IP Library Granted Patent US 7,416,718
Granted Patent B2
US 7,416,718 · App. 11/512,464 · Granted Aug 26, 2008

Auto-oxidation production of hydrogen peroxide via oxidation in a microreactor

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Quick Facts
Patent No.
US 7,416,718
App. No.
11/512,464
Granted
Aug 26, 2008
Kind
B2
Abstract

Hydrogen peroxide is prepared by an auto-oxidation method via oxidation in a microreactor. A working solution containing a reactive carrier compound is hydrogenated with hydrogen in a first step and is subsequently oxidized in a microreactor to produce hydrogen peroxide.

Claims (30)

1. A method for the production of hydrogen peroxide comprising effecting oxidation of a working compound in a microreactor to produce hydrogen peroxide and recovering the hydrogen peroxide.

2. A cyclic method for the production of hydrogen peroxide comprising the steps of

catalytically hydrogenating a working compound to yield a hydrogenated working compound;

oxidizing the hydrogenated working compound in an oxidation microreactor, to produce hydrogen peroxide;

separating the resulting hydrogen peroxide from the oxidized working compound and recovering the hydrogen peroxide in an aqueous solution; and

recycling the oxidized working compound to the hydrogenation step.

3. The method of claim 1 wherein the working compound is selected from the group consisting of amino-substituted aromatic hydrazo compounds, dihydrophenazine, alkylated dihydrophenazine derivatives, alkyl anthrahydroquinones, hydroalkyl anthrahydroquinones, mixtures of alkyl anthrahydroquinones and hydroalkyl anthrahydroquinones, and primary and secondary alkyl alcohols and aryl alcohols.

4. The method of claim 2 wherein the working compound is selected from the group consisting of amino-substituted aromatic azo compounds, phenazine, alkylated phenazine derivatives, alkyl anthraquinones and hydroalkyl anthraquinones and mixtures of alkyl anthraquinones and hydroalkyl anthraquinones.

5. The method of claim 1 or 2 wherein the oxidation uses an oxidizing agent selected from the group consisting of air, oxygen and oxygen-rich gas.

6. The method of claim 1 or 2 wherein the microreactor contains one or more microchannels, in which the oxidation is carried out.

7. The method of claim 6 wherein the microchannel has at least one cross sectional dimension within the range of from 1 micron to 5 mm.

8. The method of claim 6 wherein the microchannel has at least one cross sectional dimension within the range of from 5 microns to 2 mm.

9. The method of claim 6 wherein the microchannel has at least one cross sectional dimension within the range of from 5 microns to 1 mm.

10. The method of claim 6 wherein the oxidation microreactor contains an inlet to one or more linked microchannels and an outlet from such microchannels, for respectively introducing the working compound to the microreactor and removing oxidized working compound from the microreactor.

11. The method of claim 6 wherein the microreactor further contain at least one additional passageway adjacent to at least one oxidation microchannel for effecting heat transfer and oxidation temperature control using a heat transfer fluid during the oxidation reaction.

12. The method of claim 6 wherein the microreactor comprises layered sheets that contain an interconnected microchannel network.

13. The method of claim 1 or 2 wherein the working compound is carried in an organic solvent.

14. The method of claim 13 wherein the working compound is selected from the group consisting of alkyl anthraquinones and hydroalkyl anthraquinones and mixtures of alkyl anthraquinones and hydroalkyl anthraquinones and the working compound is carried in a solvent mixture of(i) an aromatic C 9 -C 11 hydrocarbon solvent and (ii) a second solvent component selected from the group consisting of alkylated ureas, cyclic urea derivatives, organic phosphates, carboxylic acid esters, C 4 -C 12 alcohols, cyclic amides and alkyl carbamates and mixtures thereof.

15. The method of claim 13 wherein the oxidation of the working compound in an organic solvent is also carried out in the presence of water.

16. The method of claim 1 or 2 wherein the oxidation is facilitated by an oxidation catalyst, used in combination with the working compound.

17. The method of claim 16 wherein the catalyst is selected from the group consisting of secondary and tertiary amines, alkali metal hydroxides, alkaline earth hydroxides, sodium carbonate, sodium hydroxide and ammonium hydroxide.

18. The method of claim 1 or 2 wherein the oxidation is carried out at temperatures within the range of about 20° C. to about 100° C.

19. The method of claim 1 or 2 wherein the oxidation is carried out at a pressure in the range of about 5 psig to about 300 psig.

20. The method of claim 19 wherein the oxidation is carried out at a pressure of less than about 150 psig.

21. The method of claim 1 wherein the hydrogen peroxide is separated from the oxidized working compound by extraction with water, to produce an aqueous extract containing hydrogen peroxide.

22. A cyclic method for the production of hydrogen peroxide comprising the steps of

catalytically hydrogenating an anthraquinone working solution, comprising an anthraquinone derivative carried in an organic solvent, to yield a hydrogenated working solution;

oxidizing the hydrogenated working solution in an oxidation microreactor, to produce hydrogen peroxide;

separating the hydrogen peroxide from the working solution via aqueous extraction and recovering an aqueous solution of hydrogen peroxide; and

recycling the working solution to the hydrogenation step.

Assignments (8)
RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT R/F 050605/0305 Recorded Feb 3, 2020
From: BARCLAYS BANK PLC, AS ADMINISTRATIVE AGENT
To: PEROXYCHEM LLC
Reel/Frame 051777/0957 →
SECURITY INTEREST Recorded Oct 2, 2019
From: PEROXYCHEM LLC
To: BARCLAYS BANK PLC, AS ADMINISTRATIVE AGENT
Reel/Frame 050605/0305 →
RELEASE OF SECURITY INTEREST Recorded Oct 2, 2019
From: BANK OF AMERICA, N.A., AS AGENT
To: PEROXYCHEM LLC
Reel/Frame 050606/0329 →
RELEASE OF SECURITY INTEREST Recorded Nov 4, 2015
From: MACQUARIE US TRADING LLC, AS COLLATERAL AGENT
To: PEROXYCHEM LLC
Reel/Frame 036953/0766 →
SECURITY INTEREST Recorded Oct 21, 2015
From: PEROXYCHEM LLC
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 036847/0594 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 31, 2014
From: FMC CORPORATION
To: PEROXYCHEM LLC
Reel/Frame 032558/0681 →
SHORT FORM PATENT SECURITY AGREEMENT Recorded Mar 3, 2014
From: PEROXYCHEM LLC
To: MACQUARIE US TRADING LLC
Reel/Frame 032379/0931 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 28, 2008
From: SETHI, DALBIR S.; DADA, EMMANUEL A.; HAMMACK, KEVIN; ZHOU, XINLIANG
To: FMC CORPORATION
Reel/Frame 020722/0797 →