Propylene glycol


Propylene glycol[1]
Propylene glycol chemical structure.png
PropyleneGlycol-stickAndBall.png PropyleneGlycol-spaceFill.png
IUPAC name propane-1,2-diol
Other names propylene glycol, 1,2-propanediol, 1,2-Dihydroxypropane, methyl ethyl glycol (MEG), methylethylene glycol, PG, Sirlene, Dowfrost
Identifiers
CAS number [57-55-6]
RTECS number TY6300000
SMILES CC(O)CO
Properties
Molecular formula C3H8O2
Molar mass 76.09 g/mol
Density 1.036 g/cm³
Melting point

-59 °C

Boiling point

188.2 °C

Solubility in water fully miscible
Solubility in ethanol fully miscible
Solubility in diethyl ether fully miscible
Solubility in acetone fully miscible
Solubility in chloroform fully miscible
Thermal conductivity 0.34 W/m-K (50% H2O @ 90°C)
Hazards
MSDS External MSDS
NFPA 704

NFPA 704.svg

1
0
0
 
S-phrases S24 S25
Related Compounds
Related glycols Ethylene glycol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Propylene glycol, also known by the systematic name propane-1,2-diol, is an organic compound with the chemical formula C3H8O2. Under standard conditions (temperature of 25°C and pressure of 100 kPa), it is a colorless, odorless, viscous liquid.

This chemical has many applications. It is used as a moisturizer in food, medications, and various personal care products. It is a good coolant in liquid cooling systems, a solvent for food colorings and flavorings, and a solvent for photographic chemicals. It is a carrier in fragrance oils and the main ingredient in deodorant sticks. It is used for de-icing aircraft and producing artificial smoke. It is also a working fluid in hydraulic presses.

Contents

Propylene glycol has negligible toxicity if taken orally through food and medicines. In addition, it does not irritate the skin even on prolonged contact. However, high intake of the substance over a relatively short period of time can have toxic effects.

Nomenclature

As noted above, the systematic name for propylene glycol is propane-1,2-diol, as endorsed by the International Union of Pure and Applied Chemistry (IUPAC). In addition, it is referred to as PG, 1,2-propanediol, 1,2-dihydroxypropane, methyl ethyl glycol (MEG), or methylethylene glycol.

Properties

The properties of propylene glycol are similar to those of ethylene glycol (monoethylene glycol, or MEG).[2]

Propylene glycol is miscible with water and various organic solvents such as ethanol, ether, acetone, and chloroform. Moreover, it is hygroscopic, that is, it readily absorbs water from the surrounding air. It has a boiling point of 188.2°C and a melting point of -59°C.

Each molecule of propylene glycol consists of a chain of three carbon atoms (as in propane), with two hydroxyl (or "alcohol," OH) functional groups attached to two adjacent carbon atoms. It is therefore classified as a "diol." The chemical formula may be written out as CH2OH-CHOH-CH3.

Isomers

In each molecule of propylene glycol, the central carbon is attached to four different groups of atoms, and it is therefore an asymmetric atom. Consequently, the molecule exists in two forms that are known as stereoisomers. The commercial product is a mixture of both forms, called a racemic mixture. Pure optical isomers can be obtained by hydration of optically pure propylene oxide.[3]

Production

Industrially, propylene glycol is produced by the hydration of propylene oxide. Manufacturers may use a noncatalytic, high-temperature process at 200-220°C, or a catalytic route that proceeds at 150-180°C in the presence of an ion exchange resin or small amounts of sulfuric acid or alkali. The final products contain 20 percent 1,2-propanediol, 1.5 percent dipropylene glycol, and small amounts of other polypropylene glycols.[3] Propylene glycol can also be converted from glycerol, a biodiesel by-product.

Applications

Propylene glycol has a variety of applications. It is used:

  • As a moisturizer in medications, cosmetics, food, toothpaste, mouthwash, and tobacco products
  • In hand sanitizers, antibacterial lotions, and saline solutions
  • As the main ingredient in deodorant sticks
  • As an emulsification agent in Angostura and orange bitters
  • As a solvent for food colors and flavorings
  • As a solvent for mixing photographic chemicals, such as film developers
  • As a humectant food additive, labeled as E number E1520
  • As a coolant in liquid cooling systems, such as in glycol-jacketed fermentation tanks for beer and wine
  • In cryonics
  • As a less-toxic antifreeze (compared with ethylene glycol)
  • As a carrier in fragrance oils
  • As a working fluid in hydraulic presses
  • As the killing and preserving agent in pitfall traps, usually used to capture ground beetles
  • To treat livestock ketosis
  • To de-ice aircraft.[4]
  • In smoke machines to make artificial smoke for use in firefighters' training and theatrical productions
  • In electronic cigarettes to make the vapor resemble cigarette smoke

Safety

The oral toxicity of propylene glycol is very low. In one study, rats were provided with feed containing as much as 5 percent PG over a period of 104 weeks and they showed no apparent ill effects.[5] However, there have been cases of propylene glycol poisoning, resulting from either inappropriate intravenous use or accidental ingestion by children.[6]

Serious toxicity occurs only at extremely high intakes over a relatively short period of time, when its concentration in blood plasma rises above 4 g/L.[7] Such levels of ingestion would not be possible when consuming reasonable amounts of a food product or dietary supplement containing at most 1 g/kg propylene glycol.

The U.S. Food and Drug Administration (FDA) has categorized propylene glycol as "generally recognized as safe" for use in food, cosmetics, and medicines. Like ethylene glycol, propylene glycol affects the body's chemistry by increasing the amount of acid. Propylene glycol is metabolized into pyruvic acid, which is a normal metabolite in the breakdown of glucose, while ethylene glycol is metabolized into oxalic acid, which is toxic.

However, propylene glycol is not approved for use in cat food. The U.S. Food and Drug Administration has determined that propylene glycol in or on cat food has not been shown by adequate scientific data to be safe for use. Use of propylene glycol in or on cat food causes the feed to be adulterated and in violation of the Federal Food, Drug, and Cosmetic Act. 21CFR589.1001

Prolonged contact with propylene glycol is essentially non-irritating to the skin. Undiluted propylene glycol is minimally irritating to the eye, and can produce slight transient conjunctivitis (the eye recovers after the exposure is removed). Exposure to mists may cause eye irritation, as well as upper respiratory tract irritation. Inhalation of the propylene glycol vapors appears to present no significant hazard in ordinary applications. However, limited human experience indicates that inhalation of propylene glycol mists could be irritating to some individuals. Therefore, inhalation exposure to mists of these materials should be avoided. Some research has suggested that propylene glycol not be used in applications where inhalation exposure or human eye contact with the spray mists of these materials is likely, such as fogs for theatrical productions or antifreeze solutions for emergency eye wash stations.

Propylene glycol does not cause sensitization and it shows no evidence of being a carcinogen or of being genotoxic.[8][9]

Recent Clinical Journal of Medicine article states two cases of adult men experiencing psychosis from use of propylene glycol used in phenytoin injection USP. Both patients had to be switched to Cerebyx (Fosphenytoin Sodium) in order to avoid propylene glycol co-solvent.

Allergic reaction

Research has suggested that individuals who cannot tolerate propylene glycol probably experience a special form of irritation, but that they only rarely develop allergic contact dermatitis. Other investigators believe that the incidence of allergic contact dermatitis to propylene glycol may be greater than 2 percent in patients with eczema.[10]

Patients with vulvodynia and interstitial cystitis may be especially sensitive to propylene glycol. Women struggling with yeast infections may also notice that some OTC creams can cause intense burning.[11] Post-menopausal women who require the use of an estrogen cream may notice that brand name creams made with propylene glycol often create extreme, uncomfortable burning along the vulva and perianal area. In these cases, patients can request that a local compounding pharmacy make a "propylene glycol free" cream.

See also

Notes

  1. Merck Index, 11th Edition, 7868.
  2. Note that propylene glycol is sometimes also given the acronym MEG, but as an abbreviation of methyl ethyl glycol.
  3. 3.0 3.1 1,2-propanediol. CHEMINDUSTRY.RU. Retrieved January 12, 2009.
  4. What's that Stuff?: Aircraft Deicers. C&EN News. Retrieved January 12, 2009.
  5. I.F. Gaunt, et al, April 1972. "Long-term toxicity of propylene glycol in rats," Food and Cosmetics Toxicology. 10(2): 151-162.
  6. National Library of Medicine. 2005. Human Toxicity Excerpts: CAS Registry Number: 57-55-6 (1,2-Propylene Glycol). Selected toxicity information from HSDB.
  7. Flanagan, R.J., et al. 1995. The International Programme on Chemical Safety: Basic Analytical Toxicology. WHO.
  8. 1,2-Dihydroxy propane. SIDS Initial Assessment Report for 11th SIAM, U.S.A. January 23-26, 2001, page 21. UNEP Publications. Retrieved January 12, 2009.
  9. Title 21, U.S. Code of Federal Regulations. 1999.
  10. American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994, 1224.
  11. Elizabeth Vliet, 1995, Screaming To Be Heard: Hormonal Connections That Women Suspect and Doctors Ignore. New York: M. Evans and Company.

References

  • McMurry, John. 2004. Organic Chemistry, 6th ed. Belmont, CA: Brooks/Cole. ISBN 0534420052.
  • Morrison, Robert T., and Robert N. Boyd. 1992. Organic Chemistry, 6th ed. Englewood Cliffs, NJ: Prentice Hall. ISBN 0136436692.
  • Solomons, T.W. Graham, and Craig B. Fryhle. 2004. Organic Chemistry, 8th ed. Hoboken, NJ: John Wiley. ISBN 0471417998.
  • Yaws, Carl L. 2005. The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals: Physical Properties for More Than 41,000 Organic and Inorganic Chemical Compounds: Coverage for C1 to C100 Organics and Ac to Zr Inorganics. Houston: Gulf Pub. Co. ISBN 9780976511373.

External links

All links retrieved June 5, 2015.

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