US 12,516,009 B2 · Sustainable process for the manufacture of 1,1,4,4-tetramethoxy-2-butene

Abstract

The present invention is directed to a process for the manufacture of 1,1,4,4-tetramethoxy-2-butene from 2,5-dimethoxy-2,5-dihydrofuran with methanol in the presence of an acidic ion exchanger as catalyst, whereby the molar ratio of 2,5-dimethoxy-2,5-dihydrofuran to methanol is ≥1:45. The present invention is further directed to a process of separating 1,1,4,4-tetramethoxy-2-butene, methanol and 2,5-dimethoxy-2,5-dihydrofuran from each other and H2O whereby a basic compound, preferably a basic metal salt or a basic ion exchanger, is present. Both processes can be carried out on an industrial scale, batch-wise or in continuous mode and are sustainable since the selectivity and the space-time-yields are high and less waste compared to known processes is produced. Further objects of the present invention are the use of a basic compound in the distillation of a mixture comprising H2O, 1,1,4,4-tetramethoxy-2-butene and 2,5-dimethoxy-2,5-dihydrofuran, as well as the use of an acidic ion exchanger as catalyst in a reaction of 2,5-dimethoxy-2,5-dihydrofuran with methanol to 1,1,4,4-tetramethoxy-2-butene, whereby the molar ratio of 2,5-dimethoxy-2,5-dihydrofuran to methanol is ≥1:45.

Claims17

Dependent claims

A process for manufacturing 1,1,4,4-tetramethoxy-2-butene comprising the following steps:

a) providing 2,5-dimethoxy-2,5-dihydrofuran (DMDF optionally comprising 1,1,4,4-tetramethoxy-2-butene;
b) reacting the DMDF optionally comprising 1,1,4,4-tetramethoxy-2-butene provided in step a) with methanol in a molar ratio of the DMDF to methanol being ≥1:45, in the presence of an acidic ion exchanger as catalyst and optionally in the presence of water, with a mixture comprising water and 1,1,4,4-tetramethoxy-2-butene until at most 79% of DMDF has been reacted to 1,1,4,4-tetramethoxy-2-butene to obtain a reaction mixture comprising water, methanol, 1,1,4,4-tetramethoxy-2-butene and DMDF;
c) bringing the reaction mixture comprising water, methanol, 1,1,4,4-tetramethoxy-2-butene and DMDF into contact with a basic compound;
c) distilling the reaction mixture comprising water, methanol, 1,1,4,4-tetramethoxy-2-butene and DMDF in the presence of the basic compound to thereby separate these compounds from each other and obtain 1,1,4,4-tetramethoxy-2-butene, methanol and un-reacted DMDF, wherein
step c) is practiced by adding the basic compound to the reaction mixture obtained in step b) or before or during the distillation of step d), and wherein
the process is conducted in the absence of any acetalization agent except for the presence of the methanol.

3 more elements

Dependencies are inferred from the claim text.

Sustainable process for the manufacture of 1,1,4,4-tetramethoxy-2-butene

Life of this patent

Sustainable process for the manufacture of 1,1,4,4-tetramethoxy-2-butene

Life of this patent

Abstract

Claims17