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US4888447A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for preparing alkoxylated tertiary amines

Assignee: Albemarle Corp
•
Filing: 1988-06-30
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Granted: 1989-12-19
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Expires: 2008-06-30
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Abstract

Abstract A process is described for selectively preparing alkoxylated tertiary amine compounds, such as aminated ethoxylated amines, at ambient pressure by reacting an oxyalkylated alcohol with a secondary amine in the presence of a reductive amination catalyst at above ambient temperature using, as a reductive amination catalyst, a combination of Raney nickel and molybdenum.

Inventors

  • 👤 Kim R. Smith

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 22:18
CPC Classifications
C; C07; C07C; C07C213/00; C07C213/02

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 247 words
A process for selectively preparing at ambient pressure an alkoxylated tertiary amine having the formula: ##STR7## or a mixture of such amines which comprises reacting an oxyalkylated alcohol of the formula: ##STR8## or a mixture of such alcohols, with a secondary amine of the formula HNR 3 R 4 at elevated temperature in the presence of a catalytic quantity of an amination catalyst consisting of a combination of Raney nickel and molybdenum wherein R is a straight or branched chain alkyl group having from 1 to 20 carbon atoms, a cyclic alkyl group having from 5 to 10 carbon atoms, an aryl hydrocarbon group having up to 12 carbon atoms, or an aralkyl or alkaryl hydrocarbon group having up to 18 carbon atoms, R 1 is a single unit or a series of units of the formula: ##STR9## wherein in each unit R 5 is independently selected from the group consisting of hydrogen and a straight or branched chain alkyl group having from 1 to 12 carbon atoms and x is a integer of from 0 to 40, R 2 is hydrogen or a straight or branched chain alkyl group having from 1 to 12 carbon atoms, R 3 and R 4 are each independently selected from the group consisting of straight and branched chain alkyl groups having from 1 to 12 carbon atoms, cyclic alkyl groups having from 5 to 10 carbon atoms, 1 to 4 carbon atom alkyl substituted or unsubstituted benzyl groups and allyl.
Claim 2
Dependent Claim 247 words
A process for selectively preparing at ambient pressure an alkoxylated tertiary amine having the formula: ##STR7## or a mixture of such amines which comprises reacting an oxyalkylated alcohol of the formula: ##STR8## or a mixture of such alcohols, with a secondary amine of the formula HNR 3 R 4 at elevated temperature in the presence of a catalytic quantity of an amination catalyst consisting of a combination of Raney nickel and molybdenum wherein R is a straight or branched chain alkyl group having from 1 to 20 carbon atoms, a cyclic alkyl group having from 5 to 10 carbon atoms, an aryl hydrocarbon group having up to 12 carbon atoms, or an aralkyl or alkaryl hydrocarbon group having up to 18 carbon atoms, R 1 is a single unit or a series of units of the formula: ##STR9## wherein in each unit R 5 is independently selected from the group consisting of hydrogen and a straight or branched chain alkyl group having from 1 to 12 carbon atoms and x is a integer of from 0 to 40, R 2 is hydrogen or a straight or branched chain alkyl group having from 1 to 12 carbon atoms, R 3 and R 4 are each independently selected from the group consisting of straight and branched chain alkyl groups having from 1 to 12 carbon atoms, cyclic alkyl groups having from 5 to 10 carbon atoms, 1 to 4 carbon atom alkyl substituted or unsubstituted benzyl groups and allyl.
Claim 3
Dependent Claim 43 words
A process according to claim 1 wherein R is a straight chain alkyl group having from 8 to 16 carbon atoms, R 1 is a ##STR10## group with x being 7 and R 2 , R 3 and R 4 are methyl groups.
Claim 4
Dependent Claim 12 words
A process according to claim 2 wherein R 1 is a ##STR11##
Claim 5
Dependent Claim 26 words
A process according to claim 1 wherein the process is conducted at a temperature in the range of from about 150° C. to about 350° C.
Claim 6
Dependent Claim 32 words
A process according to claim 1 wherein the amination catalyst is employed in an amount of from about 0.01 to about 50 wt % based on the weight of said oxyalkylated alcohol.
Claim 7
Dependent Claim 28 words
A process according to claim 1 wherein the amination catalyst contains from about 0.1 to about 50 wt % molybdenum based on the total weight of the catalyst.
Claim 8
Dependent Claim 36 words
In a process of producing alkoxylated tertiary amines by reacting an alkoxylated alcohol with a secondary amine, the improvement which comprises conducting the reaction at ambient pressure in the presence of a molybdenum-containing Raney nickel catalyst.
Claim 9
Dependent Claim 36 words
In a process of producing alkoxylated tertiary amines by reacting an alkoxylated alcohol with a secondary amine, the improvement which comprises conducting the reaction at ambient pressure in the presence of a molybdenum-containing Raney nickel catalyst.
Claim 10
Dependent Claim 25 words
A process according to claim 7 wherein the alkoxylated alcohol is an ethoxylated primary alcohol in which the alkanol has up to 20 carbon atoms.
Claim 11
Dependent Claim 30 words
A process according to claim 7 wherein the alkoxylated alcohol is an ethoxylated alcohol in which the alkanol is predominantly a mixture of C 12 and C 14 linear alkanols.
Claim 12
Dependent Claim 18 words
A process according to claim 9 wherein the ethoxylated alkanol has an approximate degree of ethoxylation of 6.5.
Claim 13
Dependent Claim 12 words
A process according to claim 7 wherein the secondary amine is dimethylamine.
Claim 14
Dependent Claim 25 words
A process according to claim 11 wherein the alkoxylated alcohol is an ethoxylated primary alcohol in which the alkanol has up to 20 carbon atoms.
Claim 15
Dependent Claim 30 words
A process according to claim 11 wherein the alkoxylated alcohol is an ethoxylated alcohol in which the alkanol is predominantly a mixture of C 12 and C 14 linear alkanols.
Claim 16
Dependent Claim 18 words
A process according to claim 13 wherein the ethoxylated alkanol has an approximate degree of ethoxylation of 6.5.

References Cited (Backward Citations)

US3347921A Cited
US3442950A Cited
US4181682A Cited
US4495369A Cited
EP0180455A2 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1992-12-18 1993-06-19 1993-12-19 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1996-12-18 1997-06-19 1997-12-19 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2000-12-18 2001-06-19 2001-12-19 $7700.00 Window Closed / Lapsed

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