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An important chemical product.
Colorless; irritating odor and sour corrosive liquids.
More than 1000 BC, humans had begun to use acetate bacteria for wine fermentation to make vinegar.
CAS: 55896-93-0
MF: C4H7ClO4S
MW: 186.61
EINECS: 818-924-5
Synonyms
VOLATILE ACIDS STANDARD;VINEGAR ACID;TCLP EXTRACTION FLUID 2;RARECHEM AL BE 0544;ACETIC ACID R;ACETIC ACID CAS 55896-93-0;(2S)-2-amino-3-{4-[(4-methylbenzenesulfonyl)oxy]phenyl}propanoic acid;ACIDUM ACETICUM
Ethanolic acid has a acetic acid content of 2% to 12%.
In 1911, Germany used acetaldehyde oxidation method to create the world's first synthetic acetic acid plant.
In 1966 Monsanto, the United States developed the methanol low-pressure carbonylation process (built in 1970), which has become the main method of synthesizing acetic acid, accounting for more than 50% of the total output.
In 1999, the world's Ethanolic acid production was about 5 million tons.
China began producing acetic acid in the 1950s, producing about 60,000 tons in the 1960s and increasing to 861,300 tons in 2001.
The vast majority of Ethanolic acid has been converted into derivatives for application.
40% to 50% has been used for the production of vinyl acetate in China and the United States.
Both acetate ester and cellulose acetate accounts for 10% to 12%; solvent application accounts for 20% to 25%.
Ethanolic acid has anti-bacterial and fungal infections. 2% to 5% solution has a bactericidal effect on Haemophilus and Pseudomonas.
Ethanolic acid also has effect on Candida, Aspergillus and Trichomonas.
Ethanolic acid also has spermicidal effect.
Various concentrations can be used for the treatment of various skins shallow bacterial or fungal infections, but also for vaginal trichomoniasis, burn wound infection, prevention of flu or flu and contraception.
Ethanolic acid is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH (also written as CH3CO2H, C2H4O2, or HC2H3O2).
Ethanolic acid is the active component of vinegar.
Historically, Ethanolic acid was produced from the third century BC, making acetic acid likely the first acid to be produced in large quantities.
Ethanolic acid is the second simplest carboxylic acid (after formic acid).
Ethanolic acid is an important chemical reagent and industrial chemical across various fields, used primarily in the production of cellulose acetate for photographic film, polyvinyl acetate for wood glue, and synthetic fibres and fabrics.
In households, diluted acetic acid is often used in descaling agents.
In the food industry, acetic acid is controlled by the food additive code E260 as an acidity regulator and as a condiment.
In biochemistry, the acetyl group, derived from acetic acid, is fundamental to all forms of life.
When bound to coenzyme A, Ethanolic acid is central to the metabolism of carbohydrates and fats.
The global demand for Ethanolic acid as of 2023 is about 17.88 million metric tonnes per year (t/a).
Most of the world's Ethanolic acid is produced via the carbonylation of methanol.
Ethanolic acid's production and subsequent industrial use poses health hazards to workers, including incidental skin damage and chronic respiratory injuries from inhalation.
Ethanolic acid, CH3COOH, also known as ethanoic acid, is an organic acid which has a pungent smell.
Ethanolic acid is a weak acid, in that it is only partially dissociated in an aqueous solution.
Pure, Ethanolic acid is hygroscopic (absorbs moisture from the air) and freezes at 16.5C to a colourless crystalline solid.
Ethanolic acid Chemical Properties
Melting point: 16.2 °C(lit.)
Boiling point: 117-118 °C(lit.)
Density: 1.049 g/mL at 25 °C(lit.)
Vapor density: 2.07 (vs air)
Vapor pressure: 11.4 mm Hg ( 20 °C)
Refractive index: n20/D 1.371(lit.)
Fp: 104 °F
Storage temp.: Inert atmosphere,2-8°C
Solubility: Benzene, Chloroform
pka: 4.76(at 25℃)
Form: Liquid
Color: Colorless
Odor: Characteristic vinegar, pungent; vinegar-like; sharp.
Relative polarity: 0.648
Exposure limits ACGIH: TWA 10 ppm; STEL 15 ppm
OSHA: TWA 10 ppm(25 mg/m3)
NIOSH: IDLH 50 ppm; TWA 10 ppm(25 mg/m3); STEL 15 ppm(37 mg/m3)
Stability: Moisture Sensitive, Hygroscopic
CAS DataBase Reference: 55896-93-0(CAS DataBase Reference)
Acidity
The hydrogen centre in the carboxyl group (−COOH) in carboxylic acids such as Ethanolic acid can separate from the molecule by ionization:
CH3COOH ⇌ CH3CO−2 + H+
Because of this release of the proton (H+), Ethanolic acid has acidic character.
Ethanolic acid is a weak monoprotic acid.
In aqueous solution, Ethanolic acid has a pKa value of 4.76.
Ethanolic acid's conjugate base is acetate (CH3COO−).
A 1.0 M solution (about the concentration of domestic vinegar) has a pH of 2.4, indicating that merely 0.4% of the acetic acid molecules are dissociated.
Structure
In solid Ethanolic acid, the molecules form chains of individual molecules interconnected by hydrogen bonds.
In the vapour phase at 120 °C (248 °F), dimers can be detected.
Dimers also occur in the liquid phase in dilute solutions with non-hydrogen-bonding solvents, and to a certain extent in pure acetic acid, but are disrupted by hydrogen-bonding solvents.
The dissociation enthalpy of the dimer is estimated at 65.0–66.0 kJ/mol, and the dissociation entropy at 154–157 J mol−1 K−1.
Other carboxylic acids engage in similar intermolecular hydrogen bonding interactions.
Solvent properties
Ethanolic acid is a hydrophilic (polar) protic solvent, similar to ethanol and water.
With a relative static permittivity (dielectric constant) of 6.2, Ethanolic acid dissolves not only polar compounds such as inorganic salts and sugars, but also non-polar compounds such as oils as well as polar solutes.
Ethanolic acid is miscible with polar and non-polar solvents such as water, chloroform, and hexane.
With higher alkanes (starting with octane), acetic acid is not miscible at all compositions, and solubility of acetic acid in alkanes declines with longer n-alkanes.
The solvent and miscibility properties of acetic acid make Ethanolic acid a useful industrial chemical, for example, as a solvent in the production of dimethyl terephthalate.
Biochemistry
At physiological pHs, Ethanolic acid is usually fully ionized to acetate in aqueous solution.
The acetyl group, formally derived from acetic acid, is fundamental to all forms of life. Typically, Ethanolic acid is bound to coenzyme A by acetyl-CoA synthetase enzymes, where Ethanolic acid is central to the metabolism of carbohydrates and fats.
Unlike longer-chain carboxylic acids (the fatty acids), acetic acid does not occur in natural triglycerides.
Most of the acetate generated in cells for use in acetyl-CoA is synthesized directly from ethanol or pyruvate.
However, the artificial triglyceride triacetin (glycerine triacetate) is a common food additive and is found in cosmetics and topical medicines; this additive is metabolized to glycerol and acetic acid in the body.
Ethanolic acid is produced and excreted by acetic acid bacteria, notably the genus Acetobacter and Clostridium acetobutylicum.
These bacteria are found universally in foodstuffs, water, and soil, and acetic acid is produced naturally as fruits and other foods spoil.
Ethanolic acid is also a component of the vaginal lubrication of humans and other primates, where it appears to serve as a mild antibacterial agent.
Uses
Used in the manufacture of vinyl acetate monomer (VAM), this accounts for one-third of acetic acid consumption.
As a food additive (condiment, ingredient) or as a preservative, Ethanolic acid is found in Vinegar solutions, usually between 3-9% in concentration.
In the production of various synthetic materials, Ethanolic acid is a precursor and solvent for various glues and plastics such as polyvinyl acetate, cellulose acetate, nylon and dimethyl terephthalate.
As an agent widely used in the manufacture of organic compounds which are constituent parts of food ingredients, various dye stuffs and perfumes, Rayon fibre, synthetic fibres and textiles, inks and dyes, soft drinks bottles, rubbers and plactics, and pesticides.
In waste water treatment, Ethanolic acid may be dosed to correct highly alkaline pH from where caustic soda has been dosed to the fluid stream.
For testing blood in clinical laboratory
For the treatment of outer ear infections from the growth of fungus and bacteria
Ethanolic acid is an acid produced chemically from the conversion of alcohol to acetaldehyde to acetic acid.
Ethanolic acid is the principal component of vinegar which contains not less than 4 g of acetic acid in 100 cm3 at 20°c.
The approved salts include sodium acetate, calcium acetate, sodium diacetate, and calcium diacetate.
Ethanolic acid is used as a preservative, acidulant, and flavoring agent in catsup, mayonnaise, and pickles.
Ethanolic acid can be used in conjunction with leavening agents to release carbon dioxide from sodium bicarbonate.
Colorless liquid prepared by the distillation of wood or the oxidation of dilute ethyl alcohol.
Ethanolic acid has a very pungent smell, and the vapors are flammable.
When obtained in full strength (99 percent), it congeals as an ice-like solid at 16.7°C.
For this reason the term glacial is also used to describe this acid.
Ethanolic acid is soluble in water, alcohol, ether, chloroform, and gelatin.
Acetic acid was used as a restrainer for the physical development of calotypes, Niépceotypes, and collodion plates.
Photographers also used Ethanolic acid to retard non-image reduction of these processes by adding it to the silver nitrate solution.
Ethanolic acid is used as a stop bath and as a solvent for gelatin.
Ethanolic acid is a chemical reagent for the production of chemical compounds.
The largest single use of Ethanolic acid is in the production of vinyl acetate monomer, closely followed by acetic anhydride and ester production.
The volume of Ethanolic acid used in vinegar is comparatively small.
Vinyl acetate monomer
The primary use of Ethanolic acid is the production of vinyl acetate monomer (VAM).
In 2008, this application was estimated to consume a third of the world's production of acetic acid.
The reaction consists of ethylene and Ethanolic acid with oxygen over a palladium catalyst, conducted in the gas phase.
2 H3C−COOH + 2 C2H4 + O2 → 2 H3C−CO−O−CH=CH2 + 2 H2O
Ethanolic acid can be polymerized to polyvinyl acetate or other polymers, which are components in paints and adhesives.
Ester production
The major esters of Ethanolic acid are commonly used as solvents for inks, paints and coatings.
The esters include ethyl acetate, n-butyl acetate, isobutyl acetate, and propyl acetate.
They are typically produced by catalyzed reaction from acetic acid and the corresponding alcohol:
CH3COO−H + HO−R → CH3COO−R + H2O, R = general alkyl group
For example, acetic acid and ethanol gives ethyl acetate and water.
CH3COO−H + HO−CH2CH3 → CH3COO−CH2CH3 + H2O
Most acetate esters, however, are produced from acetaldehyde using the Tishchenko reaction.
In addition, ether acetates are used as solvents for nitrocellulose, acrylic lacquers, varnish removers, and wood stains.
First, glycol monoethers are produced from ethylene oxide or propylene oxide with alcohol, which are then esterified with acetic acid.
The three major products are ethylene glycol monoethyl ether acetate (EEA), ethylene glycol monobutyl ether acetate (EBA), and propylene glycol monomethyl ether acetate (PMA, more commonly known as PGMEA in semiconductor manufacturing processes, where it is used as a resist solvent).
This application consumes about 15% to 20% of worldwide acetic acid.
Ether acetates, for example EEA, have been shown to be harmful to human reproduction.
Medical use
Ethanolic acid injection into a tumor has been used to treat cancer since the 1800s.
Ethanolic acid is used as part of cervical cancer screening in many areas in the developing world.
Ethanolic acid is applied to the cervix and if an area of white appears after about a minute the test is positive.
Ethanolic acid is an effective antiseptic when used as a 1% solution, with broad spectrum of activity against streptococci, staphylococci, pseudomonas, enterococci and others.
Ethanolic acid may be used to treat skin infections caused by pseudomonas strains resistant to typical antibiotics.
While diluted Ethanolic acid is used in iontophoresis, no high quality evidence supports this treatment for rotator cuff disease.
As a treatment for otitis externa, Ethanolic acid is on the World Health Organization's List of Essential Medicines.
Foods
Ethanolic acid has 349 kcal (1,460 kJ) per 100 g.
Vinegar is typically no less than 4% acetic acid by mass.
Legal limits on acetic acid content vary by jurisdiction.
Ethanolic acid is used directly as a condiment, and in the pickling of vegetables and other foods.
Table vinegar tends to be more diluted (4% to 8% acetic acid), while commercial food pickling employs solutions that are more concentrated.
The proportion of acetic acid used worldwide as Ethanolic acid is not as large as industrial uses, but Ethanolic acid is by far the oldest and best-known application.
Pharmacological effects
Ethanolic acid has anti-bacterial and fungal infections.
5% solution has a bactericidal effect on Haemophilus and Pseudomonas.
0.5% ~ 2% solution has antiseptic effect on lavage wound sterilization; different concentrations of acetate can be used to treat various skin shallow fungal infections; the product has bactericidal efficacy.
Production
Using methanol as a raw material, Ethanolic acid is produced by low-pressure carbonylation.
Methanol carbonylation is the main method for production of acetic acid.
There are also many other synthetic ways industrially, which are listed as follows:
Acetaldehyde oxidation
Using acetaldehyde as a raw material, adopt liquid phase oxidation with air at 70° C. and 1 MPa, in order to prevent the occurrence of explosion caused by peroxide, cobalt acetate or manganese acetate could be used as a peroxide decomposer under an exothermic reaction.
Cool and control the reaction temperature at 70 °C, Ethanolic acid can be obtained by the following concentration and distillation.
Celanese
With butane as raw material, manganese acetate is used as a catalyst at 150-250°C and 6MPa to oxidize with air to obtain acetic acid.
BP Chemical
Using oils containing more than 40% C4-C8 aliphatic hydrocarbons as a raw material, adopt the liquid phase oxidation in the presence of manganese acetate or cobalt acetate at a temperature of 160-170° C. and 4.0 MPa, and yields of acetic acid, formic acid, propionic acid, and butyric acid are generated.
Operation of distillation and refining are followed to get acetic acid.
Ethanolic acid can be prepared using ethylene as raw material, palladium as catalyst and vanadium as co-catalyst under oxidation reaction.
Biotechnological Production
Ethanolic acid is produced for beverage, food, and feed applications almost entirely using the traditional vinegar process.
First, ethanol is produced by fermentation with Saccharomyces cerevisiae in the absence of oxygen.
Then, Ethanolic acid is generated from ethanol by acetic acid bacteria, such as Acetobacter aceti, Acetobacter pasteurianus, or Gluconacetobacter europaeus, under aerobic conditions.
Different substrates, such as malt, fruits, and sugarcane, are used for Ethanolic acid production.
Today, processes with two stages (e.g. two-tank cycle fermentation or two-stage submerged fermentation) are generally employed on an industrial scale.
In a first step, biomass is produced in parallel to the acetic acid production.
In the second part of the process, mainly acidification takes place.
Ethanolic acid concentrations up to 200 g.L-1 can be achieved.
The vinegar process has been well studied over many decades.
However, there are still attempts to enhance vinegar production, especially regarding productivity and cost minimization through alternative substrates, new process concepts (e.g. immobilized cells or mixed cultures of yeasts and acetic acid bacteria, and optimized acetic acid bacteria.
Ethanolic acid can be produced under anaerobic conditions by some microorganisms such as Clostridium thermoaceticum.
In free-cell batch fermentations, acetate concentrations of 50 g.L-1 were reached in less than 192 h.
Ethanolic acid concentrations of 83–100 g.L-1, a yield of 0.74–0.80 g acetic acid per gram glucose, and a productivity of 0.60–0.85 g.L-1.h-1 were observed under optimized conditions in a cell-recovered fed-batch process with pH-control using glucose as substrate.
