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In its industrial synthesis, acetylene reacts with two equivalents of formaldehyde to form 1,4-butynediol, also known as but-2-yne-1,4-diol. This type of acetylene-based process is illustrative of what is known as "Reppe chemistry", after German chemist Walter Reppe. Hydrogenation of 1,4-butynediol gives 1,4-butanediol.

LyondellBasell manufactures 1,4-butanediol in a proprietary, multi-step process without the use of acetylene. First, propylene oxide is converted to allyl alcohol. The allyl alcohol is then hydroformylated to 4-hydroxybutyraldehyde. Hydrogenation of the 4-hydroxybutyraldehyde yields 1,4-butanediol.[4]

It is also manufactured on an industrial scale from maleic anhydride, which is first converted to the methyl maleate ester, then hydrogenated. Other routes are from butadiene, allyl acetate and succinic acid[5].

Genomatica (a San Diego-based company) has genetically engineered E. coli to metabolize sugar into 1,4-butanediol. They expect to build and begin operating a pilot plant by the end of 2009. Genomatica CEO Christopher Gann said the process consumes 32,000 BTU per pound of 1,4-butanediol (75 MJ/kg), far less than the acetylene-based process, and does not have any by-products.[6][7]

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1,4-Butanediol is used industrially as a solvent and in the manufacture of some types of plastics, elastic fibers and polyurethanes. In organic chemistry, 1,4-butanediol is used for the synthesis of ¦Ã-butyrolactone (GBL). In the presence of phosphoric acid and high temperature, it dehydrates to the important solvent tetrahydrofuran.[8] At about 200 ¡ãC in the presence of soluble ruthenium catalysts, the diol undergoes dehydrogenation to form butyrolactone.[9]

World production of 1,4-butanediol is about one million metric tons per year and market price is about 2,000 USD (1,600 EUR) per ton (2005). Almost half of it is dehydrated to tetrahydrofuran to make fibers such as Spandex.[10] The largest producer is BASF.[11]
2Â¥2011-08-30 09:43:31
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