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CAS NO: 79-14-1
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.
Synonyms:
2-Hydroxyacetic acid; 2-Hydroxyethanoic acid; α-hydroxyacetic acid; alpha-Hydroxyacetic acid; Glycolic acid; GLYCOLIC ACID; Glycollic acid; HOCH2COOH; Hydroxyacetic acid; Hydroxyethanoic acid
A glycolate or glycollate is a salt or ester of glycolic acid.
The name "glycolic acid" was coined in 1848 by 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).
Glycolic acid was first prepared in 1851 by German chemist Adolph Strecker (1822–1871) and Russian chemist Nikolai Nikolaevich Sokolov (1826–1877). They produced it by 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" (Benzoglykolsäure; also benzoyl glycolic acid). They boiled the ester for days with dilute sulfuric acid, thereby obtaining benzoic acid and glycolic acid (Glykolsäure).
Glycolic acid can be synthesized in various ways. The predominant approaches use a catalyzed reaction of formaldehyde with synthesis gas (carbonylation of formaldehyde), for its low cost.
It is also prepared by the reaction of chloroacetic acid with sodium hydroxide followed by re-acidification.
Other methods, not noticeably in use, include hydrogenation of oxalic acid, and hydrolysis of the cyanohydrin derived from formaldehyde. 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.
Glycolic acid can also be prepared using an enzymatic biochemical process that may require less energy.
Glycolic acid is slightly stronger than acetic acid due to the electron-withdrawing power of the terminal hydroxyl group. The carboxylate group can coordinate to metal ions forming coordination complexes. Of particular note are the complexes with Pb2+ and Cu2+ which are significantly stronger than complexes with other carboxylic acids. This indicates that the hydroxyl group is involved in complex formation, possibly with the loss of its proton.
Glycolic acid is used in the textile industry as a dyeing and tanning agent 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. Glycolic acid is often included in 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. It is the active ingredient in the household cleaning liquid.
Due to its capability to penetrate skin, glycolic acid finds applications in skin care products, most often as a chemical peel. 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 low as 2.5. 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.
Glycolic acid is 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). Commercially, important derivatives include the methyl and ethyl esters which are readily distillable (boiling points 147–149 °C 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.
Many plants make glycolic acid during photorespiration. Its role consumes significant amounts of energy. In 2017 researchers announced a process that employs a novel protein to reduce energy consumption/loss and prevent plants from releasing harmful ammonia. The process converts glycolate into glycerate without using the conventional BASS6 and PLGG1 route.
Glycolic acid is a water-soluble alpha hydroxy acid (AHA) that is derived from sugar cane. It is one of the most well-known and widely used alpha-hydroxy acids in the skincare industry. Other alpha-hydroxy acids include lactic acid, malic acid, tartaric acid, and citric acid.
Glycolic acid has the smallest sized molecules of all the alpha-hydroxy acids
Because of these super tiny molecules, glycolic acid can easily penetrate the skin. This allows glycolic acid to exfoliate the skin more effectively than other AHAs.
It works by speeding up cell turnover It helps dissolve the bonds that hold skin cells together, allowing dead skin cells to slough off more rapidly than they would on their own.
Glycolic acid also stimulates your skin to create more collagen. Collagen is the protein that gives skin its firmness, plumpness, and elasticity. (Collagen is also the protein that gives strength to your bones and connective tissues.)
As you age, collagen production naturally slows down. It's also destroyed by excessive sun exposure. Using glycolic acid regularly can help prevent this breakdown of collagen
Glycolic acid is an incredibly popular treatment because of the many benefits it has for the skin. It has effective skin-renewing properties, so it is often used in anti-aging products. It can help smooth fine wrinkles and improve the skin's tone and texture.1 Glycolic acid plumps the skin and helps boost hydration levels.
It's not just an anti-aging treatment, though. Glycolic acid can also help fight sun damage. It's often used to fade minor fade hyperpigmentation.1
Because it's an effective exfoliator, using glycolic acid regularly can help brighten the complexion. It's this exfoliating property that also makes it an effective preventative against ingrown hairs. If you have large pores, glycolic acid can help make those appear smaller as well.
Many acne treatment products also contain glycolic acid. It isn't an acne treatment per se, but glycolic acid can help keep pores clear from blockages, preventing comedones, blackheads, and inflamed breakouts from forming.
Although many sources claim glycolic acid gets rid of scars, this is one thing it simply can't do. Glycolic acid can lighten dark discolorations left by acne or other wounds, and may soften the look of raised scars and pitted scars, but it will not make them disappear.3
For a more efficient treatment of scars, your best bet would be professional strength glycolic acid peels or a completely different scar treatment altogether
If you're looking for glycolic acid, you have choices—and lots of them. This skincare darling can be found in a multitude of over-the-counter products.
Try your local drug store, department store, or skin spa and you'll find plenty of cleansers, masks, toners, and moisturizers that contain this ingredient. Over-the-counter glycolic acid products typically come in strength of up to 10%.4
For stronger treatments, glycolic acid is also utilized in chemical peels available at the salon or your dermatologist's office. Light duty glycolic acid peels up to 30% strength can be done by an esthetician at the salon or skin spa. Stronger peels of up to 70% can be had at the dermatology office.
Can you make a glycolic acid peel yourself? While glycolic acid is obtained from sugar cane (and also naturally found in some fruits) the sugar you buy at the store is not the same as glycolic acid.
Rubbing your face with sugar manually exfoliates the skin and will leave the skin feeling smoother. But it's not going to give you the same results as glycolic acid treatment.
Skincare products contain other thoughtfully chosen ingredients to give a specific end result. You can definitely make your own skincare products, but they won't give you results on par with a professional glycolic product or peel.
The glycolic acid treatment you choose depends a lot on your skin type and what your end goals are. If you are simply wanting brighter, healthier-looking skin (or a reduction in breakouts and fine lines) an over-the-counter product is effective enough without stronger pro peels.
Using low concentrations of glycolic acid over long periods of time creates a cumulative effect; your skin will look better the longer you use it.
For treating specific skin issues like noticeable sun damage, dark spots or acne marks, and deeper lines and wrinkles, or for marked improvement of the skin quickly, a professional peel is a good option. But because peels deliver a higher percentage of glycolic acid than daily use products they will be more irritating and have a greater chance of side effects.5
When choosing any glycolic acid treatment, the percentage of glycolic acid is just one factor. The product's pH is the other. A more acidic product will deliver a stronger and more effective treatment than a less acidic product, regardless of the percentage of glycolic acid.
So a product containing a low percentage of glycolic acid but with a lower (i.e. more acidic) pH will be more effective than a high percentage but low acidity product.
Unfortunately, the vast majority of skincare products simply list the percentage of glycolic acid used. They are not required to list the pH, so it can make it difficult to compare products apples-to-apples.
Glycolic acid OTC products and professional peels have been around a long time and have a safe and effective track record. Most skin types can use them without much trouble.
If you have very sensitive skin, you may want to stick with wash-off glycolic acid products like cleansers. These aren't quite as irritating as leave-on glycolic acid treatments and allow your skin to build up a tolerance without (hopefully) too much irritation.
While glycolic acid is a wonderful skincare ingredient, if you're looking for powerful anti-aging or anti-acne treatments, topical retinoids will give you more bang for your buck. They are prescription-only, though.
If you need any help choosing a glycolic acid product, your dermatologist can help you do so.
Glycolic acid is an Alpha Hydroxy Acid (AHA). The word acid might scare you, but glycolic acid usually comes in lower concentrations for at-home use. It works as an exfoliant to turn over dead skin cells and reveal new skin cells.
It’s also one of the smallest AHAs, meaning that it can penetrate deeply to give you the best results. And it’s water-soluble, so you can “remove” it by rinsing your face with water.
Glycolic acid should always be applied in the evening, as it makes your skin sensitive to sunlight. Applying it at night gives ample time for it to do its magic without a higher risk or damaging your skin in the sun. But you should still always apply an SPF moisturizer in the morning.
There are three ways glycolic acid can be used in a skincare routine: as a face wash, as a toner, and as a mask. You should decide between using glycolic acid as a wash or as a toner every day, because they both have lower concentrations that are meant for daily use, then add a glycolic acid mask weekly. This will give you the full benefits of the acid while being safe for your skin.
Glycolic acid is the smallest α-hydroxy acid (AHA). This colorless, odorless, and hygroscopic crystalline solid is highly soluble in water. It is found in some sugar-crops.It is one of the most well-known and widely used alpha-hydroxy acids in the skincare industry.
Glycolic acid is slightly stronger than acetic acid due to the electron-withdrawing power of the terminal hydroxyl group. The carboxylate group can coordinate to metal ions forming coordination complexes. Of particular note are the complexes with Pb2+ and Cu2+ which are significantly stronger than complexes with other carboxylic acids. This indicates that the hydroxyl group is involved in complex formation, possibly with the loss of its proton.
Glycolic acid enhances cleaning and descaling processes in oil field and petroleum refining applications. This acid also provides metal complexing in a biodegradable form without adding undesirable biological or chemical oxygen demand to formulated products.
Glycolic acid's slower reactivity compared to mineral acids helps with acid finishing during well completion. Desalting crude oil, well acidizing, and synthetic drilling mud also rely on glycolic acid.
Glycolic acid is phosphate-free, biodegradable, and doesn't accumulate in the environment. This nonflammable, corrosion-resistant glycolic acid 70% tech grade has:
• Low odor
• Low toxicity
• Low vapor pressure
Glycolic acid can be used with hydrochloric or sulfamic acids to prevent iron precipitation in cleaning operations or water flooding. It also effectively eliminates harmful deposits while minimizing corrosion damage to steel or copper systems.
Glycolic acid reacts more slowly and thus penetrates more deeply into formations before fully reacting. That characteristic leads to enhanced worm holing, because glycolic acid dissolves the equivalent amount of calcium carbonate (CaCO₃) as hydrochloric acid without the resulting corrosion.
Gypsum Removal
Gypsum, or calcium sulfate (CaSo₄) scale, is a hard deposit that blocks pipes and is difficult to remove. In a case study that used a descaling solution of ammonium glycolate, ammonium malate, and water, the descaling solution was injected into a pipe and left to set for 22 hours. This one-step procedure resulted in 85 to 100% removal of the CaSo₄ scale, with a lower process downtime (24 hours rather than the usual 48 to 72 hours descaling often takes).
Metal Naphthenate Dissolution
Naphthenate is a carboxylic acid containing saturated cyclic hydrocarbons like cyclopentane and cyclohexane. Glycolic acid competes with naphthenate for metal cations to form water-soluble glycolate salt. Glycolic acid can also increase protonation by changing the solubility and phase partition of the naphthenates. Protonated naphthenic acids are much more oil soluble than ionized napthenates.
Removal of Water Soluble Organics
Oil consists mainly of dispersed organics—but some organics dissolve in water in measurable concentrations. Gravity-based separation methods do not remove water-soluble organics (WSO). These WSO are soluble in water at typical operating pH values and exist in produced water.
Oil pumped out of the ground is mixed with water, which the industry refers to as "produced water." In offshore platforms, produced water is cleaned to a low-enough water soluble organic (WSO) level and discharged overboard. WSO are the polar part of the evaporated hexane extract and include dissolved and polar organics in produced water.
Produced water overboard discharge—while permitted in much of the world—is subject to discharge limits. For example, in the Gulf of Mexico, hydrocarbons in produced water are limited to 29 mg/l (monthly average). US regulations define hydrocarbons as compounds that extract into n-hexane solvent from water at a pH >2 and that remain after the solvent has been boiled away.
Using glycolic acid in WSO removal is preferable to other methods because glycolic acid is:
• Far less corrosive
• Non-volatile
• Non-scaling
• Compatible with existing water clarifier treatments, unlike quaternary ammonium compounds (QACs)
• Effective in a wide treatment range, unlike QACs
• Usable in combination with anionic surfactants or mineral acids
Glycolic acid offers a versatile, effective solution for many institutional cleaning applications.
Institutions—like hospitals, food processing plants, public gyms, and locker rooms—have hard surfaces that can’t be removed for washing, so cleaning must be done onsite. These surfaces include:
• Shower doors and stalls
• Toilet bowls
• Sinks
• Countertops
• Ceramic tile
• Grout
• Porcelain tubs
Glycolic acid improves the cleaning and penetrating effectiveness of other organic and inorganic acids like citric acid and sulfamic acid. It also offers ease of formulation and compatibility with a wide range of cleaner components like solvents, fragrances, surfactants, and colorants. Additional attributes that make it effective for institutional cleaning include:
• Cleaning efficacy, removing soils easily and thoroughly
• Low odor, color, toxicity, and corrosiveness
• Good biodegradability
• Chemical stability
• Great water solubility
How Glycolic Acid Enhances the Efficacy of Institutional Cleaning Agents
Chemours has worked to develop a versatile, effective solution for a broad range of cleaning and industrial applications. For institutional cleaning, glycolic acid can enhance scale and iron stain removal by itself or when it's blended with other acids. Its low pKa facilitates the removal of soap scum, residues, and other mineral scales.
Applications That Benefit from Chemours' Glycolic Acid Solution
Hard Surfaces
Dirt and scale build up on hard surfaces like tiles, toilets, counters, and shower stalls over time. Soils—complex mixtures of hard water minerals including iron, calcium, and magnesium, or soap residues—become difficult to remove. Glycolic acid demonstrates its synergistic power by enabling other acid blends to work better than acid alone.
Chemours' glycolic acid is the choice in acid-based institutional cleaners because of its:
• Ease of formulation
• Stability
• Efficacy
• Low toxicity
Laundry Sour Applications
Modern laundry systems require a dependable, flexible liquid sour. Glycolic acid provides far greater solubility than silicafluorides or hydrofluosilicic acid. It permits higher concentrations of acid in solution than citric acid for greater neutralizing efficiency while avoiding salting or rust discoloration problems.
Glycolic acid reaches a final pH of 5-6 more quickly than silicafluorides, especially at lower wash temperatures. High solubility means a lower possibility of damaged fabric—even if it’s ironed while wet. Glycolic acid liquid doesn’t cake in storage and measures easily out of automatic dispensing equipment.
Glycolic acid fulfills many roles across a wide range of industries, thanks to its low odor and toxicity, biodegradability, phosphate-free composition, and ability to chelate metal salts. Compatible with many additives, it’s also:
• Completely water soluble
• Easily rinsable
• Environmentally friendly
Electronics manufacture requires ultra-high purity materials—even the smallest amounts of metallic impurities can severely damage sensitive components. In such demanding and critical applications, choosing the right cleaning and complexing agent is essential.
Glycolic acid is important for applications that require low levels of metallic impurities. Designed for cleaning copper substrates in electronics, glycolic acid uses hydroxyl and carboxylic acid groups to form five-member ring complexes (chelates) with polyvalent metals. This complexing ability facilitates the cleaning of copper substrates to provide an excellent surface for further processing.
Glycolic acid offers:
• Good complexing of metal ions
• Low corrosion rates
• An efficient pH adjustment profile
• Good environmental, safety, and handling properties
Standard Tech Grade
The versatile glycolic acid technical grade 70% offers zero chloride content and provides basic electronics cleaning and copper substrate preparation. Its characteristics include acid and alcohol functionality, low toxicity and corrosiveness, and excellent soil removal properties.
Glycolic acid Electronics
This electronics-grade glycolic acid offers favorable chelating properties on copper surfaces and substrates in electronic applications. Applications like flat-panel, thin-film transistor (TFT) processing—which require ppm-level metal impurities and are used in the manufacture of flat panel televisions—also benefit from its use.
Glycolic acid enables and improves many formulations used in semiconductor fabrication. Glycolic acid is used to remove etch residues (like polymers or particles) from semiconductor wafer substrates. These substrates are cleaned with a solution containing glycolic acid that removes particles such as photoresist residues and other contaminants.
Glycolic acid is used to make polyglycolic acid (PGA) polymer. With its unique physical properties polyglycolic acid is applied to difficult applications in a range of industries, including the medical, oil and gas, pharmaceutical, and food and beverage sectors.
The leather industry depends on glycolic acid as a dyeing and tanning agent to achieve high-quality results because it:
• Removes calcium oxide (CaO) efficiently in deliming
• Is a powerful chrome complexant for pickling
• Offers economic advantages due to reduced consumption of expensive dyes
Additionally, the nonvolatile, biodegradable glycolic acid:
• Offers better dye color matching, color distribution, and color intensity
• Has low corrosiveness
• Offers an improved safety profile over many other acids
Glycolic Acid Enhances Leather Dyeing and Tanning Processes
Glycolic acid 70% tech grade is a solution of 70% glycolic acid and 30% water, useful in processes that require pH control and low volatility.
• In tanning, glycolic acid is efficient for bath pH adjustment, which is critical in the production of sole leather and other vegetable tanning. Its sodium salt is effective as a masking agent.
• In deliming, glycolic acid penetrates hides rapidly to reduce operation time. Its properties improve grain quality by eliminating excessive pelt swelling that causes wrinkles and reduces tear resistance.
• In pickling, glycolic acid forms metal complexes with chrome and alum mordants, which is beneficial in fur and leather finishing.
• In dyeing, the low volatility of glycolic acid requires lower usage than volatile agents like acetic and formic acids; heat does not produce corrosive fumes, and pH levels are easier to maintain.
Glycolic Acid: The Best Choice for Dyeing
In several pilot tests that compared the use of glycolic acid with formic acid:
• Articles dyed with glycolic acid offered a more intense color hue
• Dye usage was reduced when glycolic acid was used in processing
• Hides dyed with glycolic acid were softer
• The physical properties of leather were not significantly changed when using glycolic acid
IUPAC NAMES
2-hydroxy acetic acid; 2-Hydroxyacetic acid; 2-hydroxyacetic acid; 2-Hydroxyethanoic acid; 2-hydroxyethanoic acid; glycol acid; GLYCOLIC ACID; Glycolic Acid; Glycolic acid; Glycolic Acid; Glycolic acid; glycolic acid; GLYCOLLIC ACID; Glycollic acid; glycollic acid; Glycollic acid; glycollic acid; Glykolsäure; Glykolsäure ... %; Hydroxyacetic Acid
TRADE NAMES
Glycolic acid; Glycos Basic 57; Glycos Basic 70; Glycos Clear 70; Glypure 70; Glytech Basic 57; Glytech Basic 70
OTHER NAMES
1033720-45-4; 1033720-45-4; 1033720-48-7; 1033720-48-7; 259744-22-4; 259744-22-4; 702627-33-6; 702627-33-6; 79-14-1
