Epichlorohydrin, manufacturing process and use

• US 20100168379A1
• Filed: 06/11/2008
• Published: 07/01/2010
• Est. Priority Date: 06/12/2007
• Status: Active Grant

• Current Assignee: Solvay SA (Solvac SA)
• Original Assignee: Solvay SA (Solvac SA)
• Inventors: Boulos, Noel, Gilbeau, Patrick, Krafft, Philippe, Balthasart, Dominique
• Granted Patent: US 8,399,692 B2
• Time in Patent Office: Days
• US Class Current: 528/397
• 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, wherein the amount of trichloropropane is of less than 0.01 g of trichloropropane per kg of product, a process for manufacturing the product and its use in various applications.

Claims

1. - A product containing epichlorohydrin and trichloropropane, wherein the amount of trichloropropane is of less than 0.01 g of trichloropropane per kg of product.

2. - The product according to claim 1, containing in addition at least one or more of the following compounds:

(A) halogenated hydrocarbon compounds different from trichloropropane selected from the group consisting of chloropropene, trichloropropane, chloropropanol, chloropropenol, dichloropropene, dichloropropane, dichloropropanol, monochloropropanediol, chloroethers, monochlorobenzene, and any mixture of at least two of them, and/or

(B) compounds selected from the group consisting of acrolein, methyl glycidyl ether, chloroacetone, glycerol, hydroxyacetone, glycidol, cyclopentanone, and any mixture of at least two of them.

3. - The product according to claim 1, wherein the trichloropropane is selected from the group consisting of 1,2,3-trichloropropane, 1,1,1-trichloropropane, 1,1,3-trichloropropane, 1,1,2-trichloropropan;

and any mixtures of at least two of them.

4. - The product according to claim 1, containing more than 900 g of epichlorohydrin per kg of product.

5. - A process for manufacturing the product according to claim 1, comprising the following steps:

a) in a liquid reaction medium, a mixture of dichloropropanol containing 1,3-dichloro-2-propanol and 2,3-dichloro-1-propanol, in which the 1,3-dichloro-2-propanol content, relative to the sum of the 1,3-dichloro-2-propanol and 2,3-dichloro-1-propanol contents, is at least 10 wt %, is reacted with at least one basic compound in order to form epichlorohydrin and at least one salt;

b) at least one part of the liquid reaction medium from step a) is subjected to a settling operation in which a first fraction containing most of the epichlorohydrin which was contained in the part of the reaction medium from step a) before the settling operation is separated from a second fraction containing most of the salt which was contained in the part of the reaction medium from step a) before the settling operation; and

c) the first fraction separated in step b) is subjected to at least one supplementary treatment chosen from dilution, concentration, evaporation, distillation, stripping, liquid/liquid extraction and adsorption operations, alone or in combination.

6. - The process according to claim 5, wherein the reaction from step a) is carried out in at least two reaction zones, in which the volumes are assembled in a single jacket, and in which each of the reaction zones is supplied with the dichloropropanol mixture and/or with the basic compound.

7. - The process according to claim 5, wherein, in step c), the first fraction separated in step b) is subjected to at least one of the treatments selected from the group consisting of:

a treatment comprising at least one liquid/liquid extraction operation with an aqueous composition, and in which a first part containing most of the epichlorohydrin which was contained in the first fraction separated in step b) before the extraction operation, is separated from a second part containing most of the water;

a treatment comprising at least two distillation operations, of which at least one is an operation for drying by azeotropic distillation, and, at the end of the treatment, at least a first portion containing most of the epichlorohydrin which was contained in the first fraction before the distillation operations is obtained; and

a treatment which comprises at least one adsorption operation and at least one distillation operation, and, at the end of the treatment, at least a first cut containing most of the epichlorohydrin which was contained in the first fraction before the treatment is obtained.

8. - The process according to claim 5, wherein the first fraction separated in step b) contains dichloropropanol and said fraction is subjected to at least one of the treatments selected from the group consisting of:

a treatment comprising at least one liquid/liquid extraction operation with an aqueous composition, and in which a first part containing most of the epichlorohydrin which was contained in the first fraction separated in step b) before the extraction operation, is separated from a second part containing most of the water;

a treatment comprising at least two distillation operations, preferably at least two distillation operations of which at least one is an operation for drying by azeotropic distillation, and, at the end of the treatment, at least a first portion containing most of the epichlorohydrin which was contained in the first fraction before the distillation operations, and at least a second portion containing most of the dichloropropanol which was contained in the first fraction before the distillation operations, are obtained; and

a treatment which comprises at least one adsorption operation and at least one distillation operation, and, at the end of the treatment, at least a first cut containing most of the epichlorohydrin which was contained in the first fraction before the treatment, and at least a second cut containing most of the dichloropropanol which was contained in the first fraction before the treatment, are obtained.

9. - A method for the manufacture of epoxy resins or glycidyl esters or glycidyl ethers or glycidyl amides or glycidyl imides or coagulants or wet-strength resins or cationization agents or flame retardants or detergent ingredients or epichlorohydrin elastomers, comprising utilizing the product according to claim 1.

10. - The method according to claim 9, wherein the product containing epichlorohydrin is subjected to a reaction with a compound containing at least one active hydrogen atom, selected from the group consisting of monoalcohols, monocarboxylic acids, polyols, polyamines, amino alcohols, polyimides and amides, polycarboxylic acids, and mixtures thereof, in order to obtain an epoxy resin or a glycidyl ether or a glycidyl ester or glycidyl amides or glycidyl imides.

11. - The method according to claim 9 wherein the product containing epichlorohydrin is reacted with ammonia, an amine, a polyaminoamide, or a polyimine in order to obtain a coagulant, or wherein the product containing epichlorohydrin is reacted with a polyamine, a polyamide, or a polyaminoamide in order to obtain a wet-strength resin, or wherein the product containing epichlorohydrin is reacted with an amine, an amine salt, or a mixture thereof in order to obtain a cationization agent.

12. - The method according to claim 9, wherein the product containing epichlorohydrin is reacted with a compound selected from the group consisting of phosphoric acid, a phosphoric acid salt, a phosphorus oxychloride, a phosphoric acid ester, a phosphonic acid, a phosphonic acid ester, a phosphonic acid salt, a phosphinic acid, a phosphinic acid ester, a phosphinic acid salt, a phosphine oxide, a phosphine, and a mixture thereof, in order to obtain a flame retardant.

13. - The method according to claim 9, wherein the product containing epichlorohydrin is reacted with a monoalcohol containing from 12 to 16 carbon atoms or an ethoxylated alcohol or with an amine selected from the group consisting of linear alkylamines, branched alkylamines, cycloalkylamines, alkoxyamines, amino alcohols, cyclic amines containing at least one nitrogen atom in a ring structure, alkylenediamines, polyetherdiamines, and polyalkylenepolyaminesamine in order to produce a detergent ingredient.

14. - The method according to claim 9, wherein the product containing epichlorohydrin is reacted with an alkylene or phenylene oxide or with an alkylene or phenylene oxide and a glycidyl ether or homopolymerized in order to obtain an epichlorohydrin elastomer.

15. - A method for the manufacture of glycidyl amides or glycidyl imides or coagulants or wet-strength resins or cationization agents, or flame retardants, or of detergent ingredients, comprising utilizing epichlorohydrin obtained from glycerol.