Glycolic Acid

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Template:Chembox E numberTemplate:Chembox SolubilityInWater
Glycolic acid
IUPAC name 2-Hydroxyethanoic acid
Other names Dicarbonous acid

glycolic acid,
hydroxyacetic acid

Identifiers
3D model (JSmol)
ChEBI
ChEMBL
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KEGG
RTECS number MC5250000
UNII
Properties
C2H4O3
Molar mass 76.05 g/mol
Appearance white, powdery solid
Density 1.49 g/cm3[1]
Melting point
Boiling point
Solubility in other solvents alcohols, acetone,
acetic acid and
ethyl acetate[2]
Acidity (pKa) 3.83
Hazards
Main hazards Corrosive (C)
R-phrases R22-R34
S-phrases S26-S36/37/39-S45
Flash point {{{value}}}
Related compounds
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Glycolic acid (or hydroxyacetic acid); chemical formula C2H4O3 (also written as HOCH2COOH), is the smallest α-hydroxy acid (AHA). This colorless, odorless, and hygroscopic crystalline solid is highly soluble in water. It is used in various skin-care products. Glycolic acid is found in some sugar-crops. A glycolate is a salt or ester of glycolic acid.

Preparation

There are multiple routes of synthesis of glycolic acid that are practiced today. The majority of the world's supply of glycolic acid is made in a catalyzed reaction of formaldehyde with synthesis gas (carbonylation of formaldehyde) is a particularly economical preparative route.[4]

It is also prepared by the reaction of chloroacetic acid with sodium hydroxide followed by re-acidification.

In this way, a few million kilograms are produced annually. Other methods, not apparently in use, include hydrogenation of oxalic acid with nascent hydrogen and the hydrolysis of the cyanohydrin derived from formaldehyde.[5] Some of today's glycolic acids are formic acid-free. Glycolic acid can be isolated from natural sources, such as sugarcane, sugar beets, pineapple, cantaloupe, and unripe grapes.[6]

Glycolic acid can also be prepared using an enzymatic biochemical process which produces fewer impurities compared to traditional chemical synthesis, requires less energy in production and produces less co-product.[7] Each route can be evaluated for its relative costs and benefits.

Uses

Glycolic acid is used in the textile industry as a dyeing and tanning agent,[8] in food processing as a flavoring agent and as a preservative, and in the pharmaceutical industry as a skin care agent. It is also used in adhesives and plastics.[9] Glycolic acid is often included into emulsion polymers, solvents and additives for ink and paint in order to improve flow properties and impart gloss. It is used in surface treatment products that increase the coefficient of friction on tile flooring.

Due to its excellent capability to penetrate skin, glycolic acid finds applications in skin care products, most often as a chemical peel performed by a dermatologist, plastic surgeon or licensed aesthetician in concentrations of 20 to 70% or at-home kits in lower concentrations between 10 and 20%. In addition to concentration, pH also plays a large part in determining the potency of glycolic acid in solution. Physician-strength peels can have a pH as low as 0.6 (strong enough to completely keratolyze the epidermis), while acidities for home peels can be as high as 2.5. Glycolic acid is used to improve the skin's appearance and texture. It may reduce wrinkles, acne scarring, hyperpigmentation and improve many other skin conditions, including actinic keratosis, hyperkeratosis, and seborrheic keratosis[citation needed]. Once applied, glycolic acid reacts with the upper layer of the epidermis, weakening the binding properties of the lipids that hold the dead skin cells together. This allows the stratum corneum to be exfoliated, exposing live skin cells. Highly purified grades of glycolic acid are commercially available for personal care applications.

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 used as a monomer in the preparation of polyglycolic acid and other biocompatible copolymers (e.g. PLGA). From the commercial perspective, important derivatives include the methyl (CAS#[96-35-5) and ethyl (CAS# 623-50-7) esters which are readily distillable (b.p. 147-9 and 158–159 °C, respectively), unlike the parent acid. The butyl ester (b.p. 178–186 °C) is a component of some varnishes, being desirable because it is nonvolatile and good dissolving properties.[5]

Safety

Glycolic acid is a strong irritant depending on the pH levels.[10] Like ethylene glycol, it is metabolized to oxalic acid, which could make it dangerous if ingested.

References

  1. United States National Library of Medicine "Hydroxyacetic Acid" in TOXNET Hazardous Substances Data Bank (HSDB), citing Gerhartz, W. (exec ed.), Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA13 509.
  2. "DuPont Glycolic Acid Technical Information". Retrieved 2006-07-06.
  3. "Glycolic Acid MSDS". University of Akron. Retrieved 2006-09-18.
  4. D.J. Loder, Template:US Patent (1939).
  5. 5.0 5.1 Karlheinz Miltenberger "Hydroxycarboxylic Acids, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
  6. 3Dchem: Glycolic acid
  7. Glycolic Acid at CrossChem.net
  8. http://www2.dupont.com/Glycolic_Acid/en_US/uses_apps/industrial/ind_pgs/leather_tanning.html
  9. thefreedictionary.com
  10. "Glycolic Acid MSDS". ICSC:NENG1537 International Chemical Safety Cards (WHO/IPCS/ILO). CDC/NIOSH. Retrieved 2006-06-08.

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