Process for manufacturing dianhydrohexitol crystals with a step of evaporative crystallization of the first crystallization mother liquors

Patent metadata

Field	Value
Publication number	US-10526340-B2
Application number	US-201716095300-A
Country	US
Kind code	B2
Filing date	Apr 21, 2017
Priority date	Apr 25, 2016
Publication date	Jan 7, 2020
Grant date	Jan 7, 2020

Abstract

A process for manufacturing crystals of 1,4:3,6-dianhydrohexitols, by manufacturing a solution of an internal dehydration product of at least one hexitol, distilling the solution, crystallizing, and wherein the crystallization mother liquors undergo a step of evaporative crystallization. Unlike the prior art processes that seek to recycle the crystallization mother liquors, evaporative crystallization economically and efficiently replaces the succession of steps consisting of at least one concentration, then at least one step of purification by distillation, chromatography, or crystallization.

First claim

The invention claimed is:

1. A process for producing 1,4:3,6-dianhydrohexitol crystals, comprising:
a) obtaining a solution of an internal dehydration product of at least one hexitol,
b) distilling the solution resulting from step a) so as to obtain a solution of at least one 1,4:3,6-dianhydrohexitol,
c) crystallizing the 1,4:3,6-dianhydrohexitol resulting from step b),
d) draining the 1,4:3,6-dianhydrohexitol crystals resulting from step c), which results in a crystal-rich stream (1) and a mother liquor stream (1 bis),
and wherein all or part of the mother liquor stream (1 bis) undergoes an evaporative crystallization step e) in the presence of a solvent, which results in the formation of a solvent stream (2) and in the formation of a stream rich in 1,4:3,6-dianhydrohexitol crystals (2 bis).

2. The process as claimed in claim 1 , wherein all of the mother liquor stream (1 bis) resulting from the draining step d) undergoes an evaporative crystallization step e).

3. The process as claimed in claim 1 , wherein a part of the mother liquor stream (1 bis) resulting from the draining step d) undergoes an evaporative crystallization step e), from 50% to 99.9% by weight of the stream undergoing the evaporative crystallization step, and from 0.1% to 50% by weight of the stream being reintroduced into the distillate at the crystallization step c).

4. The process as claimed in claim 1 , wherein the solvent in the evaporative crystallization step e) is chosen from a C 1 -C 4 linear or branched aliphatic alcohol.

5. The process as claimed in claim 1 , wherein the crystals of the stream rich in 1,4:3,6-dianhydrohexitol crystals (2 bis) resulting from the evaporative crystallization step e) are drained at a step f), which results in the formation, on the one hand, of a main stream (3) rich in 1,4:3,6-dianhydrohexitol crystals and, on the other hand, in the formation of a mother liquor stream (3 bis).

6. The process as claimed in claim 5 , wherein this main stream (3) rich in 1,4:3,6-dianhydrohexitol crystals is reintroduced into the distillate at step c).

7. The process as claimed in claim 5 , wherein the crystals of the main stream (3) are recovered.

8. The process as claimed in claim 5 , wherein the mother liquor stream (3 bis) is reintroduced at the evaporative crystallization step e).

9. The process as claimed in claim 5 , wherein the mother liquor stream (3 bis) is reintroduced at step a) of providing the starting solution of the internal dehydration product of the hexitol and/or at step b) of distilling the solution of the internal dehydration product of the hexitol, after having removed therefrom the crystallization solvent.

10. The process as claimed in claim 1 , wherein the entire process is carried out continuously.

11. The process as claimed in claim 1 , wherein the hexitol is chosen from sorbitol, mannitol and iditol, and mixtures thereof.

12. The process as claimed in claim 1 , wherein the 1,4:3,6-dianhydrohexitol is isosorbide, isomannide, isoidide or mixtures thereof.

Assignees

• Roquette Freres

Inventors

• Wyart Hervé
• Lesur Thomas
• Ibert Mathias

Classifications

• C07D493/04 Primary

  Ortho-condensed systems · CPC title