Method for making an epoxide

• US 8,519,198 B2
• Filed: 03/22/2012
• Issued: 08/27/2013
• Est. Priority Date: 05/20/2005
• Status: Expired due to Fees

• Current Assignee: Solvay SA (Solvac SA)
• Original Assignee: Solvay SA (Solvac SA)
• Inventors: Gilbeau, Patrick
• Primary Examiner(s): Price, Elvis O
• Application Number:
  US13/427,082
• Publication Number:
  US 20120199786A1
• Time in Patent Office: 523 Days
• Field of Search: 514/724, 568/841
• US Class Current: 568/841
• CPC Class Codes: C07C 29/62 by introduction of halogen; by substitution of halogen atoms by other halogen atoms
• CPC Class Codes: C07C 29/76 by physical treatment
• CPC Class Codes: C07C 29/82 by azeotropic distillation
• CPC Class Codes: C07C 31/36 the halogen not being fluorine
• CPC Class Codes: C07D 301/26 Y being hydrogen
• CPC Class Codes: C07D 303/08 with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals

Abstract

A mixture of compounds containing 1,3-dichloropropan-2-ol, 2,3-dichloropropan-1-ol, and a halogenated ketone, where the halogenated ketone content of the mixture is at least 0.0001% by weight and less than or equal to 0.1% by weight relative to the 1,3-dichloropropan-2-ol and 2,3-dichloropropan-1-ol.

Claims

1. A mixture of compounds comprising 1,3-dichloropropan-2-ol, 2,3-dichloropropan-1-ol, and a halogenated ketone, wherein the halogenated ketone content of said mixture is at least 0.0001% by weight and less than or equal to 0.1% by weight relative to the 1,3-dichloropropan-2-ol and 2,3-dichloropropan-1-ol.

2. The mixture of compounds according claim 1, whose halogenated ketone content is of less than or equal to 0.04% by weight.

3. The mixture of compounds according claim 1, whose halogenated ketone content is of less than or equal to 0.005% by weight.

4. The mixture of compounds according to claim 1, wherein the halogenated ketone contains 3 to 18 carbon atoms and in which one or more hydrogen atoms have been replaced by a halogen atom.

5. The mixture of compounds according to claim 4, wherein the halogenated ketone is a chlorinated ketone.

6. The mixture of compounds according to claim 5, wherein the chlorinated ketone is chloroacetone.

7. The mixture of compounds according to claim 1, containing more than 50% by weight of 1,3-dichloropropan-2-ol and 2,3-dichloropropan-1-ol.

8. The mixture of compounds according to claim 1, containing more than 50% by weight of 1,3-dichloropropan-2-ol and 2,3-dichloropropan-1-ol and wherein the halogenated ketone is chloroacetone.

9. The mixture of compounds according to claim 1, further comprising water.

10. The mixture of compounds according to claim 1, wherein the mass ratio between 1,3-dichloropropan-2-ol and 2,3-dichloropropan-1-ol is greater than or equal to 0.4.

11. A process for preparing the mixture of compounds according to claim 1, by hydrochlorinating glycerol, wherein during the process a halogenated ketone is formed as a by-product and which comprises at least one treatment to remove at least part of the halogenated ketone formed.

12. The process according to claim 11, wherein the glycerol is obtained starting from renewable raw materials.

13. The process according to claim 11, wherein the glycerol is obtained during the production of biodiesel or during conversions of animal or vegetable oils and fats, the conversions being selected from saponification, transesterification and hydrolysis reactions.

14. The process according to claim 13, wherein the transesterification reaction is performed in the presence of a heterogeneous catalyst.

15. The process according to claim 11, wherein the treatment to remove at least part of the halogenated ketone comprises a distillation, evaporation and/or stripping, in the presence of water, enabling the removal of a fraction composed essentially of water and halogenated ketone and the recovery of the mixture of compounds having a reduced halogenated ketone content.

16. The process according to claim 15, wherein the treatment to remove at least part of the halogenated ketones is an azeotropic distillation in the presence of water.

17. The process according to claim 16, wherein the halogenated ketone is chloroacetone.