Abstract: In the preparation of substituted 2-cyanocinnamic esters by the Knoevenagel condensation of cyanoacetic esters and carbonyl compounds, the reaction times for obtaining high yields can be considerably reduced by using C.sub.3 -C.sub.6 -monocarboxylic acids and ammonium compounds as catalysts.
Type:
Grant
Filed:
April 22, 1994
Date of Patent:
September 19, 1995
Assignee:
Haarmann & Reimer GmbH
Inventors:
Walter Kuhn, Werner Marks, Thomas Thielmann, Erich Dilk
Abstract: This invention provides an improved method for recovering an organic acid as a salt from various process streams by addition of a crystallizing base to a concentrated solution of neutralized organic acid. The addition of such a base causes crystallization of the salt. This process provides more efficient recovery of organic acid salt from a fermentation process stream than traditional crystallization and it may be used essentially as a one step purification process. The improved method is particularly applicable to the recovery of trisodium or tripotassium citrate from process streams produced in the fermentation and recovery of citric acid, with the addition of a crystallizing base such as sodium hydroxide, sodium carbonate, potassium hydroxide, or ammonia. The resulting product may be combined with an anticaking agent and/or dried to provide a particularly free flowing product.
Type:
Grant
Filed:
May 27, 1994
Date of Patent:
September 12, 1995
Assignee:
Haarmann & Reimer Corp.
Inventors:
Steven W. Felman, Chetna Patel, Bhalchandra H. Patwardhan, David J. Solow
Abstract: Ferulic acid, vanillic acid, coniferyl alcohol and coniferyl aldehyde can be prepared from eugenol with the aid of a new Pseudomonas species.
Abstract: The invention relates to new derivatives of macrocyclic lactones, a process for their preparation, a pyrolysis process using these new derivatives and the use of the pyrolysis products for the preparation of saturated macrocyclic lactones.
Type:
Grant
Filed:
April 29, 1992
Date of Patent:
June 7, 1994
Assignee:
Haarmann & Reimer GmbH
Inventors:
Rudolf Hopp, Horst Finkelmeier, Oskar Koch, Alfred Korber
Abstract: Ketals, preferably glycerol ketals such as, for example, 1-menthone glycerol ketal or 3,3,5-trimethylcyclohexanone glycerol ketal, have a physiological cooling effect and are therefore suitable as active compounds in compositions which are intended to cause a sensation of freshness on human skin or mucous membrane.
Type:
Grant
Filed:
April 3, 1992
Date of Patent:
November 30, 1993
Assignee:
Haarmann & Reimer GmbH
Inventors:
Helmut Grub, Ralf Pelzer, Rudolf Hopp, Roland Emberger, Heinz-Jurgen Bertram
Abstract: The invention discloses an antimicrobial composition composed of a hypothiocyanate generating system adjusted to a pH between about 1.5 and about 5 with a di or tricarboxylic acid. This composition provides synergistically improved antimicrobial action. With the addition of the organic acid, the antimicrobial composition provides effective cidal activity against Gram negative microorganisms in 20 minutes or less. The composition is particularly effective against Salmonella and may be used to provide greater than 6 logs reduction in viable cell count.
Abstract: Ethers of 1-hydroxy-hex-5-en-2-one are useful odoriferous substances which have a very complex fragrance pattern and allow an interesting variation in the scent of perfume oils.
Type:
Grant
Filed:
June 18, 1992
Date of Patent:
September 28, 1993
Assignee:
Haarmann & Reimer GmbH
Inventors:
Rudolf Hopp, Thomas Thielmann, Wilhelm Gottsch
Abstract: New nitriles which are odoriferous substances having an extremely fresh note are accessible by Knoevenagel condensation of 2-cyclopentyl-cyclopentanone and cyanoacetic acid and decarboxylation of the reaction product.
Type:
Grant
Filed:
April 2, 1992
Date of Patent:
May 18, 1993
Assignee:
Haarmann & Reimer GmbH
Inventors:
Rudolf Hopp, Thomas Thielmann, Wilhelm Gottsch
Abstract: Dimethylfuryl-dihydro-1,3,5-dithiazines are useful flavorings having low taste threshold values. They impart a coffee or mocha taste, in particular to drinks, confectionery and bakery products.
Type:
Grant
Filed:
October 15, 1991
Date of Patent:
November 24, 1992
Assignee:
Haarmann & Reimer
Inventors:
Jurgen Bruning, Roland Emberger, Matthias Guntert, Rudolf Hopp, Manfred Kopsel, Peter Werkhoff
Abstract: The invention relates to new thio-alkanones of the formula ##STR1## in which X represents an oxygen or sulphur atom,R.sub.1 represents hydrogen or a C.sub.1 -C.sub.2 -alkyl group and the broken lines represent a single bond or no bond,to a process for their preparation and their use as flavorings.
Type:
Grant
Filed:
May 16, 1991
Date of Patent:
September 8, 1992
Assignee:
Haarmann & Reimer
Inventors:
Roland Emberger, Matthias Gunter, Rudolf Hopp, Manfred Kopsel, Walter Kuhn, Peter Werkhoff
Abstract: Disclosed is an improved method for preparing a particulate citric acid or an alkali metal alkaline earth metal salt thereof. The method involves spray granulating citric acid or a salt thereof from its partially purified fermentation broth to form granules which are freer flowing and less inclined to fracture than is citric acid or its salts prepared by crystallization techniques which properties render the material prepared by the present method suitable for handling in bulk.
Type:
Grant
Filed:
April 29, 1991
Date of Patent:
April 14, 1992
Assignee:
Haarmann & Reimer
Inventors:
Helmut A. Mothes, Bhalchandra H. Patwardhan, Theo G. Schroeder, David J. Solow
Abstract: The invention relates to new alkadienenitriles of the formula ##STR1## in which n is an integer from 5 to 9, a process for their preparation and their outstanding suitability as odororiferous substances.
Type:
Grant
Filed:
September 12, 1990
Date of Patent:
April 14, 1992
Assignee:
Haarmann & Reimer GmbH
Inventors:
Rudolf Hopp, Thomas Thielmann, Wilhelm Gottsch
Abstract: Disclosed are 1- and 2-mono esters of citric acid and methods for preparing them in the pure form. These novel compounds are useful as surfactants.
Abstract: Disclosed is an improved method for preparing a particulate citric acid material. The method involves spray granulating citric acid from its partially purified fermentation broth to form granules which are freer flowing and less inclined to fracture than is citric acid prepared by crystallization techniques which properties render this material suitable for handling in bulk.
Type:
Grant
Filed:
October 5, 1990
Date of Patent:
September 3, 1991
Assignee:
Haarmann & Reimer Corp.
Inventors:
Helmut A. Mothes, Bhalchandra H. Patwardhan, Theo G. Schroeder, David J. Solow
Abstract: The invention discloses an antimicrobial composition composed of an antimicrobial polypeptide and a hypothiocyanate component. Synergistic activity is seen when the composition is applied at between about 30 and 40 degrees Centigrade at a pH between about 3 and about 5. The composition is useful against gram negative bacteria such as Salmonella. A preferred composition is nisin, lactoperoxidase, thiocyanate and hydrogen peroxide. Such a composition is capable of reducing the viable cell count of Salmonella by greater than 6 logs in 10 to 20 minutes.
Type:
Grant
Filed:
June 13, 1990
Date of Patent:
August 27, 1991
Assignee:
Haarmann & Reimer Corp.
Inventors:
Nancy L. Bycroft, Graham S. Byng, Stephen R. Good
Abstract: Alkali metal citrates are prepared by the addition of an alkaline alkali metal base or salt to citric acid solutions and recovered in solid form by the addition of a C.sub.1 to C.sub.5 alcohol to the solution to cause precipitation.
Abstract: A process for the preparation of natural vanillin is disclosed wherein eugenol and/or isoeugenol is oxidized microbially to vanillin using microorganisms of the genera Serratia, Klebsiella or Enterobacter.
Abstract: Disclosed is a method for inhibiting the contamination of processed meat products by pathogenic or spoilage microorganisms which method involves treating the surface of the meat product with a lanthionine bacteriocin.
Type:
Grant
Filed:
April 23, 1990
Date of Patent:
May 14, 1991
Assignee:
Haarmann & Reimer Corp.
Inventors:
Mark W. Collison, Terry F. Farver, Christine A. McDonald, Paula J. Herald, Daniel J. Monticello
Abstract: Disclosed is a composition comprising a mixture of acylated diesters of dl-malic acid corresponding to the formula: ##STR1## where P is palmityl and S is stearyl.
Type:
Grant
Filed:
December 14, 1989
Date of Patent:
May 14, 1991
Assignee:
Haarmann & Reimer Corp.
Inventors:
Donald F. Hershberger, Richard A. Plunkett