Ozonolysis operations for generation of reduced and/or oxidized product streams

Patent metadata

Field	Value
Publication number	US-9604898-B2
Application number	US-201314415327-A
Country	US
Kind code	B2
Filing date	Jul 19, 2013
Priority date	Jul 19, 2012
Publication date	Mar 28, 2017
Grant date	Mar 28, 2017

Abstract

The present invention relates to methods for safe and efficient use of hydrogen and oxygen in ozonolysis operations. The invention also relates to an ozonolysis process involving elements of both reductive and oxidative ozonolysis which are integrated in a continuous process. In one embodiment, the ozonolysis process of the present invention uses hydrogen and/or oxygen generated from water and electricity, which may be recycled to generate water and/or electricity.

First claim

What is claimed is:

1. A method comprising:
a) providing oxygen and hydrogen, wherein said oxygen treated with electricity to generate ozone; wherein said ozone is used in ozonolysis of a fatty acid or a fatty acid ester in an ozone reactor;
b) inputting said fatty acid into said ozone reactor, in which said fatty acid or fatty acid ester absorbs said ozone, thereby forming a mixture comprising ozonated product stream comprising one or more compounds selected from ozonide, peroxide, aldehyde, ester, and acid; and
c) generating partially reduced products comprising a linear alkyl aldehyde and oxygenated products comprising a diacid or acid-ester from said ozonated product stream by:
i. partially reducing said ozonated product stream after said ozonated product stream enters a hydrogenation chamber to generate said partially reduced products comprising largely a linear alkyl aldehyde, and contacting said partially reduced products with water, forming two layers comprising an organic phase while leaving the hydrogenation chamber;
j. fractionating said organic phase to separate said linear alkyl aldehyde from the remaining organic phase; and
k. oxidizing the remaining organic phase after fractionation at step (j) after the remaining organic phase enters into an oxidation chamber, resulting in the generation of said oxygenated products comprising said diacid or acid-ester;
thereby generating said linear alkyl aldehyde and said diacid or acid-ester from said ozonated product stream,

wherein the linear aldehyde, oxo-acid, oxo-ester, acid-ester, or diacid is more than about 95% pure.

2. The method of claim 1 , wherein the linear aldehyde, oxo-acid, oxo-ester, acid-ester, or diacid is more than about 99% pure.

Assignees

• P2 Science Inc

Inventors

• Foley Patrick
• Yang Yonghua

Classifications

• C07C45/40 Primary

  by oxidation with ozone; by ozonolysis · CPC title

• C07C51/34

  by oxidation with ozone; by hydrolysis of ozonides · CPC title

• C07C51/373 Primary

  by introduction of functional groups containing oxygen only in doubly bound form · CPC title

• C07C47/02

  Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen · CPC title

• C07C55/18

  Azelaic acid · CPC title