CA2228859A1 - Synthesis of tertiary amine oxides - Google Patents

Synthesis of tertiary amine oxides

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Publication number
CA2228859A1
CA2228859A1 CA002228859A CA2228859A CA2228859A1 CA 2228859 A1 CA2228859 A1 CA 2228859A1 CA 002228859 A CA002228859 A CA 002228859A CA 2228859 A CA2228859 A CA 2228859A CA 2228859 A1 CA2228859 A1 CA 2228859A1
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CA
Canada
Prior art keywords
tertiary amine
amine oxide
amine
solvent
oxide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002228859A
Other languages
French (fr)
Other versions
CA2228859C (en
Inventor
Vaikunth S. Prabhu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lanxess Solutions US Inc
Original Assignee
General Electric Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by General Electric Co filed Critical General Electric Co
Publication of CA2228859A1 publication Critical patent/CA2228859A1/en
Application granted granted Critical
Publication of CA2228859C publication Critical patent/CA2228859C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
    • C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
    • C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds

Abstract

A process is provided for the manufacture of free-flowing solid tertiary amine oxides having N-nitrosodimethylamine levels of less than about 250 ppb. The process comprises heating a mixture of a tertiary amine, a polar hydroxy alkyl solvent, an organic acid, and aqueous hydrogen peroxide, followed by removal of the solvent and water, preferably by azeotropic removal. The resultant tertiary amine oxides have good color without bleaching and are useful without further purification.

Claims (22)

1. A process for producing amine oxides, wherein said process comprises reacting a tertiary amine of the formula wherein R1 and R2 are each independently a C8-30 alkyl moiety, with aqueous hydrogen peroxide and an amount of an organic carboxylic acid effective to catalyze the oxidation of the tertiary amine to produce a tertiary amine oxide, wherein said reaction is done in at least one polar hydroxy alkyl solvent;
wherein said solvent can form an azeotrope of at least one percent by weight water;
and isolating the tertiary amine oxide by removal of said solvent.
2. The process of claim 1, wherein the amine oxide after isolation is a solid at 23°C.
3. The process of claim 1, wherein the amine oxide after isolation contains less that about 100 ppb of N-nitrosodimethylamine.
4. The process of claim 1, where in the solvent is removed with a vaccum.
5. The process of claim 1, wherein the amine oxide has the formula wherein R1 and R2 are each C16-18 alkyl moieties; and wherein the amine oxide picks up less than about 10% by weight water when stored at 23°C and 80% relative humidity, and remains a solid at 23°C.
6. The process of claim 1, wherein the amine oxide has the formula wherein R1 and R2 are each C20-22 alkyl moieties; and wherein the amine oxide picks up less than about 5% by weight water when stored at 23°C and 80% relative humidity, and remains a solid at 23°C.
7. The process of claim 1, wherein the amine oxide has the formula wherein R1 and R2 are each a C10 alkyl moiety; and wherein the amine oxide has a 10% weight loss rating of at least about 120°C, when measured at a heating rate of 20°C/minute.
8. The process of claim 1, wherein the amine oxide has the formula wherein R1 and R2 are each a C16-18 alkyl moiety; and wherein the amine oxide has a 10% weight loss rating of at least about 145°C, when measured at a heating rate of 20°C/minute.
9. The process of claim 1, wherein the amine oxide has the formula wherein R1 and R2 are each a C20-22 alkyl moiety; and wherein the amine oxide has a 10% weight loss rating of at least about 220°C, when measured at a heating rate of 20°C/minute.
10. The process of claim 1, wherein the polar hydroxy alkyl solvent is selected from the group consisting of C1-8 alcohols containing one or more hydroxyl groups.
11. A process for making solid tertiary amine oxides, said process comprising heating under a nitrogen atmosphere a tertiary amine, an polar hydroxy alkyl solvent, an organic acid, and aqueous hydrogen peroxide to a temperature between about 50°C and about 100°C untilat least about 95% of the tertiary amine oxide has reacted and removing the polar hydroxy alkyl solvent, the organic acid, and water as an azeotrope to yield a free-flowing solid tertiary amine oxide.
12. The process of claim 11, wherein the solid tertiary amine oxide comprises at least 90% tertiary amine oxide.
13. The process of claim 11, wherein the polar hydroxy alkyl solvent is selected from the group consisting of C1-8 alcohols containing one or more hydroxyl groups.
14. The process of claim 11, wherein the organic acid is at least one acid selected from the group consisting of acetic acid, formic acid, and propionic acid.
15. The process of claim 11, wherein the aqueous hydrogen peroxide contains between about 20% to 90% by weight hydrogen peroxide.
16. The process of claim 11, wherein the molar ratio of the tertiary amine to hydrogen peroxide is between about 1:1 to about 1: 2.
17. The process of claim 11, wherein said process produces less than about 250 parts per billion of a nitrosamine based upon the weight of the tertiary amine oxide.
18. The process of claim 11, wherein the weight ratio of the tertiary amine to the organic acid is between about 50:1 to about 500:1.
19. The process of claim 11, wherein the tertiary amine is at least one amine of the formula:

wherein R1 and R2 are each independently a C1-30 alkyl moiety, and wherein at least one of R1 and R2 may optionally contain at least one -O-, -S-, -SO-, -CO2-, -CO-, or -CON- moiety.
20. The process of claim 19, wherein the weight ratio of the tertiary amine to the organic acid is between about 50:1 to about 500:1.
21. A process for making solid tertiary amine oxides, said process comprising heating under a nitrogen atmosphere a tertiary amine, iso-propyl alcohol, acetic acid, and aqueous hydrogen peroxide to a temperature between about 50°C and about 100°C until at least about 95% of the tertiary amine oxide has reacted, and removing the iso-propyl alcohol and water to yield a free-flowing solid tertiary amine oxide.
22. The process of claim 21, wherein the tertiary amine is at least one tertiary amine selected from the group consisting of didecyl methyl amine, dicocoalkyl methyl amine, ditallowalkyl methyl amine, dieicosyl methyl amine, and didocosanyl methyl amine.
CA2228859A 1997-03-20 1998-02-05 Synthesis of tertiary amine oxides Expired - Fee Related CA2228859C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/820,871 US5866718A (en) 1997-03-20 1997-03-20 Synthesis of tertiary amine oxides
US08/820,871 1997-03-20

Publications (2)

Publication Number Publication Date
CA2228859A1 true CA2228859A1 (en) 1998-09-20
CA2228859C CA2228859C (en) 2010-04-27

Family

ID=25231941

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2228859A Expired - Fee Related CA2228859C (en) 1997-03-20 1998-02-05 Synthesis of tertiary amine oxides

Country Status (10)

Country Link
US (2) US5866718A (en)
EP (1) EP0866058B1 (en)
JP (1) JP4272722B2 (en)
KR (1) KR100570861B1 (en)
CN (1) CN1089753C (en)
CA (1) CA2228859C (en)
DE (1) DE69830437T2 (en)
ID (1) ID20077A (en)
TW (1) TW495497B (en)
ZA (1) ZA981887B (en)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6752983B1 (en) * 1997-09-17 2004-06-22 Eastman Chemical Company Hair spray and consumer sprays with reduced volatile organic compounds
US6007727A (en) * 1998-03-06 1999-12-28 Lucent Technologies Inc. Process for treating by-product of optical fiber fabrication
US6054616A (en) * 1999-03-26 2000-04-25 Clariant Finance (Bvi) Limited Process for reducing residual raw material impurities in tertiary amine oxides
US6498221B1 (en) 2000-03-30 2002-12-24 Equistar Chemicals, Lp Single-site catalysts containing chelating N-oxide ligands
DE10020630A1 (en) * 2000-04-27 2001-11-08 Merck Patent Gmbh Process for the oxidation of tertiary amines and nitrogen-containing aromatic heterocycles
JP4045774B2 (en) * 2000-10-27 2008-02-13 住友化学株式会社 Process for producing carboxylic acids and their catalysts
US7198844B2 (en) * 2003-01-17 2007-04-03 Crompton Corporation Microporous polymeric resin containing stabilizers and method for making thereof
US20040147650A1 (en) * 2003-01-24 2004-07-29 General Electric Company Process for stabilization of polymer compositions
JP2008074722A (en) * 2006-09-19 2008-04-03 Mitsubishi Gas Chem Co Inc Method for producing 2-amino-5-iodobenzoic acid
BRPI0807747B1 (en) * 2007-03-05 2019-03-06 The Procter & Gamble Company CATALASE DECOMPOSITION OF HYDROGEN PEROXIDE IN TENSOTIVES.
CN101549265B (en) * 2009-04-13 2011-05-11 江南大学 Preparation of surface active agent of double long-chain alkyl amine oxide and applications thereof
CN104507909B (en) * 2012-07-24 2017-05-31 宝洁公司 Prepare the continuation method of amine oxide
CN103012219B (en) * 2012-12-20 2015-02-11 北京桑普生物化学技术有限公司 Preparation method for trimethylamine oxide
US11130709B2 (en) 2015-05-19 2021-09-28 Gcp Applied Technologies Inc. Polyalkoxylated polyamine oxide defoaming compositions
CN106390853B (en) * 2016-08-30 2018-10-23 四川花语精细化工有限公司 A method of preparing low nitrite, high activity alkyl amine oxide
EP3339288A1 (en) * 2016-12-23 2018-06-27 Aurotec GmbH Production of an amine oxide by oxidation of a tertiary amine
EP3363784B1 (en) 2017-02-16 2020-10-28 Clariant International Ltd Dimethyl farnesyl amine oxide and its use as surfactant or wetting agent
US10961180B2 (en) * 2018-01-12 2021-03-30 Eastman Chemical Company Branched trialkyl amine oxides
CN109096143B (en) * 2018-10-09 2021-08-27 南京工业大学 Method for synthesizing diethylhydroxylamine by adopting peroxyacetic acid
CN113277949B (en) * 2020-02-19 2023-03-14 科莱恩丰益脂肪胺(连云港)有限公司 Method for processing, producing or refining aliphatic hydrocarbon amines or derivatives thereof

Family Cites Families (74)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2169976A (en) * 1934-01-26 1939-08-15 Ig Farbenindustrie Ag Process of producing assistants in the textile and related industries
US2497061A (en) * 1947-03-24 1950-02-14 Henry B Kellog Alkanedione dioximes as antioxidants for preserving organic compositions which tend to deteriorate by the absorption of oxygen from the air
US2586236A (en) * 1949-11-25 1952-02-19 James P Lewis Lawn mower sharpener
US2586238A (en) * 1950-06-30 1952-02-19 Chemstrand Corp Copolymers of acrylonitrile and amine oxides
US3047579A (en) * 1958-07-18 1962-07-31 Shell Oil Co Process for preparing n-oxides
NL254590A (en) * 1959-08-08
NL283760A (en) * 1961-09-29
US3309399A (en) * 1964-04-15 1967-03-14 Miles Lab Tertiary amine oxides
US3432578A (en) * 1964-10-05 1969-03-11 Shell Oil Co Conjugated diene polymer compositions stabilized with certain hydroxylamines
CA785805A (en) * 1964-10-09 1968-05-21 Armour And Company Derivatives of fatty acids
US3408422A (en) * 1964-11-04 1968-10-29 Shell Oil Co Stabilization of unsaturated polyesters and resulting products
US3457312A (en) * 1965-10-24 1969-07-22 Armour Ind Chem Co Amine oxides
US3468869A (en) * 1966-04-08 1969-09-23 Atlas Chem Ind Antistatic materials
US3576877A (en) * 1967-11-07 1971-04-27 Pennwalt Corp Nitro-n,n-dialkyl aniline-n-oxides
US3776959A (en) * 1967-11-30 1973-12-04 Akzona Inc Preparation of amine oxides in non-polar solvent systems
US3558710A (en) * 1967-11-30 1971-01-26 Armour Ind Chem Co Preparation of amine oxides in nonpolar solvent
US3501426A (en) * 1967-12-21 1970-03-17 Dow Chemical Co Diffusion process for making foamable styrene polymer granules
US3644278A (en) * 1968-03-04 1972-02-22 Ciba Geigy Corp Substituted hydroxylamine stabilizers
US3957873A (en) * 1969-01-16 1976-05-18 Celanese Corporation Peracetic acid oxidation of amines to amine oxides
US3644244A (en) * 1969-12-15 1972-02-22 Du Pont Polybutadiene-polynitrile graft copolymer dispersions stabilized with hydroxylamines
US3778464A (en) * 1972-10-10 1973-12-11 P Klemchuk Substituted hydroxylamine anti-oxidants
US3926909A (en) * 1974-08-16 1975-12-16 Globe Mfg Co Dibenzyl hydroxyl amine stabilizer for spandex
CA1078862A (en) * 1976-03-04 1980-06-03 James F. York Preparation of organic phosphites
LU75333A1 (en) * 1976-07-08 1978-02-08
JPS5528968A (en) * 1978-08-24 1980-02-29 Nissan Chem Ind Ltd Production of amine oxide
US4263177A (en) * 1979-06-27 1981-04-21 Sherex Chemical Company, Inc. Amine oxide foam stabilizers for alkyl benzene sulfonate foaming agents
US4316996A (en) * 1980-11-17 1982-02-23 The Goodyear Tire & Rubber Company Discoloration prevention of phenolic antioxidants
US4395373A (en) * 1981-04-07 1983-07-26 Jordan Chemical Company Phosphated amine oxides
US4504666A (en) * 1981-07-03 1985-03-12 Sherex Chemical Company, Inc. High yield preparation of aromatic amine oxides
US4386224A (en) * 1981-08-31 1983-05-31 Monsanto Company Color stabilization of monoalkyl phenols
DE3145734A1 (en) * 1981-11-19 1983-05-26 Hoechst Ag, 6230 Frankfurt BIS-BETAIN-AMINOXIDE, METHOD FOR THE PRODUCTION THEREOF AND CLEANING AGENTS CONTAINING THE SAME
US4403053A (en) * 1982-05-07 1983-09-06 Borg-Warner Corporation Stabilized olefin polymers
US4443572A (en) * 1982-09-22 1984-04-17 Phillips Petroleum Company Polyolefin stabilizers
US4590231A (en) * 1983-10-11 1986-05-20 Ciba-Geigy Corporation Polyolefin compositions stabilized against degradation using hydroxylamine derivatives
JPS60120848A (en) * 1983-12-01 1985-06-28 Mitsubishi Petrochem Co Ltd Preparation of mixed tertiary amine oxide
US5166435A (en) * 1983-12-06 1992-11-24 Akzo N.V. Process for the preparation of a hydroxylamine
US4565891A (en) * 1984-07-19 1986-01-21 The Procter & Gamble Company Oxidation of tertiary amines using octacyanomolybdate or iron (III) salts as catalysts
US4668721A (en) * 1984-07-23 1987-05-26 Ciba-Geigy Corporation Polyolefin compositions stabilized against degradation using hydroxylamine derivatives
US4649221A (en) * 1984-07-23 1987-03-10 Ciba-Geigy Corporation Polyhydroxylamines
US4612393A (en) * 1985-04-29 1986-09-16 Ciba-Geigy Corporation Bis(substituted thioalkyl)hydroxylamines and stabilized polyolefin compositions
US4659565A (en) * 1985-07-01 1987-04-21 Ethyl Corporation Amine oxide hair conditioner
US4970340A (en) * 1985-07-01 1990-11-13 Ethyl Corporation Amine oxide process and composition
IE58999B1 (en) * 1985-07-22 1993-12-15 Rolland Sa A Novel N-oxyde of NN-dimethyl ethylamine, a process for it's production and the pharmaceutical compositions containing it
US4696964A (en) * 1986-04-11 1987-09-29 Ciba-Geigy Corporation Compositions stabilized with ethers of di- and tri-substituted hydroxylamines
US4748275A (en) * 1986-09-08 1988-05-31 Ethyl Corporation Non-hygroscopic trialkylamine oxides
US4970341A (en) * 1987-02-24 1990-11-13 Ethyl Corporation Amine oxide process
US4782105A (en) * 1987-04-10 1988-11-01 Ciba-Geigy Corporation Long chain N,N,-dialkylhydroxylamines and stabilized compositions
US4826506A (en) * 1987-12-09 1989-05-02 Exxon Research And Engineering Company Use of polyhydric alcohols to reduce loss of amine oxides from liquid hydrocarbon fuels
US4994614A (en) * 1987-12-14 1991-02-19 Ethyl Corporation Amine oxide process
US4876300A (en) * 1987-12-30 1989-10-24 Ciba-Geigy Corporation Polyolefin compositions stabilized with long chain N,N-dialkylhydroxylamines
US4889954A (en) * 1988-06-30 1989-12-26 Ethyl Corporation Amine oxide process
US4942260A (en) * 1988-08-29 1990-07-17 Ethyl Corporation Amine oxide process with CO2 and aluminum
US5130488A (en) * 1989-04-26 1992-07-14 Ethyl Corporation Process for preparing tert-amine oxides
CA2014201A1 (en) * 1989-04-26 1990-10-26 Albemarle Corporation Solid non-hygroscopic trialkylamine oxides
US4960934A (en) * 1989-10-27 1990-10-02 Ethyl Corporation Amine oxide process
US5208374A (en) * 1989-10-30 1993-05-04 Ethyl Corporation Amine oxide process
US5268114A (en) * 1990-04-24 1993-12-07 Ciba-Geigy Corporation N-alkenyl substituted amine-N-oxide stabilizers
US5292954A (en) * 1990-05-17 1994-03-08 Ethyl Corporation Amine oxide composition and process
US5120469A (en) * 1990-05-17 1992-06-09 Ethyl Corporation Amine oxide composition and process
US5055614A (en) * 1990-05-18 1991-10-08 Ethyl Corporation Amine oxide composition and process
US5068430A (en) * 1990-07-26 1991-11-26 Ethyl Corporation Bleaching of colored amine oxides
US5149774A (en) * 1990-07-31 1992-09-22 Ciba-Geigy Corporation Method for recycling discolored polyolefins
US5059625A (en) * 1990-10-01 1991-10-22 Olin Corporation Polyglycidol amine oxide surfactants having antimicrobial activity
US5134183A (en) * 1990-10-22 1992-07-28 Ciba-Geigy Corporation Sterically hindered oxime color improvers for polyolefin processing
GB9102311D0 (en) * 1991-02-02 1991-03-20 Albright & Wilson Nitrosamine inhibition
US5254735A (en) * 1991-02-08 1993-10-19 Ethyl Corporation Process for preparing solid amine oxides
DE4124134A1 (en) * 1991-07-20 1993-01-21 Hoechst Ag CONCENTRATED, AQUEOUS DISPERSIONS OF TETRAFLUORETHYLENE POLYMERS, METHOD FOR THE PRODUCTION AND USE THEREOF
DE4140259A1 (en) * 1991-12-06 1993-06-09 Basf Ag, 6700 Ludwigshafen, De METHOD FOR PRODUCING TERTIA AMINOXIDES
AT396930B (en) * 1992-01-23 1993-12-27 Chemiefaser Lenzing Ag AMINOXIDE
GB9202057D0 (en) * 1992-01-31 1992-03-18 Albright & Wilson Synergistic inhibition of nitrosamines and nitrites
AT399349B (en) * 1993-08-26 1995-04-25 Chemiefaser Lenzing Ag METHOD FOR CLEANING AQUEOUS AMINOXIDE SOLUTIONS
US5466870A (en) * 1993-10-29 1995-11-14 The Procter & Gamble Company Process for reducing the levels of nitrite contaminants in amine oxide surfactants
US5389306A (en) * 1994-04-22 1995-02-14 The Procter & Gamble Company Process for making solid formulations containing amine oxide surfactants
US5583258A (en) * 1995-02-15 1996-12-10 The Procter & Gamble Company Process for preparing mono-long chain amine oxide surfactants

Also Published As

Publication number Publication date
CN1089753C (en) 2002-08-28
US5866718A (en) 1999-02-02
EP0866058A3 (en) 2002-08-14
CA2228859C (en) 2010-04-27
EP0866058B1 (en) 2005-06-08
KR100570861B1 (en) 2006-08-14
KR19980080445A (en) 1998-11-25
CN1197794A (en) 1998-11-04
DE69830437T2 (en) 2005-10-20
JPH1129546A (en) 1999-02-02
TW495497B (en) 2002-07-21
DE69830437D1 (en) 2005-07-14
ZA981887B (en) 1998-09-21
US5955633A (en) 1999-09-21
ID20077A (en) 1998-09-24
EP0866058A2 (en) 1998-09-23
JP4272722B2 (en) 2009-06-03

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