Purification Or Recovery Patents (Class 568/438)
  • Patent number: 11492737
    Abstract: A method of dissolving lignocellulosic biomass waste includes obtaining raw lignocellulosic biomass waste, reducing a size of the biomass waste to provide a biomass particle size of less than about 200 ?m; using dimethyl sulfoxide (DMSO), sodium hydroxide (NaOH) and trifluoroacetic acid (TFA) solvents to dissolve the biomass particles and achieve a dissolved lignocellulose solution. The present method dissolves at least about 94% of the lignocellulose fraction in the waste biomass. In an embodiment, the biomass particle size can be about 180 ?m.
    Type: Grant
    Filed: August 19, 2021
    Date of Patent: November 8, 2022
    Assignee: UNITED ARAB EMIRATES UNIVERSITY
    Inventors: Emmanuel Galiwango, Ali H. Al-Marzouqi, Sabeera Haris
  • Patent number: 9394211
    Abstract: A process for isolating at least one target compound, such as manool, geranyl linalool, ethyl guaiacol, eugenol, veratraldehyde, squalene, terpin, cholesterol, beta-sitosterol, campesterol, stigmasterol, stigmastenol and dehydroabietic acid, from biomass, the process including steps of: obtaining a condensate from a recovery evaporator, a reverse osmosis retentate of a condensate of a pulp and paper mill, or both, the condensate, retentate or both being substantially free of higher molecular weight (approximately >1000 Da) cellulose and/or lignin and/or lignin-derived material; optionally pH adjusting and filtering the condensate to collect insoluble material; extracting the condensate, the collected insoluble material, or both, with solid phase extraction (SPE), liquid-liquid extraction or solid-liquid extraction to produce an extract containing the at least one target compound; and optionally purifying the extract containing the at least one target compound by thermal fractionation, chromatographic separ
    Type: Grant
    Filed: March 5, 2015
    Date of Patent: July 19, 2016
    Inventors: Craig Brennan Milestone, Deborah L. MacLatchy, L. Mark Hewitt
  • Patent number: 9006494
    Abstract: The present invention relates to a process for producing vanillin from an aqueous, basic vanillin-comprising composition, in particular from a composition as arises in the oxidation, especially in the oxidation by electrolysis, of aqueous alkaline lignin-comprising compositions, comprising at least one treatment of an aqueous, basic vanillin-comprising composition, in particular the treatment of a composition as arises in the oxidation, especially in the oxidation by electrolysis, of aqueous alkaline lignin-comprising compositions, with a basic adsorbent, in particular an anion exchanger.
    Type: Grant
    Filed: July 3, 2013
    Date of Patent: April 14, 2015
    Assignee: BASF SE
    Inventors: Florian Stecker, Andreas Fischer, Axel Kirste, Agnes Voitl, Chung Huan Wong, Siegfried Waldvogel, Carolin Regenbrecht, Dominik Schmitt, Marius Franziskus Hartmer
  • Patent number: 8993809
    Abstract: A process for isolating at least one target compound, such as manool, geranyl linalool, ethyl guaiacol, eugenol, veratraldehyde, squalene, terpin, cholesterol, beta-sitosterol, campesterol, stigmasterol, stigmastenol and dehydroabietic acid, from biomass, the process including steps of: obtaining a condensate from a recovery evaporator, a reverse osmosis retentate of a condensate of a pulp and paper mill, or both, the condensate, retentate or both being substantially free of higher molecular weight (approximately >1000 Da) cellulose and/or lignin and/or lignin-derived material; optionally pH adjusting and filtering the condensate to collect insoluble material; extracting the condensate, the collected insoluble material, or both, with solid phase extraction (SPE), liquid-liquid extraction or solid-liquid extraction to produce an extract containing the at least one target compound; and optionally purifying the extract containing the at least one target compound by thermal fractionation, chromatographic separ
    Type: Grant
    Filed: April 7, 2011
    Date of Patent: March 31, 2015
    Assignee: Her Majesty the Queen in Right of Canada, as Represented by the Minister of Environment
    Inventors: Craig Brennan Milestone, Deborah L. MacLatchy, L. Mark Hewitt
  • Patent number: 8884069
    Abstract: A process for the preparation of an aromatic aldehyde by means of the oxidation of the corresponding starting compound in aqueous medium, and separation of said aldehyde from said medium by pervaporation is disclosed together a plant for its carrying out. Advantageously, the process of the present invention allows control of oxidation reaction and recovery of the product with high selectivity and purity. Among others, benzaldehyde, anisaldehyde and vanillin can advantageously be prepared by this process.
    Type: Grant
    Filed: June 10, 2011
    Date of Patent: November 11, 2014
    Assignee: Alma Mater Studiorum Universita di Bologna
    Inventors: Giovanni Camera Roda, Vincenzo Augugliaro, Vittorio Loddo, Giovanni Palmisano, Leonardo Palmisano
  • Patent number: 8692026
    Abstract: A new synthesis of 4-bromo-2-methoxybenzaldehyde is reported from 1,4 dibromo 2-fluorobenzene. First, 2-fluoro-4-bromobenzaldehyde is prepared through metal halogen exchange and formylation with a formyl source at 0° C. After crystallization, this intermediate is reacted with methanol in the presence of potassium carbonate. Subsequently, 4-bromo-2-methoxy-benzaldehyde is crystallized.
    Type: Grant
    Filed: July 1, 2011
    Date of Patent: April 8, 2014
    Assignee: Albemarle Corporation
    Inventors: Thierry J. Giard, Vincent L. Mutterer, Christophe Durvaux
  • Publication number: 20140046099
    Abstract: The present invention relates to a process for producing vanillin from an aqueous, basic vanillin-comprising composition, in particular from a composition as arises in the oxidation, especially in the oxidation by electrolysis, of aqueous alkaline lignin-comprising compositions, comprising at least one treatment of an aqueous, basic vanillin-comprising composition, in particular the treatment of a composition as arises in the oxidation, especially in the oxidation by electrolysis, of aqueous alkaline lignin-comprising compositions, with a basic adsorbent, in particular an anion exchanger.
    Type: Application
    Filed: July 3, 2013
    Publication date: February 13, 2014
    Inventors: Florian Stecker, Andreas Fischer, Axel Kirste, Agnes Voitl, Chung Huan Wong, Siegfried Waldvogel, Carolin Regenbrecht, Dominik Schmitt, Marius Franziskus Hartmer
  • Publication number: 20130123546
    Abstract: A process for the preparation of an aromatic aldehyde by means of the oxidation of the corresponding starting compound in aqueous medium, and separation of said aldehyde from said medium by pervaporation is disclosed together a plant for its carrying out. Advantageously, the process of the present invention allows control of oxidation reaction and recovery of the product with high selectivity and purity. Among others, benzaldehyde, anisaldehyde and vanillin can advantageously be prepared by this process.
    Type: Application
    Filed: June 10, 2011
    Publication date: May 16, 2013
    Applicant: ALMA MATER STUDIORUM UNIVERSITA DI BOLOGNA
    Inventors: Giovanni Camer Roda, Vincenzo Augugliaro, Vittorio Loddo, Giovanni Palmisano, Leonardo Palmisano
  • Publication number: 20130090498
    Abstract: A new synthesis of 4-bromo-2-methoxybenzaldehyde is reported from 1,4 dibromo 2-fluorobenzene. First, 2-fluoro-4-bromobenzaldehyde is prepared through metal halogen exchange and formylation with a formyl source at 0° C. After crystallization, this intermediate is reacted with methanol in the presence of potassium carbonate. Subsequently, 4-bromo-2-methoxy-benzaldehyde is crystallized.
    Type: Application
    Filed: July 1, 2011
    Publication date: April 11, 2013
    Applicant: Albemarle Corporation
    Inventors: Thierry J. Giard, Vincent L. Mutterer, Christophe Durvaux
  • Publication number: 20130072724
    Abstract: A process for isolating at least one target compound, such as manool, geranyl linalool, ethyl guaiacol, eugenol, veratraldehyde, squalene, terpin, cholesterol, beta-sitosterol, campesterol, stigmasterol, stigmastenol and dehydroabietic acid, from biomass, the process including steps of: obtaining a condensate from a recovery evaporator, a reverse osmosis retentate of a condensate of a pulp and paper mill, or both, the condensate, retentate or both being substantially free of higher molecular weight (approximately >1000 Da) cellulose and/or lignin and/or lignin-derived material; optionally pH adjusting and filtering the condensate to collect insoluble material; extracting the condensate, the collected insoluble material, or both, with solid phase extraction (SPE), liquid-liquid extraction or solid-liquid extraction to produce an extract containing the at least one target compound; and optionally purifying the extract containing the at least one target compound by thermal fractionation, chromatographic separ
    Type: Application
    Filed: April 7, 2011
    Publication date: March 21, 2013
    Applicant: Her Majesty The Queen in the Right of Canada, as Represented by the Minister of Environment
    Inventors: Craig Brennan Milestone, Deborah L. MacLatchy, L. Mark Hewitt
  • Publication number: 20120192880
    Abstract: The invention provides a tobacco composition for use in a smoking article or a smokeless tobacco composition that comprises an extract derived from a component of a plant of the Nicotiana species. The invention also provides smoking articles and smokeless tobacco compositions that include the extracts described herein, and methods for preparing extracts derived from a component of a plant of the Nicotiana species for addition to a tobacco composition.
    Type: Application
    Filed: January 28, 2011
    Publication date: August 2, 2012
    Inventors: Michael Francis Dube, William Monroe Coleman, III
  • Publication number: 20110268652
    Abstract: The present invention relates to an integrated method for producing cellulose and at least one low-molecular-weight reusable material, in which a starting material containing lignocellulose is provided and subjected to a decomposition with a processing medium. A fraction enriched with cellulose and a fraction depleted of cellulose is then isolated from the decomposition material, the depleted fraction of cellulose being subjected to a treatment during which at least one low-molecular-weight reusable material is obtained.
    Type: Application
    Filed: September 7, 2009
    Publication date: November 3, 2011
    Applicant: BASF SE
    Inventors: Otto Machhammer, Jochem Henkelmann, Wolfgang Rohde, Mario Emmeluth, Sonja Giesa
  • Publication number: 20110263696
    Abstract: Compositions comprising proanthocyanidin compositions (e.g. those extracted from cinnamomum species) that are observed to bind tau and inhibit its aggregation as well as methods for making and using such compositions are disclosed. In certain embodiments of the invention, the proanthocyanidins can be used as a probe to identify and/or characterize tau isoforms in a variety of contexts. In other embodiments of the invention, these compositions are used in methods designed to treat neurological disorders associated with tau aggregation (e.g. Alzheimer's disease).
    Type: Application
    Filed: March 31, 2008
    Publication date: October 27, 2011
    Inventors: Donald J. Graves, John Lew
  • Patent number: 7910780
    Abstract: The present invention relates to a method for purifying terephthalaldehyde which comprises a first step of dissolving terephthalaldehyde containing impurities in an aromatic solvent at high temperature to prepare a solution; and a second step of quenching the solution to re-crystallize it into terephthalaldehyde. In accordance with the present invention, high pure terephthalaldehyde may be economically prepared.
    Type: Grant
    Filed: November 15, 2007
    Date of Patent: March 22, 2011
    Assignee: LG Chem, Ltd.
    Inventors: Seong Hoon Kang, In Kyu Park, Yeong Dae Kim, Jong Suh Park
  • Publication number: 20110021613
    Abstract: Compounds obtainable from plants, e.g. of the genus Eucalyptus, or from microorganisms are shown to be useful as CNS activity modulators useful e.g. in the treatment of depression, for lifting mood and/or for increasing behavioural initiative and the like. This use and related aspects form embodiments of the invention. Also compounds as such are presented. The compounds useful are acylphloroglucine derivatives of the formula I, wherein the substituents are as defined in the description.
    Type: Application
    Filed: December 11, 2007
    Publication date: January 27, 2011
    Applicant: INTERMED DISCOVERY GMBH
    Inventors: Ernst Roemer, Torsten Grothe
  • Publication number: 20100130791
    Abstract: The present invention relates to a method for purifying terephthalaldehyde which comprises a first step of dissolving terephthalaldehyde containing impurities in an aromatic solvent at high temperature to prepare a solution; and a second step of quenching the solution to re-crystallize it into terephthalaldehyde. In accordance with the present invention, high pure terephthalaldehyde may be economically prepared.
    Type: Application
    Filed: November 15, 2007
    Publication date: May 27, 2010
    Applicant: LG CHEM, LTD.
    Inventors: Seong-Hoon Kang, In-Kyu Park, Young-Dae Kim, Jong-Suh Park
  • Patent number: 7714173
    Abstract: The present invention relates to a method for preparing high-purity terephthalaldehyde which comprises re-crystallizing terephthalaldehyde crystals containing impurities, using an anti-solvent. Specifically, the present invention relates to a method for preparing terephthalaldehyde which comprises dissolving low-purity terephthalaldehyde prepared by a conventional method in dimethylsulfoxide and then re-crystallizing the solution, using water as an anti-solvent. The present invention is not only environment-friendly because it uses water only as an anti-solvent, but also economical because it may simply prepare high-purity terephthalaldehyde in a short time.
    Type: Grant
    Filed: June 14, 2007
    Date of Patent: May 11, 2010
    Assignee: LG Chem, Ltd.
    Inventors: Seong-Hoon Kang, In-Kyu Park, Jong-Suh Park, Young-Dae Kim, Jong-Hyun Chae
  • Patent number: 7696372
    Abstract: This invention relates to a process for preparing R-gossypol L-phenylalaninol dienamine using non-chromatographic purification methods. In particular, the invention is directed to resolution of R- and S-gossypol L-phenylalaninol dienamine by crystallization. R-gossypol L-phenylalaninol dienamine is a useful intermediate for the preparation of R-(?)-gossypol and R-(?)-gossypol acetic acid co-crystal. R-(?)-Gossypol acetic acid and its co-crystal is useful for inducing apoptosis in cells and for sensitizing cells to the induction of apoptotic cell death.
    Type: Grant
    Filed: October 1, 2008
    Date of Patent: April 13, 2010
    Assignee: Ascenta Therapeutics, Inc.
    Inventors: Ming Guo, Shuguang Zhu, Laure Navarre, Régis Périon
  • Publication number: 20100048958
    Abstract: The present invention relates to a method for preparing high-purity terephthalaldehyde which comprises re-crystallizing terephthalaldehyde crystals containing impurities, using an anti-solvent. Specifically, the present invention relates to a method for preparing terephthalaldehyde which comprises dissolving low-purity terephthalaldehyde prepared by a conventional method in dimethylsulfoxide and then re-crystallizing the solution, using water as an anti-solvent. The present invention is not only environment-friendly because it uses water only as an anti-solvent, but also economical because it may simply prepare high-purity terephthalaldehyde in a short time.
    Type: Application
    Filed: June 14, 2007
    Publication date: February 25, 2010
    Applicant: LG CHEM, LTD.
    Inventors: Seong-Hoon Kang, In-Kyu Park, Jong-Suh Park, Young-Dae Kim, Jong-Jyun Chae
  • Publication number: 20090298927
    Abstract: The present invention is related to a thermal extract of a plant material and methods of extraction thereof. The method of producing a thermal extract from a plant starting material by means of a thermal extraction of the starting material wherein the improvement consists in requiring smaller amounts of costly and/or toxic organic solvents for the extraction and partitioning steps.
    Type: Application
    Filed: April 2, 2007
    Publication date: December 3, 2009
    Applicant: Pharmatherm Chemicals Inc.
    Inventors: David Boulard, Robert G. Graham, Barry Freel
  • Patent number: 7402708
    Abstract: A method for producing aqueous ortho-phthalaldehyde solutions which comprises introducing an acetal of the o-phthalaldehyde into water and subsequently setting a pH <7 by adding an acid, whereupon, then at a temperature between 10° C. and 90° C., the acetal is converted into the o-phthalaldehyde by eliminating the corresponding alcohol, and also use of OPA acetals for producing these solutions.
    Type: Grant
    Filed: January 25, 2006
    Date of Patent: July 22, 2008
    Assignee: DSM Fine Chemicals Austria NFG GmbH & Co KG
    Inventors: Karlheinz Giselbrecht, Wolfgang Hillisch
  • Patent number: 7399889
    Abstract: The present invention provides a process for the preparation of Vanillin (4-hydroxy-3-methoxy benzaldehyde) by a single-step oxidation of ferulate moiety of rice straw, a renewable agricultural waste. This is a chemical method where vanillin is produced from a renewable resource in a single-step using a green oxidizing reagent and green solvent. Apart from that the water and the inorganic compounds can be recycled.
    Type: Grant
    Filed: February 12, 2007
    Date of Patent: July 15, 2008
    Assignee: Council of Scientific and Industrial Research
    Inventor: Naleen Borthakur
  • Patent number: 7393983
    Abstract: The present invention relates to a method and an apparatus for continuously separating aromatic dialdehyde from a reaction mixture obtained by gas-phase oxidation of dimethylbenzene. The method for continuously separating aromatic dialdehyde includes the steps of congealing aromatic dialdehyde by cooling the gas-phase reaction mixture including the aromatic dialdehyde, which is obtained by gas-phase oxidation of dimethylbenzene, to 5-70° C. and separating the congealed aromatic dialdehyde from the remaining reaction mixture. Using the method and apparatus in accordance with the present invention, aromatic dialdehyde can be effectively and selectively separated from a reaction mixture obtained by gas-phase oxidation of dimethylbenzene in high yield.
    Type: Grant
    Filed: May 9, 2006
    Date of Patent: July 1, 2008
    Assignee: LG Chem, Ltd.
    Inventors: Jong-Hyun Chae, Won-Ho Lee, Dong-Il Lee, Hyun-Kyung Yoon
  • Patent number: 7183442
    Abstract: The present invention relates to a method for preparing high-purity terephthalaldehyde from terephthalaldehyde crystal containing impurities by recrystallization using an antisolvent. Low-purity terephthalaldehyde prepared by a conventional method, which contains a small amount of impurities, is dissolved in a solvent and recrystallized using water as antisolvent to obtain high-purity terephthalaldehyde. The invention is significantly advantageous in using water only as antisolvent. Also, the purification process takes short time and is economical and environment-friendly.
    Type: Grant
    Filed: December 6, 2005
    Date of Patent: February 27, 2007
    Assignee: LG Chem, Ltd.
    Inventors: Hyun-kyung Yoon, Won-ho Lee, Jong-hyun Chae, Dong-il Lee
  • Patent number: 7145043
    Abstract: Methods, compositions, and devices for alleviating the problems of toxic discharge of aldehydes present in waste streams are disclosed. The methods relate to forming neutralized aldehydes by treating aldehydes with oxidizing agents. The oxidizing agents offer a simple, effective, fast and inexpensive solution for treatment of toxic aldehydes prior to disposal into the environment.
    Type: Grant
    Filed: December 16, 2004
    Date of Patent: December 5, 2006
    Assignee: Ethicon, Inc.
    Inventor: Peter Zhu
  • Patent number: 6727391
    Abstract: A liquid output from a continuous hydroformylation, which comprises essentially aldehydes, high-boiling by-products, a homogeneously dissolved hydroformylation catalyst, unreacted olefins, low-boiling by-products and dissolved synthesis gas, is worked up by a process in which a) the liquid hydroformylation output is depressurized in a first depressurization stage to a pressure which is from 2 to 20 bar below the reactor pressure, resulting in separation into a liquid phase and a gas phase, and b) the liquid phase obtained in the first depressurization stage is depressurized in a second depressurization stage to a pressure which is lower than the pressure of the first depressurization stage, resulting in separation into a liquid phase comprising essentially high-boiling by-products of the hydroformylation, the homogeneously dissolved hydroformylation catalyst and small amounts of hydroformylation product and unreacted olefin and a gas phase comprising essentially the major part of the hydroformylation produc
    Type: Grant
    Filed: August 8, 2002
    Date of Patent: April 27, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl-Heinz Walczuch, Rolf Müller, Roland Krokoszinski, Bernhard Geissler
  • Patent number: 6686507
    Abstract: A process for the purification of 2-methoxy-5-trifluoro-methoxy benzaldehyde oil in which the oil is converted to amine by reaction of a nitroaniline with the oil; the imine is isolated as a solid; and the solid imine is converted back to the 2-methoxy-5-trifluoromethoxy benzaldehyde oil. The nitroaniline is selected from the group consisting of 3-nitroaniline, 3-methyl-2-nitroaniline, 4-methyl-2-nitroaniline, 2 methyl-3-nitroaniline and 4-methyl-3-nitroaniline.
    Type: Grant
    Filed: December 9, 2002
    Date of Patent: February 3, 2004
    Assignee: Pfizer Inc
    Inventors: Timothy J. N. Watson, Patrice Arpin, Michael G. Vetelino
  • Patent number: 6670510
    Abstract: The present invention recites a process for the of 2,5-dimethoxy-benzaldehyde by reacting a 2-hydroxy-5 methoxy-benzaldehyde with a suitable metal hydroxide in the presence of a suitable solvent to make a metal salt of 2-hydroxy-5-methoxy benzaldehyde comprising. The invention further provides a method for alkylating said metal salts with dimethylsulfate in the presence of a suitable solvent so as to provide a 2,5-dimethoxy benzaldehyde.
    Type: Grant
    Filed: April 18, 2002
    Date of Patent: December 30, 2003
    Assignee: Eastman Chemical Company
    Inventors: Thomas Elbert Shanks, Robert Joseph Maleski
  • Patent number: 6624330
    Abstract: The present invention relates to a method for stabilizing phenylacetaldehyde by adding at least one additive, in which case the additive contains one or more polybasic carboxylic acids.
    Type: Grant
    Filed: December 4, 2001
    Date of Patent: September 23, 2003
    Assignee: Haarmann & Reimer GmbH
    Inventor: Walter Kuhn
  • Patent number: 6531634
    Abstract: Methods, compositions, and devices for alleviating the problems of toxic discharge of aldehydes present in waste streams are disclosed. The methods relate to forming neutralized aldehydes by treating aldehydes with oxidizing agents. The oxidizing agents offer a simple, effective, fast and inexpensive solution for treatment of toxic aldehydes prior to disposal into the environment.
    Type: Grant
    Filed: June 29, 2001
    Date of Patent: March 11, 2003
    Inventor: Peter Zhu
  • Patent number: 6486358
    Abstract: Improved process for the purification and formulation of o-phthalaldehyde in which crude o-phthalaldehyde, obtained by cleavage of an acetal of o-phthalaldehyde by means of acidic hydrolysis, is, optionally by adding an aqueous basic solution, adjusted to a pH of from 1 to 8, and then, after phase separation has taken place, water is distilled off from the phase which contains the aldehyde with very short thermal stress of less than 1 minute at a pressure of between 100 mbar and atmospheric pressure and a temperature of from room temperature to 180° C. on a thin-layer overhead evaporator and o-phthalaldehyde is then stripped off from the distillation bottom which remains with very short thermal stress of less than 1 minute at a pressure of from 0.5 to 50 mbar and a jacket temperature of from 80 to 80° C. via a thin-layer evaporator and the resulting o-phthalaldehyde melt is pelleted at atmospheric pressure and a temperature of from 60 to 80° C.
    Type: Grant
    Filed: May 15, 2002
    Date of Patent: November 26, 2002
    Assignee: DSM Fine Chemicals Austria NFG GmbH & CO KG
    Inventors: Karlheinz Giselbrecht, Walter Raml, Rudolf Hermanseder
  • Patent number: 6437176
    Abstract: An aromatic carboxylic acid, aromatic aldehyde, and aromatic alcohol are simultaneously and efficiently prepared by liquid phase oxidizing an aromatic compound represented by formula (I) with a gas containing molecular oxygen, in a presence of a catalyst comprising transition metal compound, tertiary amine and bromide compound:
    Type: Grant
    Filed: March 19, 2001
    Date of Patent: August 20, 2002
    Assignee: Toray Industries, Inc.
    Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
  • Patent number: 6355843
    Abstract: The invention is directed to the process of purifying 4′-chloro-4-biphenylcarboxaldehyde.
    Type: Grant
    Filed: October 10, 2000
    Date of Patent: March 12, 2002
    Assignee: Eli Lilly and Company
    Inventor: Richard Alan Berglund
  • Patent number: 6245945
    Abstract: A process for the selective hydrolysis of acetals in the presence of phthalides comprises reacting a mixture (M) comprising a) a phthalide of the formula (I) where: R1,R2,R3 and R4: are independently hydrogen, C1-C4-alkyl or halogen, and b) an acetal or ketal of the formula (II) where: R5 and R6: are independently C1-C6-alkyl, C6-C10-aryl or together ethylene, and R7 and R8: are independently C1-C6-alkyl, or one radical is a hydrogen and the other is a phenyl radical where from 1 to 3 hydrogen atoms of the phenyl radical may be replaced by C1-C6-alkyl radicals or C1-C4-alkoxy radicals, or R7 and R8 are together C3-C6-alkanediyl, and a hydrogen atom may be replaced by a hydroxyl group, at from 10 to 200° C. in the presence of from 1 to 10 mol of water, based on the amount of acetal or ketal of the formula (II), to hydrolyze the acetal or ketal of the formula (II) to the corresponding aldehyde or ketone.
    Type: Grant
    Filed: August 25, 2000
    Date of Patent: June 12, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Weiper-Idelmann, Heinz Hannebaum, Hermann Pütter
  • Patent number: 6153789
    Abstract: The present invention provides a method of purifying an aqueous dye solution having an aldehyde and/or ketone impurity including a step of reacting the impurity with a hydrazine derivative, forming a water-insoluble hydrazone compound. The hydrazone compound is then removed from the solution to form a dye having an increased purity.
    Type: Grant
    Filed: June 29, 1999
    Date of Patent: November 28, 2000
    Assignee: BASF Corporation
    Inventors: Kevin P. Cusack, Kwang Kim, Dennis L. Edie, Benjamin S. Tennyson
  • Patent number: 5872153
    Abstract: A process for preparing an aqueous o-phthalaldehyde-glutaraldehyde solution which comprises converting an acetal of the o-phthalaldehyde in a 10 to 60% strength aqueous glutaraldehyde solution into o-phthalaldehyde at room temperature up to 100.degree. C. by eliminating the corresponding alcohol, and removing the eliminated alcohol to give the aqueous o-phthalaldehyde-glutaraldehyde solution.
    Type: Grant
    Filed: November 26, 1997
    Date of Patent: February 16, 1999
    Assignee: DSM Chemie Linz GmbH
    Inventors: Karl Heinz Giselbrecht, Eduard Perndorfer
  • Patent number: 5861286
    Abstract: The present invention relates to a process for the preparation of aromatic substances having formula (I), characterized in that a substrate having formula (II) is subjected to an oxydation in the presence of at least one protein and at least one metal ion, formula wherein R.sub.1 may be a radical --H, --CH.sub.3, --CH.sub.2 OH, --CHO, --COOH, --OCH.sub.3, or --COO--CH(COOH)--CH.sub.2 --C.sub.6 H.sub.3 (OH).sub.2 ; R.sub.2 may be a radical --H, --OH, or --OCH.sub.3 ; R.sub.3 may be a radical --H, --OH, --OCH.sub.3, or O-glucosid; R.sub.4 may be a radical --H, --OH, or --OCH.sub.3.
    Type: Grant
    Filed: September 25, 1997
    Date of Patent: January 19, 1999
    Assignee: V. Mane Fils
    Inventors: Jean Mane, Joseph Zucca
  • Patent number: 5772909
    Abstract: Vanillin is difficult to separate from second organic chemicals produced therewith such as parahydroxybenzaldehyde by conventional distillation or rectification because of the proximity of their boiling points. Vanillin can now be readily separated from such second organic chemicals by azeotropic distillation using as an effective azeotropic distillation agent, dibenzyl ether.
    Type: Grant
    Filed: November 2, 1995
    Date of Patent: June 30, 1998
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Thomas Jones, Jeffrey L. Finnan, Joseph Arvizzigno
  • Patent number: 5773664
    Abstract: A process for separating off poorly soluble by-products from reaction mixtures which are produced in the oxidation of p-cresol with oxygen or an oxygen-containing gas in methanol as solvent in the presence of alkali metal hydroxide and in the presence of metal compounds as catalyst, is characterized in that, after the oxidation, excess alkali is neutralized to the extent that a salt precipitate forms and this salt precipitate is separated off together with the poorly soluble by-products.
    Type: Grant
    Filed: January 26, 1996
    Date of Patent: June 30, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albert Schnatterer, Helmut Fiege, Frank Jelitto, Peter Skornia, Karl-Heinz Theisen
  • Patent number: 5510006
    Abstract: Vanillin is difficult to separate from second organic chemicals produced therewith such as parahydroxybenzaldehyde by conventional distillation or rectification because of the proximity of their boiling points. Vanillin can now be readily separated from such second organic chemicals by azeotropic distillation using as an effective azeotropic distillation agent, dibenzyl ether.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: April 23, 1996
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Thomas Jones, Jeffrey L. Finnan, Joseph Arvizzigno
  • Patent number: 5463137
    Abstract: A propylene stream which contains propane as an impurity is contacted with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst thereby producing a product stream containing butyraldehyde and/or n-butyl alcohol, unreacted propylene and propane. A gas mixture containing propylene and propane is separated from the product stream and subjected to adsorption at a temperature of 0.degree. to 250.degree. C. in a bed of adsorbent which selectively adsorbs propylene, thereby adsorbing substantially all of the propylene from the gas mixture. The propylene is desorbed from the adsorbent and recycled to the reaction zone. The process is operated on a low per pass conversion with recycle of unreacted propylene. In the system of the invention the propylene adsorption unit may be upstream or downstream of the hydroformylation reactor.
    Type: Grant
    Filed: April 22, 1994
    Date of Patent: October 31, 1995
    Assignee: The BOC Group, Inc.
    Inventors: Ramakrishnan Ramachandran, Loc H. Dao
  • Patent number: 5430194
    Abstract: The present invention relates to a process for producing an optically active aldehyde (first aldehyde) containing a reduced amount of the corresponding enantiomeric aldehyde (second aldehyde) which process comprises: (1) providing an initial solution containing a non-eutectic mixture of the first aldehyde and the second aldehyde, which mixture has a composition in the compositional region where only the first aldehyde crystallizes when its solubility limit in the solution is exceeded, and (2) maintaining the solution at a temperature above the eutectic temperature of the mixture and under conditions such that the solubility limit of the first aldehyde is exceeded so as to form a crystalline first aldehyde containing relatively less of the second aldehyde than was present in the initial solution.
    Type: Grant
    Filed: June 24, 1994
    Date of Patent: July 4, 1995
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Bruce A. Barner, John R. Briggs, Jonathan J. Kurland, Charles G. Moyers, Jr.
  • Patent number: 5410090
    Abstract: A method for removing cobalt values from the crude product of a cobalt-catalyzed hydroformylation reaction by the application of an airless cobalt demetalling step upstream of the stripping step of a Cobalt Flash hydroformylation catalyst recovery process for C.sub.4 to C.sub.14 olefins, whereby no oxygen is required to oxidize cobalt carbonyls to their cobaltous form. This airless demetalling step may also be used downstream of the stripping step in the case of C.sub.7 to C.sub.20 olefins to remove carbonyls from a water soluble cobaltous salt and carbon carbonyl stream which is taken as bottoms from the stripper reactor.
    Type: Grant
    Filed: April 8, 1994
    Date of Patent: April 25, 1995
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Stephen W. Beadle, William H. Summerlin, Eddy T. A. Van Driessche
  • Patent number: 5354909
    Abstract: A process for isolating 4-hydroxybutanal and 3-hydroxy-2-methylpropanal from aqueous mixtures of the isomers is disclosed. Reaction of the aqueous mixture with a hydroxy compound in the presence of an acidic catalyst and a nonpolar organic solvent gives a product aqueous solution of 3-hydroxy-2-methylpropanal and an organic solution containing a 2-oxytetrahydrofuran derived from 4-hydroxybutanal. The 4-hydroxybutanal can be regenerated by acidic hydrolysis of the 2-oxytetrahydrofuran.
    Type: Grant
    Filed: August 17, 1993
    Date of Patent: October 11, 1994
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Jeffrey A. Klang, Ann P. Lawson
  • Patent number: 5162577
    Abstract: A novel process for the lithiation of 1,3-bis(trifluoro-methyl)benzene in a solvent is described, said process comprising carrying out the lithiation with the lithium salt of an amine of the general formulaR.sup.1 R.sup.2 NH Iwherein R.sup.1 and R.sup.2 are secondary or tertiary lower alkyl or secondary or tertiary lower alkyl substituted by a lower alkyl or lower cycloalkyl or lower cycloaklyl substituted by a lower alkyl, or R.sup.1 and R.sup.2 taken together form a C.sub.6-14 -alkylene group in which the two carbon atoms linked with the nitrogen atom are secondary or tertiary and are separated from each other by 2 to 4 carbon atoms.The solution of the lithiated 1,3-bis(trifluoromethyl)-benzene obtained can be reacted with an electrophile which is suitable for the substitution of lethiated benzene derivatives, whereby a compound of the formula ##STR1## wherein R.sup.3 signifies the residue of an electrophile which is suitable for the substitution of lithiated benzene derivatives, is obtained.
    Type: Grant
    Filed: February 1, 1991
    Date of Patent: November 10, 1992
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Raffaello Masciadri
  • Patent number: 5149882
    Abstract: 2-chloro-5-nitrobenzaldehyde or an acetal thereof is isolated from a mixture of isomers thereof at a temperature of from -10.degree. to +140.degree. C., by suspending the mixture of isomers in a solvent or solvent mixture.
    Type: Grant
    Filed: June 4, 1991
    Date of Patent: September 22, 1992
    Inventors: Bernd Schaefer, Wolfgang Freund, Gernot Reissenweber
  • Patent number: 5077441
    Abstract: A method for the treatment of plant material to provide a protein-rich product and oil relatively free of gossypol. The process includes the steps of:a. contacting plant material with an aqueous monohydric alcohol solvent to extract oil and gossypol from the plant material and form a miscella fraction including the solvent, oil and gossypol, and a plant material fraction having gossypol removed therefrom;b. separating the solvent from the oil and gossypol in the miscella, preferably by membrane separation under pressure in a membrane separation unit, to form a first (retentate) fraction comprising the oil and gossypol, and a second (permeate) fraction comprising the solvent; andc. contacting the first fraction with an adsorbent effective to separate the gossypol from the oil therein.The plant material and oil remaining after the process are relatively free of gossypol and may be recovered for subsequent use. The plant material is especially valuable as a protein-rich food product or feed.
    Type: Grant
    Filed: October 5, 1990
    Date of Patent: December 31, 1991
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Myong S. Kuk, Robert J. Hron, Sr., George Abraham
  • Patent number: 5059717
    Abstract: The method according to the present invention comprises purification of 2,2'-di-(1,6,7-trihydroxy-3-methyl-5-isopropyl-8-naphthaldehyde) by crystallization from a solution thereof in diethyl ether with a concentration of 0.002-0.2 g/ml by adding 0.25-3 parts of hexane by volume (of diethyl ether) keeping the mixture at a temperature of from 10.degree. to 30.degree. C., separation of the resulting precipitate and drying thereof to give the desired product.
    Type: Grant
    Filed: July 16, 1990
    Date of Patent: October 22, 1991
    Inventors: Bakhtiyar T. Ibragimov, Samat A. Talipov, Rustam G. Mardanov, Takhir F. Aripov
  • Patent number: 4933499
    Abstract: The invention relates to a process for the purification of alkenyl aromatic compounds which contain benzaldehyde as an impurity. This process comprises steps for contacting a benaldehyde-containing alkenyl aromatic compound with a bisulphite treating agent, and separating the resulting benzaldehyde-bisulphite addition product from the alkenyl aromatic compound. In certain preferred embodiments, the treating agent is a modified anion-exchange resin containing bound bisulphite ions. Optionally, the process then further comprises a step for recovering the benzaldehyde from the resin addition product by contact with an aqueous sodium carbonate solution or by steam distillation.
    Type: Grant
    Filed: February 27, 1989
    Date of Patent: June 12, 1990
    Assignee: Shell Oil Company
    Inventors: Paul A. M. Grotenhuis, Brian L. Goodall
  • Patent number: 4929767
    Abstract: A process for treating an organic solution of a partially deactivated solubilized rhodium-tertiary organophosphine complex hydroformylation catalyst with an organic reagent in order to improve the extractability of rhodium therefrom into an aqueous solution containing an ionic organophosphine ligand.
    Type: Grant
    Filed: October 6, 1988
    Date of Patent: May 29, 1990
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventors: David J. Miller, David R. Bryant, Ernst Billig, Bernard L. Shaw