Title:
PROCESS FOR THE PREPARATION OF 3,3-DIMETHYLBUTANAL
Document Type and Number:
WIPO Patent Application WO2001002332
Kind Code:
A3
Abstract:
3,3-Dimethylbutanal is prepared from 3,3-dimethylbutanol. Intermediate 3,3-dimethylbutanol is obtained by reacting ethylene, isopropylene and a mineral acid to produce a 3,3-dimethylbutyl ester which is hydrolyzed to the alcohol. The hydrolysis step is effectively carried out by reactive distillation. Alternatively, 3,3-dimethylbutanal is prepared from 3,3-dimethylbutanol obtained by reduction of the corresponding carboxylic acid or 1,2-epoxy-3,3-dimethylbutane, or by hydrolysis of 1-halo-3,3-dimethylbutane. Fixed bed gas phase and stirred tank liquid phase processes are provided for converting 3,3-dimethylbutanol to 3,3-dimethylbutanal by catalytic dehydrogenation.
Inventors:
EBNER JERRY R
GUO ZHI
HERSHMAN ARNOLD
KLEIN LORAINE M
MCGHEE WILLIAM D
PASTER MARK D
PRAKASH INDRA
GUO ZHI
HERSHMAN ARNOLD
KLEIN LORAINE M
MCGHEE WILLIAM D
PASTER MARK D
PRAKASH INDRA
Application Number:
PCT/US2000/017946
Publication Date:
March 22, 2001
Filing Date:
June 29, 2000
Export Citation:
Assignee:
NUTRASWEET CO (US)
International Classes:
C07C45/29; C07B61/00; C07C17/275; C07C29/06; C07C29/09; C07C29/12; C07C29/124; C07C29/132; C07C29/147; C07C31/125; C07C45/00; C07C45/38; C07C47/02; C07C229/24; C07C303/24; C07K1/113; C07K5/072; C07K5/075; C07C305/08; (IPC1-7): C07C47/02; C07C45/00; C07C45/38; C07C303/24; C07C303/26; C07C29/12; C07C229/24; C07C29/147; C07C29/124; C07C29/09; C07C29/36; C07C29/132
Foreign References:
| US5856584A | 1999-01-05 | |||
| GB693390A | 1953-07-01 | |||
| US4433175A | 1984-02-21 | |||
| US4590313A | 1986-05-20 | |||
| US5510508A | 1996-04-23 |
Other References:
R. F. NYSTROM ET AL: "Reduction of organic compounds by lithium aluminium hydride. II. Carboxylic acids", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 69, 1947, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC., US, pages 2548 - 2549, XP002154210, ISSN: 0002-7863
V. N. IPATIEFF ET AL: "Study in the terpene series. X. Isomerization accompanying hydrogenolysis of alcohols", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 73, 1951, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC., US, pages 553 - 555, XP002154211, ISSN: 0002-7863
A . BRÄNDSTRÖM: "A method for the preparation of tert-alkylacetic acids", ACTA CHEMICA SCANDINAVICA., vol. 13, no. 3, 1959, MUNKSGAARD, COPENHAGEN., DK, pages 608 - 610, XP002154212, ISSN: 0904-213X
CHEMICAL ABSTRACTS, vol. 43, no. 16, 1949, Columbus, Ohio, US; abstract no. 6155b, M. S. MALINOVSKII ET AL: "Preparation of alcohols by the Grignard method from olefin oxides. II. Synthesis of 3,3-dimethyl-1-butanol and 4,4-dimethyl-1-pentanol from ethylene oxide and 2-heptanol, and of 5-methyl-5-hexanol from propylene oxide" page 6155; column 1; XP002154213
V. N. IPATIEFF ET AL: "Study in the terpene series. X. Isomerization accompanying hydrogenolysis of alcohols", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 73, 1951, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC., US, pages 553 - 555, XP002154211, ISSN: 0002-7863
A . BRÄNDSTRÖM: "A method for the preparation of tert-alkylacetic acids", ACTA CHEMICA SCANDINAVICA., vol. 13, no. 3, 1959, MUNKSGAARD, COPENHAGEN., DK, pages 608 - 610, XP002154212, ISSN: 0904-213X
CHEMICAL ABSTRACTS, vol. 43, no. 16, 1949, Columbus, Ohio, US; abstract no. 6155b, M. S. MALINOVSKII ET AL: "Preparation of alcohols by the Grignard method from olefin oxides. II. Synthesis of 3,3-dimethyl-1-butanol and 4,4-dimethyl-1-pentanol from ethylene oxide and 2-heptanol, and of 5-methyl-5-hexanol from propylene oxide" page 6155; column 1; XP002154213
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