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79-14-1

Basic Information
CAS No.: 79-14-1
Name: Glycolic acid
Article Data: 660
Cas Database
Molecular Structure:
Molecular Structure of 79-14-1 (Glycolic acid)
Formula: C2H4O3
Molecular Weight: 76.052
Synonyms: Aceticacid, hydroxy- (9CI);Glycolic acid (7CI,8CI);2-Hydroxyacetic acid;2-Hydroxyethanoic acid;GlyPure;GlyPure 70;GlyPure 99;Glycocide;Hydroxyaceticacid;Hydroxyethanoic acid;NSC 166;a-Hydroxyacetic acid;
EINECS: 201-180-5
Density: 1.416 g/cm3
Melting Point: 75-80 °C(lit.)
Boiling Point: 265.6 °C at 760 mmHg
Flash Point: 128.7 °C
Solubility: H2O: 0.1 g/mL, clear
Appearance: Light yellow to amber liquid
Hazard Symbols: CorrosiveC
Risk Codes: 34-22
Safety: 26-36/37/39-45-23
Transport Information: N/A
PSA: 57.53000
LogP: -0.93670
Synthetic route
141-46-8

Glycolaldehyde

79-14-1

glycolic Acid

Conditions
ConditionsYield
With sodium chlorite; dimethyl sulfoxide In aq. phosphate buffer at 0 - 20℃; pH=4;100%
With 5 % platinum on carbon In water at 80℃; under 7500.75 Torr; for 6h; Temperature; Time; Reagent/catalyst; Autoclave;78%
With oxygen In water at 180℃; under 3750.38 Torr; for 1h; Autoclave;50%

N-acetyl-N-nitrosoglycine

A

79-14-1

glycolic Acid

B

64-19-7

acetic acid

Conditions
ConditionsYield
With water at 25℃;A 100%
B 100%
With water-d2 at 25℃; Rate constant; Kinetics; half life; reactions of derivatives under var. conditions;A 100%
B 100%
96-35-5

glycolic acid methyl ester

79-14-1

glycolic Acid

Conditions
ConditionsYield
With water at 95 - 97℃; under 760.051 Torr; for 2h; Reactive distillation;100%
With water; Candida rugosa lipase In aq. phosphate buffer at 45℃; for 30h; pH=7.2; Enzymatic reaction;
With water In methanol at 100℃;
50-00-0

formaldehyd

201230-82-2

carbon monoxide

79-14-1

glycolic Acid

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; acetic acid at 140℃; under 13689.1 - 52476.2 Torr; for 4h; Catalytic behavior; Pressure; Temperature; Time; Reagent/catalyst; Concentration; Autoclave;99.9%
With trifluorormethanesulfonic acid; acetic acid at 140℃; under 13689.1 - 52476.2 Torr; for 4h; Catalytic behavior; Pressure; Temperature; Time; Reagent/catalyst; Concentration; Autoclave;99.9%
With trifluorormethanesulfonic acid; acetic acid at 140℃; under 13689.1 - 52476.2 Torr; for 4h; Catalytic behavior; Pressure; Temperature; Time; Reagent/catalyst; Concentration; Autoclave;99.9%
107-21-1

ethylene glycol

79-14-1

glycolic Acid

Conditions
ConditionsYield
Stage #1: ethylene glycol With Rh(OTf)(trop2NH)(PPh3); water; cyclohexanone; sodium hydroxide at 20℃; for 2h; Inert atmosphere;
Stage #2: With hydrogenchloride In water Inert atmosphere;
99%
Wird durch verschiedene Essigbakterien;
With ruthenium trichloride; N-Bromosuccinimide; perchloric acid; mercury(II) diacetate; acetic acid In water Thermodynamic data; Mechanism; Kinetics; ΔE(excit.), ΔS(excit.), ΔH(excit.), and ΔF(excit.);
35249-89-9

glycolic acid ammonium salt

79-14-1

glycolic Acid

Conditions
ConditionsYield
With water98%
With sulfuric acid In water; 4-methyl-2-pentanone; kerosene at 25 - 75℃; for 0.5 - 1h; pH=2 - 3; Purification / work up;
With sulfuric acid In water; toluene at 25 - 75℃; for 0.5h; pH=2 - 3; Purification / work up;
79-14-1

glycolic Acid

Conditions
ConditionsYield
With aluminum trihydroxide; water at 165℃; for 3h; Mechanism;92%
With water at 99.84℃; for 18h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Sealed tube; Green chemistry;91%
With alkali
107-16-4

glycolonitrile

79-14-1

glycolic Acid

Conditions
ConditionsYield
With sulfuric acid; water at 105 - 110℃; for 6h; Temperature;92%
With water; microbial enzyme at 40℃; for 12h; Product distribution / selectivity;10 - 99 %Chromat.
Stage #1: glycolonitrile With sulfuric acid In water for 2191.5h; pH=3;
Stage #2: With sodium hydroxide pH=7;
Stage #3: With water; microbial enzyme at 40℃; for 12h; Product distribution / selectivity;
99 %Chromat.
With nitrilase from Hoeflea phototrophica DFL-43; water In aq. phosphate buffer; dimethyl sulfoxide at 30℃; for 0.166667h; pH=8; Enzymatic reaction;
56-81-5

glycerol

A

79-14-1

glycolic Acid

B

473-81-4

glyceric acid

C

96-26-4

dihydroxyacetone

Conditions
ConditionsYield
With oxygen In water at 60℃; Catalytic behavior; Reagent/catalyst; Autoclave; chemoselective reaction;A 8.9%
B 89.9%
C 6.8%
With oxygen In water at 80℃; under 7500.75 Torr; for 2h; pH=6.7; Reagent/catalyst; Autoclave;
With oxygen In water at 60℃; under 3750.38 Torr; for 24h; Catalytic behavior; Kinetics; Reagent/catalyst; Time; High pressure;A 7.8 %Chromat.
B 55.4 %Chromat.
C 7.7 %Chromat.
30379-58-9

benzyl glycolate

79-14-1

glycolic Acid

Conditions
ConditionsYield
With hydrogen Hydrogenolysis;88%
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Chemistry

Product Name: Glycolic acid (CAS NO.79-14-1)

Molecular Formula: C2H4O3
Molecular Weight: 76.05g/mol
Mol File: 79-14-1.mol
EINECS: 201-180-5
Appearance: colourless crystalline solid
Melting Point: 75-80 °C(lit.)
Boiling point: 265.6 °C at 760 mmHg
Flash Point: 128.7 °C
Density: 1.416 g/cm3
Refractive index: n20/D 1.424
Water Solubility: SOLUBLE
Sensitive: Hygroscopic
Stability: Stable. Incompatible with bases, oxidizing agents and reducing agents
Index of Refraction: 1.449 
Molar Refractivity: 14.41 cm
Molar Volume: 53.6 cm3 
Surface Tension: 61.3 dyne/cm
Enthalpy of Vaporization: 58.47 kJ/mol
Vapour Pressure: 0.00125 mmHg at 25°C
XLogP3-AA: -1.1
H-Bond Donor: 2
H-Bond Acceptor: 3
Structure Descriptors of Glycolic acid (CAS NO.79-14-1):
  IUPAC Name: 2-hydroxyacetic acid
  Canonical SMILES: C(C(=O)O)O
  InChI: InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5) 
  InChIKey: AEMRFAOFKBGASW-UHFFFAOYSA-N
Product Categories: Pharmaceutical Intermediates; Roxatidine Acetate; omega-Hydroxycarboxylic Acids; omega-Functional Alkanols, Carboxylic Acids, Amines & Halides; Hydroxycarboxylic Acids (for High-Performance Polymer Research); Functional Materials; Reagent for High-Performance Polymer Research; Cosmetic Ingredients & Chemicals

Uses

 Glycolic acid (CAS NO.79-14-1)  can be used in various skin-care products.Due to its excellent capability to penetrate skin.
Glycolic acid is also a useful intermediate for organic synthesis, in a range of reactions including: oxidation-reduction, esterification and long chain polymerization.    It is also used as a monomer in the preparation of polyglycolic acid and other biocompatible copolymers. Glycolic acid is often included into emulsion polymers, solvents and additives for ink and paint in order to improve flow properties and impart gloss.Other uses :in the textile industry as a dyeing and tanning agent, in food processing as a flavoring agent and as a preservative.

Production

  Glycolic acid (CAS NO.79-14-1)  is prepared by the reaction of chloroacetic acid with sodium hydroxide followed by re-acidification as follows:
ClCH2CO2H + NaOH → HOCH2CO2H + NaCl
In this way, a few million kilograms are produced annually. Other methods, include hydrogenation of oxalic acid and the hydrolysis of the cyanohydrin derived from formaldehyde.but not apparently in use. Glycolic acid can be isolated from natural sources, such as sugar beets, sugarcane, canteloupe, pineapple, and unripe grapes.
Glycolic acid,we can also  using an enzymatic biochemical process,compared to traditional chemical synthesis,it produces fewer impurities , requires less energy in production and produces less co-product.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intravenous 1gm/kg (1000mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 656, 1986.
guinea pig LD50 oral 1920mg/kg (1920mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 259, 1941.
rat LC50 inhalation 7100ug/m3/4H (7.1mg/m3) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Inhalation Toxicology. Vol. 9, Pg. 435, 1997.
rat LD50 oral 1950mg/kg (1950mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 259, 1941.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Moderately toxic by ingestion. A severe eye irritant. A skin and mucous membrane irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
Safety Information of Glycolic acid (CAS NO.79-14-1):
Hazard Codes: CCorrosive
Risk Statements: 34-22   
R34: Causes burns. 
R22: Harmful if swallowed.
Safety Statements: 26-36/37/39-45-23
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S23: Do not breathe vapour.
RIDADR: UN 3265 8/PG 3
WGK Germany: 1
RTECS: MC5250000
HazardClass: 8
PackingGroup: II

Specification

 Glycolic acid , its CAS NO. is 79-14-1, the synonyms are 2-Hydroxyacetic acid ; Acetic acid, hydroxy- ; EPA Pesticide Chemical Code 000101 ; Glycollic acid ; Hydroxyacetic acid ; Hydroxyethanoic acid ; Kyselina glykolova ; Kyselina hydroxyoctova .

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