Abstract: N—[N-(3,3-dimethylbutyl)-L-?-aspartyl]-L-phenylalanine 1-methyl ester is produced by hydrogenation of L-?-aspartyl-L-phenylalanine 1-methyl ester and 3,3-dimethylbutyraldehyde produced in situ by the hydrolysis or cleavage of a 3,3-dimethylbutyraldehyde precursor. The production method is efficient and low cost, as compared with conventional N—[N-(3,3-dimethylbutyl)-L-?-aspartyl]-L-phenylalanine 1-methyl ester synthesis.
Type:
Grant
Filed:
May 12, 2010
Date of Patent:
October 11, 2011
Assignee:
The NutraSweet Company
Inventors:
Indra Prakash, Kenneth E. Furlong, Handley E. Jackson, III
Abstract: N—[N-(3,3-dimethylbutyl)-L-?-aspartyl]-L-phenylalanine 1-methyl ester is produced by hydrogenation of L-?-aspartyl-L-phenylalanine 1-methyl ester and 3,3-dimethylbutyraldehyde produced in situ by the hydrolysis or cleavage of a 3,3-dimethylbutyraldehyde precursor. The production method is efficient and low cost, as compared with conventional N—[N-(3,3-dimethylbutyl)-L-?-aspartyl]-L-phenylalanine 1-methyl ester synthesis.
Type:
Application
Filed:
May 12, 2010
Publication date:
September 2, 2010
Applicant:
THE NUTRASWEET COMPANY
Inventors:
INDRA PRAKASH, KENNETH E. FURLONG, HANDLEY E. JACKSON, III
Abstract: The present invention relates to a process of oxidation of alcohols selectively to aldehydes or ketones with molecular oxygen using a TEMPO based catalyst, Fe-bipyridyl or Fe-phenantroline co-catalyst and N-bromosuccinimide promoter in acetic acid solvent. The oxidation takes places at high rates and high aldehyde selectivity at temperatures in the range 45-50° C. and oxygen or air pressures of 0-15 psi. The alcohol conversion of 95-100% and aldehyde selectivity higher than 95% are achieved over 3-4 hours reaction time. Aldehydes such as 3,3-dimethyl-1-butanal can be produced efficiently using the present invention.
Type:
Grant
Filed:
February 24, 2005
Date of Patent:
April 1, 2008
Assignee:
The NutraSweet Company
Inventors:
Setrak K. Tanielyan, Robert L. Augustine, Indra Prakash, Kenneth E. Furlong, Handley E. Jackson
Abstract: 3,3-Dimethylbutanal is prepared from 3,3-dimethybutanol. 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 converted 3,3-dimethylbutanol to 3,3-dimethylbutanal by catalytic dehydrogenation.
Type:
Grant
Filed:
October 24, 2006
Date of Patent:
March 25, 2008
Assignee:
The Nutrasweet Company
Inventors:
Jerry R. Ebner, Zhi Guo, Arnold Hershman, Loraine M. Klein, William D. McGhee, Mark D. Paster, Indra Prakash
Abstract: N—[N-(3,3-dimethylbutyl)-L-?-aspartyl]-L-phenylalanine 1-methyl ester is produced by hydrogenation of L-?-aspartyl-L-phenylalanine 1-methyl ester and 3,3-dimethylbutyraldehyde produced in situ by the hydrolysis or cleavage of a 3,3-dimethylbutyraldehyde precursor. The production method is efficient and low cost, as compared with conventional N—[N-(3,3-dimethylbutyl)-L-?-aspartyl]-L-phenylalanine 1-methyl ester synthesis.
Type:
Application
Filed:
September 19, 2007
Publication date:
February 21, 2008
Applicant:
THE NUTRASWEET COMPANY
Inventors:
INDRA PRAKASH, KENNETH FURLONG, HANDLEY JACKSON
Abstract: This invention provides a method for preparing a liquid composition of N-[N-(3,3-dimethylbutyl)-L-?-aspartyl]-L-phenylalanine 1-methyl ester comprising the steps of (a) providing a liquid carrier; and (b) mixing N-[N-(3,3-dimethylbutyl)-L-?-aspartyl]-L-phenylalanine 1-methyl ester with said liquid carrier in a ratio of up to 3:2 by weight to produce a liquid composition. The resulting liquid composition would be capable of fully dissolving or suspending neotame and may be mixed with or added to a food or beverage product in an amount effective to sweeten the food or beverage product. This invention is also directed to the novel liquid compositions prepared by the process of this invention and to the food and beverage products sweetened thereby. The liquid carriers of this invention include water, alcohol and mixtures thereof.
Type:
Grant
Filed:
July 13, 2001
Date of Patent:
February 5, 2008
Assignee:
The Nutrasweet Company
Inventors:
Stephen A. Schroeder, Run Wang, Subbaroa V. Ponakala, Vinod Chaudhary
Abstract: N-[N-(3,3-dimethylbutyl)-L-?-aspartyl]-L-phenylalanine 1-methyl ester is produced by hydrogenation of L-?-aspartyl-L-phenylalanine 1-methyl ester and 3,3-dimethylbutyraldehyde produced in situ by the hydrolysis or cleavage of a 3,3-dimethylbutyraldehyde precursor. The production method is efficient and low cost, as compared with conventional N-[N-(3,3-dimethylbutyl)-L-?-aspartyl]-L-phenylalanine 1-methyl ester synthesis.
Type:
Grant
Filed:
April 30, 2004
Date of Patent:
October 30, 2007
Assignee:
The Nutrasweet Company
Inventors:
Indra Prakash, Kenneth E. Furlong, Handley E. Jackson, III
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 converted 3,3-dimethylbutanol to 3,3-dimethylbutanal by catalytic dehydrogenation.
Type:
Application
Filed:
October 24, 2006
Publication date:
May 10, 2007
Applicant:
The Nutrasweet Company
Inventors:
Jerry Ebner, Zhi Guo, Arnold Hershman, Loraine Klein, William McGhee, Mark Paster, Indra Prakash
Abstract: Synthesis of N-[N-(3,3-dimethylbutyl)-L-?-aspartyl]-L-phenylalanine 1-methyl ester by treating N-(3,3-dimethylbutyl)-L-aspartic acid with ketones to give oxazolidinone derivatives, which are condensed with L-phenylalanine methyl ester.
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.
Type:
Grant
Filed:
March 27, 2003
Date of Patent:
January 16, 2007
Assignee:
The Nutrasweet Company
Inventors:
Jerry R. Ebner, Zhi Guo, Arnold Hershman, Loraine M. Klein, William D. McGhee, Mark Paster, Indra Prakash
Abstract: A process for the production of 3,3-dimethylbutyraldehyde is disclosed. The 3,3-dimethylbutyraldehyde is obtained by the reduction of 3,3-dimethylbutyric acid using trimethylacetic anhydride and a phosphine. The 3,3-dimethylbutyric acid is preferably obtained by a process in which tert-butanol and vinylidene chloride are reacted in the presence of sulfuric acid. The disclosed process has improved cost and yield.
Type:
Grant
Filed:
March 18, 2003
Date of Patent:
April 18, 2006
Assignee:
The NutraSweet Company
Inventors:
Indra Prakash, Robert L. Augustine, Setrak K. Tanielyan
Abstract: The present invention relates to a process of oxidation of alcohols selectively to aldehydes or ketones with NaOCl using a TEMPO—borate catalyst system. It is shown that the oxidation can be efficiently carried out without KBr additives under solvent free conditions. Aldehydes such as 3,3-dimethylbutyraldehyde can be produced efficiently using the present invention.
Type:
Grant
Filed:
January 29, 2004
Date of Patent:
November 30, 2004
Assignee:
The NutraSweet Company
Inventors:
Indra Prakash, Setrak K. Tanielyan, Robert L. Augustine, Kenneth E. Furlong, Robert C. Scherm, Handley E. Jackson
Abstract: N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is produced by hydrogenation of L-&agr;-aspartyl-L-phenylalanine 1-methyl ester and 3,3-dimethylbutyraldehyde produced in situ by the hydrolysis or cleavage of a 3,3-dimethylbutyraldehyde precursor. The production method is efficient and low cost, as compared with conventional N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester synthesis.
Type:
Application
Filed:
April 30, 2004
Publication date:
November 25, 2004
Applicant:
NUTRASWEET COMPANY
Inventors:
Indra Prakash, Kenneth E. Furlong, Handley E. Jackson
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.
Type:
Grant
Filed:
May 29, 2003
Date of Patent:
October 12, 2004
Assignee:
The Nutrasweet Company
Inventors:
Jerry R. Ebner, Zhi Guo, Arnold Hershman, Loraine M. Klein, William D. McGhee, Mark Paster, Indra Prakash
Abstract: This invention relates to the purification of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester by slurrying a mixture containing N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester with organic or aqueous organic solvents.
Abstract: Processes for using modified catalysts with improved functionality in the production of neotame are disclosed. The modified catalysts surprisingly have been found to improve the selectivity over conventional catalysts and to reduce the level of certain impurities in neotame production processes.
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.
Type:
Application
Filed:
March 27, 2003
Publication date:
January 8, 2004
Applicant:
The Nutrasweet Company
Inventors:
Jerry R. Ebner, Zhi Guo, Arnold Hershman, Loraine M. Klein, William D. McGhee, Mark D. Paster, Indra Prakash
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.
Type:
Application
Filed:
May 29, 2003
Publication date:
December 11, 2003
Applicant:
The Nutrasweet Company
Inventors:
Jerry R. Ebner, Zhi Guo, Arnold Hershman, Loraine M. Klein, William D. McGhee, Mark D. Paster, Indra Prakash
Abstract: N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is produced by hydrogenation of a mixture of 3,3-dimethylbutyraldehyde and a precursor of L-&agr;-aspartyl-L-phenylalanine 1-methyl ester. In particular, N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is produced using an acid salt of L-&agr;-aspartyl-L-phenylalanine 1-methyl ester or N-protected L-&agr;-aspartyl-L-phenylalanine 1-methyl ester. The production method is efficient and low cost, as compared with conventional N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester synthesis.
Type:
Grant
Filed:
May 18, 2001
Date of Patent:
November 4, 2003
Assignee:
The NutraSweet Company
Inventors:
Indra Prakash, Zhi Guo, Steve Schroeder, Kurt L. Wachholder