Chloroacetic Acid 氯乙酸

CAS 79-11-8 MFCD00002683

化学结构图

79-11-8
SMILES: O=C(O)CCl

化学属性

Mol. FormulaC2H3ClO2
Mol. Weight94
Boiling Point189
Melting Point62-66
Density1.404
Flash Point126°(258°F)
TSCAYes
SolubilitySoluble in water, alcohols, benzene, chloroform, ether
Vapor Density3.26 (vs air)
Vapor Pressure0.75 mmHg ( 20 °C)
Refractive index1.4330

别名和识别编码

Chemical NameChloroacetic Acid
CAS Number79-11-8
Synonym 2-chloro-aceticacid AKOS BBS-00004063 Acide chloracetique Acide monochloracetique CHLOROACETIC ACID CROPTEX STEEL Chloracetic acid Chloroacetic acid Chloroacetic acid (ß) MKhUK MONCHLOROACETIC ACID Monochloracetic acid Monochloressigsäure Monochloroacetic acid Monochloroethanoic acid NCI-C60231 RARECHEM AL BO 0100 TZR-701阻燃润滑剂 acetic acid, chloro- aceticacid,chloro- acidechloracetique acidechloroacetique(french) acidemonochloracetique(french) acidemonochloracetique(solide) acidemonochloracetique(solutions) chloroethanoic acid monochloroacetic acid α 异氰尿酸蜜
PubChem Substance ID24865140
EC Number201-178-4
Beilstein Registry Number605438
MDL NumberMFCD00002683
Merck Number14,2112
Chemical Name Translation氯乙酸
Wiswesser Line NotationQV1G
LabNetwork Molecule IDLN00193507
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分类

  • {SNA} ACS Grade, Chemical Synthesis, Essential Chemicals, Inorganic Salts, Solutions and Reagents, Organic Acids, Research Essentials, Synthetic Reagents
  • {SA} Chemical Synthesis, Organic Acids, Synthetic Reagents
  • {uni_hamburg} no charge; carboxylic acid; 1fragment
  • Aliphatic halogenated, Alpha Sort, Alphabetic, Analytical Standards, Analytical/Chromatography, C, CH, Chromatography, Environmental Standards, Herbicides, Pesticides & Metabolites, Volatiles/ Semivolatiles
  • {Chemicalbook} 农药中间体: 杀虫剂中间体: 有机磷类杀虫剂

相关文献及参考

  • Merck 14 ,2112
  • Beil. 2 ,IV,474
  • Aldrich MSDS 1 , 365:D / Corp MSDS 1 (1), 726:C / FT-IR 2 (1), 789:C / FT-IR 1 (1), 508:A / FT-NMR 1 (1), 790:B / IR-Spectra (3), 298:B / NMR-Reference 2 (1), 444:D / RegBook 1 (1), 555:A / Sax 6 , 676 / Sigma FT-IR 1 (1), 1378:A / Structure Index 1 , 78:D:8 / Vapor Phase 3 , 591:B
  • Short: II/14a Title: Molecular Constants: Diamagnetic Molecules Author: Demaison, J.; Dubrulle, A.; Hüttner, W.; Tiemann, E. Editor: Hellwege, K.-H.; Hellwege, A.M. Source: Landolt-Börnstein, New Series Volume: II/14a Page: 1-788 Year: 1982 Keyword: organic compounds; molecular constants; spectroscopy; microwave spectroscopy ISBN: 3-540-11365-7 ISBN: 978-3-540-11365-2 Internet Resource: DOI:10.1007/b19966 RefComment: 196 figs., XI
  • Short: II/25B Title: Structure Data Of Free Polyatomic Molecules: Molecules containing One or Two Carbon Atoms Author: Graner, G.; Hirota, E.; Iijima, T.; Kuchitsu, K.; Ramsay, D.A.; Vogt, J.; Vogt, N. Editor: Kuchitsu, K. Source: Landolt-Börnstein, New Series Volume: II/25B Year: 1999 Keyword: Free Polyatomic Molecules; Carbon Atoms; Molecules ISBN: 3-540-63645-5 ISBN: 978-3-540-63645-8 Internet Resource: DOI:10.1007/b68834 RefComment: IX, 512 pages. Hardcover Abstract: Volume II/25 is a supplemented and revised edition of the preceding volumes II/7, II/15, II/21 and II/23 contain
  • A convenient one-pot alternative to the Knoevenagel or Horner-Wadsworth-Emmons reactions for the synthesis of ɑ-unsubstituted cinnamic acids involves the reaction of chloroacetic acid with dimethyl phosphite in the presence of sodium methoxide, and treatment of the resulting phosphonoacetate salt with a benzaldehyde: J. Org. Chem., 46, 2514 (1981):
  • For a more general version of this reaction, applicable to the synthesis of a variety of substituted acrylic acids, see 2-Bromopropionic acid, A17569.

安全信息

Hazard statements
  • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
  • H400 Verytoxictoaquaticlife 对水生生物毒性非常大。
  • H331 Toxic if inhaled 吸入中毒
  • H311 Toxic in contact with skin 皮肤接触中毒
  • H301 Toxic if swallowed 吞食有毒
Hazard Codes 6.1 T,N T,N,Xi,F
GHS Symbol
WGK Germany3
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P2 (EN 143) respirator cartridges, type P3 (EN 143) respirator cartridges
Signal word Danger
RTECSAF8575000
Precautionary statements
  • P234 Keep only in original container. 只保留在原来的容器中。
  • 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。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
  • P273 Avoid release to the environment. 避免释放到环境中。
  • 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。
  • P301+P310
  • P301+P330+P331
  • 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。
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Safety Statements
  • S23 Do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) 不要吸入气体/烟雾/蒸汽/喷雾;
  • 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;
  • 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;
  • S37 Wear suitable gloves 戴适当手套;
  • 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);
  • S61 Avoid release to the environment. Refer to special instructions/safety data sheet 避免释放到环境中,参考特别指示/安全收据说明书;
  • S63
UN Number 1751
Risk Statements
  • R23/24/25 Toxic by inhalation, in contact with skin and if swallowed 吸入,皮肤接触及吞食都有毒
  • R34 Causes burns 会导致灼伤
  • R50 Very toxic to aquatic organisms 对水生生物极毒
Storage condition 0-6°C Hygroscopic
Packing GroupII
Hazard Class6.1
Restrict 剧毒化学品
TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1300 mg/kg/65W-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Tumorigenic - tumors at site of application
REFERENCE :
   JNCIAM Journal of the National Cancer Institute.  (Washington, DC)  V.1-60,
   1940-78.  For publisher information, see JJIND8.  Volume(issue)/page/year:
   53,695,1974

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 100 mg/kg
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Lungs, Thorax, or Respiration - tumors
   Liver - tumors
REFERENCE :
   NTIS** National Technical Information Service.  (Springfield, VA 22161)
   Formerly U.S. Clearinghouse for Scientific & Technical Information.
   Volume(issue)/page/year: PB223-159

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 16600 ug/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   RPTOAN Russian Pharmacology and Toxicology (English Translation).
   Translation of FATOAO.  (Euromed Pub., 33, Woodlands Rd., Surbiton, Surrey,
   UK)  V.30-    1967-  Volume(issue)/page/year: 41,113,1978

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 55 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   GTPZAB Gigiena Truda i Professional'nye Zabolevaniya.  Labor Hygiene and
   Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR)
   V.1-36, 1957-1992. For publisher

TYPE OF TEST            : LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE       : Inhalation
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 180 mg/m3
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   GTPZAB Gigiena Truda i Professional'nye Zabolevaniya.  Labor Hygiene and
   Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR)
   V.1-36, 1957-1992. For publisher information, see MTPEEI
   Volume(issue)/page/year: 18(9),32,1974

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 5 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   TXAPA9 Toxicology and Applied Pharmacology.  (Academic Press, Inc., 1 E.
   First St., Duluth, MN 55802) V.1-    1959-  Volume(issue)/page/year:
   22,303,1972

TYPE OF TEST            : Mutation in mammalian somatic cells
TEST SYSTEM             : Rodent - mouse Lymphocyte
DOSE/DURATION           : 400 mg/L
REFERENCE :
   ENMUDM Environmental Mutagenesis.  (New York, NY)  V.1-9, 1979-87.  For
   publisher information, see EMMUEG.  Volume(issue)/page/year: 9,143,1987

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Rodent - mouse Lymphocyte
DOSE/DURATION           : 548 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 97,49,1982

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Rodent - hamster Ovary
DOSE/DURATION           : 160 mg/L
REFERENCE :
   EMMUEG Environmental and Molecular Mutagenesis.  (Alan R. Liss, Inc., 41 E.
   11th St., New York, NY 10003)  V.10-    1987-  Volume(issue)/page/year:
   10(Suppl 10),1,1987

Warnings 危险化学品

其他信息

  • 蒸气压:0.75 mm Hg ( 20 °C)
  • Acros Organics:氯乙酸 Chloroacetic acid, 99+%(79-11-8)
  • 上游原料:盐酸 --> 乙酸 --> 氯 --> 硫磺 --> 2-氯乙醇 --> 三氯乙烯 --> 二氯化二硫 --> 三氯乙酸 --> 乙醇酸 --> 二氯乙酸 --> 1,1,2,2-四氯乙烷 --> 二氯乙酸甲酯
  • MOL 文件:79-11-8.mol
  • Sigma Aldrich:79-11-8(sigmaaldrich)
  • 方法二:工业生产氯乙酸有三种主要方法。(1)乙酸氯化法是在碘、磷、硫或磷和硫的卤化物等催化剂存在下,用氯气将乙酸直接氯化而得。除生成氯乙酸外,还有深度氯化的副产物如二氯乙酸、三氯乙酸。此法原料消耗较低,工艺简单,氯乙酸产率可达92%。(2)三氯乙烯水合法是以93%的硫酸为催化剂,反应温度约160-180℃。此法可得高纯度的氯乙酸,产率可达90%,但副产盐酸较多。(3)氯乙醇氧化法是在60℃用60%的硝酸氧化,氯乙酸收率超过90%。在北美洲以乙酸氯化法为主,西欧以三氯乙烯水合法为主。我国采用乙酸氯化法生产:将定量的冰醋酸加入反应锅,以冰醋酸重量的3.5%硫黄粉作催化剂,预热至90℃以上,开始通入适量的氯气,两只反应锅串联通氯,主锅控制温度为98±2℃,副锅为85-90℃,通氯速度约70kg/h,待反应锅内物料的相对密度为1.350(80℃)时,即反应到达终点。将反应物抽至酸罐,冷却结晶,液相为少量乙酸、二氯乙酸、氯化硫和少量氯乙酸,分离出结晶体,再在38℃以下把母液抽尽即为成品。每吨产品约产生150公斤母液,可进一步氯化制成二氯乙酸、二氯乙酸甲酯及氯仿。三氯乙烯水合法同时进行水的加成和水解:反应温度160-180℃,反应中硫酸浓度应保持在93%,控制三氯乙烯和水的比例。硫酸消耗不超过50kg,副产30%的盐酸2.57t。工业品氯乙酸为无色或略带淡黄色结晶体。原料消耗定额:冰醋酸(98%)730kg/t、氯气860kg/t、硫磺26kg/t。
  • 用途四:用于广泛的有机合成原料。染料工业用于生产靛蓝、萘氨基乙酸类染料;在制药工业用于合成咖啡因、巴比妥、肾上腺素、维生素B6、氨基乙酸、丙二酸酯等药物和中间体;在农药工业用于生产除草剂2,4-D、丁酯、2,4,5-T、硫氰乙酸、α-萘乙酸、草甘磷、甲草胺、乙草胺、丁草胺及杀虫剂乐果等20多种农药;在合成纤维工业用于生产羧甲基纤维素(CMC)和有色金属浮选剂Z-200#,还可用作色层分析试剂等,也可用于食品添加剂、洗涤剂、冷烫精等产品。详见本条附表氯乙酸系列产品。
  • 类别:腐蚀物品
  • 用途三:氯乙酸是一种有机化工原料,在农药生产上广泛应用,可用于合成有机磷杀虫剂乐果、氧乐
  • 储运特性:库房通风低温干燥; 与氧化剂、碱类分开
  • F:3
  • 海关编码:29154000
  • 毒性分级:高毒
  • 可燃性危险特性:遇热, 明火燃烧; 受热分解产生有毒光气; 有腐蚀性
  • 用途三:氯乙酸是一种有机化工原料,在农药生产上广泛应用,可用于合成有机磷杀虫剂乐果、氧乐果的中间体氯乙酸甲酯,喹硫磷的中间体2-羟基喹啉,除草
  • 方法一:氯乙酸的合成方法较多,有乙酸氯化法、乙酐催化氯化法、三氯乙烯水解法、羟基乙酸氯化法、四氯乙烷水解等,国内工业生产上主要采用乙酸氯化法,该法的优点是不使用硫酸,且原料价格便宜,CH 3 COOH+Cl 2 →ClCH 2 COOH+HCl 将定量冰醋酸加入反应锅,以冰醋酸质量的3.5%硫磺粉作催化剂,预热至90℃以上,开始通入适量的氯气,两只反应锅串联通氯气,主锅控制温度为(98±2)℃,副锅为85~90℃,通氯气速度约70kg/h。待反应锅内物料相对密度为1.350(80℃)时,即到达反应终点。将反应物抽至酸罐,冷却结晶,分离出结晶体,再在38℃以下把母液抽尽,即得到成品氯乙酸。此外,也有实验表明,除硫磺粉外,乙酐也可在相同条件下对上述氯化反应起到较好的催化作用,且效果优于硫磺粉。 还有三氯乙烯水合法。三氯乙烯与浓硫酸反应,反应温度160~180℃,保持硫酸含量为93%,控制三氯乙烯和水的比例,反应历程经硫酸加成、水解而得到一氯乙酸。

系列性分类


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