Method for phase transfer synthesis of organic peroxides

• US 9,550,731 B2
• Filed: 05/22/2015
• Issued: 01/24/2017
• Est. Priority Date: 05/22/2014
• Status: Active Grant

• Current Assignee: Honeywell Federal Manufacturing & Technologies, LLC (Honeywell International Inc.)
• Original Assignee: Honeywell Federal Manufacturing & Technologies, LLC (Honeywell International Inc.)
• Inventors: Lampe, Matt, Robison, Thomas
• Primary Examiner(s): Parsa, Jafar
• Assistant Examiner(s): Bonaparte, Amy C
• Application Number:
  US14/719,364
• Publication Number:
  US 20150336886A1
• Time in Patent Office: 613 Days
• Field of Search: 558/263, 558/264, 568/558, 568/566, 568/567, 568/568, 568/578, 560/302
• US Class Current: 1/1
• CPC Class Codes: C07C 407/00 Preparation of peroxy compounds
• CPC Class Codes: C07C 409/38 the —O—O— group being bound between a >C=O group and a carbon atom, not further substituted by oxygen atoms, i.e. esters of peroxy acids

Abstract

Processes and systems for synthesizing organic peroxides are provided. One or more of the reactions described herein may be performed in a continuous reactor, optionally including at least one microscale reaction channel. Additionally, at least one phase transfer catalyst may be used to facilitate reaction of components present in a multiphase reaction mixture.

Claims

1. A process for synthesizing an organic peroxide, said process comprising:

reacting an organic hydroperoxide with at least one organic reactant in a multiphase reaction mixture to thereby form an organic peroxide,

wherein said multiphase reaction mixture comprises a first reaction phase and a second reaction phase at least partially immiscible in said first reaction phase, wherein said organic hydroperoxide is more miscible in one of said first and second reaction phases than in the other,

wherein said multiphase reaction mixture further comprises at least one catalyst for facilitating mass transfer between said first and said second reaction phases,

wherein said reacting is carried out in a reaction zone comprising at least two reaction channels, wherein each of said reaction channels includes no turns or bends having an angle greater than 80°

, wherein said reaction channels are arranged in a parallel configuration and each of said reaction channels has one or more of the following characteristics (i) through (iii)—

(i) a total channel volume of less than 75 mL;

(ii) a length-to-width ratio of at least 20;

1; and

/or

(iii) an average channel cross-sectional area of less than 10 mm².

2. The process of claim 1, wherein said organic reactant is more miscible in said first reaction phase and said organic hydroperoxide is more miscible in said second reaction phase, wherein said second reaction phase is an aqueous reaction phase.

3. The process of claim 2, wherein at least one of said first and said second reaction phases further comprises at least one pH modifying agent.

4. The process of claim 1, wherein said organic reactant comprises an organic halide.

5. The process of claim 1, wherein said reacting includes heating said multiphase reaction mixture to a temperature of at least 40°

C.

6. The process of claim 1, wherein said reacting includes cooling said multiphase reaction mixture to a temperature of less than 40°

C.

7. The process of claim 1, wherein said reacting comprises passing said multiphase reaction mixture through said reaction channel, wherein the Reynolds Number of the reaction mixture passing through said reaction channel is greater than 5,000.

8. The process of claim 1, wherein said reaction zone comprises at least 5 reaction channels.

9. The process of claim 8, wherein each of said reaction channels comprises a substantially straight reaction channel, wherein none of said reaction channels includes any bends or turns having an angle greater than 80°

.

10. The process of claim 1, wherein at least one of said reaction channels is a substantially straight reaction channel having a tortuosity factor of less than 1.5.

11. The process of claim 1, wherein said reaction channels have at least two of characteristics (i) through (iii).

12. The process of claim 1, wherein said reaction channels have all three of characteristics (i) through (iii).

13. A process for synthesizing an organic peroxide, said process comprising:

(a) providing a first reactant mixture comprising at least one organic reactant selected from the group consisting of alcohols, ketones, acids, esters, ethers, or halides or anhydrides thereof;

(b) providing a second reactant mixture comprising at least one pH modifying agent, wherein said first and said second reactant mixtures are at least partially immiscible with one another, and wherein at least one of said first and second reactant mixtures include at least one organic hydroperoxide;

(c) reacting at least a portion of said organic reactant with said organic hydroperoxide in a reaction zone in the presence of at least one phase transfer catalyst to thereby provide said organic peroxide,

wherein said reaction zone is at least partially defined within at least one continuous microscale reactor, wherein said microscale reactor includes at least two reaction channels, wherein each of said reaction channels includes no turns or bends having an angle greater than 80°

, and wherein said reaction channels are arranged in a parallel configuration.

14. The process of claim 13, wherein said second reactant mixture comprises said organic hydroperoxide and water.

15. The process of claim 13, wherein said pH modifying agent is a base.

16. The process of claim 13, further comprising combining said first reactant mixture and said second reactant mixture to form a combined reactant mixture and reacting said combined reactant mixture during said reacting of step (c).

17. The process of claim 13, wherein each of said channels is a substantially straight channel having a tortuosity factor of less than 1.5:

1.

18. A process for synthesizing an organic peroxide, said process comprising:

(a) reacting an organic hydroperoxide with at least one organic reactant in a multiphase reaction mixture in a reaction zone to thereby form an organic peroxide, wherein the average residence time of said reaction mixture in said reaction zone is less than 5 minutes; and

(b) recovering at least a portion of said organic peroxide from at least a portion of said reaction mixture,

wherein said multiphase reaction mixture comprises a first reaction phase and a second reaction phase at least partially immiscible in said first reaction phase, wherein said organic hydroperoxide is more miscible in one of said first and second reaction phases than in the other,

wherein said multiphase reaction mixture further comprises at least one catalyst for facilitating mass transfer between said first and said second reaction phases, and

wherein each of said reacting and said recovering is performed in a continuous manner, and wherein said reaction zone comprises at least two substantially straight reaction channels arranged in a parallel configuration, wherein each of said reaction channels includes no turns or bends having an angle greater than 80 degrees, and wherein said organic peroxide comprises t-butyl-peroxy-2-methylbenzoate.

19. The process of claim 18, wherein said first reaction phase is an organic phase comprising said organic reactant and wherein said second reaction phase is an aqueous phase comprising said organic hydroperoxide.

20. The process of claim 19, wherein said multiphase reaction mixture further comprises at least one pH modifying agent.

21. The process of claim 18, wherein said recovering includes separating said multiphase reaction mixture into a product stream and a waste stream;

and washing at least a portion of said product stream to provide said organic peroxide.