Title:
PROCESS FOR MAKING TERTIARY AMINOALCOHOL COMPOUNDS
Document Type and Number:
WIPO Patent Application WO/2013/012777
Kind Code:
A3
Abstract:
A process for making a tertiary aminoalcohol compound is disclosed. The process comprises using an excess amount of a carbonyl compound in a condensation step between the carbonyl compound and a nitroalkane in the presence of a catalytic amount of a tertiary aminoalcohol compound, and conducting a hydrogenation/alkylation step to produce the tertiary aminoalcohol. The tertiary aminoalcohol compound used to catalyze the condensation step is preferably the same tertiary aminoalcohol compound produced in the hydrogenation/alkylation step. The process uses fewer steps than conventional processes.
Inventors:
MOORE DAVID W (US)
SPIEKER CHRISTIAN (DE)
GUMMRE JOHN D (US)
SPIEKER CHRISTIAN (DE)
GUMMRE JOHN D (US)
Application Number:
PCT/US2012/046855
Publication Date:
March 21, 2013
Filing Date:
July 16, 2012
Export Citation:
Assignee:
ANGUS CHEMICAL (US)
ANGUS CHEMIE GMBH (DE)
MOORE DAVID W (US)
SPIEKER CHRISTIAN (DE)
GUMMRE JOHN D (US)
ANGUS CHEMIE GMBH (DE)
MOORE DAVID W (US)
SPIEKER CHRISTIAN (DE)
GUMMRE JOHN D (US)
International Classes:
C07C45/55; C07C47/04; C07C201/12; C07C205/15; C07C213/00; C07C215/08
Domestic Patent References:
| WO1997000900A1 | 1997-01-09 |
Foreign References:
| US4067905A | 1978-01-10 | |||
| GB1056589A | 1967-01-25 | |||
| GB730602A | 1955-05-25 | |||
| CN101307074A | 2008-11-19 |
Other References:
WHEATLEY W B: "alpha,alpha-Dimethylcholine: Esters and Carbamates", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, ACS PUBLICATIONS, US, vol. 76, 20 May 1954 (1954-05-20), pages 2832 - 2834, XP002539600, ISSN: 0002-7863, DOI: 10.1021/JA01639A068
J. K. N. JONES ET AL: "378. Reactions of nitroparaffins. Part II. The reaction of 2-nitropropane with formaldehyde and ammonia", JOURNAL OF THE CHEMICAL SOCIETY (RESUMED), 1 January 1949 (1949-01-01), pages 1766, XP055038961, ISSN: 0368-1769, DOI: 10.1039/jr9490001766
KLEIN G ET AL: "Activation of nitroaldol reactions by diethylzinc and amino alcohols or diamines as promoters", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 43, no. 42, 14 October 2002 (2002-10-14), pages 7503 - 7506, XP004383405, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(02)01768-9
LUZZIO F A: "The Henry reaction: recent examples", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 57, no. 6, 4 February 2001 (2001-02-04), pages 915 - 945, XP004316522, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(00)00965-0
J. K. N. JONES ET AL: "378. Reactions of nitroparaffins. Part II. The reaction of 2-nitropropane with formaldehyde and ammonia", JOURNAL OF THE CHEMICAL SOCIETY (RESUMED), 1 January 1949 (1949-01-01), pages 1766, XP055038961, ISSN: 0368-1769, DOI: 10.1039/jr9490001766
KLEIN G ET AL: "Activation of nitroaldol reactions by diethylzinc and amino alcohols or diamines as promoters", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 43, no. 42, 14 October 2002 (2002-10-14), pages 7503 - 7506, XP004383405, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(02)01768-9
LUZZIO F A: "The Henry reaction: recent examples", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 57, no. 6, 4 February 2001 (2001-02-04), pages 915 - 945, XP004316522, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(00)00965-0
Attorney, Agent or Firm:
SARUSSI, Steven, J. (300 South Wacker DriveChicago, IL, US)
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