IP Library Granted Patent US 9,604,898
Granted Patent B2
US 9,604,898 · App. 14/415,327 · Granted Mar 28, 2017

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

Inventors: Patrick Foley (New Haven, CT); Yonghua Yang (New Haven, CT)
Assignee: P2 Science, Inc.
C07C51/373C07C45/40C07C51/34
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Quick Facts
Patent No.
US 9,604,898
App. No.
14/415,327
Granted
Mar 28, 2017
Kind
B2
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.

Claims (10)

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.

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Feb 6, 2023
From: HG VENTURES LLC
To: P2 SCIENCE, INC.
Reel/Frame 062650/0301 →
SECURITY INTEREST Recorded Dec 3, 2022
From: P2 SCIENCE, INC.
To: HG VENTURES LLC
Reel/Frame 062050/0152 →
SECURITY INTEREST Recorded May 15, 2020
From: P2 SCIENCE, INC.
To: WEBSTER BANK, NATIONAL ASSOCIATION
Reel/Frame 052678/0391 →
CORRECTIVE ASSIGNMENT TO CORRECT THE NATURE OF CONVEYANCE PREVIOUSLY RECORDED ON REEL 035025 FRAME 0307. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT OF SECURITY INTEREST. Recorded Dec 21, 2016
From: P2 SCIENCE, INC.
To: CONNECTICUT INNOVATIONS, INCORPORATED
Reel/Frame 041163/0706 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 8, 2015
From: FOLEY, PATRICK; YANG, YONGHUA
To: P2 SCIENCE, INC.
Reel/Frame 035851/0233 →
Continuity (3)
Provisional Application 61673411 · Jul 19, 2012
Provisional Application 61784376 · Mar 14, 2013
Related Publication 20150183707A1 · Jul 2, 2015