PROCESS FOR THE MANUFACTURE OF EPICHLOROHYDRIN

• US 20110137055A1
• Filed: 07/09/2009
• Published: 06/09/2011
• Est. Priority Date: 08/01/2008
• Status: Active Grant

• Current Assignee: Westlake Epoxy Incorporated (TTWF LP)
• Original Assignee: Hexion Incorporated (Hexion Intermediate Holding 2, Inc.)
• Inventors: Muppa, Prasad, Postma, Ron
• Granted Patent: US 8,802,873 B2
• Time in Patent Office: Days
• US Class Current: 549/531
• CPC Class Codes: B01J 21/00 Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
• CPC Class Codes: B01J 23/34 Manganese
• CPC Class Codes: C07D 255/02 not condensed with other rings
• CPC Class Codes: C07D 301/12 with hydrogen peroxide or inorganic peroxides or peracids

Abstract

The invention relates to a process for the manufacture of epichlorohydrin (“ECH”)

• • by catalytic oxidation of allyl chloride (“AC”) with an oxidant wherein the catalytic oxidation is performed in an aqueous reaction medium, wherein a water-soluble manganese complex is used as oxidation catalyst,
  • followed by the isolation of epichlorohydrin.

Claims

1. A process for the manufacture of epichlorohydrin, comprising:

reacting allyl chloride (“

AC”

) with an oxidant in the presence of a catalyst in an aqueous reaction medium, wherein the catalyst comprises a water-soluble manganese complex and the molar ratio of allyl chloride to oxidant is from 1;

1 to 10;

1; and

isolating an epichlorohydrin product.

2. The process of claim 1, wherein the epichlorohydrin product or a part of the epichlorohydrin product is isolated as an organic phase, wherein the organic phase comprises epichlorohydrin product or a mixture of allyl chloride and epichlorohydrin product.

3. The process of claim 1, wherein the catalyst comprises a mononuclear manganese complex of the general formula (I):

[LMnX₃]Y 

 

(I)

or a binuclear manganese complex of the general formula (II);

[LMn(μ

−

X)₃MnL]Y₂ 

 

(II)

wherein Mn is a manganese;

L or each L independently is a polydentate ligand;

each X independently is a coordinating species; and

each μ

−

X independently is a bridging coordinating species, selected from the group consisting of;

RO⁻

, Cl⁻

, Br⁻

, I⁻

, F⁻

, NCS⁻

, N₃⁻

, I₃⁻

, NH₃, NR₃, RCOO⁻

, RSO₃⁻

, RSO₄⁻

, OH⁻

, O²⁻

, O₂²⁻

, HOO⁻

, H₂O, SH⁻

, CN⁻

, OCN⁻

, and S4²⁻

and combinations thereof, wherein R is a C₁-C₂₀ radical selected from the group consisting of alkyl, cycloalkyl, aryl, benzyl and combinations thereof, and Y is an oxidatively-stable counterion.

4. The process of claim 3, wherein each polydentate ligand is independently selected from acyclic compounds containing at least 7 atoms in the backbone or cyclic compounds containing at least 9 atoms in the ring, wherein each polydentate ligand having 3 nitrogen atoms with the nitrogen atoms separated by at least two carbon atoms.

5. The process of claim 3, wherein a binuclear water-soluble manganese complex is used as the catalyst.

6. The process of claim 1, wherein the catalyst is used in a molar ratio of the catalyst (Mn) to the allyl chloride from 1:

10 to 1;

10,000,000.

7. The process of claim 1, wherein the aqueous reaction medium is a water phase.

8. The process of claim 1, wherein the aqueous reaction medium further comprises a buffer system and a pH in the range of from 2.5 to 8.0.

9. The process of claim 1, wherein the reaction is carried out at temperatures in the range from −

5°

C. and 30°

C.

10. The process of claim 1, wherein the oxidant is hydrogen peroxide.

11. The process of claim 10, wherein the hydrogen peroxide is used as an aqueous solution in a concentration of from 15% to 98%.

12. The process of claim 1, wherein the allyl chloride and the oxidant are reacted at a molar ratio of the allyl chloride to the oxidant in the range from 1:

0.1 to 1;

0.8.

13. The process of claim 1, wherein the oxidant is added to the aqueous reaction medium at a rate about equal to the reaction rate.

14. The process of claim 1, wherein the reaction is performed in a batch process, in a continuous process or in a semi-continuous process.

15. The process of claim 1, wherein the reaction is carried out based on the following mass balance:

epichlorohydrin of about 11000 kg/h,

allyl chloride of about 9100 kg/h,

H₂O₂ (35%) of about 6457 kg/h, and

H₂O of about 2140 kg/h.