79-11-8 Usage
Description
Chloroacetic acid (CAA) is a monohalogenated acetic acid
(m-HAA) that is used as a photosensitizing agent and in
industrial synthesis of certain organic chemicals such as indigoid
dyes. The m-HAAs are a major class of drinking water
disinfection by-products during chlorination of drinking water.
Chemical Properties
Different sources of media describe the Chemical Properties of 79-11-8 differently. You can refer to the following data:
1. colourless or white crystals
2. Chloroacetic acid is a colorless to white crystalline solid. It has a strong vinegar-like odor and an Odor
Threshold of 0.15 milligram per cubic meter.
Uses
Different sources of media describe the Uses of 79-11-8 differently. You can refer to the following data:
1. Herbicide, preservative, bacteriostat, intermediate in production of carboxymethylcellulose; ethyl
chloroacetate, glycine, synthetic caffeine, sarcosine, thioglycolic acid, EDTA, 2,4-D, 2,4,5-T.
2. Chloroacetic acid behaves as a very strong monobasic acid and is used as a strong acid catalyst for diverse reactions. The Cl function can be displaced in base-catalyzed reactions.
3. CAA is one of these agents used in the topical treatment of
warts in most European countries and also as an herbicidal
agent and a bleaching agent for silkworm cocoons. It can be
found in wines and beers using static headspace extraction
coupled with gas chromatography–mass spectrometry. CCA is
the main toxic metabolite of vinyl chloride. CAA and volatile
organochlorines are suspected to contribute to forest dieback
and stratospheric ozone destruction.
Definition
Different sources of media describe the Definition of 79-11-8 differently. You can refer to the following data:
1. A colorless crystalline
solid made by substituting one of the hydrogen
atoms of the methyl group of
ethanoic acid with chlorine, using red
phosphorus. It is a stronger acid than
ethanoic acid because of the electron-withdrawing
effect of the chlorine atom.
Dichloroethanoic acid (dichloroacetic
acid, CHCl2COOH) and trichloroethanoic
acid (trichloroacetic acid,CCl3COOH) are
made in the same way. The acid strength
increases with the number of chlorine
atoms present.
2. ChEBI: A chlorocarboxylic acid that is acetic acid carrying a 2-chloro substituent.
Production Methods
Chloroacetic acid can be synthesized by the radical chlorination of acetic acid, treatment of trichloroethylene with concentrated H2SO4, oxidation of 1,2-dichloroethane or chloroacetaldehyde, amine displacement from glycine, or chlorination of ketene.
General Description
Chloroacetic acid, solution is a colorless solution of the white crystalline solid. The acid concentration can be up to 80%.It is used in manufacturing dyes and in medicine. Chloroacetic acid is toxic by inhalation, ingestion and skin contact. Chloroacetic acid is corrosive to metals and tissue. Chloroacetic acid is used as an herbicide, preservative and bacteriostat.
Air & Water Reactions
Water soluble.
Reactivity Profile
These organic compounds donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Chloroacetic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.
Hazard
Use in foods prohibited by FDA. Irritating and corrosive to skin. Upper respiratory tract
irritant. Questionable carcinogen.
Health Hazard
Inhalation causes mucous membrane irritation. Contact with liquid causes severe irritation and burns of the eyes and irritation and burns of skin. Ingestion causes burns of mouth and stomach.
Fire Hazard
Special Hazards of Combustion Products: Toxic gases, such as hydrogen chloride, phosgene and carbon monoxide, may be generated.
Flammability and Explosibility
Nonflammable
Safety Profile
Poison by ingestion,
inhalation, subcutaneous, and intravenous
routes. A corrosive skin, eye, and mucous
membrane irritant. Questionable carcinogen
with experimental tumorigenic data.
Mutation data reported. Combustible liquid
when exposed to heat or flame. To fight
fire, use water spray, fog, mist, dry chemical, foam. When heated to decomposition it
emits toxic fumes of Cl-. See also
CHLORIDES.
Potential Exposure
This haloacetic acid can be a byproduct
of drinking water disinfection and may increase the risk of
cancer. Monochloracetic acid is used primarily as a chemical
intermediate in the synthesis of sodium carboxymethyl cellulose; and such other diverse substances as ethyl chloroacetate,
glycine, synthetic caffeine, sarcosine, thioglycolic acid, and
various dyes. Hence, workers in these areas are affected. It is
also used as an herbicide. Therefore, formulators and applicators of such herbicides are affected.
Environmental Fate
CCA by inhibition of the pyruvate-dehydrogenase, aconitase,
and a-ketoglutarate dehydrogenase that contribute in tricarboxylic
acid cycle and also inhibition of glyceraldehyde-
3-phosphate dehydrogenase can impair production of
cellular energy and conversion to anaerobic glycolysis, resulting
in increasing acidosis with accumulation of glycolic
acid, oxalate, and lactate production. CCA can also affect
cellular components via sulfhydryl groups. Both of these
effects may contribute to central nervous system (CNS),
cardiovascular, renal, and hepatic effects. The metabolites
glycolic acid and oxalate may contribute to CNS and renal
toxicity (myoglobin and oxalate precipitation in the tubuli).
Binding of calcium to oxalates probably causes the hypocalcemia,
but hypocalcemia can be secondary to rhabdomyolysis.
CAA by reduction of cellular glutathione can cause
oxidative stress. Inhibition of mitochondrial aconitase causes
hypoglycemia.
Shipping
UN1750 (liquid) & UN1751 (solid) Chloroacetic
acid, solid or liquid, Hazard class: 6.1; Labels: 6.1-Poison
Inhalation Hazard, 8-Corrosive material.
Purification Methods
Crystallise the acid from CHCl3, CCl4, *benzene or water. Dry it over P2O5 or conc H2SO4 in a vacuum desiccator. Further purification is by distillation from MgSO4, and by fractional crystallisation from the melt. Store it under vacuum or under dry N2. [Bernasconi et al. J Am Chem Soc 107 3621 1985, Beilstein 2 IV 474.]
Toxicity evaluation
Occupational exposure to CAA can occur through inhalation
and dermal contact with this compound at workplaces where
it is produced or used. The general population can be exposed
to CAA via ingestion of chlorinated or chloraminated drinking
water.The atmospheric photochemical oxidation of some volatile
organochlorine compounds is one source of CAAs in the
environment. CAA can be generated during water disinfection
processes and during metabolic detoxification of industrial
solvents such as trichloroethylene.
Incompatibilities
Compounds of the carboxyl group react
with all bases, both inorganic and organic (i.e., amines)
releasing substantial heat, water, and a salt that may be
harmful. Incompatible with arsenic compounds (releases
hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, sulfides (releasing
heat, toxic, and possibly flammable gases), thiosulfates,
and dithionites (releasing hydrogen sulfate and oxides of
sulfur). The solution in water is a strong acid. Contact with
strong oxidizers, strong bases; and strong reducing agents
such as hydrides can cause violent reactions. Chloracetic
acid decomposes on heating, producing toxic and corrosive
hydrogen chloride, phosgene, and carbon monoxide gases.
Attacks metals in the presence of moisture.
Check Digit Verification of cas no
The CAS Registry Mumber 79-11-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 9 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 79-11:
(4*7)+(3*9)+(2*1)+(1*1)=58
58 % 10 = 8
So 79-11-8 is a valid CAS Registry Number.
InChI:InChI=1/C2H3ClO2/c3-1-2(4)5/h1H2,(H,4,5)/p-1
79-11-8Relevant articles and documents
Study on Gas-phase mechanism of chloroacetic acid synthesis by catalysis and chlorination of acetic acid
Xue, Jian-Wei,Zhang, Jian-Peng,Wu, Bo,Li, Fu-Xiang,Lv, Zhi-Ping
, p. 475 - 480 (2014)
The process of acetic acid catalysis and chlorination for synthesizing chloroacetic acid can exist in not only gas phase but also liquid phase. In this paper, the gas-phase reaction mechanism of the synthesis of chloroacetic acid was studied. Due to the high concentration of acetic acid and the better reaction mass transfer in the liquid-phase reaction, the generation amount of the dichloroacetic acid was higher than that in the gas-phase reaction. Under the solution distillation, the concentration of acetyl chloride, whose boiling point is very low, was very high in the gas phase, sometimes even up to 99 %, which would cause the acetyl chloride to escape rapidly with the hydrogen chloride exhaust, so that the reaction slowed down. Therefore, series reactions occured easily in the gas-phase reaction causing the amount of the dichloroacetic acid to increase.
Microwave synthesis of chloroacetic acid with various cocatalysts in acetic anhydride catalyzing method
Song, Guo-Qiang,Wang, Li-Sheng,Li, Fu-Xiang
, p. 3923 - 3926 (2014)
In this paper, we introduce a method of synthesizing chloroacetic acid using acetyl chloride as catalyst and anhydrous ferric chloride, ferric chloride hexahydrate, zinc chloride and concentrated sulfuric acid (98 % H 2SO4) as cocatalysts respectively with a variable frequency microwave oven as heater. From investigating the influences of cocatalysts in reaction, we draw a optimal condition that the yield and selectivity of chloroacetic acid are 98.11 and 98.58 % respectively when adding 0.4 g FeCl3 in mixture after reacting 3.5 h and in comparable with the corresponding percentages, 96.9 and 96.87 %, with 0.7 g ZnCl2 adding, the adding amount of 1.5 g 98 % H2SO4 result in a little lower percentages of 95.71 and 95.61 % correspondingly. We have speculated the cocatalytic mechanisms in chlorination.
Reductive dechlorination of trichloroacetic acid (TCAA) by electrochemical process over Pd-In/Al2O3 catalyst
Liu, Yanzhen,Mao, Ran,Tong, Yating,Lan, Huachun,Zhang, Gong,Liu, Huijuan,Qu, Jiuhui
, p. 13 - 21 (2017)
Electrochemical reduction treatment was found to be a promising method for dechlorination of Trichloroacetic acid (TCAA), and acceleration of electron transfer or enhancement of the concentration of atomic H* significantly improve the electrochemical dechlorination process. Bimetallic Pd-based catalysts have the unique property of simultaneously catalyzing the production of atomic H* and reducing target pollutants. Herein, a bimetallic Pd–In electrocatalyst with atomic ratio of 1:1 was evenly deposited on an Al2O3 substrate, and the bimetallic Pd-In structure was confirmed via X-ray photoelectron spectroscopy (XPS). Electrochemical removal of trichloroacetic acid (TCAA) by the Pd-In/Al2O3 catalyst was performed in a three-dimensional reactor. 94% of TCAA with the initial concentration of 500?μg?L?1 could be degraded within 30?min under a relatively low current density (0.9?mA?cm?2). In contrast to the presence of refractory intermediates (dichloroacetic acid (DCAA)) found in the Pd/Al2O3 system, TCAA could be thoroughly reduced to monochloroacetic acid (MCAA) using Pd-In/Al2O3 catalysts. According to scavenger experiments, an electron transfer process and atomic H* formation function both existed in the TCAA reduction process, and the enhanced indirect atomic H* reduction process (confirmed by ESR signals) played a chief role in the TCAA removal. Moreover, the synergistic effects of Pd and In were proven to be able to enhance both direct electron transfer and indirect atomic H* formation, indicating a promising prospect for bimetallic electrochemical reduction treatment.
Reaction of Lithium Acylate α-Carbanions with Carbon Tetrachloride
Zorin,Zaynashev,Zorin
, p. 42 - 46 (2019/04/27)
Metalation of acetic, butanoic, or 2-methylpropanoic acid with lithium diisopropylamide in tetrahydrofuran under argon gave the corresponding lithium acylate α-carbanions which reacted with carbon tetrachloride at 20–25°C for 2 h to afford butanedioic acid or its 2,3-diethyl and 2,2,3,3-tetramethyl derivatives, as well as the corresponding α-chlorocarboxylic acids and chloroform. A radical mechanism was proposed for the formation of dicarboxylic and α-chlorocarboxylic acids.
Catalytic Oxidative Cracking of Benzene Rings in Water
Shimoyama, Yoshihiro,Ishizuka, Tomoya,Kotani, Hiroaki,Kojima, Takahiko
, p. 671 - 678 (2019/01/08)
Efficient degradation of harmful benzene rings in water is indispensable for achieving a clean water environment. We report herein unprecedented catalytic oxidative benzene cracking (OBC) in water using a ruthenium(II)-aqua complex having an N-heterocyclic carbene ligand as a catalyst and a cerium(IV) salt as a sacrificial oxidant under mild conditions. The OBC reactions produced carboxylic acids such as formic acid, which can be converted to dihydrogen directly from the OBC solution using a rhodium(III) catalyst with adjustment of the solution pH to 3.3. The OBC reactions can be applied to monosubstituted benzene derivatives such as ethylbenzene, chlorobenzene, and benzoic acid. Initial rates of the OBC reactions showed a linear relationship in the Hammett plot with a negative slope, indicating the electrophilicity of a Ru(III)-oxyl complex as the reactive species in the catalytic OBC reaction. Also, we discuss a plausible mechanism of the catalytic OBC reactions based on the kinetic analysis and the product stoichiometry for the OBC reaction of nonvolatile sodium m-xylene sulfonate. The addition of an electrophilic radical to the aromatic ring to form arene oxide/oxepin is proposed as the initial step of the OBC reaction.