Sorbic Acid Per Se Or Salt Thereof Patents (Class 562/601)
  • Patent number: 8404890
    Abstract: Described is a method of making sorbic acid, pentadiene, or 3-penten-2-one. The method includes partially hydrogenating 4-hydroxy-6-methyl-2-pyrone (HMP) to yield 5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one (4-DHMMP). Then, if 3-penten-2-one is desired, thermally decomposing the 4-DHMMP to yield 3-penten-2-one. If sorbic acid or pentadiene are desired, the 4-DHMMP is hydrogenated to yield 4-hydroxy-6-methyltetrahydro-2-pyrone (4-HMTHP). The 4-HMTHP is then dehydrated by contacting it with a solid acid catalyst to yield parasorbic acid (PSA). The PSA can then be ring-opened by contacting it with a solid acid catalyst. The reaction conditions of the ring-opening reaction can be controlled to yield sorbic acid and/or pentadiene.
    Type: Grant
    Filed: November 10, 2010
    Date of Patent: March 26, 2013
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James A. Dumesic, Mei Chia
  • Publication number: 20120328708
    Abstract: The present invention concerns a disinfectant or antimicrobial composition for use in dental treatment, such as treatment and/or prevention of periodontitis, gingivitis or other forms of oral infection. The present Inventor found that microorganisms that infect the dental tissues and cause inflammation thereof, are susceptible to osmotic stress, to such extent that the application of a hypertonic composition is effective in curing or preventing infection and/or inflammations. It was furthermore found that these microorganisms are also susceptible to acidic stress. The present invention therefore provides compositions that induce osmotic stress in microorganisms causing infection of dental tissue when topically applied thereto, preferably osmotic as well as acidic stress. The present invention also concerns the methods and uses involving the compositions of the invention.
    Type: Application
    Filed: February 18, 2011
    Publication date: December 27, 2012
    Applicant: Nikinc Pharma B.V.
    Inventors: Suzette Veronica Van Der Waal, Stanley Brul, Johannes Jacob De Soet, Lucas Wilhelmus Maria Van Der Sluis
  • Publication number: 20120264660
    Abstract: A traceable treatment composition for treating a subterranean formation having multiple zones penetrated by a well bore comprising a homogenous blend of a tracking composition and a resin composition. The tracking composition comprises a substantially non-radioactive tracking material selected from the group consisting of a metal salt. The metal portion of the metal salt may be selected from the group consisting of gold, silver, lithium, molybdenum, and vanadium.
    Type: Application
    Filed: June 27, 2012
    Publication date: October 18, 2012
    Applicant: Halliburton Energy Seervices, Inc.
    Inventors: Philip D. Nguyen, Jimmie D. Weaver, Johnny A. Barton
  • Publication number: 20120157370
    Abstract: The invention relates to the use of radical traps in detergents and cleaners in order to improve cleaning performance, in particular for dirt containing polymerizable dyes.
    Type: Application
    Filed: February 23, 2012
    Publication date: June 21, 2012
    Applicant: Henkel AG & Co. KGaA
    Inventors: Christian Kropf, Andreas Buhl, André Hätzelt
  • Publication number: 20120116119
    Abstract: Described is a method of making sorbic acid, pentadiene, or 3-penten-2-one. The method includes partially hydrogenating 4-hydroxy-6-methyl-2-pyrone (HMP) to yield 5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one (4-DHMMP). Then, if 3-penten-2-one is desired, thermally decomposing the 4-DHMMP to yield 3-penten-2-one. If sorbic acid or pentadiene are desired, the 4-DHMMP is hydrogenated to yield 4-hydroxy-6-methyltetrahydro-2-pyrone (4-HMTHP). The 4-HMTHP is then dehydrated by contacting it with a solid acid catalyst to yield parasorbic acid (PSA). The PSA can then be ring-opened by contacting it with a solid acid catalyst. The reaction conditions of the ring-opening reaction can be controlled to yield sorbic acid and/or pentadiene.
    Type: Application
    Filed: November 10, 2010
    Publication date: May 10, 2012
    Inventors: James A. Dumesic, Mei Chia
  • Publication number: 20100221398
    Abstract: The invention relates to use of a compound of Formula (I) as a preservative, or to enhance the anti-mould efficacy of another preservative and a product comprising a compound of Formula (I), wherein: the second carbon is optionally substituted; the bond between R and the second carbon is unsaturated; R is a C1 to C20 alkyl, aryl, alkaryl, alkenyl or alkynyl; and wherein R may be optionally substituted; Z is H or OH; and when Z is OH, the bond between R and the second carbon is a triple bond.
    Type: Application
    Filed: June 6, 2008
    Publication date: September 2, 2010
    Inventors: David Brian Archer, Malcolm Stratford, Andrew Plumridge
  • Publication number: 20080051453
    Abstract: The present invention relates to a pharmaceutical co-crystal comprising an active pharmaceutical ingredient and a co-crystal agent having the structure R1—C(?O)XH.
    Type: Application
    Filed: August 22, 2007
    Publication date: February 28, 2008
    Inventors: Annette Bak, Drazen Ostovic
  • Patent number: 6794540
    Abstract: A process for the preparation of sorbic acid by thermal cleavage of the polyester prepared from crotonaldehyde and ketene, in the presence of a solvent and of an amine as catalyst with simultaneous distillation out of the sorbic acid formed and of the solvent through a rectification column with reflux, wherein only the solvent rather than the distillate is used as reflux, leads to high yields of sorbic acid and to a reduced consumption of amine catalyst.
    Type: Grant
    Filed: January 3, 2003
    Date of Patent: September 21, 2004
    Assignee: Nutrinova Nutrition Specialties & Food Ingredients GmbH
    Inventor: Christoph Mollenkopf
  • Patent number: 6673963
    Abstract: The invention relates to a process for preparing sorbic acid by thermal cleavage in a solvent of the polyester prepared from crotonaldehyde and ketene, the cleavage of the polyester being carried out in the presence of 20 to 100% by weight of a secondary or tertiary aliphatic, alicyclic nitrogen- and/or oxygen-containing amine, or aliphatic-aromatic substituted amine, as catalyst.
    Type: Grant
    Filed: September 9, 2002
    Date of Patent: January 6, 2004
    Assignee: Nutrinova Nutrition Specialties & Food Ingredients GmbH
    Inventors: Daniel Decker, Guenter Roscher, Christoph Mollenkopf, Erwin Weiss, Stefan Purps
  • Patent number: 6652820
    Abstract: A method of making a cesium salt is described and involves reacting a cesium sulfate containing solution with lime to form 1) a solution containing at least cesium hydroxide and 2) a residue comprising calcium sulfate. The method further involves removing the residue from the solution and converting the cesium hydroxide that is present in the solution to at least one type of cesium salt. The present invention further relates to uses of the cesium salt as well as methods of making cesium hydroxide using lime. Also, methods of making alkali metal salts and alkali metal hydroxides are also described.
    Type: Grant
    Filed: April 2, 2001
    Date of Patent: November 25, 2003
    Assignee: Cabot Corporation
    Inventor: Bart F. Bakke
  • Patent number: 6652921
    Abstract: The present invention relates to wood which contains a sorbic acid store and to processes for producing the sorbic acid store in the wood or on the surface of the wood. The present invention also relates to a process for using sorbic acid and its salts for protecting wood from microbially induced degradation.
    Type: Grant
    Filed: November 8, 2001
    Date of Patent: November 25, 2003
    Assignee: Nutrinova Nutrition Specialties & Food Ingredients GmbH
    Inventors: Nico N. Raczek, Katrin Saelzer
  • Publication number: 20030212296
    Abstract: A one-step polymerization process, leading directly to highly branched polyesters with unsaturated, either acrylate or sorbate end groups is described, which is based on the Diels-Alder reaction of polyfunctional sorbic esters with acrylates in defined ratios. A preferred embodiment of the invention is the Diels-Alder polymerization in aqueous emulsion.
    Type: Application
    Filed: February 21, 2003
    Publication date: November 13, 2003
    Inventors: Rainer Bruno Frings, Gerwald F. Grahe, Ou Shibata
  • Patent number: 6590122
    Abstract: The invented process for producing a polyester supplies a crotonaldehyde with a purity of 95% by weight or more to a reaction system in the reaction of ketene with crotonaldehyde. In this process, unreacted crotonaldehyde may be recovered from a reaction mixture obtained by the reaction of ketene with crotonaldehyde and may be recycled to the reaction system. The &agr;vinylcrotonaldehyde content of the crotonaldehyde to be supplied to the reaction system is, for example, less than 0.5% by weight, and the paraldehyde content of the crotonaldehyde to be supplied to the reaction system is, for example, less than 5% by weight. By decomposing the above-prepared polyester with, for example, hydrochloric acid, a sorbic acid having a satisfactory hue can be efficiently obtained.
    Type: Grant
    Filed: May 26, 2000
    Date of Patent: July 8, 2003
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Noboru Kamei, Akira Yamashita, Mitsuhiro Kouno
  • Patent number: 6545180
    Abstract: The invented process for producing sorbic acid includes the step of decomposing a polyester at temperatures of 100° C. or less with hydrochloric acid, which polyester is obtained from ketene and crotonaldehyde. In the process, the reaction temperature after the initiation of a polyester decomposition reaction is controlled by adding a hydrochloric acid to a reaction mixture, which hydrochloric acid has a temperature lower than that of the reaction mixture, for example, a temperature of 50° C. or less. Such hydrochloric acid for reaction control may have a concentration of, for example, 23% by weight or more. This process can yield sorbic acid in a short time in a high yield and can highly efficiently produce sorbic acid.
    Type: Grant
    Filed: May 24, 2000
    Date of Patent: April 8, 2003
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Akira Yamashita, Mitsuhiro Kouno
  • Publication number: 20030065218
    Abstract: The invention relates to a process for preparing sorbic acid by cleaving the sorbic acid polyester prepared from crotonaldehyde and ketene, the sorbic acid polyester being distilled and the cleavage being catalyzed by an amine, which comprises separating off the amine from the distillation residue by distillation under reduced pressure and at a temperature which is higher than the temperature of the polyester distillation and recovering it.
    Type: Application
    Filed: September 9, 2002
    Publication date: April 3, 2003
    Inventors: Christoph Mollenkopf, Erwin Weiss, Thomas Beck, Andreas Schneider, Klaus Fahrner, Stefan Purps
  • Patent number: 6525218
    Abstract: A process produces sorbic acid by hydrolyzing a polyester with an aqueous hydrochloric acid solution having a concentration of 15% by weight or less under the application of pressure or at a temperature of 100° C. or higher, which polyester is obtained by reaction between crotonaldehyde and ketene. In this process, the polyester may be hydrolyzed with a 3 to 10% by weight aqueous hydrochloric acid solution at a temperature of from 115° C. to 140° C. A reaction mixture after hydrolysis of the polyester may be subjected to solid-liquid separation and the resulting filtrate may be recycled and reused in the hydrolysis reaction of the polyester. This process can significantly reduce the amount of tar formed during decomposition of the polyester, can produce sorbic acid in a high yield, and can reduce the load on the treatment of waste filtrates formed during purification operation.
    Type: Grant
    Filed: August 7, 2001
    Date of Patent: February 25, 2003
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Mitsuhiro Kouno, Tadayuki Mitani, Noboru Kamei
  • Patent number: 6512142
    Abstract: A granulated product of potassium sorbate (i) has an overall pore volume of 0.3 ml/g or less, (ii) has an Na content of 450 ppm or less, or (iii) has an overall pore volume of 0.4 ml/g or less, or a granule hardness of 15% or less, and an Na content of 1000 ppm or less. The granulated product is obtained, for example, (i) by granulating a potassium sorbate aqueous solution through fluidized bed granulation drying, (ii) by neutralizing sorbic acid with a potassium sorbate having a molar ratio of Na to K (Na/K) of 0.0024 or less to yield potassium sorbate, and granulating the potassium sorbate, or (iii) by neutralizing sorbic acid with a potassium sorbate having a molar ratio of Na to K (Na/K) of 0.006 or less to yield potassium sorbate, and moisture-conditioning 100 parts by weight of the potassium sorbate with 1 to 8.5 parts by weight of water and 1 to 8 parts by weight of a water-soluble organic solvent and subjecting the resulting mixture to extrusion granulation.
    Type: Grant
    Filed: May 18, 2000
    Date of Patent: January 28, 2003
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Mitsuhiro Kouno, Masayuki Okada, Kazuyuki Matsuoka, Noboru Kamei
  • Patent number: 6509498
    Abstract: The invented process produces sorbic acid or its salt through the decomposition of a polyester obtained from ketene and aldehyde, and includes the step of treating a solution containing-sorbic acid or its salt with a chemically activated carbon, which sorbic acid or its salt is produced by the decomposition of the polyester. The treatment with activated carbon is performed, for example, at pH ranging from 5.8 to 7.5 at temperatures ranging from 30° C. to 80° C. The invented process can efficiently remove colored substances and can easily yield a high quality sorbic acid having a satisfactory hue in a high yield.
    Type: Grant
    Filed: May 26, 2000
    Date of Patent: January 21, 2003
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Akira Yamashita, Mitsuhiro Kouno
  • Patent number: 6495718
    Abstract: Compositions which comprise sorbic acid and/or one or more sorbates, and a flavonoid and/or flavonoid derivative, a method for the preparation thereof, and their use.
    Type: Grant
    Filed: May 25, 2000
    Date of Patent: December 17, 2002
    Assignee: Nutrinova Nutrition Specialties & Food Ingredients GmbH
    Inventor: Ralf Schmidt
  • Patent number: 6495717
    Abstract: A process produces sorbic acid or its salt and includes the step of retaining a slurry or solution containing sorbic acid or its salt while holding an oxygen concentration of a gaseous phase at 4% by volume or less, the gaseous phase being in contact with the slurry or solution containing sorbic acid or its salt. In the process, the oxygen concentration of the gaseous phase may be held at 4% by volume or less while introducing an inert gas into a gaseous phase of a reservoir holding the slurry or solution and/or of a conduit adjacent to the reservoir. Such an inert gases includes, for example, nitrogen gas. The oxygen concentration of the gaseous phase is preferably held at 1% by volume or less. The process can prevent the formation of new color-inducing substances in a purification operation of sorbic acid or its salt, and the obtained sorbic acid or its salt has a minimized degree of coloring and a minimized deterioration of hue over time.
    Type: Grant
    Filed: May 18, 2000
    Date of Patent: December 17, 2002
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Mitsuhiro Kouno, Noboru Kamei
  • Patent number: 6489509
    Abstract: An aqueous potassium sorbate solution has a dissolved oxygen concentration of not more than 3.0 mg/l. The aqueous potassium sorbate solution can be obtained (i) by degassing an aqueous potassium sorbate solution to thereby control the dissolved oxygen concentration to 3.0 mg/l or less, or (ii) by performing a reaction in a system, in which the oxygen concentrations of the gas phase and of materials to be reacted are reduced, in the production of an aqueous potassium sorbate solution by a reaction of sorbic acid and potassium hydroxide in the presence of water. The resulting aqueous potassium sorbate solution exhibits successively stable hue.
    Type: Grant
    Filed: May 3, 2001
    Date of Patent: December 3, 2002
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Mitsuhiro Kouno, Noboru Kamei
  • Patent number: 6462233
    Abstract: The invented process produces sorbic acid. The process includes the steps of adding a crude sorbic acid to a hot water having a temperature exceeding 100° C., which crude sorbic acid is obtained by the decomposition of a polyester formed through a reaction of ketene with crotonaldehyde, and performing at least one treatment selected from (A) a hot water extraction treatment for extracting sorbic acid with the hot water, and (B) a treatment with an activated carbon in the hot water. The temperature of the hot water is, for example, 120° C. or lower. The amount of sorbic acid to be treated is, for example, equal to or less than the saturated dissolution amount of sorbic acid with respect to the hot water at a treating temperature. The invented process can easily and efficiently remove tar substances and other impurities by-produced in the decomposition of the polyester and can produce a highly purified sorbic acid with a high productivity.
    Type: Grant
    Filed: May 26, 2000
    Date of Patent: October 8, 2002
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Akira Yamashita, Mitsuhiro Kouno
  • Patent number: 6455733
    Abstract: Crude sorbic acid produced in a decomposition step 1 is subjected to a crystallization step 2 to precipitate crystalline sorbic acid, and the crystalline sorbic acid is separated from a mother liquor (filtrate). The mother liquor was subjected to an extraction step 3 in which a specific extractant is employed, and an extract (organic phase) is subjected to a back extraction step 4 and treated with an alkaline solution to extract the sorbic acid into an aqueous phase in the form of a salt. The aqueous phase is neutralized in a neutralization step 6 and the produced sorbic acid is recovered in a separation step 7. As the extractant, use can be made of an organic solvent which is separable from water and has a solubility in water of not more than 1% by weight and in which not less than 0.5% by weight of sorbic acid is dissolvable (e.g., aliphatic C6-20 alcohols, ketones, esters, aromatic ethers).
    Type: Grant
    Filed: January 18, 2000
    Date of Patent: September 24, 2002
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Hiroshi Miura
  • Patent number: 6437182
    Abstract: The invented process produces sorbic acid by hydrolysis of a polyester in the presence of an acid, which polyester is obtained from ketene and crotonaldehyde. The process includes the step of subjecting a decomposition reaction mixture of the polyester to solid-liquid separation at temperatures ranging from 30° C. to 60° C. to yield sorbic acid as a solid. The process may further include the step of rinsing the sorbic acid obtained by solid-liquid separation with an aqueous solution containing sorbic acid, which aqueous solution is formed in a purification process of sorbic acid subsequent to the solid-liquid separation. The invented process can easily and efficiently remove tar substances by-produced in the reaction and can mitigate loads on a purification process.
    Type: Grant
    Filed: May 24, 2000
    Date of Patent: August 20, 2002
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Akira Yamashita, Mitsuhiro Kouno
  • Publication number: 20010047109
    Abstract: An aqueous potassium sorbate solution has a dissolved oxygen concentration of not more than 3.0 mg/l. The aqueous potassium sorbate solution can be obtained (i) by degassing an aqueous potassium sorbate solution to thereby control the dissolved oxygen concentration to 3.0 mg/l or less, or (ii) by performing a reaction in a system, in which the oxygen concentrations of the gas phase and of materials to be reacted are reduced, in the production of an aqueous potassium sorbate solution by a reaction of sorbic acid and potassium hydroxide in the presence of water. The resulting aqueous potassium sorbate solution exhibits successively stable hue.
    Type: Application
    Filed: May 3, 2001
    Publication date: November 29, 2001
    Inventors: Mitsuhiro Kouno, Noboru Kamei
  • Patent number: 5891921
    Abstract: Wood preservative systems comprising (a) a biocidal effective amount of (i) at least one di C.sub.8 -C.sub.12 alkyl quaternary ammonium carboxylate having the formula ##STR1## wherein R.sup.1 and R.sup.2 are a C.sub.8 -C.sub.12 alkyl group; R.sup.3 is a substituted or unsubstituted, interrupted or uninterrupted C.sub.1 -C.sub.100 group; l and q independently are 1, 2 or 3 and (l) (q) is 1, 2, or 3; and n is 0 or an integer from 1 to 50; (ii) at least one di C.sub.8 -C.sub.12 alkyl quaternary ammonium borate having the formula ##STR2## wherein R.sup.1 and R.sup.2 are defined as above, and a is 2 or 3, but when a is 2, b is 0 or 1, and when a is 3, b is 0, 1, or 2; or (iii) a combination of (i) and (ii); and (b) a solvent are provided. These carboxylate quats as well as carboxylate quats wherein R.sup.1 is a C.sub.1 -C.sub.20 alkyl or aryl-substituted alkyl group and R.sup.2 is a C.sub.8 -C.sub.20 alkyl group are preferably prepared by an indirect or a direct synthesis.
    Type: Grant
    Filed: April 18, 1996
    Date of Patent: April 6, 1999
    Assignee: Lonza Inc.
    Inventor: Leigh E. Walker
  • Patent number: 5354902
    Abstract: Stabilized aqueous solutions containing sorbic acid or salt thereof in an antimicrobial proportion, and further containing from 0.1, and preferably from 0.2, to about 5 ppm of manganous ion, said manganous ion being in an amount sufficient to inhibit oxidation of said sorbic acid or salt thereof to oxidative products such as acetaldehyde.
    Type: Grant
    Filed: April 28, 1993
    Date of Patent: October 11, 1994
    Assignee: McNeil-PPC, Inc.
    Inventors: Mel Merciadez, Kas Mohammed, Francois Y. Maniere
  • Patent number: 5200559
    Abstract: A process for producing sorbic acid from a polyester obtained by reaction of crotonaldehyde with ketene using an organic acid zinc salt as catalyst is provided, which process comprises dissolving the polyester in an aromatic hydrocarbon solvent having an azeotropic temperature of the solvent with water of 92.degree. to 100.degree. C., followed by washing the polyester solution with water or a mineral acid water to remove zinc matter and continuously contacting the solution with a strongly acidic porous ion exchange resin, the process being simple, commercially profitable, making possible a long term operation of the polyester decomposition apparatus, capable of easily purifying sorbic acid and affording sorbic acid with a good yeild.
    Type: Grant
    Filed: September 16, 1991
    Date of Patent: April 6, 1993
    Assignee: Chisso Corporation
    Inventor: Masahiro Nakajima
  • Patent number: 5191115
    Abstract: To produce a carboxylic acid R.sup.1 --COOH, in which R.sup.1 is a tertiary branched alkyl residue or a cycloalkyl residue with one or more rings, which may be attached, and possibly substituted by at least one alkyl residue, the alpha carbon atom of the carbonyl group being a tertiary carbon atom, a branched or cyclic alkane R.sup.1 H, in which R.sup.1 is a branched alkyl residue or a cycloalkyl residue with one or more rings, which may be attached, and possibly substituted by at least one alkyl residue, the alpha carbon atom of the hydrogen atom being a tertiary carbon atom or a secondary carbon atom capable of being rearranged during reaction to a tertiary atom, is reacted in the presence of an acid catalyst with a formiate H(CO)O(CR.sup.2 R.sup.3 R.sup.4), in which R.sup.2, R.sup.3 and R.sup.4 denote hydrogen or alkyl, under the three following conditions: that R.sup.2, R.sup.3 and R.sup.
    Type: Grant
    Filed: February 5, 1991
    Date of Patent: March 2, 1993
    Assignee: Atochem
    Inventors: Veronique Lazzeri, Roger Gallo, Rachid Jalal
  • Patent number: 4929755
    Abstract: In the process of hydrocarboxylating an .alpha.-enamide with CO and H.sub.2 O or an organic hydroxyl compound to produce an N-acyl-.alpha.-amino acid or ester, respectively, the improvement comprising using as the .alpha.-enamide reactant, an .alpha.-enamide which has a chiral center that is essentially all L or D, thereby producing a reaction mixture containing diastereomeric N-acyl-.alpha.-amino acids or esters having two chiral centers, said mixture having essentially no enantiomeric pairs.
    Type: Grant
    Filed: December 19, 1986
    Date of Patent: May 29, 1990
    Assignee: The Standard Oil Company
    Inventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
  • Patent number: 4822913
    Abstract: Esters of carboxylic acids of the formula RCH.sub.2 COOR"' and R'CH:C(R")COOR"' are reacted to form a carboxylic acid and an aliphatic alcohol R"'OH wherein R, R', and R" are individually selected from the group consisting of --H, alkyl moieties of from 1 to 18 carbon atoms and aralkyl moieties, cycloalkyl moieties and alkylaryl moieties of 3 to 18 carbon atoms and R"' is an alkyl moiety of 1 to 18 carbon atoms in the presence of an AMS-1B borosilicate crystalline molecular sieve catalyst under reaction conditions.
    Type: Grant
    Filed: October 28, 1983
    Date of Patent: April 18, 1989
    Assignee: Amoco Corporation
    Inventor: Gary P. Hagen
  • Patent number: 4740617
    Abstract: Preparation of sorbic acid from precursors by contact with acid catalysts is improved by utilizing crystallization to separate sorbic acid during the preparation.
    Type: Grant
    Filed: December 21, 1981
    Date of Patent: April 26, 1988
    Assignee: Monsanto Company
    Inventor: Richard C. Hallcher
  • Patent number: 4736063
    Abstract: Butadiene and acetic acid are reacted with metal ion oxidant to prepare acetoxyhexenoic acids which are then converted to sorbic acid.
    Type: Grant
    Filed: January 2, 1981
    Date of Patent: April 5, 1988
    Assignee: Monsanto Company
    Inventors: James P. Coleman, Richard C. Hallcher, Dudley E. McMackins
  • Patent number: 4639294
    Abstract: A process for producing sorbic acid is described, by first reacting crotonaldehyde with ketene to prepare a polyester, then decomposing the polyester with hydrochloric acid, separating the crude sorbic acid from the reaction solution, and purifying the separated sorbic acid, said purifying step comprising the following steps:(a) continuously dissolving the crude sorbic acid in petroleum at a temperature in the range of from 100.degree. to 140.degree. C. while evaporating the residual water and hydrochloric acid from the solution of the sorbic acid in petroleum;(b) separating the tar content from the petroleum solution in a separation column at a temperature in the range of from 100.degree. to 140.degree. C.; and(c) subjecting the mixture of sorbic acid and petroleum to flash evaporation in a film-type evaporator at a reduced pressure in the range of from 20 to 60 mmHg, with the evaporation residue being withdrawn from the bottom of the evaporator and recycled to step (a).
    Type: Grant
    Filed: July 16, 1985
    Date of Patent: January 27, 1987
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Noboru Kamei, Kinjiro Ikeda, Keishi Aoyama, Seitaro Hamano
  • Patent number: 4506095
    Abstract: This invention provides a process for producing alkenoate products in the presence of an ethylaluminum dichloride type catalyst, such as the production of methyl 5-hexenoate by the reaction between propylene and methyl acrylate.
    Type: Grant
    Filed: March 17, 1983
    Date of Patent: March 19, 1985
    Assignee: Celanese Corporation
    Inventor: Gerald S. Koermer
  • Patent number: 4502993
    Abstract: The invention relates to a process for the preparation of unsaturated aliphatic carboxylic acids by thermal cracking of the polymeric intermediate product ("polyester") which is formed in the catalytic reaction of aldehydes or ketones with ketene. The reaction mixture containing polyester is heated with water, and the polyester is then isolated and subjected to cracking. Or the polyester is first isolated and then heated with water and finally subjected to cracking. In both cases the temperature when the mixture is heated with water is the same as the boiling point, or is less than 40.degree. C. below the boiling point, of the aqueous mixture.
    Type: Grant
    Filed: May 19, 1982
    Date of Patent: March 5, 1985
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hermann Neu, G/u/ nter Roscher
  • Patent number: 4460787
    Abstract: The acid conversion of certain precursors, e.g. .gamma.-vinyl-.gamma.-butyrolactone, to sorbic acid is improved by presence of copper or silver ions along with the acid.
    Type: Grant
    Filed: December 21, 1981
    Date of Patent: July 17, 1984
    Assignee: Monsanto Company
    Inventors: James P. Coleman, Richard C. Hallcher
  • Patent number: 4380650
    Abstract: Acyloxyhexenoic acids are converted to .gamma.-vinyl-.gamma.-butyrolactone.
    Type: Grant
    Filed: January 2, 1981
    Date of Patent: April 19, 1983
    Assignee: Monsanto Company
    Inventors: James P. Coleman, Richard C. Hallcher, Dudley E. McMackins
  • Patent number: 4309357
    Abstract: Dienoic acids are prepared by reaction of salts of 3-butenoic acid and vinyl halides, in the presence of catalysts which are phosphinic complexes of rhodium or nickel.
    Type: Grant
    Filed: March 7, 1980
    Date of Patent: January 5, 1982
    Assignee: Montedison S.p.A.
    Inventors: Gian P. Chiusoli, William Giroldini, Giuseppe Salerno
  • Patent number: 4296243
    Abstract: A process for producing sorbic acid and its derivatives, which comprises reacting crotonaldehyde with ketene in the presence of a catalyst and decomposing or hydrolyzing the resulting adduct, said catalyst comprising a zinc salt of an aliphatic carboxylic acid and a phosphine or a pyridine.
    Type: Grant
    Filed: July 27, 1979
    Date of Patent: October 20, 1981
    Assignee: Daicel Ltd.
    Inventor: Kazuo Sato
  • Patent number: 4244776
    Abstract: Granular potassium sorbate is continuously manufactured by spraying an aqueous potassium sorbate solution into or onto a bed of potassium sorbate particles fluidized by heated air.
    Type: Grant
    Filed: March 8, 1979
    Date of Patent: January 13, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Noltner, Horst Oehme, Rudolf Lademann, Heinz Wendt
  • Patent number: 4158741
    Abstract: Process for preparing sorbic acid which comprises contacting .gamma.-vinyl-.gamma.-butyrolactone with at least one catalyst selected from the group consisting of (A) solid acids, (B) transition metal oxides, (C) metals of Group VIII of the Periodic Table and (D) halides of metals of Groups I-B, II-B, III-B, IV-B, V-B, VI-B and VIII of the Periodic Table.
    Type: Grant
    Filed: October 29, 1976
    Date of Patent: June 19, 1979
    Assignee: Nippon Gohsei Kagaku Kogyo Kabushiki Kaisha
    Inventors: Mitsuhiro Goi, Masahiko Miyashita, Tokio Hashimoto
  • Patent number: 4132733
    Abstract: Process for the manufacture of a molecular compound of sorbic acid -- potassium sorbate by means of crystallization from a solution of sorbic acid and potassium sorbate.
    Type: Grant
    Filed: June 10, 1975
    Date of Patent: January 2, 1979
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans Fernholz, Hans-Joachim Schmidt, Friedrich Wunder