1,4-Butanediol(1,4-BD) Overview





1,4-butanediol (1,4-BD) is a colorless, viscous liquid derived from butane by placement of alcohol groups at each end of its molecular chain and is one of four stable isomers of butanediol.


  • 1,4-BD has widespread industrial use. It is used in the production of spandex fibers, urethane elastomers, and copolyester ethers. Sizable quantities of 1,4-BD are also used to make gamma-butyrolactone (GBL), which has outlets in electronics, pharmaceuticals, and agrochemicals, as well as high-performance polymers. Miscellaneous uses include its use in solvents, coating resins, and as pharmaceutical intermediates.

  • Worldwide production capacity for 1,4-BD is measured in the millions of metric tons/year.

  1. Substance identification


1)Chemical Abstract Service (CAS) Registry Number

2)Other Names

1,4-Butanediol; Butane-1,4-diol; 1,4-Butylene glycol; Tetramethylene glycol; 110-63-4; 1,4-Dihydroxybutane; 1,4-Tetramethylene glycol; BDO; Butanediol-1,4;1,4-BD; 1,4-BDO; 1,4-Tetramethylene

3)Street Names

1,4-BD has been associated with street names including:

"BlueRaine", "Dream On", "Fubar", "Pine Needle Oil", "Rejuv@Nite","Thunder", “Cleaner”, “Enliven”, “Inner G”, “One Comma Four", "One Four Bee", "One Four B-D-O", “Revitalize Plus”, “Serenity”, “SomatoPro”, "Soma Solution", “Sucol B”, “Thunder Nectar”, “Weight Belt Cleaner”, “White Magic”.

4)Physical properties

1,4-BD is a colorless, almost odorless, waxy solid to oily liquid depending on temperature (melting point 20.4°C and boiling point of 235°C).

2. Chemistry


1)Chemical description

1,4-Butanediol is the organic compound with the formula HOCH2CH2CH2CH2OH. This colorless viscous liquid is derived from butane by placement of alcohol groups at each end of the chain. It is one of four stable isomers of butanediol.

2) Chemical properties

Readily soluble in water (1.0x106 mg/L at 20 deg °C), alcohols, ketones, glycol ethers, and glycol ether acetates; less soluble in diethyl ether and esters; not miscible with aliphatic and aromatic hydrocarbons and chlorinated hydrocarbons.


3. Therapeutic applications and extent of therapeutic use and epidemiology of medical use

1,4-BD itself has no recognized therapeutic application. However, the dimethanesulfate (1,4-butanediol dimethanesulfonate; busulfan) is available in oral (Busulfan; Myleran, GlaxoSmithKline) and intravenous (Busulfex IV, Otsuka America Pharmaceutical, Inc.) forms for the treatment of chronic myeloid leukemia (CML). When given orally, except for seizures, adverse central nervous system effects (i.e. CNS stimulations ordepression) are not typically indicated. This suggests that busulfan is not readily converted to GHB, at least not at clinical doses up to those producing severe effects.

4. Industrial use

1,4-Butanediol's largest use is within tetrahydrofuran (THF) production, used to make polytetramethylene ether glycol, which goes mainly into spandex fibers, urethane elastomers, and copolyester ethers. The next largest outlet is engineering plastic polybutylene terephthalate (PBT). Sizable quantities of 1,4-BD are also used to make gamma-butyrolactone, which has outlets in electronics, pharmaceuticals, and agrochemicals, as well as high-performance polymers. Miscellaneous uses include solvents, coating resins, and pharmaceutical intermediates. The 2008 WHO questionnaire for review of psychoactive substances, identified seven countries legitimated it for technical use. Sales in the United States alone in 1992 totaled 56,847,000 kg. Worldwide production capacities for 1,4-butanediol in 2006 were measured in millions of metric tons/year. During 1978 to 1985 U.S. production of 1,4-butanediol reported in the Chemical Economics Handbook or to the U.S. International Trade Commission ranged from 138.2 to 353.5 million pounds annually while the quantity imported for the same period of time ranged from 2.0 to 27.7 million pounds annually.

References


1. Buggia I, Locatelli F, Regazzi MB, Zecca M. Busulfan. Ann Pharmacother, 1994, 28: 1055-1062.

2. Hazardous Substances Data Bank [Internet]. 1,4-Butanediol. Bethesda, MD: National Library of Medicine (US), Division of Specialized Information Services; 1986- [cited 2014 March 15].

3. PubMed Health. Busulfan (by mouth). National Center for Biotechnology Information (NCBI) at the U.S. National Library of Medicine (NLM); 2014.

4. Bishop JB, Wasson JS. Toxicological review of busulfan (Myleran). Mutat Res, 1986, 168: 15-45.

5. World Health Organization. 1,4-Butanediol (1,4-BD) Pre-Review Report: Expert Committee on Drug Dependence Thirty-fifth Meeting. Geneva: World Health Organization; 2012. Report No.: 35th ECDD (2012) Agenda item 5.5.

6. Irwin RD. A review of evidence leading to the prediction that 1,4-butanediol is not a carcinogen. J Appl Toxicol, 2006, 26: 72-80.