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Glycolic acid

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Glycolic acid
Chemical structure of glycolic acid
Chemical structure of glycolic acid
Ball-and-stick model of glycolic acid
Ball-and-stick model of glycolic acid
Names
IUPAC name
2-Hydroxyethanoic acid
Other names
dicarbonous acid
glycolic acid
hydroxyacetic acid
hydroacetic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.073 Edit this at Wikidata
KEGG
RTECS number
  • MC5250000
UNII
  • InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5) checkY
    Key: AEMRFAOFKBGASW-UHFFFAOYSA-N checkY
  • InChI=1/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)
    Key: AEMRFAOFKBGASW-UHFFFAOYAR
  • C(C(=O)O)O
Properties
C2H4O3
Molar mass 76.05 g/mol
Appearance white, powdery solid
Density 1.49 g/cm3[1]
Melting point 75 °C (167 °F; 348 K)
Boiling point decomposes
70% solution
Solubility in other solvents alcohols, acetone,
acetic acid and
ethyl acetate[2]
Acidity (pKa) 3.83
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive (C)
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability (yellow): no hazard codeSpecial hazards (white): no code
3
1
Flash point 129 °C (264 °F; 402 K) [3]
Related compounds
Lactic acid
Related compounds
 Glycolaldehyde
Acetic acid
Glycerol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Glycolic acid (hydroacetic acid or hydroxyacetic acid); chemical formula C2H4O3 (also written as HOCH2CO2H), 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 or glycollate is a salt or ester of glycolic acid.

The name "glycolic acid" was coined in 1848 by the French chemist Auguste Laurent (1807–1853). He proposed that the amino acid glycine — which was then called glycocolle — might be the amine of a hypothetical acid, which he called "glycolic acid" (acide glycolique).[4] When the team of Strecker and Sokolov finally produced glycolic acid in 1851, they bestowed, on their acid, the name of Laurent's hypothetical acid.[5]

Preparation

Glycolic acid was first prepared in 1851 by the team of the German chemist Adolph Strecker (1822–1871) and the Russian chemist Nikolai Nikolaevich Sokolov (1826–1877), who produced it by a treating hippuric acid with nitric acid and nitrogen dioxide to form an ester of benzoic acid and glycolic acid (C6H5C(=O)OCH2COOH), which they called "benzoglycolic acid" (Benzoglycolsäure), also called benzoyl glycolic acid. They then boiled the ester for days with dilute sulfuric acid, thereby obtaining benzoic acid and glycolic acid (Glycolsäure).[6]

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), as this is a particularly economical preparative route.[7]

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, and the hydrolysis of the cyanohydrin derived from formaldehyde.[8] 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.[9]

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.[10] 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,[11] 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.[12] 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 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 has good dissolving properties.[8]

Safety

Glycolic acid is a strong irritant depending on the pH levels.[13] 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. ^ Laurent, Auguste (1848) "Sur les acides amidés et le sucre de gélatine" (On aminated acids and the sugar of gelatine [i.e., glycine]), Annales de Chimie et de Physique, 3rd series, 23 : 110–123. From p. 112: "Appelons ce dernier acide glycolique … " (Let us call the latter "glycolic acid" … )
  5. ^ (Socoloff and Strecker, 1851), p. 37.
  6. ^ Socoloff, Nicolaus and Strecker, Adolph (1851) "Untersuchung einiger aus der Hippursäure entstehenden Producte" (Investigation of some products that arise from hippuric acid), Annalen der Chemie und Pharmacie, 80 : 17–43. For their production of glycolic acid, see pp. 34–37. Note: Strecker and Sokolov's empirical formula for glycolic acid (viz, C4H4O6) was incorrect, because like many chemists at that time, they used the wrong atomic masses for carbon (6 instead of 12) and for oxygen (8 instead of 16).
  7. ^ D.J. Loder, U.S. patent 2,152,852 (1939).
  8. ^ a b Karlheinz Miltenberger "Hydroxycarboxylic Acids, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
  9. ^ 3Dchem: Glycolic acid
  10. ^ Glycolic Acid at CrossChem.net
  11. ^ http://www2.dupont.com/Glycolic_Acid/en_US/uses_apps/industrial/ind_pgs/leather_tanning.html
  12. ^ thefreedictionary.com
  13. ^ "Glycolic Acid MSDS". ICSC:NENG1537 International Chemical Safety Cards (WHO/IPCS/ILO). CDC/NIOSH. Retrieved 2006-06-08.
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