Glycerol treatment process

• US 20110237773A1
• Filed: 12/07/2009
• Published: 09/29/2011
• Est. Priority Date: 12/08/2008
• Status: Abandoned Application

• Current Assignee: Solvay SA (Solvac SA)
• Original Assignee: Solvay SA (Solvac SA)
• Inventors: Gilbeau, Patrick
• Application Number:
  US13/131,516
• Publication Number:
  US 20110237773A1
• Time in Patent Office: Days
• US Class Current: 528/421
• CPC Class Codes: C07C 29/62 by introduction of halogen; by substitution of halogen atoms by other halogen atoms
• CPC Class Codes: C07C 29/88 by treatment giving rise to a chemical modification of at least one compound chemisorption C07C29/76
• CPC Class Codes: C07C 31/225 Glycerol
• CPC Class Codes: C07C 31/36 the halogen not being fluorine
• CPC Class Codes: C08G 59/022 characterised by the preparation process or apparatus used
• CPC Class Codes: C08G 59/025 characterised by the purification methods used
• CPC Class Codes: C08G 59/04 of polyhydroxy compounds with epihalohydrins or precursors thereof

Abstract

Process for treating a glycerol product contaminated with at least one glycerol alkyl ether in order to convert at least one portion of the glycerol alkyl ether to glycerol, in which the glycerol product is subjected to a reaction with at least one halo-de-alkoxylation agent introduced during the treatment, and in which the molar ratio of the total amount of the halo-de-alkoxylation agent to the total amount of the glycerol alkyl ether present in the glycerol product before the treatment, is greater than or equal to 0.1 and less than or equal to 1 000 000.

Claims

1. A process for treating a glycerol product contaminated with at least one glycerol alkyl ether in order to convert at least one portion of the glycerol alkyl ether to glycerol, in which the glycerol product is subjected to a reaction with at least one halo-de-alkoxylation agent, and in which the molar ratio of the total amount of the halo-de-alkoxylation agent which is introduced during the treatment to the total amount of the glycerol alkyl ether present in the glycerol product before the treatment, is greater than or equal to 0.1 and less than or equal to 1 000 000.

2. The process according to claim 1, in which, in addition, at least one compound is formed that contains the alkyl group of the glycerol alkyl ether and that is neither a glycerol alkyl ether nor an alkyl ether of a glycerol halohydrin.

3. The process according to claim 1, wherein the glycerol alkyl ether is chosen from the group consisting of glycerol alkyl monoethers, glycerol alkyl diethers, glycerol alkyl triethers, and any mixture of at least two of them, and in which the alkyl groups of the glycerol alkyl ethers are selected independently from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl groups, and any combination of at least two of them.

4. The process according to claim 1, wherein the content of alkyl ether in the glycerol product before the treatment is greater than or equal to 0.001 g per kg of contaminated glycerol product and less than or equal to 100 g per kg of contaminated glycerol product.

5. The process according to claim 1, wherein the halo-de-alkoxylation agent contains at least one hydrogen halide.

6. The process according to claim 5, wherein the hydrogen halide contains hydrogen chloride.

7. The process according to claim 6, wherein the hydrogen chloride is used in the form of an aqueous solution, and wherein the amount of hydrogen chloride relative to the sum of the amounts of hydrogen chloride and of water is higher than or equal to 40% by weight.

8. The process according to claim 6, wherein the hydrogen chloride is used in gas form optionally in admixture with at least one other gaseous compound selected from the group consisting of nitrogen, oxygen, carbon dioxide, steam, a noble gas, and any mixture of at least two of them.

9. The process according to claim 8, wherein the hydrogen chloride in the gas mixture is higher than or equal to 99% mol.

10. The process according to claim 2, wherein the compound containing the alkyl group of the glycerol alkyl ether is an alkyl halide.

11. The process according to claim 1, being carried out in batch or continuous mode, wherein the reaction is performed under at least one of the following conditions:

at a temperature greater than or equal to 20°

C. and less than or equal to 160°

C.;

at a pressure greater than or equal to 0.3 bar absolute and less than or equal to 100 bar absolute;

for a time greater than or equal to 1 h and less than or equal to 100 h when the process is carried out in batch mode, or for a residence time greater than or equal to 1 h and less than or equal to 100 h when the process is carried out in continuous mode.

12. A process for manufacturing an epoxide, comprising:

a) a first step of treating a glycerol product contaminated with at least one glycerol alkyl ether according to the process of claim 1;

b) optionally, a second step in which at least one portion of the glycerol present at the end of step a) is subjected to at least one separation operation so as to separate the glycerol from the compound(s) containing the alkyl group of the glycerol alkyl ether;

c) a third step in which at least one portion of the treated glycerol product obtained at the end of step a) and/or at least one portion of the separated glycerol obtained at the end of step b) is subjected to a reaction with hydrogen chloride so as to convert at least one portion of the glycerol to glycerol chlorohydrin,

in which the glycerol chlorohydrin thus obtained is subjected to a dehydrochlorination reaction.

13. The process according to claim 12, wherein the halo-de-alkoxylation agent used in step a) and the hydrogen chloride used at step c) are gaseous hydrogen chloride.

15. A process for manufacturing an epoxy derivative selected from the group consisting of epoxy resins, glycidyl ethers, glycidyl esters, glycidyl amides, glycidyl imides, glycidyl amines, products that can be used as coagulants, wet-strength resins, cationization agents, flame retardants, ingredients for detergents, epichlorohydrin elastomers, halogenated polyethers-polyols, monochloropropanediol and any mixtures of at least two of them, comprising carrying out the process according to claim 13, wherein the epoxide is epichlorohydrin and wherein the epichlorohydrin is subjected to a reaction with at least one compound selected from the group consisting of monoalcohols, monocarboxylic acids, polyols, polyamines, amino alcohols, polyimides, polyamides, polycarboxylic acids, ammonia, amines, polyaminoamides, polyimines, amine salts, phosphoric acid, phosphoric acid salts, phosphorus oxychlorides, phosphoric acid esters, phosphonic acids, esters of phosphonic acids, salts of phosphonic acids, phosphinic acids, esters of phosphinic acids, salts of phosphinic acids, phosphine oxides, phosphines, ethoxylated alcohols, alkylene or phenylene oxides, and mixtures of at least two of them, or wherein epichlorohydrin is subjected to a homopolymerization reaction, or wherein epichlorohydrin is subjected to a reaction selected from the group consisting of oligomerisation, co-oligomerisation, condensation, dehydrochlorination, and hydrolysis, with water, or with a di- or polyhydroxylated compound which may optionally be halogenated and/or have ether oxide bonds and/or double bonds capable of being halogenated in a subsequent stage, or wherein epichlorohydrin is subjected to a reaction with water.

16. The process according to claim 12, wherein the epoxide is epichlorohydrin, and wherein the glycerol chlorohydrin is dichloropropanol.

14. (canceled)