Epichlorohydrin-based product and process for manufacturing this product

• US 6,288,248 B1
• Filed: 11/25/1998
• Issued: 09/11/2001
• Est. Priority Date: 11/27/1997
• Status: Expired due to Term

• Current Assignee: Solvay SA (Solvac SA)
• Original Assignee: Solvay SA (Solvac SA)
• Inventors: Gilbeau, Patrick, Catinat, Jean-Pierre, Strebelle, Michel
• Primary Examiner(s): Rotman, Alan L.
• Assistant Examiner(s): DESAI, RITA J
• Application Number:
  US09/199,570
• Time in Patent Office: 1,021 Days
• Field of Search: 549/516, 549/524, 549/525, 549/518
• US Class Current: 549/518
• CPC Class Codes: C07D 301/12 with hydrogen peroxide or inorganic peroxides or peracids
• CPC Class Codes: C07D 301/32 Separation; Purification
• CPC Class Codes: C07D 303/08 with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals

Abstract

Epichlorohydrin-based product containing at least 99.9% by weight of epichlorohydrin and a total amount of chloro impurities of less than or equal to 150 ppm by weight, and process for manufacturing this product by reaction of allyl chloride with a peroxide compound in the presence of water, a catalyst and a diluent in at least one reactor, and separation of the epichlorohydrin formed.

Claims

1. A purified epichlorohydrin product produced by reaction between allyl chloride and a peroxide in water and methanol, during which reaction methyl glycidyl ether is produced in a contaminating amount, wherein said product comprises at least 99.9% by weight of epichlorohydrin;

a total amount of chloro impurities of less than or equal to 150 ppm by weight and an amount of methyl glycidyl ether which is less than said contaminating amount.

2. Product according to claim 1, further comprising methyl glycidyl ether which is present in an amount of less than or equal to 250 ppm by weight.

3. Product according to claims 1 or 2, further comprising 2-methoxy-1-propanol which is present in an amount of less than or equal to 100 ppm by weight.

11. Product according to claim 2, containing an amount of 2-methoxy-1-propanol of less than or equal to 100 ppm by weight.

17. Epichlorohydrin-based product according to claim 1, in which the chloro impurities are by-products formed by reaction between epichlorohydrin and water or optionally the diluent.

18. Epichlorohydrin-based product according to claim 17, in which the chloro impurities are 1-chloro-2-methoxy-3-propanol, 1,3-dichloro-2-propano, 2,3-dichloropropanol and 1-chloro-2,3-dihydroxypropane.

4. Process for manufacturing an epichlorohydrin-based product containing at least 99.9% by weight of epichlorohydrin and a total amount of chloro impurities of less than or equal to 150 ppm by weight, which comprises

a) reacting allyl chloride with a peroxide compound in the presence of water, a catalyst which is a titanium silicalite, and a diluent in at least one reactor, to produce a reaction mixture comprising epichlorohydrin contaminated with an amount of methyl glycidyl ether and

b) subjecting the reaction mixture of a) to a treatment to separate out the epichlorohydrin;

and

c) recovering a purified epichlorohydrin product with a reduced amount of methyl glycidyl ether, compared to that in said reaction mixture.

5. Process according to claim 4, in which the epichlorohydrin separation treatment (b) is carried out by extraction using an extraction solvent and in which an extract containing at least some of the extraction solvent, at least 10% of the epichlorohydrin produced, possibly an excess of allyl chloride and traces of the diluent, on the one hand, and a raffinate containing at least some of the diluent, at least some of the water, and traces of epichlorohydrin and of by-products, on the other hand, are collected after extraction in step (b).

6. Process according to claim 5, in which the extract is subjected to a distillation treatment (c) in order to separate a first fraction containing the epichlorohydrin produced, the excess allyl chloride, if any, and traces of diluent from a second fraction containing the extraction solvent, which is recycled into the extraction step (b).

7. Process according to claim 6, in which the first fraction obtained in the distillation step (c) is subjected to a distillation treatment (d) in order to remove the excess allyl chloride, if any, and the traces of diluent, which are recycled into the epoxidation step (a), and an epichlorohydrin-based product is collected and then dried in an azeotropic column.

8. Process according to claim 5, in which the raffinate obtained in the extraction step (b) is subjected to a distillation (e) in order to separate a first fluid containing the water and by-products from a second fluid containing the diluent and traces of epichlorohydrin, which are recycled into the epoxidation step (a).

9. Process according to claim 8, in which the first fluid is subjected to a purification treatment (f) in order to remove the by-products and in which the purification treatment is carried out by distillation in the presence of an organic compound or by extraction using an extraction liquid.

10. Process according to claim 4, in which the diluent is methanol and the peroxide compound is hydrogen peroxide.

12. Process according to claim 5, in which the diluent is methanol and the peroxide compound is hydrogen peroxide.

13. Process according to claim 6, in which the diluent is methanol and the peroxide compound is hydrogen peroxide.

14. Process according to claim 7, in which the diluent is methanol and the peroxide compound is hydrogen peroxide.

15. Process according to claim 8, in which the diluent is methanol and the peroxide compound is hydrogen peroxide.

16. Process according to claim 9, in which the diluent is methanol and the peroxide compound is hydrogen peroxide.

19. Process for manufacturing an epichlorohydrin-based purified product containing at least 99.9% by weight of epichlorohydrin and a total amount of chloro impurities of less than or equal to 150 ppm by weight, selected from the group consisting of 1-chloro-2-methoxy-3-propanol, 1,3-dichloro-2-propano, 2,3-dichloropropanol 1-chloro-2,3-dihydroxypropane and admixtures thereof, which comprises

a) reacting allyl chloride with a peroxide compound in the presence of water, a catalyst which is a titanium silicalite, and methanol in at least one reactor, to produce a reaction mixture comprising epichlorohydrin contaminated with an amount of methyl glycidyl ether and an amount of chloro impurities;

and

b) subjecting the reaction mixture of a) to a treatment to separate out the epichlorohydrin; and

c) recovering a purified epichlorohydrin product with a reduced amount of methyl glycidyl ether, compared to that in said reaction mixture;

d) distilling the epichlorohydrin to reduce the amount of chloro impurities.

20. The process of claim 19, wherein the peroxide compound comprises hydrogen peroxide.

21. The process of claim 19, wherein the reacting of a) is undertaken at a temperature of less than 150°

C.

22. The process of claim 19, wherein the reacting of a) is undertaken at a temperature of 0 to 120°

C.

23. A purified epichlorohydrin product produced by reaction between allyl chloride and a peroxide in water and methanol, during which reaction methyl glycidyl ether and chloro impurities are produced in a contaminating amount,

wherein said product comprises epichlorohydrin, chloro impurities and methylglycidyl ether,

wherein the product comprises at least 99.9% by weight of epichlorohydrin;

a total amount of chloro impurities of less than or equal to 150 ppm by weight and an amount of methyl glycidyl ether which is less than said contaminating amount.

24. A purified epichlorohydrin product produced by reaction between allyl chloride and a peroxide in water and methanol, during which reaction methyl glycidyl ether and chloro impurities are produced in a contaminating amount,

wherein said product comprises epichlorohydrin, methylglycidyl ether, and chloro impurities selected from the group consisting of 1-chloro-2-methoxy-3-propanol, 1,3-dichloro-2-propano, 2,3-dichloropropanol 1-chloro-2,3-dihydroxypropane and admixtures thereof,

wherein the product comprises at least 99.9% by weight of epichlorohydrin;

a total amount of chloro impurities of less than or equal to 150 ppm by weight and an amount of methyl glycidyl ether which is less than said contaminating amount.