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64-19-7

Basic Information
CAS No.: 64-19-7
Name: Acetic acid glacial
Article Data: 3647
Cas Database
Molecular Structure:
Molecular Structure of 64-19-7 (Acetic acid glacial)
Formula: C2H4O2
Molecular Weight: 60.0526
Synonyms: Acetic acid, diluted;Acetic acid, aqueous solution;Ethanoic acid;Ethanoic acid monomer;Ethylic acid;Glacial acetic acid;Methanecarboxylic acid;Vinegar acid;Glacial acetic acid (JP14);Acetic acid;
EINECS: 200-580-7
Density: 1.069 g/cm3
Melting Point: 16-16.5 °C
Boiling Point: 117.065 °C at 760 mmHg
Flash Point: 40 °C
Solubility: Miscible with water
Appearance: Clear colorless liquid
Hazard Symbols: CorrosiveC,IrritantXi
Risk Codes: 34-42-35-10-36/38
Safety: 26-36/37/39-45-23-24/25
Transport Information: UN 1792 8/PG 2
PSA: 37.30000
LogP: 0.09090
Synthetic route
56-81-5

glycerol

A

64-19-7

acetic acid

B

107-02-8

acrolein

Conditions
ConditionsYield
With offretite impregnated with 4.7 wt.percent vanadium In water at 320℃; under 760.051 Torr; for 2h; Flow reactor;A n/a
B 24.2%
With Cs-doped silicotungstic acid supported on α-Al2O3 at 300℃; for 1.5h;
With mesoporous siliconiobium phosphate In water at 250℃; under 760.051 Torr; for 4h; Reagent/catalyst; Inert atmosphere;
67-56-1

methanol

201230-82-2

carbon monoxide

A

79-20-9

acetic acid methyl ester

B

64-19-7

acetic acid

Conditions
ConditionsYield
With methyl iodide; rhodium(III) chloride In 3-butyl-1-methylimidazolium bis(trifluoromethylsulfonyl) amide; water at 130℃; under 22502.3 Torr; for 2h; Compressed gas;A 0.5%
B 99.5%
With methyl iodide; rhodium(III) chloride In 3-butyl-1-methylimidazolium bis(trifluoromethylsulfonyl) amide; water at 130℃; under 22502.3 Torr; for 2h; Compressed gas;A 3.9%
B 96.1%
With methyl iodide; rhodium(III) chloride In 3-butyl-1-methylimidazolium bis(trifluoromethylsulfonyl) amide at 130℃; under 22502.3 Torr; for 2h; Compressed gas;A 3%
B 96%
56-81-5

glycerol

A

75-07-0

acetaldehyde

B

64-19-7

acetic acid

C

79-10-7

acrylic acid

D

107-02-8

acrolein

Conditions
ConditionsYield
With zeolite-β impregnated with 4.2 wt.% vanadium In water at 320℃; under 760.051 Torr; for 2h; Reagent/catalyst; Flow reactor;A n/a
B n/a
C 6.1%
D 52.8%
With water; oxygen at 290℃; for 1.5h; Reagent/catalyst; Temperature; Inert atmosphere; Flow reactor;A n/a
B n/a
C 51 %Chromat.
D n/a
With oxygen In water at 266℃; under 760.051 Torr; Temperature; Flow reactor;A n/a
B n/a
C 32.5 %Chromat.
D 23.6 %Chromat.
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Specification

Acetic acid, also known as glacial acetic acid, is clear colorless liquid with distinctive sour taste and cpungent smell. It is one of the simplest carboxylic acids which is the main component of vinegar. It is completely soluble in water, ethanol, ether, carbon tetrachloride and other common organic solvents, insoluble in carbon disulfide, and more than C12 aliphatic hydrocarbons. What's more, acetic acid can dissolve most resins and essential oils. It has a relatively high freezing point of 16.7 Degrees Celsius and this should be borne in mind when storing the material. Acetic acid is an important chemical reagent and industrial chemical which is mainly used in the production of cellulose acetate for photographic film and polyvinyl acetate for wood glue, as well as synthetic fibres and fabrics. 

Physical properties about Acetic acid are: (1)ACD/LogP: -0.322; (2)ACD/LogD (pH 5.5): -1.11; (3)ACD/LogD (pH 7.4): -2.90; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 2.61; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)Index of Refraction: 1.376 ; (11)Molar Refractivity: 12.879 cm3; (12)Molar Volume: 56.175 cm3; (13)Polarizability: 5.106 10-24cm3; (14)Surface Tension: 31.9169998168945 dyne/cm; (15)Density: 1.069 g/cm3; (16)Flash Point: 40 °C; (17)Enthalpy of Vaporization: 23.7 kJ/mol; (18)Boiling Point: 117.065 °C at 760 mmHg; (19)Vapour Pressure: 13.8739995956421 mmHg at 25°C

Preparation of Acetic acid: Acetic acid is widely distributed in nature. For example: In fruit or vegetable oils, it mainly exists with the form of esters; In animal tissues, faeces and blood, it exists with the form of free acid. Many microbes can convert different organic matter to acetic acid by fermentation. The main methods of industrial production of acetic acid are acetaldehyde oxidation, methanol low-pressure carbonylation, methanol high-pressure carbonylation, and alkanes liquid-phase oxidation.

1. Acetaldehyde oxidation: Use acetaldehyde as raw material and oxygen or air as the oxidant. Then go through liquid-phase oxidation in the presence of manganese acetate at 50-80 °C and 0.6-1.0 MPa in bubble tower reactor.

2. Methanol low-pressure carbonylation: Use catalyst system consisting of rhodium carbonyl compounds and iodide. The methanol reacts with carbon monoxide in water-acetic acid medium at about 175 °C and lower than 3.0MPa to obtain acetic acid. As the high activity and selectivity of catalyst, the side effect is very few. After a series of treatment, the end-product acetic acid can be obtained by distillation and purified from crude product. The yield is more than 99% on the calculation of methanol. This method has following advantages: cheap materials, mitigatory operating conditions, high productivity, good product quality, and simple process. Currently, it is the most advanced method to produce acetic acid. However, reaction media is serious corrosive, so it needs for expensive special steel.

3. Methanol high-pressure carbonylation: Methanol and carbon monoxide reacts in acetic acid aqueous solution in the presence of catalyst cobalt carbonyl and cocatalyst methyl iodide at 250 °C and 70MPa. After separation, acetic acid can be obtained. The yield can reach 90% on the calculation of methanol.

4. Alkanes liquid-phase oxidation: Use butane as raw material, acetic acid as solvent, and air as oxidant. Then go through liquid-phase oxidation in the presence of catalyst acetic acid cobalt at 170-180 °C and 5.5MPa. You can also use liquefied petroleum gas or light oil as raw material. The raw material of this method is cheaper, but it has long process, severe corrosion, and low yield.

In addition, acetic acid also can be obtained by ethylene.

acetic acid can be obtained by ethylene

Uses of Acetic acid:
1. Acetic acid is a popular product and one of the most important organic acids. It is mainly used for the production of ethyl acetate, chloroacetic acid, vinyl acetate, acetic anhydride, acetate, Cellulose acetate, etc. Polyvinyl acetate can be made into films and adhesives, and also the raw material for synthetic fibers. Cellulose acetate can produce rayon and filmstrip. The acetate formed by lower alcohol is an excellent solvent which is widely used in paint industry.

2. Acetic acid is usually used as acidity regulator used for complex seasonings, vinegar, can, jelly and cheese, which is properly used according to production needs.

3. Acetic acid is used as analysis reagent, non-aqueous titration solvent, and chromatography reagent. It is an excellent polar protic solvent which is frequently used for recrystallization to purify organic compounds. What's more, glacial acetic acid is used in analytical chemistry for the estimation of weakly alkaline substances such as organic amides.

4. Acetic acid is an important organic chemical raw material which can produce a variety of organic chemical products. It also can be used in pharmaceutical and dyes industry for a variety of pharmaceuticals and industrial dyes. There are many organic or inorganic salts produced from acetic acid. Such as: Sodium acetate is used in the textile industry and as a food preservative (E262); Copper(II) acetate is used as a pigment and a fungicide; Silver acetate is used as a pesticide; Palladium(II) acetate is used as a catalyst for organic coupling reactions such as the Heck reaction; Aluminium acetate and iron(II) acetate is used as mordants for dyes.

When you are using this chemical, please be cautious about it as the following: Acetic acid may cause severe burns and sensitization by inhalation. Please do not breathe vapour. And it is irritating to eyes and skin. These burns or blisters may not appear until hours after exposure. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. Moreover, you should wear suitable protective clothing, gloves and eye/face protection to avoid contact with skin and eyes. In case of accident or if you feel unwell, please seek medical advice immediately (show the label whenever possible.)

You can still convert the following datas into molecular structure:
1. Smiles:C(=O)(C)O
2. InChI:InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo rectal 281uL/kg (0.281mL/kg) GASTROINTESTINAL: ALTERATION IN GASTRIC SECRETION

LIVER: LIVER FUNCTION TESTS IMPAIRED

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Journal of Toxicology, Clinical Toxicology. Vol. 82, Pg. 333, 1994.
human TCLo inhalation 816ppm/3M (816ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
AMA Archives of Industrial Health. Vol. 21, Pg. 28, 1960.
human TDLo oral 1470ug/kg (1.47mg/kg) GASTROINTESTINAL: CHANGE IN STRUCTURE OR FUNCTION OF ESOPHAGUS

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE
American Industrial Hygiene Association Journal. Vol. 33, Pg. 624, 1972.
man LDLo unreported 308mg/kg (308mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LC50 inhalation 5620ppm/1H (5620ppm) SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BLOOD: OTHER CHANGES
Medicina del Lavoro. Industrial Medicine. Vol. 48, Pg. 559, 1957.
mouse LD50 intravenous 525mg/kg (525mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Acta Pharmacologica et Toxicologica. Vol. 18, Pg. 141, 1961.
rabbit LD50 skin 1060uL/kg (1.06mL/kg)   Union Carbide Data Sheet. Vol. 8/7/1963,
rabbit LDLo oral 600mg/kg (600mg/kg)   Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 83, Pg. 136, 1920.
rabbit LDLo rectal 600mg/kg (600mg/kg)   Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 83, Pg. 136, 1920.
rabbit LDLo subcutaneous 600mg/kg (600mg/kg)   Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 83, Pg. 136, 1920.
rat LCLo inhalation 16000ppm/4H (16000ppm)   American Industrial Hygiene Association Quarterly. Vol. 17, Pg. 129, 1956.
rat LD50 oral 3310mg/kg (3310mg/kg)   Delaware State Medical Journal. Vol. 31, Pg. 276, 1959.