Plural Oxygens Bonded Directly To The Same Carbon (e.g., Acetals, Ketals, Orthoesters, Orthocarbonates, Etc.) Patents (Class 568/591)
  • Publication number: 20150065753
    Abstract: In a process for separating a mixture comprising cyclohexanone and phenol, at least a portion of the mixture is distilled in the presence of a solvent including at least two alcoholic hydroxyl groups attached to non-adjacent saturated carbon atoms and at least one hemiketal defined by the formula (I) or the formula (II): wherein R1, the same or different at each occurrence, is independently an alkylene group having from 2 to 10 carbon atoms, R2 is an alkylene group having from 4 to 10 carbon atoms, and R3 is hydrogen or the following group: and/or an enol-ether derived from the hemiketal defined by the formula (I) or the formula (II), wherein the total concentration of the hemiketal and the enol-ether, expressed in terms of weight percentage on the basis of the total weight of the feed to the distilling step (a), is at least 0.01%.
    Type: Application
    Filed: April 9, 2013
    Publication date: March 5, 2015
    Inventors: Keith H. Kuechler, Francisco M. Benitez, Krystle J. Chavez, Christopher L. Becker, John L. Heidman, JR.
  • Publication number: 20140378359
    Abstract: The present invention relates to a composition of matter comprising at least 95% w/w of at least one compound of formula (I), wherein R group is a C1—6 alkyl group optionally comprising an ether functional group; and wherein each carbon-carbon double bond of said compound, independently from each other, can be in a configuration Z or E; which is a useful perfuming ingredient.
    Type: Application
    Filed: January 9, 2013
    Publication date: December 25, 2014
    Applicant: FIRMENICH SA
    Inventors: Peter Fankhauser, Olivier Etter
  • Patent number: 8859824
    Abstract: Compounds are provided herein which are coordination complexes of the formula, AxByCit2Fz.mH2O, wherein A is a cation selected from certain IA or IIA metal ions in the Periodic Table; B is a cation selected from certain IIA metal ions and certain divalent d-block transition metal ions; A and B are different; “Cit” is tribasic citric acid anion; the stoichiometric ratio of x to y is equal or higher than 1.0 but lower than 8.0; m is 0-12; and z is selected such that electroneutrality is preserved. Compounds provided herein are useful to treat dietary deficiencies, osteoporosis, osteopenia, bone loss, and risk of bone loss, as well as other medical conditions involving the need for administration of the various ions. In addition, the compounds can be used as fluoride sources for dental use and to fluoridate water systems.
    Type: Grant
    Filed: January 4, 2010
    Date of Patent: October 14, 2014
    Assignee: Mission Pharmacal Company
    Inventors: Mary Ann Walter, Jian Gao, Neill Bailey Walsdorf
  • Patent number: 8563780
    Abstract: Allyl and propargyl ethers of the formula X—C(R1)(R2)—O—C(CH3)(R3)—OCH3 (I), wherein X is an ethynyl or vinyl group, R1 is methyl or ethyl, R2 is a saturated or unsaturated linear or cyclic aliphatic hydrocarbon residue and R3 is methyl or ethyl, a method for their preparation and their use in the manufacture of ?-ketoallenes, ?,?-unsaturated carbonyl compounds and ?,?-unsaturated ketones.
    Type: Grant
    Filed: May 12, 2009
    Date of Patent: October 22, 2013
    Assignee: DSM IP Assets B.V.
    Inventors: Werner Bonrath, Rolf Kuenzi
  • Patent number: 8420290
    Abstract: An acetal compound of formula (1) is provided wherein R1 is H, methyl or trifluoromethyl, R2 is a monovalent C1-C10 hydrocarbon group, R3 and R4 are H or a monovalent C1-C10 hydrocarbon group, R2 and R3 may together form an aliphatic hydrocarbon ring, and X1 is a single bond or a divalent C1-C4 hydrocarbon group. A polymer comprising recurring units derived from the acetal compound is used as a base resin to formulate a resist composition which exhibits a high resolution when processed by micropatterning technology, especially ArF lithography.
    Type: Grant
    Filed: November 25, 2009
    Date of Patent: April 16, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd
    Inventors: Koji Hasegawa, Masaki Ohashi, Takeshi Kinsho, Tsunehiro Nishi, Masayoshi Sagehashi
  • Publication number: 20130090390
    Abstract: A compound of formula (I) is described and use thereof as fragrance, especially as lily-of-the-valley fragrance and/or as an agent for increasing the substantivity and/or the retention of a fragrance preparation and/or as a fixative.
    Type: Application
    Filed: October 5, 2012
    Publication date: April 11, 2013
    Applicant: SYMRISE AG
    Inventors: Emilie Singer, Bernd Holscher
  • Patent number: 8288596
    Abstract: Acetals are formed from an aldehyde hydrogenation product mixture comprising alcohols and at most 2% of alde-hydes and the product is distilled to yield purified alcohols and a second stream containing acetals and/or unsaturated ethers.
    Type: Grant
    Filed: February 27, 2008
    Date of Patent: October 16, 2012
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Ronald Dean Garton, Corey W. Reed, Krishna Kulai Rao, Bruce D. Lilly, Ramzi Yanni Saleh, Raphael Frans Caers
  • Patent number: 8236749
    Abstract: Acetal derivatives of 2,2,3,6-tetramethyl-1-cyclohexane/ene-carbaldehyde of formula (I): for use in the perfumery industry as well as the resulting compositions or articles containing one or more of these compounds. In formula (I), one dotted line indicates the presence of a carbon-carbon single or double bond and the other dotted line indicates the presence of a carbon-carbon single bond, R1 represents a hydrogen atom or a methyl or ethyl group; and each R, taken alone, simultaneously or independently, represents a C1-3 alkyl or alkenyl group, or the R groups, taken together, represent a C2-6 hydrocarbon group optionally including an oxygen atom.
    Type: Grant
    Filed: April 14, 2010
    Date of Patent: August 7, 2012
    Assignee: Firmenich SA
    Inventors: Philippe Dupau, Murielle Haldimann Sanchez
  • Publication number: 20120029240
    Abstract: Allyl and propargyl ethers of the formula X—C(R1)(R2)—O—C(CH3)(R3)—OCH3 (I), wherein X is an ethynyl or vinyl group, R1 is methyl or ethyl, R2 is a saturated or unsaturated linear or cyclic aliphatic hydrocarbon residue and R3 is methyl or ethyl, a method for their preparation and their use in the manufacture of ?-ketoallenes, ?,?-unsaturated carbonyl compounds and ?,?-unsaturated ketones.
    Type: Application
    Filed: May 12, 2009
    Publication date: February 2, 2012
    Inventors: Werner Bonrath, Rolf Kuenzi
  • Publication number: 20120010114
    Abstract: Acetal derivatives of 2,2,3,6-tetramethyl-1-cyclohexane/ene-carbaldehyde of formula (I): for use in the perfumery industry as well as the resulting compositions or articles containing one or more of these compounds. In formula (I), one dotted line indicates the presence of a carbon-carbon single or double bond and the other dotted line indicates the presence of a carbon-carbon single bond, R1 represents a hydrogen atom or a methyl or ethyl group; and each R, taken alone, simultaneously or independently, represents a C1-3 alkyl or alkenyl group, or the R groups, taken together, represent a C2-6 hydrocarbon group optionally including an oxygen atom.
    Type: Application
    Filed: April 14, 2010
    Publication date: January 12, 2012
    Inventors: Philippe Dupau, Murielle Haldimann Sanchez
  • Publication number: 20110190544
    Abstract: A modified carbonaceous material having chemically bound on its surface at least one fluoropolyoxyalkylene chain (chain Rf) and a process for the modification of a carbonaceous material [material (C)]. The process comprises: contacting the material (C) with a (per)fluoropolyether peroxide comprising at least one peroxidic moiety comprised between sp3 carbon atoms and at least one fluoropolyoxyalkene chain (chain Rf), i.e. a fluorocarbon segment comprising ether linkages in main chain [peroxide (P)]; and heating the material (C) while in contact with the peroxide (P) at a temperature exceeding decomposition temperature of the peroxide (P).
    Type: Application
    Filed: August 4, 2008
    Publication date: August 4, 2011
    Applicant: SOLVAY SOLEXIS S.P.A.
    Inventors: Walter Navarrini, Maurizio Sansotera, Pierangelo Metrangolo, Pietro Cavallotti, Giuseppe Resnati
  • Publication number: 20100184866
    Abstract: Compounds are provided herein which are coordination complexes of the formula, AxByCit2Fz.mH2O, wherein A is a cation selected from certain IA or IIA metal ions in the Periodic Table; B is a cation selected from certain IIA metal ions and certain divalent d-block transition metal ions; A and B are different; “Cit” is tribasic citric acid anion; the stoichiometric ratio of x to y is equal or higher than 1.0 but lower than 8.0; m is 0-12; and z is selected such that electroneutrality is preserved. Compounds provided herein are useful to treat dietary deficiencies, osteoporosis, osteopenia, bone loss, and risk of bone loss, as well as other medical conditions involving the need for administration of the various ions. In addition, the compounds can be used as fluoride sources for dental use and to fluoridate water systems.
    Type: Application
    Filed: January 4, 2010
    Publication date: July 22, 2010
    Applicant: Mission Pharmacal Company
    Inventors: Mary Ann Walter, Jian Gao, Neill Bailey Walsdorf
  • Patent number: 7700814
    Abstract: Acetals are formed from a mixture comprising alcohols and aldehydes and the product is distilled to yield purified alcohols and/or acetals and/or unsaturated ethers.
    Type: Grant
    Filed: March 27, 2007
    Date of Patent: April 20, 2010
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Ronald D. Garton, Corey W. Reed, Krishna K. Rao, Bruce D. Lilly
  • Publication number: 20090105260
    Abstract: An IR spectroscopic technique provides methods for measuring the irritation potential of a formulation and to assess the ability of molecules to enhance the permeability of substances into and through skin using samples comprising stratum corneum. Molecules are screened for their performance as chemical penetration enhancers using a unique in silico procedure that may be applied iteratively in an attempt to generate molecules showing successively higher performance. Both the irritation potential and the ability of the molecule to enhance penetration are considered in the in silico approach. The invention provides specific molecules that may be used in topical or transdermal formulations to improve the delivery of actives. The structures of compounds of the invention include: Formulas (I), (II), (III), (IV), (V), (IV) and analogs thereof.
    Type: Application
    Filed: January 17, 2006
    Publication date: April 23, 2009
    Inventors: Samir Mitragotri, Pankaj Karande, Amit K. Jain
  • Patent number: 7507522
    Abstract: The present invention relates to novel unsaturated polycyclic compounds containing two fluoroalcohol substitutents. This invention also relates to homopolymers and copolymers derived from such unsaturated polycyclic compounds. The copolymers are useful for photoimaging compositions and, in particular, photoresist compositions (positive-working and/or negative-working) for imaging in the production of semiconductor devices. The polymers are especially useful in photoresist compositions having high UV transparency (particularly at short wavelengths, e.g., 157 nm) which are useful as base resins in resists and potentially in many other applications.
    Type: Grant
    Filed: May 17, 2005
    Date of Patent: March 24, 2009
    Assignee: E. I. DuPont de Nemours and Company
    Inventors: Michael Karl Crawford, Hoang Vi Tran, Frank Leonard Schadt, III, Fredrick Claus Zumsteg, Jr., Andrew Edward Feiring, Michael Fryd
  • Publication number: 20080287714
    Abstract: The present invention is an industrial process for the preparation of acetals using a simulated moving bed (SMB) reactor system to accomplish the conversion of reactants (aldehyde and alcohol) and simultaneously, the separation of the reaction products (acetal and water) by selective adsorption. The SMB reactor consists of a set of interconnected columns packed with an acid solid (or mixture of acid solids: catalysts and adsorbents) effective for catalyzing the reaction between aldehydes and alcohols and for separating the reaction products by selective adsorption of at least one product.
    Type: Application
    Filed: May 17, 2005
    Publication date: November 20, 2008
    Inventors: Alirio Egidio Rodrigues, Viviana Manuela Tenedorio Matos Da Silva
  • Patent number: 7402707
    Abstract: The synthesis of a precursor oligocene, particularly pentacene, is a two-step process. In the first step the Diels-Alder adduct of the a,b-dihydro-a,b-etheno-oligocene with a 1,1-dialkoxy-cyclopentadiene is formed. In the second step this Diels-Alder adduct is converted into the precursor oligocene, in that first the corresponding keto-compound is formed, which may be eliminated thereafter. The resulting precursor oligocene can be converted to the oligocene with a heat treatment, particularly after providing a solution hereof on a substrate. It is suitable for use as semiconductor material in a thin-film transistor. Formula (I).
    Type: Grant
    Filed: March 17, 2004
    Date of Patent: July 22, 2008
    Assignee: Koninklijke Philips Electronics N.V.
    Inventors: Wolter Ten Hoeve, Bart-Hendrik Huisman
  • Patent number: 7294448
    Abstract: The present invention provides a visible light-sensitive composition which is highly sensitive to a visible light and is useful as an electronic circuit forming material, a lithographic printing material, etc., said visible light-sensitive composition comprising (a) a polymer comprising a repeating unit represented by general formula (I): wherein R1, R2, and R3 are the same or different and each represents substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted aralkyl, or alternatively R1 and R2 form cycloalkyl together with the adjacent carbon atom, and R4 represents lower alkyl, (b) a compound that generates an acid by visible light irradiation and (c) a sensitizing dye.
    Type: Grant
    Filed: August 20, 2003
    Date of Patent: November 13, 2007
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Tsuguo Yamaoka, Katsuhiro Ito, Takeshi Iwasaki, Ikuo Shimizu
  • Patent number: 7285686
    Abstract: An improved process for the preparation of 1,3 substituted indenes which are useful intermediates in the synthesis of aryl fused azapolycyclic compounds as agents for the treatment of neurological and psychological disorders.
    Type: Grant
    Filed: November 17, 2003
    Date of Patent: October 23, 2007
    Assignee: Pfizer Inc
    Inventors: Robert Eugene Handfield, Jr., Timothy J. N. Watson, Phillip James Johnson, Peter Robert Rose
  • Patent number: 7232639
    Abstract: As a polymer exhibiting improved transparency which is suitable for a resist resin used in a chemical-amplification-type resist being applicable for photolithography using exposure light at 180 nm or shorter, this invention provides a polymer comprising a repeating unit resulting from polymerization of a monomer exhibiting a polymerization activity, wherein the monomer has a fluorine-containing acetal or ketal structure represented by general formula (1): wherein R represents an atomic group containing a carbon-carbon double bond exhibiting polymerization activity; at least one of R1 and R2 is fluorinated alkyl group or fluorinated aryl group having 1 to 20 carbon atoms; and R3 represents a radical selected from the group consisting of hydrogen atom, alkyl group, alkoxy-substituted alkyl group, fluorinated alkyl group, aryl group, fluorinated aryl group, aralkyl group and fluorinated aralkyl group having 1 to 20 carbon atoms.
    Type: Grant
    Filed: February 25, 2003
    Date of Patent: June 19, 2007
    Assignee: NEC Corporation
    Inventors: Katsumi Maeda, Kaichiro Nakano
  • Patent number: 7148385
    Abstract: A perfluoropolyether and a composition comprising the perfluoropolyether are provided in which the perfluoropolyether comprises at least one bromine or iodine atom at the primary position of the perfluoropolyether. Also provided is a process for producing the composition in which the process comprises contacting a perfluoropolyether acid fluoride moiety with a metal bromide or metal iodide or a suitable polyether secondary iodide under a condition sufficient to effect the production of a perfluoropolyether comprising at least one bromine or iodine at the primary position.
    Type: Grant
    Filed: July 25, 2003
    Date of Patent: December 12, 2006
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Jon L. Howell, Erik W. Perez, Alfred Waterfeld, Chadron Mark Friesen, Joseph Stuart Thrasher, Ireneusz Nowak
  • Patent number: 7018978
    Abstract: The present invention relates to novel heterocyclic pro-fragrances, preferably oxazolidines, tertahydro-1,3-oxazines, thiazolidines, or tetrahydro-1,3-thiazines, more preferably oxazolidines, or tertahydro-1,3-oxazines, most preferably oxazolidines, which are capable of sustained release of fragrance raw material ketones and aldehydes and to fragrance delivery systems which comprise said pro-fragrances.
    Type: Grant
    Filed: April 16, 2003
    Date of Patent: March 28, 2006
    Assignee: Procter & Gamble Company
    Inventors: Gregory Scot Miracle, Kenneth Nathan Price
  • Patent number: 7015363
    Abstract: The present invention provides the following process for producing and the like, which enables the production of an ether compound, which is useful for chemical amplification type resist compositions, synthetic intermediates of pharmaceuticals, paints, or the like, with less side reaction and in high yield. A process for producing an ether compound having a group represented by the general formula (II) wherein R1, R2 and R3 may be the same or different, and represent substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted aralkyl, or R1 and R2 form cycloalkyl together with an adjacent carbon atom, which comprises allowing a compound having a hydroxyl group (including a carboxyl group) to react with an alkenyl ether represented by the general formula (I) wherein R1, R2 and R3 have the same significances as defined above, respectively.
    Type: Grant
    Filed: July 12, 2002
    Date of Patent: March 21, 2006
    Assignee: Kyowa Yuka Co., Ltd.
    Inventors: Ikuo Shimizu, Katsuhiro Ito, Kazuyasu Osada, Tsuguo Yamaoka
  • Patent number: 6974834
    Abstract: This invention relates to a process for the synthesis of enantiomerically enriched (1S,4R) 1-acetoxy-4-hydroxycyclopent-2-ene of Formula I, a compound useful as an intermediate in the synthesis of prostaglandins and prostanoids.
    Type: Grant
    Filed: January 7, 2004
    Date of Patent: December 13, 2005
    Assignee: Agouron Pharmaceuticals Inc.
    Inventor: Kevin Edward Henegar
  • Patent number: 6919480
    Abstract: The present invention provides novel processes for preparing a fluorinated acyl fluoride and a fluorinated vinyl ether.
    Type: Grant
    Filed: December 5, 2003
    Date of Patent: July 19, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu
  • Patent number: 6822124
    Abstract: A method for producing alcoxylated carbonyl compounds of general formula (I) (compounds I): R1aR2C(OR3)b wherein R1, R2 represent hydrogen or C1-C6-alkyl, R3 independently means C1-C6-alkyl, a is 0 or 1, b 2 or 3 with the proviso that the sum of a and b is 3, by means of anodic oxidation of germinal dialcoxy compounds of general formula (II) (compounds II) wherein R4, R5, R6, R7 represent hydrogen or C1-C6-alkyl, R5, R6 represent C1-C6-alkyl or C1-C6-alcoxy, in the presence of a C1-C6-alkyl alcohol (compounds III). A usual compound (compound IV) is used as a cathodic depolarizer suitable for electrochemical oxidation. The anodic oxidation and cathodic reduction is carried out in an undivided electrolyte cell in the presence of C1-C6-alkyl alcohols.
    Type: Grant
    Filed: May 22, 2003
    Date of Patent: November 23, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Hermann Pütter, Andreas Fischer
  • Patent number: 6806392
    Abstract: A process for the preparation of acetals and ketals by reacting an aldehyde or ketone with an alcohol in the presence of an acidic catalyst and removing water by pervaporation. Manufacturing equipment for the preparation of acetals and ketones is also provided.
    Type: Grant
    Filed: November 7, 2002
    Date of Patent: October 19, 2004
    Assignee: DSM IP Assets B.V.
    Inventors: Volkmar Boesch, Juan Ramon Herguijuela, Thomas Clavey
  • Publication number: 20040181097
    Abstract: The present invention provides the following process for producing and the like, which enables the production of an ether compound, which is useful for chemical amplification type resist compositions, synthetic intermediates of pharmaceuticals, paints, or the like, with less side reaction and in high yield.
    Type: Application
    Filed: December 24, 2003
    Publication date: September 16, 2004
    Inventors: Ikuo Shimizu, Katsuhiro Ito, Kazuyasu Osada, Tsuguo Yamaoka
  • Patent number: 6756497
    Abstract: Benzoic acid derivatives useful as intermediates for the preparation of drugs and agricultural chemicals, particularly compounds having herbicidal activity; and easy and economical processes for the preparation of the same. The processes are specifically those represented by reaction formula for the preparation of compounds represented by general formulae (1) and (6).
    Type: Grant
    Filed: January 12, 2001
    Date of Patent: June 29, 2004
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Yuuki Nakagawa, Masao Yamaguchi, Hiroyuki Adachi, Hiroyuki Yamanaka, Tomio Yagihara, Masami Hatano
  • Patent number: 6753402
    Abstract: Polyester-polyether block copolymers can be prepared by catalytic addition of alkylene oxides onto H-functional initiator substances, using polyester alcohols as H-functional initiator substances and multimetal cyanide compounds as catalysts.
    Type: Grant
    Filed: April 10, 2002
    Date of Patent: June 22, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Stephan Bauer, Georg Heinrich Grosch, Gerlinde Tischer, Kathrin Harre, Eva Baum, Thomas Ostrowski, Reinhard Lorenz, Regina Pretzsch, Michael Pcolinski, Stefan Dinsch, Inge Rotermund
  • Patent number: 6747174
    Abstract: The present invention provides novel processes for preparing a fluorinated acyl fluoride and a fluorinated vinyl ether.
    Type: Grant
    Filed: January 28, 2003
    Date of Patent: June 8, 2004
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu
  • Patent number: 6747176
    Abstract: 2-Chloro-1,1,1-trialkoxyethane of formula (II): wherein R1 to R3, which may be the same or different, are alkyl, or any two of the alkyl groups taken together form a cyclic group, is prepared by reacting 1,1,1-trialkoxyethane with gaseous or liquid chlorine in the presence of alcohol solvent in an amount ranging from 0.1% to 20 wt %, based on the amount of 1,1,1-trialkoxyethane reactant.
    Type: Grant
    Filed: June 10, 2003
    Date of Patent: June 8, 2004
    Assignee: Degussa AG
    Inventors: Guenther Koehler, Karl-Heinz Bruehl, Johannes Ruwwe, Manfred Neumann
  • Patent number: 6734313
    Abstract: Ortho esters and ortho carbonates can be produced by alkylating esters and carbonates with, for example, the hexafluorophosphate salt of a trialkyl oxonium ion. The spiro species are useful intermediates in the synthesis of complex organic molecules. Synthetic pathways for the production of medically active compounds incorporates spiro ortho esters. Anti-first-pass effect materials are produced in high yield utilizing a synthetic strategy incorporating cyclic ortho ester intermediates.
    Type: Grant
    Filed: May 9, 2003
    Date of Patent: May 11, 2004
    Assignee: Bioavailability Systems, LLC
    Inventors: Robert Seemayer, Jack Liang
  • Publication number: 20040043916
    Abstract: The use of various novel oxime ethers are described as fragrance chemicals. These chemicals are suitable for use in creating fragrance, and scents in items such as perfumes, colognes and personal care products is disclosed.
    Type: Application
    Filed: August 29, 2002
    Publication date: March 4, 2004
    Inventors: Anubhav P.S. Narula, Rajamony Mahesh, Manfred Pawlak, Patrick M. Merritt, Clint Dee Winton Brooks
  • Publication number: 20040043917
    Abstract: The use of various oxime ethers are described as fragrance chemicals, suitable for use in creating fragrance, and scents in items such as perfumes, colognes and personal care products is disclosed. Novel compounds are also disclosed.
    Type: Application
    Filed: August 29, 2002
    Publication date: March 4, 2004
    Inventors: Anubhav P.S. Narula, Rajamony Mahesh, Manfred Pawlak, Clint Dee Winton Brooks
  • Publication number: 20040024260
    Abstract: An acetal or a ketal are prepared by reacting a carbonyl compound and an alcohol in the presence of an acid catalyst and water. Water and alcohol are removed from the reaction mixture in an at least two-stage pervaporation or vapor permeation process using a plurality of membranes. Additional alcohol is fed into a retentate stream of at least one of the two stages. At least one of the plurality of membranes in the two-stage pervaporation or vapor permeation process is different from the other membranes in terms of selectivity behavior in the removal of water and alcohol.
    Type: Application
    Filed: April 28, 2003
    Publication date: February 5, 2004
    Applicant: DEGUSSA AG
    Inventors: Hermann Winkler, Heinz-Guenter Poll, Manfred Neumann, Guenther Koehler, Frank Bauer
  • Patent number: 6653511
    Abstract: A perfluoropolyether and a composition comprising the perfluoropolyether are provided in which the perfluoropolyether comprises at least one bromine or iodine atom at the primary position of the perfluoropolyether. Also provided is a process for producing the composition in which the process comprises contacting a perfluoropolyether acid fluoride moiety with a metal bromide or metal iodide or a suitable polyether secondary iodide under a condition sufficient to effect the production of a perfluoropolyether comprising at least one bromine or iodine at the primary position.
    Type: Grant
    Filed: September 9, 2002
    Date of Patent: November 25, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Jon L. Howell, Erik W. Perez, Alfred Waterfeld, Chadron Mark Friesen, Joseph Stuart Thrasher, Ireneusz Nowak
  • Patent number: 6639095
    Abstract: The present invention provides a process for preparing optically active &agr;-hydroxy acids and derivatives thereof by subjecting the alkylated 1,3-dioxolanones of formula (IV) wherein R1 and R2 are the same or different and are each independently H or C1-6 alkyl; R5 is H, C1-16 alkyl, or unsubstituted or substituted phenyl; and R6 is C1-8 alkyl, C2-7 alkenyl or unsubstituted or substituted benzyl, to either alcoholysis or hydrolysis, in which the alkylated 1,3-dioxolanones are obtained by using 10-camphorsulfonamide as a chiral auxiliary.
    Type: Grant
    Filed: October 8, 2002
    Date of Patent: October 28, 2003
    Inventors: Biing-Jiun Uang, Jia-Wen Chang, Der-Pin Jang
  • Patent number: 6613918
    Abstract: Ortho esters and ortho carbonates can be produced by alkylating esters and carbonates with, for example, the hexafluorophosphate salt of a trialkyl oxonium ion. The spiro species are useful intermediates in the synthesis of complex organic molecules. Synthetic pathways for the production of medically active compounds incorporates spiro ortho esters. Anti-first-pass effect materials are produced in high yield utilizing a synthetic strategy incorporating cyclic ortho ester intermediates.
    Type: Grant
    Filed: October 22, 2001
    Date of Patent: September 2, 2003
    Assignee: Bioavailability Systems, LLC
    Inventors: Robert Seemayer, Jack Liang
  • Patent number: 6610866
    Abstract: A method is described for stereoselectively reducing an unsaturated alkyl ketone substituent attached to a fused ring base. In this method, the unsaturated alkyl ketone reacts with a chiral oxazaborolidine reagent. This reaction stereoselectively reduces the unsaturated alkyl ketone to an unsaturated alkyl alcohol. The unsaturated alkyl alcohol can be further reduced, if desired, to produce a saturated alkyl alcohol. The fused ring base can be, for example, a steroid ring base or a base of a vitamin D analog. The process in accordance with the invention can be used with an alkeneone substituent (e.g., a 22-ene-24-one substituent) or an alkyneone substituent (e.g., a 22-yne-24-one substituent) on a steroid ring base to make squalamine or other useful aminosterol compounds and intermediates for making aminosterol compounds.
    Type: Grant
    Filed: April 12, 2001
    Date of Patent: August 26, 2003
    Assignee: Magainin Pharmaceuticals, Inc.
    Inventors: William A. Kinney, Steven Jones, Xuehai Zhang, Meena N. Rao, Michel Bulliard, Harold Meckler, Nancy Lee
  • Patent number: 6551987
    Abstract: The present invention relates to fragrance delivery systems which comprise: a) one or more pro-fragrances having formula (I) wherein G1 and G2 are methyl, or a cyclic hydrocarbyl unit derived from the isomers of ionone and/or damascone; R and R1 are each independently C1-C22 substituted or unsubstituted, branched or unbranched alkyl, C2-C22 substituted or unsubstituted, branched or unbranched alkenyl, C2-C20 substituted or unsubstituted, branched or unbranched hydroxyalkyl, C7-C20 substituted or unsubstituted alkylenearyl, C3-C20 substituted or unsubstituted cycloalkyl, alkyleneoxy, C6-C20 aryl, C5-C20 heteroaryl comprising one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, and mixtures thereof; two of the units Y1, Y2, R or R1 can be taken together to form one or more aromatic or non-aromatic, heterocyclic or non-heterocyclic, single rings, fused rings, bicyclo rings, spiroannulated rings, or mixtures thereof, said rings comprising from 3 to 20 carbon atoms and one or mor
    Type: Grant
    Filed: October 22, 2001
    Date of Patent: April 22, 2003
    Assignee: The Procter & Gamble Company
    Inventors: Gregory Scott Miracle, Lon Montgomery Gray
  • Patent number: 6528025
    Abstract: A process for the preparation of acetals and ketals by reacting an aldehyde or Ketone with an alcohol in the presence of solid acid and removing water by pervaporation. Manufacturing equipment for the preparation of acetals and ketones is also provided.
    Type: Grant
    Filed: June 29, 2000
    Date of Patent: March 4, 2003
    Assignee: Roche Vitamins Inc.
    Inventors: Volkmar Boesch, Juan Ramon Herguijuela
  • Patent number: 6518464
    Abstract: The present invention relates to a continuous process for the preparation of unsaturated acetals by reacting olefinically unsaturated aliphatic compounds with allyl alcohols in a reaction column, where the reactants are only partially reacted in the reaction column, the resulting acetal is concentrated in at least two successive evaporation stages, and the recovered reactants are returned to the reaction column.
    Type: Grant
    Filed: September 5, 2001
    Date of Patent: February 11, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Jörg Therre, Gerd Kaibel, Werner Aquila, Günter Wegner, Hartwig Fuchs
  • Publication number: 20030023119
    Abstract: Formaldehyde is removed by distillation from reaction solutions containing a methylolated alkanal which was obtained from the reaction of formaldehyde with an alkanal which has at least one acidic hydrogen atom &agr; to the carbonyl function or from the reaction of a 2-alkylacrolein or acrolein with water and formaldehyde, by a process in which this reaction was carried out in the presence of catalytic amounts of an organic amine. The process permits the improved removal of formaldehyde from the reaction mixture and furthermore facilitates the hydrogenation of the alkanals thus obtained to give polyols.
    Type: Application
    Filed: June 26, 2002
    Publication date: January 30, 2003
    Inventors: Matthias Dernbach, Detlef Kratz, Achim Stammer, Gerhard Schulz
  • Patent number: 6506945
    Abstract: A process for preparing an ether-capped poly(oxyalkylated) alcohol surfactant is provided. The alcohol has the formula: RO(R1O)xCH(CH3)OR2 wherein R is selected from the group consisting of linear or branched, saturated or unsaturated, substituted or unsubstituted, aliphatic or aromatic hydrocarbon radicals having from about 1 to about 30 carbon atoms; R1 may be the same or different, and is independently selected from the group consisting of branched or linear C2 to C7 alkylene in any given molecule; x is a number from 1 to about 30; and R2 is a six membered substituted or unsubstituted, saturated or unsaturated, cyclic or aromatic hydrocarbon radical.
    Type: Grant
    Filed: December 8, 2000
    Date of Patent: January 14, 2003
    Assignee: The Procter & Gamble Company
    Inventors: Bernard William Kluesener, Mark Robert Sivik, Glenn Thomas Jordan, IV, Paul William Huber, Jr., Philippe Neyraval, Christian Priou
  • Patent number: 6495725
    Abstract: The present invention provides a simplified and convenient process for the preparation of an optically active enone such as 7,7-dimethyl-6,8-dioxabicyclo-[3,3,0]oct-3-en-2-one. The invention further provides novel optically active intermediate compounds.
    Type: Grant
    Filed: December 15, 2000
    Date of Patent: December 17, 2002
    Assignee: Chisso Corporation
    Inventor: Kunio Ogasawara
  • Patent number: 6486362
    Abstract: A process for producing oxygen-containing compounds containing at least one oxygen atom bonded to two distinct carbon atoms which are not bonded together and not comprising a multiple bond comprises a step a) for hydroformylation of a feed comprising at least one olefin containing four to seven carbon atoms to at least one aldehyde, in the presence of a catalyst and a synthesis gas under hydroformylation conditions, a step b) for hydrogenation of this aldehyde to at least one corresponding alcohol, and a step c) for transforming at least one alcohol obtained from step b) in the presence of a catalyst under conditions for producing a mixture containing at least one ether or at least one acetal.
    Type: Grant
    Filed: June 29, 2000
    Date of Patent: November 26, 2002
    Assignee: Institut Francais du Petrole
    Inventors: Alain Forestiere, Jean-Ferdinand Gaillard, Michel Barraque
  • Patent number: 6420612
    Abstract: Bicycloheptene compounds represented by general formula (1) and being useful as intermediates for the production of agricultural chemicals or drugs (wherein X is hydroxycarbonyl, hydroxymethyl, halogenomethyl, nitromethyl, or methylthiomethyl); and a process for the preparation of compounds of general formula (1), characterized by reacting 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene with a compound represented by general formula (2) (wherein X is as defined above)
    Type: Grant
    Filed: September 13, 2001
    Date of Patent: July 16, 2002
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Tomio Yagihara, Hiroyuki Yamanaka
  • Patent number: 6348606
    Abstract: The claimed invention relates to cyclic dienol ethers of formula (III). wherein R3 is hydrogen and R4 is C1-4 alkoxy or R3 and R4 together form an optionally substituted methylenedioxy group —O—C(R5)(R6)—O—, wherein R5 and R6 are each independently hydrogen, C1-4 alkyl or phenyl.
    Type: Grant
    Filed: January 17, 2001
    Date of Patent: February 19, 2002
    Assignee: Roche Vitamins Inc.
    Inventors: Bruno Burdet, August Rüttimann
  • Patent number: 6344590
    Abstract: An adamantanemethanol derivative of the invention is represented by the following formula (1), wherein Ra is a hydrogen atom or a hydrocarbon group; Rb is a hydrocarbon group having a carbon atom, to which carbon atom at least one hydrogen atom is bonded, at a bonding site with the adjacent carbon atom; Rc, Rd and Re are each a hydrogen atom, a hydroxyl group which may be protected by a protective group or the like; provided that a hydroxyl group protected by a protective group or the like is bonded to at least one carbon atom constituting the adamantane skeleton when Ra is a hydrogen atom or a methyl group and Rb is a methyl group; and at least one substituent, in addition to the HO—C(Ra)(Rb)— group indicated in the formula (1), is bonded to the adamantane ring when one of Ra and Rb is a methyl group and the other is an ethyl group.
    Type: Grant
    Filed: December 21, 1999
    Date of Patent: February 5, 2002
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Tatsuya Nakano, Hiroshi Shimojitosyo