Glycolic acid

Glycolic Acid

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Glycolic acid

Glycolic acid (or hydroxyacetic acid) is the smallest a-hydroxy acid

Alpha hydroxy acid

a-hydroxy acids, or alpha hydroxy acids , are a class of chemical compounds that consist of a carboxylic acid substituted with a hydroxyl on the adjacent carbon....
(AHA). This colorless, odorless, and hygroscopic crystalline solid is highly soluble in water

Water

Water is a common chemical substance that is essential for the survival of all known forms of life. In typical usage, water refers only to its liquid form or States of matter, but the substance also has a solid state, ice, and a gaseous state, water vapor or steam....
. It is used in various skin-care products. Glycolic acid is found in some sugar-crops.

s prepared by the reaction of chloroacetic acid

Chloroacetic acid

Chloroacetic acid is the chemical compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis....
with sodium hydroxide

Sodium hydroxide

Sodium hydroxide , also known as lye, caustic soda and sodium hydrate, is a caustic metallic Base . Sodium hydroxide forms a strong alkaline solution when dissolved in a solvent such as water, however, only the hydroxide ion is basic....
followed by re-acidification. The net reaction can be summarized as follows:

ClCH₂CO₂H + NaOH ? HOCH₂CO₂H + NaCl

In this way, a few million kilograms are produced annually.

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Encyclopedia

Glycolic acid (or hydroxyacetic acid) is the smallest a-hydroxy acid

Alpha hydroxy acid

Water

Preparation

It is prepared by the reaction of chloroacetic acid

Chloroacetic acid

Chloroacetic acid is the chemical compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis....
with sodium hydroxide

Sodium hydroxide

ClCH₂CO₂H + NaOH ? HOCH₂CO₂H + NaCl

In this way, a few million kilograms are produced annually. Other methods, not apparently in use, include hydrogenation

Hydrogenation

Hydrogenation is the chemical reaction that results from the addition of hydrogen . The process is usually employed to a redox or Saturation organic compounds....
of oxalic acid

Oxalic acid

Oxalic acid is the chemical compound with the chemical formula H2C2O4. This dicarboxylic acid is better described with the formula HOOCCOOH....
and the hydrolysis of the cyanohydrin derived from formaldehyde

Formaldehyde

Formaldehyde is a chemical compound with the chemical formula H2CO. It is the simplest aldehyde. Formaldehyde exists in several forms aside from H2CO: the cyclic trimer trioxane and the polymer Polyoxymethylene....
. Glycolic acid can be isolated from natural sources, such as sugarcane

Sugarcane

Sugarcane is a genus of 6 to 37 species of tall perennial plant Poaceae , native to warm temperate to tropical regions of the Old World. They have stout, jointed, fibrous stalks that are rich in sugar and measure 2 to 6 meters tall....
, sugar beets, pineapple

Pineapple

Pineapple is the common name for an edible tropical plant and also its fruit. It is native to the southern part of Brazil, and Paraguay. This herbaceous plant perennial plant grows to tall with 30 or more trough-shaped and pointed leaves long, surrounding a thick plant stem....
, canteloupe, and unripe grape

Grape

File:Table grapes on white.jpgA grape is the non-Climacteric #In_botany fruit that grows on the Perennial plant and deciduous woody vines of the genus Vitis....
s..

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. This process is used by the specialty chemical company CrossChem.

Uses

Due to its excellent capability to penetrate skin

Skin

The skin is the outer covering of the body, also known as the epidermis. It is the largest organ of the integumentary system made up of multiple layers of epithelial biological tissue, and guards the underlying muscles, bones, ligaments and organ s....
, glycolic acid finds applications in skin care products, most often as a chemical peel performed by a dermatologist in concentrations of 20 to 80% or at-home kits in lower concentrations of 10%. It is used to improve the skin's appearance and texture. It may reduce wrinkles, acne

Acne vulgaris

Acne vulgaris is a skin condition caused by changes in the pilosebaceous units . Severe acne is inflammation, but acne can also manifest in noninflammatory forms....
scarring, hyperpigmentation and improve many other skin conditions. 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 outer skin to "dissolve" revealing the underlying skin.

Glycolic acid is also a useful intermediate for organic synthesis, in a range of reactions including: oxidation-reduction

Redox

Redox describes all chemical reactions in which atoms have their oxidation number changed.This can be either a simple redox process such as the oxidation of carbon to yield carbon dioxide or the reduction of carbon by hydrogen to yield methane , or it can be a complex process such as the oxidation of sugar in the human body through a ser...
, esterification

Esterification

Esterification is the general name for a chemical reaction in which two reactants form an ester as the product . Esters are common in organic chemistry and biological materials, and often have a characteristic pleasant, fruity odor....
and long chain polymerization. It is used as a monomer

Monomer

A monomer is a small molecule that may become Chemistry chemical bonding to other monomers to form a polymer....
in the preparation of polyglycolic acid

Polyglycolide

Polyglycolide or Polyglycolic acid is a biodegradable, thermoplastic polymer and the simplest linear, aliphatic polyester. It can be prepared starting from glycolic acid by means of Condensation reaction or ring-opening polymerization....
and other biocompatible copolymer

Heteropolymer

A heteropolymer or copolymer is a polymer derived from two monomeric species, as opposed to a homopolymer where only one monomer is used....
s (e.g. PLGA

PLGA

PLGA or poly is a copolymer which is used in a host of Food and Drug Administration approved therapeutic devices, owing to its Biodegradation and biocompatibility....
). Among other uses this compound finds employment in the textile industry as a dye

Dye

A dye can generally be described as a colored substance that has an Chemical affinity to the Wiktionary:substrate to which it is being applied....
ing and tanning

Tanning

Tanning is the process of making leather, which does not easily Decomposition, from the skins of animals, which do. Often this uses tannin, an acidic chemical compound....
agent, in food processing as a flavor

Flavor

Flavor or flavour is the sensory impression of a food or other chemical substance, and is determined mainly by the chemical senses of taste and olfaction....
ing agent and as a preservative. Glycolic acid is often included into emulsion polymers, solvents and additives for ink and paint in order to improve flow properties and impart gloss.

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 varnish

Varnish

Varnish is a Transparency , hard, protective finish or film primarily used in wood finishing but also for other materials. Varnish is traditionally a combination of a drying oil, a resin, and a Turpentine substitute or solvent....
es, being desirable because it is nonvolatile and good dissolving properties.

Safety

Glycolic acid is a strong irritant. Like ethylene glycol

Ethylene glycol

Ethylene glycol is an alcohol with two -OH groups , a chemical compound widely used as an automobile antifreeze. In its pure form, it is an odorless, colorless, syrupy, sweet tasting, toxic liquid....
, it is metabolized to oxalic acid

Oxalic acid

Oxalic acid is the chemical compound with the chemical formula H2C2O4. This dicarboxylic acid is better described with the formula HOOCCOOH....
, which makes it dangerous if ingested.

Glycolic acid

Preparation

Uses

Safety

External links