Process for the preparation of 2-alkene-1,4-diols and 3-alkene-1

Details Process for the preparation of 2-alkene-1,4-diols and 3-alkene-1 Process for the preparation of 2-alkene-1,4-diols and 3-alkene-1

1997-07-08

1999-09-28

Shippen, Michael L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

C07C 3118

Patent

active

059591625

ABSTRACT:
This invention pertains, firstly, to the use of mixtures of hydriodic acid and organic solvent soluble iodide salts as catalysts for the hydration of .gamma.,.delta.-epoxyalkenes to form a mixture of the corresponding 2-alkene-1,4-diol and 3-alkene-1,2-diol isomers. Secondly, this invention describes the use of pH to control the 2-alkene-1,4-diol/3-alkene-1,2-diol product ratio, and achieve improved 2-alkene-1,4-diol selectivities by controlling the pH to near neutral values. Thirdly, this invention includes a catalyst recovery process whereby a liquid/liquid extraction is used to separate the product from the catalyst. In this extraction, .gamma.,.delta.-epoxyalkene, or a .gamma.,.delta.-epoxyalkene-containing organic solvent, is used to extract the catalysts from water, leaving the diol products in the aqueous phase, from which they may be subsequently recovered by distillation, extraction or by other means.

REFERENCES:
patent: 5530167 (1996-06-01), Tustin
Ross et al., "Vinyl Epoxide Hydrolysis Reactions," J. Am. Chem. Soc., vol. 102, pp. 1658-1665 (1982).
CA 101: 110030w (1984).
CA 96: 180770q (1982).
10G--Heterocyclic Compounds, 18462 (1960).
CA 91: 210877w (1979).
Compilation from SciFinder, pp. 1-6 and 1-4 (1997).
Derwent Abstracts, AN 95-099801.
Derwent Abstracts, AN 94-201497.
Derwent Abstracts, AN 95-099804.
Derwent Abstracts, AN 95-099803.

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