EP0307184A2
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Preparation of Amine Oxides
Assignee: Ethyl Corp
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Filing: 1988-09-07
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Granted: —
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Expires: 2008-09-07
Abstract
Abstract Tertiary amine oxides are made which are substantially free of nitrosamine impurities by reacting the desired tert-amine with aqueous hydrogen peroxide in the presence of carbon dioxide and at a temperature below about 45°C, especially below 40°C. Nitrosamines are suspect carcinogens and mutagens.
Inventors
- 👤 Dennis Paul Bauer
- 👤 Teresa Summerford Willard
- 👤 Kathleen Susan Laurenzo
- 👤 Frederick Richard Masterton
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-05 16:52
CPC Classifications
C; C07; C07C; C07C291/00; C07C291/02; C07C291/04
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
78 words
A process for oxidizing a tert-amine by reaction with hydrogen preoxide to form a tert-amine oxide and comprising contacting said tert-amine with aqueous hydrogen peroxide in the presence of a promoter formed by adding carbon dioxide to the reaction mixture, characterized by being conducted at a temperature below about 45°C whereby the nitrosamine content of the tert-amine oxide product is substantially reduced compared to the nitrosamine content of tert-amine oxides produced by the same process at higher temperatures.
Claim 2
Dependent Claim
78 words
A process for oxidizing a tert-amine by reaction with hydrogen preoxide to form a tert-amine oxide and comprising contacting said tert-amine with aqueous hydrogen peroxide in the presence of a promoter formed by adding carbon dioxide to the reaction mixture, characterized by being conducted at a temperature below about 45°C whereby the nitrosamine content of the tert-amine oxide product is substantially reduced compared to the nitrosamine content of tert-amine oxides produced by the same process at higher temperatures.
Claim 3
Dependent Claim
18 words
A process of Claim 1 conducted at a temperature below 40°C, preferably at a temperature of from 20-39°C.
Claim 4
Dependent Claim
105 words
A process of Claim 1 or Claim 2 wherein said tert-amine has the formula R¹R²R³N wherein R¹ is an alkyl group containing 1-30 carbon atoms and R² and R³ are alkyl groups containing 1-30 carbon atoms, cycloalkyl groups containing 5-12 carbon atoms, aryl groups containing 6-12 carbon atoms, aralkyl groups containing 7-12 carbon atoms or any two of the R groups can join to form a carbocyclic or heterocyclic ring or all three of the R groups may participate to form a pyridine ring, said process being conducted at a temperature in the range of 0-45°C whereby the formation of nitrosamine impurities is substantially inhibited.
Claim 5
Dependent Claim
51 words
A process of Claim 1 or Claim 2 wherein said tert-amine has the structure R¹R²R³N and at least R¹ of R¹ and R² is selected from primary alkyl groups containing 6-20 carbon atoms and R³ is methyl or ethyl, and , if not as defined above, R² is methyl or ethyl.
Claim 6
Dependent Claim
38 words
A process of Claim 4 wherein at least R¹ of R¹ and R² is selected from primary mainly linear alkyl groups containing 8-20 carbon atoms and R³ is methyl, and if not as defined above, R² is methyl.
Claim 7
Dependent Claim
23 words
A process of Claim 4 or Claim 5 wherein at least R¹ of R¹ and R² is decyl, dodecyl, tetradecyl, hexadecyl, or octadecyl.
Claim 8
Dependent Claim
20 words
A process of any one of Claims 1 to 6 wherein the hydrogen peroxide is 20-70 weight percent active H₂O₂.
Claim 9
Dependent Claim
30 words
A process of any one of Claims 1 to 7 wherein the amount of carbon dioxide is from 3 to 7 weight percent based on the weight of said tert-amine.
Claim 10
Dependent Claim
23 words
A process of any one of Claims 1 to 8 carried out in the presence of a co-solvent, such as a lower alcohol.
Claim 11
Dependent Claim
65 words
The use of a process for oxidizing a tert-amine by reaction with hydrogen peroxide to form a tert-amine oxide and comprising contacting said tert-amine with aqueous hydrogen peroxide in the presence of a promoter formed by adding carbon dioxide to the reaction mixture, said process being conducted at a temperature below about 45°C, in the production of an ingredient for a cosmetic or surfactant formulation.
Claim 12
Dependent Claim
65 words
The use of a process for oxidizing a tert-amine by reaction with hydrogen peroxide to form a tert-amine oxide and comprising contacting said tert-amine with aqueous hydrogen peroxide in the presence of a promoter formed by adding carbon dioxide to the reaction mixture, said process being conducted at a temperature below about 45°C, in the production of an ingredient for a cosmetic or surfactant formulation.
References Cited (Backward Citations)
No citation records indexed.
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