Product containing epichlorohydrin, its preparation and its use in various applications

• US 8,378,130 B2
• Filed: 06/11/2008
• Issued: 02/19/2013
• Est. Priority Date: 06/12/2007
• Status: Active Grant

• Current Assignee: Solvay SA (Solvac SA)
• Original Assignee: Solvay SA (Solvac SA)
• Inventors: Boulos, Noel, Krafft, Philippe, Gilbeau, Patrick, Balthasart, Dominique
• Primary Examiner(s): Listvoyb, Gregory
• Application Number:
  US12/663,744
• Publication Number:
  US 20100179300A1
• Time in Patent Office: 1,714 Days
• Field of Search: 549/518, 549/516, 549/524, 549/525
• US Class Current: 549/541
• CPC Class Codes: C07D 301/27 Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms macromolecular compounds C08
• CPC Class Codes: C07D 301/28 by reaction with hydroxyl radicals
• CPC Class Codes: C07D 303/12 with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
• CPC Class Codes: C07F 9/65502 the oxygen atom being part of a three-membered ring
• CPC Class Codes: C08G 59/00 Polycondensates containing more than one epoxy group per molecule low-molecular-weight polyepoxy compounds C07; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
• CPC Class Codes: C08G 59/02 Polycondensates containing more than one epoxy group per molecule

Abstract

Product containing epichlorohydrin and at least one alkyl glycidyl ether in an amount of less than 0.1 g/kg of product. Use of the product containing epichlorohydrin in the manufacture of epoxy resins, of glycidyl ethers, of glycidyl esters, of glycidyl amides, of glycidyl imides, of products that will be used in food and drink applications, of cationization agents, and of flame retardants, of products which will be used as detergent ingredient and of epichlorohydrin oligomers.

Claims

1. A product, comprising epichlorohydrin and an alkyl glycidyl ether in a positive amount of less than or equal to 0.08 g/kg of product,

wherein the content of epichlorohydrin is greater than or equal to 900 g/kg of product, and

wherein the alkyl glycidyl ether is methyl glycidyl ether.

2. The product according to claim 1, wherein the content of epichlorohydrin is greater than or equal to 950 g/kg of product.

3. The product according to claim 1, obtained by dehydro chlorination of a composition containing dichloropropanol and at least one chloroalkoxypropanol.

4. The product according to claim 3, wherein the chloro alkoxy propanol is selected from the group consisting of 2-chloro-3-alkoxy-propane-1-ol, 1-chloro-3-alkoxy-propane-2-ol, and mixtures thereof.

5. The product according to claim 3, wherein the composition containing dichloropropanol is obtained by hydrochlorination of a compound containing glycerol and at least one glycerol alkyl ether in an amount of less than or equal to 0.6 g/kg of compound.

6. A process for producing the product according to claim 1, comprising:

(a) reacting a composition comprising glycerol with hydrogen chloride in the presence of a carboxylic acid, in order to obtain a composition comprising dichloropropanol and at least one chloro alkoxy propanol in an amount of less than or equal to 0.1 g/kg of composition

(b) reacting the composition in (a) with a basic agent in order to obtain said product.

7. The process according to claim 6, further comprising:

(c) a vegetable fat or oil is reacted with an alcohol to obtain the composition comprising glycerol, under such conditions that ethers of glycerol are formed and are not separated from glycerol,

(d) the composition comprising glycerol obtained in (c) is further subjected to at least one treatment, optionally under reduced pressure, selected from the group consisting of evaporative concentration, evaporative crystallization, distillation, fractional distillation, stripping, and liquid-liquid extraction, in order to obtain a composition comprising glycerol and at least one glycerol alkyl ether in an amount that is lower than or equal to 0.6 g/kg.

8. The product according to claim 1, wherein the methyl glycidyl ether is present in an amount of less than or equal to 0.06 g/kg of product.

9. The product according to claim 1, wherein the methyl glycidyl ether is present in an amount of less than or equal to 0.04 g/kg of product.

10. The product according to claim 1, wherein the methyl glycidyl ether is present in an amount of less than or equal to 0.01 g/kg of product.

11. The product according to claim 1, further comprising cyclopentanone.

12. The product according to claim 11, comprising cyclopentanone in an amount greater than or equal to 0.1 mg/kg of product and less than or equal to 0.5 g/kg of product.

13. The product according to claim 1, wherein the content of epichlorohydrin is greater than or equal to 999 g/kg of product.

14. The product according to claim 1, wherein the content of epichlorohydrin is greater than or equal to 999.5 g/kg of product.

15. The product according to claim 3, wherein the chloroalkoxypropanol is chloromethoxypropanol.

16. The product according to claim 4, wherein the chloroalkoxypropanol is selected from the group consisting of 2-chloro-3-methoxy-propane-1-ol, 1-chloro-3-methoxy-propane-2-ol, and mixtures thereof.

17. The product according to claim 5, wherein the glycerol alkyl ether is glycerol methyl ether.

18. The process according to claim 6, wherein the chloro alkoxy propanol is chloromethoxypropanol.

19. The process of claim 7, wherein the glycerol alkyl ether is glycerol methyl ether.