Process for the manufacture of a 1,2-epoxide and a device for carrying out said process

• US 8,859,790 B2
• Filed: 01/26/2011
• Issued: 10/14/2014
• Est. Priority Date: 02/02/2010
• Status: Expired due to Fees

• Current Assignee: Evonik Degussa GmbH
• Original Assignee: Momentive Specialty Chemicals Incorporated (Momentive Performance Materials Holdings LLC)
• Inventors: Muppa, Prasad, Postma, Ron, Van Den Berg, Bart, Stock, Juergen, Wiederhold, Holger, Rausch, Hans, Schallenberg, Jorg, Bernhardt, Stefan
• Primary Examiner(s): Kosar, Andrew D
• Assistant Examiner(s): COVINGTON, RAYMOND K
• Application Number:
  US13/574,715
• Publication Number:
  US 20130023680A1
• Time in Patent Office: 1,357 Days
• Field of Search: 549/531, 502/200, 502/324
• US Class Current: 549/531
• CPC Class Codes: B01D 17/0208 by sedimentation
• CPC Class Codes: B01F 25/431 Straight mixing tubes with baffles or obstructions that do not cause substantial pressure drop; Baffles therefor
• CPC Class Codes: B01J 19/2435 Loop-type reactors
• CPC Class Codes: B01J 2219/00094 Jackets
• CPC Class Codes: B01J 2231/72 Epoxidation
• CPC Class Codes: B01J 4/00 Feed or outlet devices; Feed or outlet control devices feed or outlet devices for pressure vessels B01J3/02 ; feeding of particles into and evacuation of particles out of the reactor B01J8/0015
• CPC Class Codes: C07D 301/03 by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
• CPC Class Codes: C07D 301/12 with hydrogen peroxide or inorganic peroxides or peracids
• CPC Class Codes: C07D 301/14 with organic peracids, or salts, anhydrides or esters thereof
• CPC Class Codes: Y02P 20/582 Recycling of unreacted starting or intermediate materials

Abstract

Apparatus and processes are provided for forming epoxide compounds. In one embodiment, a process for the manufacture of an epoxide is provided including adding an oxidant, a water-soluble manganese complex and a terminal olefin to form a multiphasic reaction mixture, reacting the terminal olefin with the oxidant in the multiphasic reaction mixture having at least one organic phase in the presence of the water-soluble manganese complex, separating the reaction mixture into the at least one organic phase and an aqueous phase, and reusing at least part of the aqueous phase. The invention is also related to a device for performing the above process.

Claims

1. A process for the manufacture of an epoxide, comprising:

a) adding an oxidant, a water-soluble manganese complex, and a terminal olefin to form a multiphasic reaction mixture comprising at least one organic phase and an aqueous phase, wherein the water-soluble manganese complex is a mononuclear species of the general formula (I);

[LMnX₃]Y 

 

(I)

 

or a binuclear species of the general formula (II);

[LMn(μ

−

X)₃MnL](Y)_n 

 

(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, and wherein Y is a non-coordinating counter ion;

b) reacting the terminal olefin with the oxidant in the multiphasic reaction mixture having at least one organic phase in the presence of the water-soluble manganese complex;

c) separating the at least one organic phase and the aqueous phase, wherein the aqueous phase comprises the water-soluble manganese complex; and

d) reusing at least part of the aqueous phase.

2. The process according to claim 1, wherein step a) comprises the sub steps of:

a1) adding to the reaction mixture the oxidant and the water-soluble manganese complex as aqueous phase components; and

a2) dispersing the terminal olefin into the aqueous phase.

3. The process of claim 1, wherein the reaction takes place in an aqueous phase of the multiphasic reaction mixture.

4. The process of claim 1, wherein the reusing at least part of the aqueous phase comprises at least a portion of the aqueous phase obtained in step c) is recycled into step a).

5. The process of claim 2, wherein the water recycle ratio of aqueous components to reused aqueous phase is in the range of from 10:

1 to 1;

10.

6. The process according to claim 5, wherein the water recycle ratio is about 1:

3.5.

7. The process of claim 1, wherein the molar ratio of terminal olefin to oxidant is in the range of from 12:

1 to 1;

1.

8. The process of claim 1, wherein the terminal olefin has a maximum solubility at 20°

C. of about 100 g/L.

9. The process of claim 1, wherein the aqueous phase further comprises a buffer system and a pH in the range of from 1 to 8, and the buffer is added to the reaction mixture as an aqueous component.

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

5°

C. to 40°

C.

11. The process of claim 1, wherein the terminal olefin is selected from allyl bromide, allyl chloride and allyl acetate and the reaction is carried out at temperatures in the range from −

5°

C. to 40°

C.

12. The process of claim 1, wherein the terminal olefin is propylene and the reaction is carried out at temperatures in the range from −

5°

C. to 40°

C.

13. The process of claim 1, wherein the molar ratio of water-soluble manganese complex to oxidant is in the range of from 1:

10 to 1;

10,000,000.

14. The process of claim 1, wherein the oxidant is hydrogen peroxide or a precursor thereof.

15. The process of claim 1, wherein the aqueous phase comprises a pH in the range of from 1 to 5.

16. The process of claim 1, wherein each X is independently 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, and R is selected from the group consisting of C₁-C₂₀ alkyl, C₁-C₂₀ cycloalkyl, C₁-C₂₀ aryl, benzyl and combinations thereof.

17. The process of claim 1, wherein each μ

−

X is independently 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, and R is selected from the group consisting of C₁-C₂₀ alkyl, C₁-C₂₀ cycloalkyl, C₁-C₂₀ aryl, benzyl and combinations thereof.

18. The process of claim 1, wherein Y is a non-coordinating counter ion selected from the group consisting of RO⁻

, Cl⁻

, Br⁻

, I⁻

, F⁻

, SO₄²⁻

, RCOO⁻

, PF₆⁻

, acetate, tosylate, triflate, and a combination thereof, and R is selected from the group consisting of C₁-C₂₀ alkyl, C₁-C₂₀ cycloalkyl, C₁-C₂₀ aryl, benzyl and combination thereof.