Method for preparation of 1,4-sorbitan

Patent metadata

Field	Value
Publication number	US-11174236-B2
Application number	US-201917265939-A
Country	US
Kind code	B2
Filing date	Aug 26, 2019
Priority date	Aug 27, 2018
Publication date	Nov 16, 2021
Grant date	Nov 16, 2021

Abstract

The invention discloses a method for preparation of 1,4-sorbitan by dehydration of D-sorbitol, wherein one equivalent of water is removed and a cyclization occurs, followed by a treatment with ethanol and isopropanol.

First claim

The invention claimed is:

1. A method for preparation of 1,4-sorbitan with four consecutive steps STEP1, STEP2, STEP3 and STEP4, wherein
in STEP1 D-sorbitol is dehydrated in a dehydration reaction DEHYDREAC in the presence of p-toluenesulfonic acid and tetrabutylammonium bromide,
the reaction time TIME1-1 of DEHYDREAC is from 3 to 12 h;
DEHYDREAC is done at a temperature TEMP1, TEMP1 is from 95 to 130° C.,
DEHYDREAC is done at a pressure PRESS1 of 500 mbar or below,
STEP1 provides a mixture MIX1;

in STEP2 ethanol is mixed with MIX1, STEP2 provides a mixture MIX2;
in STEP3 isopropanol is mixed with MIX2, STEP3 provides a mixture MIX3;
in STEP4 1,4-sorbitan is isolated from MIX3.

2. The method according to claim 1 , wherein
the p-toluene sulfonic acid is used in form of p-toluenesulfonic acid monohydrate.

3. The method according to claim 1 , wherein
DEHYDREAC is done neat, wherein only the three components D-sorbitol, p-toluenesulfonic acid and tetrabutylammonium bromide are used for and are charged for DEHYDREAC.

4. The method according to claim 1 , wherein
DEHYDREAC is done at a temperature TEMP1, TEMP1 is from 95 to 120° C.

5. The method according to claim 1 , wherein
the reaction time TIME1-1 of DEHYDREAC is from 4 to 12 h.

6. The method according to claim 1 , wherein
DEHYDREAC is done at a pressure PRESS1 of 250 mbar or below.

7. The method according to claim 1 , wherein
water is removed during DEHYDREAC.

8. The method according to claim 1 , wherein
STEP2 is done at a temperature TEMP2 of from 60 to 90° C.

9. The method according to claim 1 , wherein
STEP3 is done at a temperature TEMP3-1 of from 10 to 30° C.

10. The method according to claim 1 , wherein
after the mixing of isopropanol, STEP3 comprises a cooling COOL3 of MIX3 to a temperature TEMP3-2 of from −5 to 5° C.

11. The method according to claim 1 , wherein
STEP3 comprises a stirring STIRR3 of MIX3, wherein STIRR3 is done for a time TIME3-2, wherein TIME3-2 is from 1 to 12 h.

12. The method according to claim 11 , wherein
STIRR3 is done after COOL3, wherein COOL3 comprises a cooling of MIX3 to a temperature TEMP3-2 of from −5 to 5° C.

13. The method according to claim 11 , wherein
STIRR3 is done at TEMP3-2, wherein TEMP3-2 is a temperature of from −5 to 5° C.

14. The method according to claim 1 , wherein
1,4-sorbitan is isolated in STEP4 from MIX3 by filtration.

15. The method according to claim 1 , wherein
STEP1, STEP2 and STEP3 are done consecutively in one and the same reactor.

16. A method for preparing prostaglandin analogues or Polysorbate comprising preparing 1,4-sorbitan according to claim 1 .

Assignees

• Lonza Guangzhou Pharmaceutical Ltd
• Lonza Ag

Inventors

• Wei Jieping
• Yang Yanling
• Shan Daniel
• Zhu Reta
• Hanselmann Paul
• Scherer Dieter

Classifications

• C07D307/20 Primary

  Oxygen atoms · CPC title