Acetic anhydride 乙酸酐(易制毒)

CAS 108-24-7 MFCD00008705

化学结构图

108-24-7
SMILES: CC(=O)OC(C)=O

化学属性

Mol. Formula(CH3CO)2O
Mol. Weight102.09
Density1.08 g/mL(lit.)
Refractive indexn20/D 1.390(lit.)
Boiling Point138-140 °C(lit.)
Melting Point-73 °C(lit.)
Flash Point49°(120°F)
TSCAYes
Autoignition Point629 °F
Vapor Density3.5 (vs air)
Vapor Pressure10 mmHg ( 36 °C)
Solubility起反应

别名和识别编码

Chemical NameAcetic anhydride
CAS Number108-24-7
EC Number203-564-8
Beilstein Registry Number385737
MDL NumberMFCD00008705
PubChem Substance ID24859248
Merck Number14,56
Synonym Cap A(12% 乙酸酐溶于乙腈) Essigsaeureanhydrid Acetyl anhydride 醋酐(乙酸酐) Octowy bezwodnik 氧化乙醯基 (CH3CO)2O aceticacidanhydride Acetic oxide Acetyl oxide Ethanoic anhydrate 无水乙酸 醋酸酐 Anhydrid kyseliny octove Acetanhydrid Acetyl ether acetylether 乙酸的,醋酸的 乙酸酐(0309限出口) AKOS BBS-00004312 ACETIC ANHYDRIDE CAPPING REAGENT A ACETIC OXIDE 乙酐 ETHANOIC ANHYDRIDE Aceticacid,anhydride 无水醋酸 氧化乙醯 Acetyl oxide; Ethanoic anhydride 醋酐 乙酸酐 Anidride acetica Anhydride acetique ACETYL OXIDE acetic Acetic anhydride AC2O 醋酐, 99+% 醋酐, ACS, 97+% Acetic acid, anhydride Acetanhydride Azijnzuuranhydride Acetyl acetate acetylanhydride
Chemical Name Translation乙酸酐(易制毒)
Wiswesser Line Notation1VOV1
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分类

  • Acylation Reagents, Amines, Analytical Reagents, Analytical/Chromatography, Derivatization Reagents, Derivatization Reagents GC, GC Derivatization Reagents, by Application, Reagents for Acylation
  • {SNA} Building Blocks, Carbonyl Compounds, Carboxylic Acid Anhydrides, Chemical Synthesis, Organic Building Blocks
  • {SNA} Acids, Acids & Bases, Chemical Synthesis, Organic Acids, Synthetic Reagents
  • {SNA} Alkaline β-elimination, Anhydrides, Chemical Deglycosylation, Deglycosylation Strategies, Fatty Acids and conjugates, Fatty Acyls, Hydrazinolysis, Protein Modification,

相关文献及参考

  • Merck 14 ,56
  • Beil. 2 ,IV,386
  • Fieser 1 ,3 / Fieser 2 ,7 / Fieser 5 ,3 / Fieser 6 ,1 / Fieser 7 ,1 / Fieser 8 ,1 / Fieser 9 ,1 / Fieser 11 ,1
  • Aldrich MSDS 1 , 10:C / Corp MSDS 1 (1), 17:D / FT-IR 2 (1), 1204:D / FT-IR 1 (1), 711:A / FT-NMR 1 (1), 1165:A / IR-Spectra (2), 368:A / IR-Spectra (3), 416:A / NMR-Reference 2 (1), 601:A / RegBook 1 (1), 827:H / Sax 6 , 85 / Sigma FT-IR 1 (2), 232:A / Structure Index 1 , 129:A:1 / Vapor Phase 3 , 760:C
  • Rates of acetylation of alcohols and phenols can be greatly increased by hypernucleophilic catalysis with DMAP (4-(Dimethyl­amino)­pyridine, A13016). See also 2-Hydroxypyridine, A14522 and Tri-n-butyl­phosphine, A12649. The use of certain metal triflates as catalysts is also effective; see, e.g. Scandium(III)­ trifluoromethanesulfonate hydrate, 40566, and Ytterbium(III)­ trifluoromethanesulfonate hydrate, 40314. CoCl2 catalysis in acetonitrile has been reported to promote selective acetylation of primary alcohols in the presence of secondary and tertiary: J. Org. Chem., 57, 2001 (1992), and formation of 1,1-diacetoxy-derivatives from aromatic aldehydes, but with aliphatic aldehydes, 1,2-diones are formed: J. Org. Chem., 56, 3283 (1991); 58, 5578 (1993).
  • Can be used to activate Dimethyl­ sulfoxide, A13280, for mild, selective oxidation of alcohols to aldehydes or ketones (Albright-Goldman oxidation) at room temperature without added base (cf Swern: Oxalyl­ chloride, A18012): J. Am. Chem. Soc., 43, 2480 (1965); J. Org. Chem., 53, 2144 (1988).

安全信息

GHS Symbol
WGK Germany1
Hazard Codes C F,Xn C,Xn,F,Xi
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H331 Toxic if inhaled 吸入中毒
  • H302 Harmful if swallowed 吞食有害
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H318 Causes serious eye damage 严重伤害眼睛
  • H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
  • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
  • H332 Harmful if inhaled 吸入有害
  • H226 Flammable liquid and vapour 易燃液体和蒸气
Personal Protective Equipment Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
RTECSAK1925000
Precautionary statements
  • P311 Call a POISON CENTER or doctor/physician. 呼叫解毒中心或医生/医师。
  • P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P305+P351+P338
  • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P304+P340+P310
  • P370+P378
Signal word Danger
UN Number 1715 UN1715 UN 2924 3/PG 2
Risk Statements
  • R10 Flammable 易燃
  • R11 Highly flammable 非常易燃
  • R37/38 Irritating to respiratory system and skin 对呼吸系统和皮肤有刺激性
  • R20/21/22 Harmful by inhalation, in contact with skin and if swallowed 吸入、皮肤接触和不慎吞咽有害
  • R19 May form explosive peroxides 可能生成易爆的过氧化物质
  • R41 Risk of serious damage to eyes 有严重损伤眼睛的危险
  • R34 Causes burns 会导致灼伤
  • R20/22 Harmful by inhalation and if swallowed 吸入和不慎吞咽有害
  • R20/21 Harmful by inhalation and in contact with skin 吸入及与皮肤接触有害
Safety Statements
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时,立即求医(可能时出示标签);
  • S16 Keep away from sources of ignition - No smoking 远离火源,禁止吸烟;
  • S39 Wear eye/face protection 戴眼睛/面孔保护装置;
  • S33 Take precautionary measures against static discharges 对静电采取预防措施;
Storage condition Moisture Sensitive Store at RT.
Packing GroupII
Hazard Class8
Restrict 易制毒 {} 易制毒化学品
Warnings 危化品目录(2015) 危险化学品
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 1780 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   AMIHBC AMA Archives of Industrial Hygiene and Occupational Medicine.
   (Chicago, IL)  V.2-10, 1950-54. For publisher information, see AEHLAU.
   Volume(issue)/page/year: 4,119,1951

TYPE OF TEST            : LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE       : Inhalation
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 1000 ppm/4H
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   34ZIAG "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York,
   Academic Press, Inc., 1969  Volume(issue)/page/year: -,607,1969

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Administration onto the skin
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 4 mL/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   UCDS** Union Carbide Data Sheet.  (Union Carbide Corp., 39 Old Ridgebury
   Rd., Danbury, CT 06817)  Volume(issue)/page/year: 8/7/1963

其他信息

  • 用途二:主要用于醋酸纤维素、药物、乙酰化剂和染料、香料的合成
  • 乙酐价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 10000317 乙酸酐(醋酸酐)(易制毒-2);乙酐;醋酐;无水醋酸酐 250ml 13元 2011/08/23 10000318 乙酸酐(醋酸酐)(易制毒-2);乙酐;醋酐;无水醋酸酐 500ml 25元 2010/06/21 222130010 乙酐 Acetic anhydride 98+% 1 LT 779元
  • F:21
  • 上游原料:乙酸乙酯 --> 乙酸 --> 氨 --> 二乙烯酮 --> 乙烯酮 --> 磷
  • Alfa Aesar:醋酐,ACS,97+% Acetic anhydride, ACS, 97+%(108-24-7)
  • 刺激数据:皮肤- 兔子 450 毫克/ 24小时 轻度; 眼睛-兔子 0.25 毫克 重度
  • 方法一:有以下几种工艺路线:1.乙酸裂解法(烯酮法) 以丙酮或乙酸为原料,首先热分解生成中间体乙烯酮,然后将含乙烯酮气体在两个串联的填充塔中用乙酸和乙酐的混合物(循环液)淬冷同时进行化学吸收,生成乙酐: H2C=C=O+CH3COOH—(CH3CO)2O工艺过程如下:将乙酸在蒸发器内气化,于20kPa,负压下与磷酸催化剂混合并通过预热分解器预热至600℃,进行分解管,在700-720℃下热分解成含水和乙酸的乙烯酮。为避免生成沸点与乙酐相近的双乙烯酮(沸点127.4℃),在预热分解管出口处通入氨,经冷却器急冷至0℃左右,分离出水和末反应的乙酸,而后将除去乙酸的反应气体送入吸收塔,与乙酸反应生成乙酐。第一吸收塔控制温度30-40℃,乙酐浓度为85%,第二吸收塔控制温度20℃,乙酐浓度为10-20%,为保持吸收塔的乙酸浓度,在第二吸收塔中定期加入冰醋酸,并将第二吸收塔的乙酸循环至第一吸收塔作吸吸夜用。自第一吸收塔循环液中抽取的粗乙酐去精留馏塔精馏,可得浓度95%以上的乙酐。此法产生步骤多,能耗大,乙酐总收率仅约70%,是较陈旧的方法。用丙酮热解时,裂解温度650-800℃,停留时间0.25-0.75s,加入少量二硫化碳以抑制碳生成,产物用乙酸淬冷.生成的乙烯酮再以乙酸吸收即成乙酐。2.乙醛氧化法院 其反应如下:2CH3CHO+O2——(CH3CO)2+H2O以乙醛为原料,以乙酸钴-乙酸铜为催化剂,在45-55℃,0.29-0.39MPa用空气或氧进行液相催化氧化,产物中乙酐占40%,如加入乙酸乙酯作稀释剂,则成品乙酐可提高50%,粗品经精制分离而得。工艺过程如下:原料乙醛加入稀释剂乙酸乙酯和催化剂乙酸钴,碳酸铜,再加入乙酸和回汽水,配成氧化料,将氧化料连续加入氧化塔底部,自塔身各节通入氧气,反应温度控制在40-60℃之间压力维持在100-300kPa,连续出料,出料的料液中含醛量应不超过2%,尾气通入吸收塔用水吸收。料液在去酯工序将反应产生的水分迅速随着乙酯馏出,防止生成的乙酐水解成乙酸。再在去催化剂塔馏出酐酸混合液,催化剂留在塔釜内,贮积较浓后蒸去塔内残存酐酸,放出催化剂处理回用。酐酸混合液在酐酸分离塔将乙酐和乙酸分开.分离塔为不锈钢真料塔,操作时间真空度53.3-80kPa,塔顶出料为乙酸,塔底出料为粗乙酐。粗乙酸在不锈钢精制制塔内减压蒸去低沸物后,收集成品乙酐。此法操作简单,同时得到副产品乙酸,是目前乙酐的主要生产方法.乙醛氧化法的消耗定额:乙醛1681kh/t,乙酸乙酯70kg/t,氧气571kg/t。3.乙酸甲酯羰化法 以甲醇和乙酸为原料,使用铑系催化剂,以铬的化合物作助催化剂,羰基化生成乙酐。工业上分两步进行:第一步是甲醇酯化为乙酸甲酯;第二步是乙酸酯羰化生成乙酐,温度175℃,压力25MPa,生成乙酐的选择性为95%。这个过程的研究和发展,被看作碳一化学的一项成就,引起各国的重视。4.乙酰氯法乙酰氯与乙酸钠反应制得。
  • 防护措施:有毒。对眼及粘膜具有强烈的刺激性,浓度为0.36mg/m3时即对眼有刺激;0.18mg/m3时,就能改变人的脑电图象。还能引起细胞组织蛋白质变质。其蒸气刺激性更强,极易烧伤皮肤及眼睛,如经常接触会引起皮炎和慢性结膜炎。对大鼠经口LD50为1780mg/kg。当溅及或粘附于皮肤时,要立即用清水或2%苏打水冲洗,全身中毒时应延医诊治。空气中最高容许浓度5ppm。设备应密封,防止泄漏。操作人员要穿戴好防护用品。
  • 类别:腐蚀物品
  • {Chemica

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