Process for the preparation of 1,4-3,6-dianhydro-hexitols

Details Process for the preparation of 1,4-3,6-dianhydro-hexitols Process for the preparation of 1,4-3,6-dianhydro-hexitols

1982-03-11

1983-10-04

Raymond, Richard

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D49304

Patent

active

044080611

ABSTRACT:
A process for the preparation of 1,4-3,6-dianhydro-hexitols from hexitols by elimination of water is described, characterized in that gaseous hydrogen halide is used as the acid dehydrating agent optionally with carboxylic acids, carboxylic acid halides and/or carboxylic acid anhydrides in quantities of up to 600 mol percent, based on the hexitols, as cocatalysts. The reaction is carried out in the absence of water and organic solvents, preferably using gaseous hydrogen chloride, temperatures of up to 300.degree. C. and pressures of up to 250 bar. Very high yields are obtained after working up of the product by distillation or extraction.

REFERENCES:
patent: 3454603 (1969-07-01), Hartmann
R. Montgomery and L. F. Wiggins, J. Chem. Soc., 1947, 433.
J. C. Goodwin, J. E. Hodge and D. Weisleder, Carbohyd. Res. 79, 133, (1980).
Fauconier, Bull. Soc. Chem., (1884), 41, 119.
L. F. Wiggins, J. Chem. Soc., 1945, 4.
Haworth, Heath and Wiggins, J. Chem. Soc., 1944, 155.
"Anhydrides of the Penitols and Hexitols", by L. F. Wiggins, in Advances in Carbohydrate Chemistry, 5 (1950), pp. 191 et seq.
"Alditol Anhydrides", by S. Soltzberg, in Advances in Carbohydrate Chemistry, 25 (1970), pp. 229 et seq.
Ropuszynski et al., Przem. Che. 48, (11), 665-668, 1969.
"Preparation of Bicyclic Hexitol Anhydride by Using Acidic Cation-Exchange Resin in a Binary Solvent", by J. C. Goodwin et al., in Carbohydrate Research, 79 (1980), pp. 133-141.

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