:
100-51-6
한글명:
벤질 알코올
동의어(한글):
벤질알코올;(하이드록시메틸)벤젠;벤젠메탄올;알BENZENEMETHANOL;알파-하이드록시톨루엔;페닐메틸알코올;페닐카빈올;벤젠카빈올;벤질알콜;벤질알코올
상품명:
Benzyl alcohol
동의어(영문):
BnOH;Bentalol;bentanol;euxylk100;FEMA 2137;benzylicum;NCI-C06111;Benzalcohol;argopore-oh;Benzylalchol
CBNumber:
CB3852587
분자식:
C7H8O
포뮬러 무게:
108.14
MOL 파일:
100-51-6.mol

벤질 알코올 속성

녹는점
-15 °C
끓는 점
205 °C
밀도
1.045 g/mL at 25 °C(lit.)
증기 밀도
3.7 (vs air)
증기압
13.3 mm Hg ( 100 °C)
굴절률
n20/D 1.539(lit.)
FEMA
2137 | BENZYL ALCOHOL
인화점
201 °F
저장 조건
2-8°C
용해도
H2O: 33 mg/mL, clear, colorless
물리적 상태
Liquid
색상
APHA: ≤20
상대극성
0.608
냄새
Mild, pleasant.
폭발한계
1.3-13%(V)
수용성
4.29 g/100 mL (20 ºC)
Merck
14,1124
JECFA Number
25
BRN
878307
노출 한도
No exposure limit is set. Because of its low vapor pressure and low toxicity, the health hazard to humans from occupational exposure should be very low.
InChIKey
WVDDGKGOMKODPV-UHFFFAOYSA-N
CAS 데이터베이스
100-51-6(CAS DataBase Reference)
NIST
Benzyl alcohol(100-51-6)
EPA
Benzenemethanol(100-51-6)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn,T
위험 카페고리 넘버 20/22-63-43-36/37/38-23/24/25-45-40
안전지침서 26-36/37-24/25-23-53
유엔번호(UN No.) UN 1593 6.1/PG 3
WGK 독일 1
RTECS 번호 DN3150000
F 고인화성물질 8-10-23-35
자연 발화 온도 817 °F
TSCA Yes
HS 번호 29062100
유해 물질 데이터 100-51-6(Hazardous Substances Data)
독성 LD50 orally in rats: 3.1 g/kg (Smyth)
그림문자(GHS):
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 P264, P270, P301+P312, P330, P501
H317 알레르기성 피부 반응을 일으킬 수 있음 피부 과민성 물질 구분 1 경고 P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H332 흡입하면 유해함 급성 독성 물질 흡입 구분 4 경고 P261, P271, P304+P340, P312
H351 암을 일으킬 것으로 의심됨 (노출되어도 암을 일으키지 않는다는 결정적인 증거가 있는 노출경로가 있다면 노출경로 기재) 발암성 물질 구분 2 경고 P201, P202, P281, P308+P313, P405,P501
예방조치문구:
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.
P272 작업장 밖으로 오염된 의복을 반출하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P281 요구되는 개인 보호구를 착용하시오
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P501 ...에 내용물 / 용기를 폐기 하시오.

벤질 알코올 C화학적 특성, 용도, 생산

용도

착향료로서 과자에 쓰인다. 특히 딸기나 편도의 향기에 배합한다.

용도

아이스크림(160ppm), 츄잉껌(1,200ppm), 크림향료(재스민향 160ppm), 사탕, 젤라틴·푸딩(20~40ppm) 등에 이용된다. 용해력이 높기 때문에 유성향료의 용해제 및 추출제, 휘발보류제로 사용되며, 빛이 차단된 밀봉용기에 담아 보존한다. 화장품·비누용의 향료로, 재스민 등 인조 화정유의 조합, 용제나 회석제, 에스터 원료로서도 사용한다. 또 국소마취제로도 쓰이는데, 농도 1∼3%의 것은 주사제의 조정에 쓰이고, 1∼2% 첨가한 것을 로션으로 만들어 가려움을 멈추게 하는 약으로 사용한다.

화학적 성질

Benzyl alcohol occurs in many essential oils and foods. It is a colorless liquid with a weak, slightly sweet odor. Benzyl alcohol can be oxidized to benzaldehyde, for example, with nitric acid. Dehydrogenation over a copper–magnesium oxide–pumice catalyst also leads to the aldehyde. Esterification of benzyl alcohol results in a number of important fragrance and flavor materials. Diphenylmethane is prepared by a Friedel–Crafts reaction of benzyl alcohol and benzene with aluminum chloride or concentrated sulfuric acid. By heating benzyl alcohol in the presence of strong acids or strong bases, dibenzyl ether is formed.
Synthesis. Benzyl alcohol is manufactured mainly by two processes.
1) Benzyl chloride is hydrolyzed by boiling with aqueous solutions of alkali or alkaline-earth hydroxides or carbonates. By-product in this process is dibenzyl ether (up to 10%).
2) Toluene is, in low conversion, oxidized, with air, in the liquid phase, to benzyl hydroperoxide, which yields mainly benzyl alcohol and some benzaldehyde upon hydrolysis, for example, in the presence of a cobalt salt. Benzyl alcohol thus obtained requires a more thorough purification for use in perfumes and flavors.
Because of its relatively weak odor, benzyl alcohol is used in fragrance and flavor compositions mainly as a solvent and for dilution. It is the starting material for a large number of benzyl esters, which are important fragrance and flavor substances.

화학적 성질

Benzyl alcohol has a characteristic pleasant, fruity odor and a slightly pungent, sweet taste; the note tends to become similar to that of benzyl aldehyde on aging.

출처

The free alcohol is often present in several essential oils and extracts of jasmine, tobacco, tea, neroli, copaiba, Acacia farnesiana Willd., Acacia cavenia Hook. and Arn., Robinia pseudacacia, ylang-ylang, Pandanus odoratissimus, Michelia champaca, Prunus laurocerasus, tuberose, orris, castoreum, violet leaves, clove buds and others. Also found in fresh apple, apricot, mandarin peel oil, high bush blueberry, raspberry, strawberry fruit, American cranberry and cooked asparagus.

용도

Esters of benzyl alcohol are used in makingperfume, soap, flavoring, lotion, and ointment.It finds application in color photography;the pharmaceuticals industry, cosmetics,and leather dyeing; and as an insect repellent.It occurs in natural products such as oils ofjasmine and castoreum.

용도

antimicrobial, antipruritic

용도

manufacture of other benzyl Compounds. Pharmaceutic aid (antimicrobial). Solvent for gelatin, casein (when hot), solvent for cellulose acetate, shellac. Used in perfumery and in flavoring (mostly in form of its aliphatic esters). In microscopy as embedding material.

용도

benzyl alcohol is a preservative against bacteria, used in concentrations of 1 to 3 percent. It can cause skin irritation.

생산 방법

Benzyl alcohol is prepared commercially by the distillation of benzyl chloride with potassium or sodium carbonate. It may also be prepared by the Cannizzaro reaction of benzaldehyde and potassium hydroxide.

정의

ChEBI: An aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent.

정의

An aromatic primary alcohol. Phenylmethanol is synthesized by Cannizzaro’s reaction, which involves the simultaneous oxidation and reduction of benzenecarbaldehyde (benzaldehyde) by refluxing in an aqueous solution of sodium hydroxide:
2C6H5CHO → C6H5CH2OH + C6H5COOH
Phenylmethanol undergoes the reactions characteristic of alcohols, especially those in which the formation of a stable carbonium ion as an intermediate (C6H5CH2 +) enhances the reaction. Substitution onto the benzene ring is also possible; the –CH2OH group directs into the 2- or 4-position by the donation of electrons to the ring.

상표명

Actamin c;Benhur;Bigram;B-neuron;Brophylline;D & m tablets;Dermaspray;Dex-a-vet;Duphaspasmin;Eclipse;Fertagyl;Hydraplex;Lidazon;Lokalin;Madinex;Omnadren;Orostat;Parkestaf;Procadolor;Reflex-spray;Solvidont;Sudocrem;Topic;Triofan.

World Health Organization (WHO)

Benzyl alcohol has been used as an antimicrobial agent in pharmaceutical preparations for many years. Parenteral administration of preparations containing 0.9% benzyl alcohol resulted in the death of 16 neonates in the USA in the early 1980s. Many countries subsequently warned against using such preparations in neonates. This decision is not applicable to the use of benzyl alcohol as a preservative in other circumstances or to its use in topical preparations and no country has placed a total ban on the compound.

Aroma threshold values

Detection: 1.2 to 1000 ppb; also 10 to 1000 ppm.

Taste threshold values

Taste characteristics at 50 ppm: chemical, fruity with balsamic nuances.

일반 설명

A clear colorless liquid with a pleasant odor. Slightly denser than water. Flash point 194°F. Boiling point 401°F. Contact may irritate skin, eyes, and mucous membranes. May be slightly toxic by ingestion. Used to make other chemicals.

공기와 물의 반응

Slightly soluble in water.

반응 프로필

Attacks plastics. [Handling Chemicals Safely 1980. p. 236]. Acetyl bromide reacts violently with alcohols or water [Merck 11th ed. 1989]. Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: an explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid [Chem. Eng. News 45(43):73 1967; J, Org. Chem. 28:1893 1963]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous-carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites [NFPA 491 M 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence [Wischmeyer 1969].

위험도

Highly toxic.

건강위험

Inhalation of vapor may cause irritation of upper respiratory tract. Prolonged or excessive inhalation may result in headache, nausea, vomiting, and diarrhea. In severe cases, respiratory stimulation followed by respiratory and muscular paralysis, convulsions, narcosis and death may result. Ingestion may produce severe irritation of the gastrointestinal tract, followed by nausea, vomiting, cramps and diarrhea; tissue ulceration may result. Contact with eyes causes local irritation. Material can be absorbed through skin with anesthetic or irritant effect.

건강위험

Benzyl alcohol is a low acute toxicant witha mild irritation effect on the skin. Theirritation in 24 hours from the pure compoundwas mild on rabbit skin and moderateon pig skin. A dose of 750 μg producedsevere eye irritation in rabbits. The toxicityof benzyl alcohol is of low order,the effects varying with the species. Oralintake of high concentrations of this compoundproduced behavioral effects in rats.The symptoms progressed from somnolenceand excitement to coma. Intravenous administrationin dogs produced ataxia, dyspnea,diarrhea, and hypermotility in the animals.
Adult and neonatal mice treated withbenzyl alcohol exhibited behavioral change,including sedation, dyspnea, and loss ofmotor function. Pretreatment with pyrazoleincreased the toxicity of benzyl alcohol. Withdisulfiram the toxicity remained unchanged.The study indicated that the acute toxicitywas due to the alcohol itself andnot to bezaldehyde, its primary metabolite(McCloskey et al. 1986).

화재위험

Benzyl alcohol is combustible.

화재위험

Flash Point (°F): 220 ℃, 213 ℃; Flammable Limits in Air (%): No data; Fire Extinguishing Agents: Alcohol foam, dry chemical, carbon dioxide; Fire Extinguishing Agents Not To Be Used: Water or foam may cause foaming; Special Hazards of Combustion Products: No data; Behavior in Fire: No data; Ignition Temperature (°F): 817; Electrical Hazard: No data; Burning Rate: 3.74 mm/min.

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.

Pharmaceutical Applications

Benzyl alcohol is an antimicrobial preservative used in cosmetics, foods, and a wide range of pharmaceutical formulations, including oral and parenteral preparations, at concentrations up to 2.0% v/v. The typical concentration used is 1% v/v, and it has been reported to be used in protein, peptide and small molecule products, although its frequency of use has fallen from 48 products in 1996, 30 products in 2001, to 15 products in 2006. In cosmetics, concentrations up to 3.0% v/v may be used as a preservative. Concentrations of 5% v/v or more are employed as a solubilizer, while a 10% v/v solution is used as a disinfectant.
Benzyl alcohol 10% v/v solutions also have some local anesthetic properties, which are exploited in some parenterals, cough products, ophthalmic solutions, ointments, and dermatological aerosol sprays.
Although widely used as an antimicrobial preservative, benzyl alcohol has been associated with some fatal adverse reactions when administered to neonates. It is now recommended that parenteral products preserved with benzyl alcohol, or other antimicrobial preservatives, should not be used in newborn infants if at all possible.

색상 색인 번호

Benzyl alcohol is mainly a preservative, mostly used in topical antimycotic or corticosteroid ointments. It is also a component catalyst for epoxy resins and is contained in the color developer C-22. As a fragrance allergen, it has to be mentioned by name in cosmetics within the EU.

Safety

Benzyl alcohol is used in a wide variety of pharmaceutical formulations. It is metabolized to benzoic acid, which is further metabolized in the liver by conjugation with glycine to form hippuric acid, which is excreted in the urine.
Ingestion or inhalation of benzyl alcohol may cause headache, vertigo, nausea, vomiting, and diarrhea. Overexposure may result in CNS depression and respiratory failure. However, the concentrations of benzyl alcohol normally employed as a preservative are not associated with such adverse effects.
Reports of adverse reactions to benzyl alcohol used as an excipient include toxicity following intravenous administration; neurotoxicity in patients administered benzyl alcohol in intrathecal preparations; hypersensitivity, although relatively rare; and a fatal toxic syndrome in premature infants.
The fatal toxic syndrome in low-birth-weight neonates, which includes symptoms of metabolic acidosis and respiratory depression, was attributed to the use of benzyl alcohol as a preservative in solutions used to flush umbilical catheters. As a result of this, the FDA has recommended that benzyl alcohol should not be used in such flushing solutions and has advised against the use of medicines containing preservatives in the newborn.
The WHO has set the estimated acceptable daily intake of the benzyl/benzoic moiety at up to 5 mg/kg body-weight daily.
LD50 (mouse, IV): 0.32 g/kg
LD50 (mouse, oral): 1.36 g/kg
LD50 (rat, IP): 0.4 g/kg
LD50 (rat, IV): 0.05 g/kg
LD50 (rat, oral): 1.23 g/kg

Chemical Synthesis

By saponification of the ester present in Tolu and Pery balsams; synthetically, it is obtained from benzyl chloride by the action of sodium or potassium carbonate.

저장

Benzyl alcohol oxidizes slowly in air to benzaldehyde and benzoic acid; it does not react with water. Aqueous solutions may be sterilized by filtration or autoclaving; some solutions may generate benzaldehyde during autoclaving.
Benzyl alcohol may be stored in metal or glass containers. Plastic containers should not be used; exceptions to this include polypropylene containers or vessels coated with inert fluorinated polymers such as Teflon.
Benzyl alcohol should be stored in an airtight container, protected from light, in a cool, dry place.

Purification Methods

It is usually purified by careful fractional distillation under reduced pressure in the absence of air. Benzaldehyde, if present, can be detected by UV absorption at 283nm. It has also been purified by shaking with aqueous KOH and extracting with peroxide-free diethyl ether. After washing with water, the extract is treated with saturated NaHS solution, filtered, washed, dried with CaO and distilled under reduced pressure [Mathews J Am Chem Soc 48 562 1926]. Peroxy compounds can be removed by shaking with a solution of Fe2+ followed by washing the alcohol layer with distilled water and fractionally distilling it. [Beilstein 6 IV 2222.]

비 호환성

Benzyl alcohol is incompatible with oxidizing agents and strong acids. It can also accelerate the autoxidation of fats. Although antimicrobial activity is reduced in the presence of nonionic surfactants, such as polysorbate 80, the reduction is less than is the case with hydroxybenzoate esters or quaternary ammonium compounds.
Benzyl alcohol is incompatible with methylcellulose and is only slowly sorbed by closures composed of natural rubber, neoprene, and butyl rubber closures, the resistance of which can be enhanced by coating with fluorinated polymers. However, a 2% v/v aqueous solution in a polyethylene container, stored at 208℃, may lose up to 15% of its benzyl alcohol content in 13 weeks. Losses to polyvinyl chloride and polypropylene containers under similar conditions are usually negligible. Benzyl alcohol can damage polystyrene syringes by extracting some soluble components

Regulatory Status

Included in the FDA Inactive Ingredients Database (dental injections, oral capsules, solutions and tablets, topical, and vaginal preparations). Included in parenteral and nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

벤질 알코올 준비 용품 및 원자재

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