Carbon To Carbon Unsaturation Containing Patents (Class 568/596)
  • Patent number: 9051254
    Abstract: The present invention describes a novel synthetic method for preparing the key intermediate 2,6,10-trimethyl-1,1-dialkoxy-3,5,9-undecatriene of lycopene. An existing synthetic method have some disadvantages that it is very difficult to gain the raw material dialkyl 4-methyl-5,5-diakoxy-1-pentene-1-phosphonate (10) because no effective synthetic method can be adopted, and furthermore the obtained target compound is composed of several cis/trans isomers. This invention relates to a process comprising a condensation step wherein a starting C10-phosphonate is changed to its carbanion completely at a temperature of ?40˜30 under an atmosphere of a non-reactive gas in an organic solvent catalyzed by base, and then C4-dialkyl is added to undergo Wittig-Horner condensation. This invention affords all trans C14-acetal and this method is characterized with the advantages of simple procedure, easy access to raw material and low cost, which makes it has the value of industrial application.
    Type: Grant
    Filed: June 11, 2012
    Date of Patent: June 9, 2015
    Assignees: HANGZHOU NORMAL UNIVERSITY, UNIVERSITY OF SHAOXING
    Inventors: Pengfei Zhang, Chao Shen, Runpu Shen, Wei Liu, Chunlei Wu
  • Patent number: 8940944
    Abstract: VDF-based curable fluoroelastomers having glass transition temperature lower than ?35° C. and an amount of —COF end groups in the polymer lower than the sensitivity limit of the method using the FT-IR spectroscopy described in the present application.
    Type: Grant
    Filed: March 22, 2012
    Date of Patent: January 27, 2015
    Assignee: Solvay Solexis S.p.A.
    Inventors: Marco Apostolo, Francesco Triulzi, Vito Tortelli, Marco Galimberti
  • Patent number: 8846968
    Abstract: The present invention relates to an intermediate (12) of lycopene of 2,6,10-trimethyl-1,1-dialkoxyl-3,5,9-undecantriene of formula, (12) and its intermediate of 4-methyl-5,5-dialkoxyl-1-pentenyl-1-phosphonic acid dialkyl ester of formula (10), and their preparation methods. The process route is simple, the starting materials are available easily, the cost is low, and it is valuable in industry.
    Type: Grant
    Filed: December 3, 2012
    Date of Patent: September 30, 2014
    Assignees: Shaoxing University, Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory
    Inventors: Runpu Shen, Chunlei Lv, Xiaoyue Jiang, Xuejun Lao, Weidong Ye, Luo Liu, Xiaohua Song, Chunlei Wu
  • Publication number: 20140005434
    Abstract: The present invention relates to an intermediate (12) of lycopene of 2,6,10-trimethyl-1,1-dialkoxyl-3,5,9-undecantriene of formula, (12) and its intermediate of 4-methyl-5,5-dialkoxyl-1-pentenyl-1-phosphonic acid dialkyl ester of formula (10), and their preparation methods. The process route is simple, the starting materials are available easily, the cost is low, and it is valuable in industry.
    Type: Application
    Filed: December 3, 2012
    Publication date: January 2, 2014
    Applicants: Shaoxing University, Zhejiang Medicine Co., Ltd. Xinchang
    Inventors: Runpu Shen, Chunlei LV, Xiaoyue Jiang, Xuejun Lao, Weidong Ye, Luo Liu, Xiaohua Song, Chunlei Wu
  • 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
  • Publication number: 20130096209
    Abstract: The present invention provides edible compositions comprising a compound of the present invention, food products comprising such edible compositions and methods of preparing such food products. The present invention also provides methods of reducing the amount of NaCl in a food product, methods of reducing the sodium intake in a diet, and methods of reducing bitter taste in a food product.
    Type: Application
    Filed: April 15, 2011
    Publication date: April 18, 2013
    Applicants: Kraft Foods Global Brands LLC, Chromocell Corporation
    Inventors: David Hayashi, William P. Jones, Jane V. Leland, Peter H. Brown, Joseph Gunnet, Daniel Lavery, Louise Slade, Kambiz Shekdar, Jessica Langer
  • Publication number: 20120316366
    Abstract: The present invention describes a novel synthetic method for preparing the key intermediate 2,6,10-trimethyl-1,1-dialkoxy-3,5,9-undecatriene of lycopene. An existing synthetic method have some disadvantages that it is very difficult to gain the raw material dialkyl 4-methyl-5,5-diakoxy-1-pentene-1-phosphonate (10) because no effective synthetic method can be adopted, and furthermore the obtained target compound is composed of several cis/trans isomers. This invention relates to a process comprising a condensation step wherein a starting C10-phosphonate is changed to its carbanion completely at a temperature of ?40˜30 under an atmosphere of a non-reactive gas in an organic solvent catalyzed by base, and then C4-dialkyl is added to undergo Wittig-Horner condensation. This invention affords all trans C14-acetal and this method is characterized with the advantages of simple procedure, easy access to raw material and low cost, which makes it has the value of industrial application.
    Type: Application
    Filed: June 11, 2012
    Publication date: December 13, 2012
    Applicants: UNIVERSITY OF SHAOXING, HANGZHOU NORMAL UNIVERSITY
    Inventors: PENGFEI ZHANG, CHAO SHEN, RUNPU SHEN, WEI LIU, CHUNLEI WU
  • Publication number: 20120226077
    Abstract: VDF-based curable fluoroelastomers having glass transition temperature lower than ?35° C. and an amount of —COF end groups in the polymer lower than the sensitivity limit of the method using the FT-IR spectroscopy described in the present application.
    Type: Application
    Filed: March 22, 2012
    Publication date: September 6, 2012
    Applicant: SOLVAY S.A.
    Inventors: Marco Apostolo, Francesco Triulzi, Vito Tortelli, Marco Galimberti
  • Patent number: 8217192
    Abstract: A problem as an object of the invention is to provide a production method of spilanthol in a large scale without using expensive reagents. The present invention provides a production method of N-isobutyl-2,6,8-decatrienamide, wherein a column chromatography purification step is not required in all processes.
    Type: Grant
    Filed: January 16, 2009
    Date of Patent: July 10, 2012
    Assignee: Takasago International Corporation
    Inventors: Shigeru Tanaka, Kenji Yagi, Hideo Ujihara, Kenya Ishida
  • 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: 20110105773
    Abstract: A problem as an object of the invention is to provide a production method of spilanthol in a large scale without using expensive reagents. The present invention provides a production method of N-isobutyl-2,6,8-decatrienamide, wherein a column chromatography purification step is not required in all processes.
    Type: Application
    Filed: January 16, 2009
    Publication date: May 5, 2011
    Applicant: TAKASAGO INTERNATIONAL CORPORATION
    Inventors: Shigeru Tanaka, Kenji Yagi, Hideo Ujihara, Kenya Ishida
  • 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
  • Patent number: 7605286
    Abstract: The present invention relates to a method of protecting a hydroxyl group, which includes reacting a hydroxyl group-containing compound with a compound represented by the formula (I): wherein R is a phenyl group optionally having substituent(s), an alkyl group optionally having substituent(s) or a benzyl group optionally having substituent(s), and X is a halogen atom, in the presence of an acid catalyst to substitute the hydrogen atom of the hydroxyl group of the hydroxyl group-containing compound with a protecting group represented by the formula (II): wherein R is as defined above. The present invention provides a method capable of introducing an acetal type protecting group into a hydroxyl group under mild conditions, and a protecting reagent therefor and a method of producing the protecting reagent.
    Type: Grant
    Filed: June 23, 2004
    Date of Patent: October 20, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tetsuya Ikemoto, Yosuke Watanabe
  • Patent number: 7501545
    Abstract: A method of producing a compound represented by formula (IV), having: subjecting a compound of formula (I) to fluorination, subjecting the resultant compound to at least one of thermal decomposition and hydrolysis, and subjecting the resultant compound to thermal decomposition, to obtain the compound of formula (IV): in which R1 and R2 each independently are a hydrogen atom, a halogen atom, or a substituent; X1 is a hydrogen atom or a halogen atom, Y is an alkoxycarbonyl group or —CH2OCOR3, R3 is a substituent, and R1F and R2F each independently are a halogen atom or a fluorine-containing group.
    Type: Grant
    Filed: March 13, 2007
    Date of Patent: March 10, 2009
    Assignee: FUJIFILM Corporation
    Inventors: Yushi Kaneko, Naoyuki Hanaki
  • Patent number: 7488851
    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: Grant
    Filed: May 17, 2005
    Date of Patent: February 10, 2009
    Assignee: Universidade Do Porto
    Inventors: Alírio Egídio Rodrigues, Viviana Manuela Tenedório Matos Da Silva
  • Patent number: 7271296
    Abstract: The invention relates to a process for preparing phytofluene of the formula I, where a) a phosphonium salt of the formula II is condensed with an aldehyde of the formula III in a Wittig reaction to give an acetal of the formula IV b) the condensation product of the formula IV is subjected to an acid-catalyzed acetal hydrolysis to give the aldehyde of the formula V c) and V is condensed in a further Wittig reaction with a phosphonium salt of the formula VI to give phytofluene where the radicals R1, R2 and R7, and X? and Y? have the meaning sated in the description.
    Type: Grant
    Filed: October 15, 2004
    Date of Patent: September 18, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Hansgeorg Ernst, Klaus Henrich
  • 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: 7022665
    Abstract: The present invention relates to an acetal of formula in which the symbols R1 represent, independently or simultaneously, a linear or branched saturated or unsaturated C1 to C4 hydrocarbon group; or the two R1 are bonded together to form a saturated ring having 5 to 7 atoms and including the oxygen atoms to which the R1 groups are bonded, this ring being possibly substituted by methyl or ethyl groups; and the wavy line indicates that the double bond in position 4 has a configuration of the type (Z) or (E) or a mixture of the two configurations. The invention relates also to the use of such compounds as perfuming or flavoring ingredients, as well as the perfumed or flavored articles or perfuming or flavoring compositions containing such compounds.
    Type: Grant
    Filed: June 21, 2004
    Date of Patent: April 4, 2006
    Assignee: Firmenich SA
    Inventors: René Decorzant, Ferdinand Naef
  • 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: 6858761
    Abstract: The present invention provides a process and its utilization in a process comprising the step of carrying out an addition reaction of an alkylene oxide to an addition-receiving substance in the presence of a resin catalyst, thereby producing the addition reaction product, when the resin catalyst as used for the reaction is persevered so as to recycle it after it is recovered, the unreacted alkylene oxide remaining in the resin catalyst can be prevented from polymerizing and solidifying during the preservation, and the resin catalyst accordingly can be preserved stably for a long time. The resin catalyst as recovered after it is used for the reaction may be preserved under any of the following conditions: 1) at a low temperature of not higher than 40° C.
    Type: Grant
    Filed: March 18, 2002
    Date of Patent: February 22, 2005
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Yukihiro Yoneda, Tokumasa Ishida, Masahiro Uemura
  • 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: 6610892
    Abstract: The invention relates to a process for preparing 2,7-dimethyl-2,4,6-octatrienal monoacetals of the general formula I which comprises a) condensing an ester phosphonium salt of the general formula II or an ester phosphonate of the general formula III with an aldehyde of the formula IV in a Wittig or Wittig-Horner reaction to give an acetal ester of the general formula V b) reducing the ester of the formula V to give an acetal alcohol of the general formula VI and c) oxidizing the alcohol to 2,7-dimethyl-2,4,6-octatrienal monoacetals of the general formula I, where the substituents have the meaning defined in the description.
    Type: Grant
    Filed: March 12, 2002
    Date of Patent: August 26, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Hansgeorg Ernst, Klaus Henrich
  • 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: 20020035298
    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: Application
    Filed: September 5, 2001
    Publication date: March 21, 2002
    Inventors: Jorg Therre, Gerd Kaibel, Werner Aquila, Gunter Wegner, Hartwig Fuchs
  • Patent number: 6313322
    Abstract: A process for preparing acetals of the formula I where a) the Rs are, independently of one another, a C1-C20-alkyl or C3-C20-alkenyl radical, or b) the two R radicals together form the members of an unsubstituted or C1-C10-alkyl-substituted 5- to 7-membered cyclic acetal, by reacting 3-methyl-2-butenal in the presence of sulfamic acid, of a N-(C1-C8-alkyl)sulfamic acid or of a N,N-di(C1-C8-alkyl)sulfamic acid as catalyst with: an alcohol of the formula R—OH (IIa), or an orthoester of the formula HC—(OR)3 (III) or a mixture of an alcohol of the formula (IIa) and an orthoester of the formula (III), or an alcohol of the formula HO—(CH2)m—OH (IIb), where m is a number from 2 to 4, and (CH2)m group in the alcohol IIb may be substituted by a C1-C10-alkyl group.
    Type: Grant
    Filed: February 1, 2000
    Date of Patent: November 6, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Gisela Hieber, Klaus Ebel
  • Patent number: 6291719
    Abstract: The present invention relates to a method of catalyzing etherification, esterification, hydration, ether cleavage, isomerization alkylation, or other reactions which are catalyzable with an acid or molecular sieve catalyst. Said reactions are conducted using a novel, dual functional catalyst prepared with active components and a small amount of binder, wherein said dual functional catalyst comprises cylindrical pellets which are molded such that a cross-section or each pellet has a window lattice shape with external teeth, or a star shape with inner spokes.
    Type: Grant
    Filed: August 29, 2000
    Date of Patent: September 18, 2001
    Assignees: China Petro-Chemical Corporation, Qilu Petro-Chemical Corporation Sinopec
    Inventors: Buliang Gao, Jinyong Zhang, Jinshan Wang, Xingren Hao, Zaiqun Yu, Wei Wang
  • Patent number: 6255535
    Abstract: The present invention describes a novel process for the preparation of perfluoro allyl ethers. The process involves providing a hydrogen-containing precursor comprising at least one 1,2-dichloro alkyl ether moiety, fluorinating the precursor to provide a perfluorinated intermediate, and dechlorinating the perfluorinated intermediate to the corresponding perfluorinated ether. A reaction product of a perfluorinated olefin and an allyl ether may also be used as a precursor. Such a reaction product is chlorinated before the fluorination step. Perfluoro vinyl or allyl ethers may be used in place of the perfluorinated olefin. Novel perfluoro alkoxy compounds are also described.
    Type: Grant
    Filed: December 22, 1999
    Date of Patent: July 3, 2001
    Assignees: Dyneon LLC, 3M Innovative Properties Company
    Inventors: Jay F. Schulz, George G. I. Moore, Werner Schwertfeger, Klaus Hintzer, Zai-Ming Qiu, Miguel A. Guerra, Erik D. Hare, Allan T. Worm
  • Patent number: 6046367
    Abstract: Novel triphenylbis(fluoroalkoxy)phosphoranes and a process for their preparation are disclosed. Also disclosed is a process for making fluorinated ketals by reacting phosphoranes with fluorinated ketones.
    Type: Grant
    Filed: October 7, 1994
    Date of Patent: April 4, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Zhen-Yu Yang
  • Patent number: 5986113
    Abstract: A process for the manufacture of polyene esters or polyene acids comprises reacting a polyene O,O-dialkylacetal of di(O,O-dialkylacetal) with a vinylketene acetal or analogue thereof in the presence of a Lewis acid, hydrolyzing the reaction mixture depending on the vinylketene acetal used, subsequently cleaving alcohol under strongly basic conditions from the polyene derivative produced at this stage and, where the desired ester or carboxy group is still not present, performing the respective conversion. Certain intermediates in this process form a further aspect of the invention. The final products are primarily carotenoids which can be used appropriately, e.g. as colorants and pigments for foodstuffs, animal products etc.
    Type: Grant
    Filed: March 26, 1998
    Date of Patent: November 16, 1999
    Assignee: Roche Vitamins Inc
    Inventor: August Ruttimann
  • Patent number: 5739394
    Abstract: The invention relates to novel 3,3-dioxy-4,4,4-trifluorobutyric acid derivatives of the formula (I) ##STR1## in which R.sup.1 and R.sup.2 independently of one another represent C.sub.1 -C.sub.10 -alkyl, or represent cyclohexyl, or represent optionally substituted C.sub.6 -C.sub.10 -aryl or C.sub.7 -C.sub.14 -arylalkyl, orR.sup.1 and R.sup.2 together represent C.sub.2 -C.sub.4 -alkylene which is optionally mono- or disubstituted by methyl, or optionally substituted ortho-arylene,R.sup.3 represents hydrogen or C.sub.1 -C.sub.10 -alkyl, or represents cycloalkyl, or represents optionally substituted C.sub.6 -C.sub.10 -aryl or C.sub.7 -C.sub.
    Type: Grant
    Filed: December 16, 1996
    Date of Patent: April 14, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventor: Norbert Lui
  • Patent number: 5731475
    Abstract: There is disclosed a process for the preparation of a lower alkyl ester of 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylic acid which comprises the steps of(a) reacting a compound of formula:CF.sub.3 --CXCl--CH(OH)--CH.dbd.C(CH.sub.3).sub.2 (I)wherein X is chloro or bromo, with a tri-lower-alkyl orthoacetate containing up to four carbon atoms in each alkyl groups in the presence of at least a catalytic amount of an acid catalyst at an elevated temperature for a sufficient time to obtain a compound of formula:CF.sub.3 --CXCl--CH.dbd.CH--C(CH.sub.3).sub.2 --CH.sub.2 CO.sub.2 R (III)wherein R is an alkyl group containing up to four carbon atoms, and(b) treating said compound of formula (III) with at least one molar equivalent of a base to obtain said alkyl ester of 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylic acid. The products are useful as intermediates for insecticides.
    Type: Grant
    Filed: April 4, 1997
    Date of Patent: March 24, 1998
    Assignee: Zeneca Limited
    Inventors: Martin Charles Bowden, Michael Drysdale Turnbull
  • Patent number: 5710345
    Abstract: Polymers and copolymers of one or more fluorinated dienes of structure CFX.sup.1 .dbd.CX.sup.2 --O--CX.sup.3 X.sup.4 --O--CX.sup.2 .dbd.CX.sup.1 F, wherein X.sup.1 and X.sup.2 are F, Cl or H, and X.sup.3 and X.sup.4 are F or CF.sub.3, wherein said dienes essentially form cyclic repetitive units, the comonomers used for preparing copolymers being ethylene unsaturated fluorinated compounds.Processes for preparing the fluorinated dienes having said structure which comprise the reaction in solution between one halogenated olefin and one hypofluorite CX.sup.3 X.sup.4 (OF).sub.2, wherein X.sup.3 and X.sup.4 are F or CF.sub.3, and the dehalogenation or dehydrohalogenation of the linear adduct between one hypofluorite molecule and two olefin molecules.The polymers and copolymers of the invention are particularly suitable for preparing coatings for applications at high temperatures.
    Type: Grant
    Filed: November 15, 1996
    Date of Patent: January 20, 1998
    Assignee: Ausimont, S.P.A
    Inventors: Walter Navarrini, Vito Tortelli, Alessandro Zedda
  • Patent number: 5600015
    Abstract: There is described a process for the manufacture of isoprene derivatives of the general formula ##STR1## wherein the asymmetric centres can each individually have the (R)- or (S)-configuration, R represents a residue of the formulae ##STR2## R.sup.1 signifies lower alkyl or both R.sup.1 's together signify ethylene or propylene and n stands for the number 0, 1 or 2,in which a compound, which is present in the (E)- or (Z)-form, of the general formula ##STR3## wherein R, n and an optionally present asymmetric centre have the above significance,is asymmetrically hydrogenated with a ruthenium complex of an optically active atropisomeric diphosphine.
    Type: Grant
    Filed: May 19, 1995
    Date of Patent: February 4, 1997
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Emil A. Broger, Robert K. M uller
  • Patent number: 5599848
    Abstract: A process for preparing a mixture of 8E,10E-dodecadienol (Ia), 8E,10Z-dodecadienol (Ib), 8Z,10E-dodecadienol (Ic) and 8Z,10Z-dodecadienol (Id),H.sub.3 C--CH.dbd.CH--CH.dbd.CH--(CH.sub.2).sub.6 --CH.sub.2 --OH(8E,10E=Ia)(8E,10Z=Ib)(8Z,10E=Ic)(8Z,10Z=Id)starting from 1,8-octanediol (II) which is converted with a halogenating agent into (III)Hal-CH.sub.2 --(CH.sub.2).sub.6 --CH.sub.2 --OH (III)where (III) is subsequently reacted with (IV),H.sub.2 C.dbd.CH--O--R (IV)to give (V)Hal-CH.sub.2 --(CH.sub.2).sub.6 --CH.sub.2 --O--CH(CH.sub.3)--OR(V),(V) is converted in the presence of magnesium and crotonaldehyde into (VI)H.sub.3 C--CH.dbd.CH--CH(OH)--(CH.sub.2).sub.8 --O--CH(CH.sub.3)--OR(VI)and the protective group R and the hydroxyl group are simultaneously eliminated from (VI) in the presence of acid, novel intermediates for this process, and methods for controlling the codling moth Cydia pomonella by interfering with mating using this mixture are described.
    Type: Grant
    Filed: August 7, 1995
    Date of Patent: February 4, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Klein, Ulrich Neumann, Wolfgang Mackenroth, Guenter Renz, Wolfgang Krieg, Christiane Mackenroth, Ernst Buschmann, Jacobus J. DeKramer, Roland Milli
  • Patent number: 5455361
    Abstract: The invention relates to a process for preparing ketene acetals by dehydrohalogenation of 2-haloaldehyde acetals. If the 2-haloaldehyde acetal is open chain, the dehydrohalogenation is carried out in the presence of an alkali metal hydroxide or alkaline earth metal hydroxide and a phase transfer catalyst and/or a secondary or tertiary alcohol or a secondary or tertiary diol. If the 2-haloaldehyde acetals is cyclic, the dehydrohalogenation is carried out in the presence of an alkali metal hydroxide or alkaline earth metal hydroxide and a phase transfer catalyst and with or without a secondary or tertiary alcohol or a secondary or tertiary diol, or carried out in the presence of an alkali metal hydroxide or alkaline earth metal hydroxide and a secondary or tertiary diol. The ketene acetals which can be prepared by the process of the invention serve as intermediates in organic synthesis and are suitable as monomers or comonomers in free radical polymerization for the production of biodegradable plastics.
    Type: Grant
    Filed: September 13, 1993
    Date of Patent: October 3, 1995
    Assignee: Wacker-Chemie GmbH
    Inventors: Gerald Fleischmann, Herbert Eck, Hermann Petersen, Siegfried Pflaum
  • Patent number: 5393867
    Abstract: Disclosed are novel polyether compounds obtained by the reaction or polymerization of 3,4-epoxy-1-butene in the presence of a palladium(O) catalyst and a nucleophilic initiator compound. The polyether compounds comprise n units of residue (1) and m units of residue (2), wherein the total value of n+m is 2 to 70, m/(n+m) is greater than 0.30 and up to 0.
    Type: Grant
    Filed: January 18, 1994
    Date of Patent: February 28, 1995
    Assignee: Eastman Chemical Company
    Inventors: James C. Matayabas, Jr., Falling: Stephen N.
  • Patent number: 5338888
    Abstract: An improved process for preparing E,Z-butenedial bis(dialkyl acetals) by reacting the corresponding 2,5-dialkoxy-2,5-dihydrofurans with the corresponding lower alkanols in the presence of an acid at elevated temperature entails carrying out the reaction in the presence of approximately equimolar amounts of a trialkyl orthoformate and in the presence of catalytic amounts of a strong mineral acid or of a strong organic acid.
    Type: Grant
    Filed: July 6, 1993
    Date of Patent: August 16, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Paust, Wolfgang Krause
  • Patent number: 5149843
    Abstract: Conjugated diene compounds of the general formula: ##STR1## which are industrially advantageous intermediates for preparing sarcophytol A useful as an anticarcinogenic promotor or antitumor agent are provided.
    Type: Grant
    Filed: June 7, 1991
    Date of Patent: September 22, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
  • Patent number: 4983748
    Abstract: Polysaccharide aldehydes having the formula Sacch--O--CH.sub.2 --CH.dbd.CH--CHO, Saach--O--CH.sub.2 --C.tbd.C--CHO, ##STR1## starch, cellulose, and gum aldehydes, are useful for imparting wet, dry, or temporary wet strength to paper. They are prepared by a non-oxidative method which involves reacting the polysaccharide base, in the presence of alkali, with a derivatizing acetal reagent having the general structure ##STR2## and then hydrolyzing the acetal by adjusting the pH to less than 7, preferably 2-4. In the formulas, n is 1-3; R.sup.11 and R.sup.12 are independently an alkyl, aryl, aralkyl, or alkaryl group when n is 1, R.sup.11 or R.sup.12 is one of the groups when n is 2, or R.sup.11 and R.sup.12 are not present when n is 3; R.sup.13 is an alkyl group, optionally containing an ether linkage, or an aralkyl group; R.sup.14 and R.sup.15 are individually a hydrogen or a methyl group; R.sup.16, R.sup.17, and R.sup.18 are individually an alkyl group; Y.sup.
    Type: Grant
    Filed: December 28, 1988
    Date of Patent: January 8, 1991
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventors: John J. Tsai, Patrick G. Jobe, Diane J. Lamb, Robert L. Billmrs, Martin M. Tessler
  • Patent number: 4948781
    Abstract: The invention is concerned with compounds of the formula: ##STR1## wherein: R represents an alkyl group of one to four carbons, an alkenyl group of two to four carbons or a 1-alkoxy-alkyl group of the formula ##STR2## R.sup.1,R.sup.2 and R.sup.3 may be the same or different and represent hydrogen, methyl or ethyl;R.sup.4 represents hydrogen, an alkyl group of from one to five carbon atoms, an alkenyl group of from two to four carbon atoms or an alkylidene group of from one to four carbon atoms;R.sup.5,R.sup.6 and R.sup.7 may be the same or different and represent hydrogen, methyl or ethyl with the proviso that the sum R.sup.5 +R.sup.6 +R.sup.7 does not exceed two carbon atoms; andR.sup.8 represents methyl or ethyl;with the proviso that at least two, but not more than three of the symbols R.sup.1,R.sup.2,R.sup.3 and R.sup.4 represent hydrogen.This invention is also concerned with odorant and flavoring compositions containing these compounds.
    Type: Grant
    Filed: January 26, 1983
    Date of Patent: August 14, 1990
    Assignee: Givaudan Corporation
    Inventors: Roman Kaiser, Dietmar Lamparsky
  • Patent number: 4876370
    Abstract: 1,3,5-Nonatriene derivatives of formula: ##STR1## in which R.sub.1 and R.sub.2, together with the carbon atom to which they are linked, form a carbonyl group, or each of R.sub.1 and R.sub.2 denotes alkoxy or R.sub.1 and R.sub.2 together form an alkylenedioxy radical, which may be made by reaction of a butadiene derivative of formula: ##STR2## in which R is alkyl or phenyl, with a butanal ketoacetal of 10 formula: ##STR3## followed by reaction of the product with a halomethyltriphenylphosphonium halide, are useful intermediates e.g. for the production of phytol.
    Type: Grant
    Filed: September 19, 1988
    Date of Patent: October 24, 1989
    Assignee: Rhone-Poulenc Sante
    Inventors: Lucette Duhamel, Pierre Duhamel
  • Patent number: 4827004
    Abstract: Novel Isoprene Derivatives which have mucosa-protective and gastric acid secretion-inhibiting properties and are useful for combatting ulcers both by treating and as a prophylaxis against gastric and/or duodenal ulcers.
    Type: Grant
    Filed: August 24, 1987
    Date of Patent: May 2, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Albert Fischli, Max Schmid, Rudolf Schmid
  • Patent number: 4642390
    Abstract: A semi-continuous process for the manufacture of acetals of chloroacetaldehyde is described. In a preferred embodiment of the invention, chloroacetaldehyde dimethyl acetal is prepared by introducing chlorine and vinyl acetate through separate inlets into the upper opening of a cooled vertical packed column to form an intermediate product. The intermediate flows through the column, and optionally a static mixer, into a cooled batch reactor precharged with an excess of methanol to form the crude acetal product. Isolation and purification of the product is accomplished by known batch-type procedures.
    Type: Grant
    Filed: May 30, 1986
    Date of Patent: February 10, 1987
    Assignee: National Starch and Chemical Corporation
    Inventor: Dennis Neigel
  • Patent number: 4634778
    Abstract: Process for preparing chlorinated ethylenic derivatives of the formula ##STR1## in which R.sub.1 represents acetyl, formyl optionally in the form of an acetal, hydroxy optionally as an ether or ester, alkyloxycarbonyl, alkyl of 1 to 12 carbon atoms substituted by one or more acetyl, formyl optionally in the form of an acetal, hydroxy optionally in the form of an ether or ester, or alkyloxycarbonyl, alkenyl of 2 to 12 carbon atoms containing one or more double bonds optionally substituted by one or more of acetyl, formyl optionally in the form of an acetal, hydroxy optionally in the form of an ether or ester, or alkyloxycarbonyl, or R.sub.1 represents 3-sulpholenyl or a radical of formula ##STR2## in which R.sub.2 denotes a hydrogen or acetyl, by reacting chlorine in a nonpolar aprotic solvent with a compound of general formula ##STR3## in which R.sub.1 is defined as above. The products of formula I, some of which are new, are useful as intermediates in the synthesis of terpene products such as vitamin E.
    Type: Grant
    Filed: November 16, 1984
    Date of Patent: January 6, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel, Pierre Chabardes
  • Patent number: 4631146
    Abstract: The invention relates to 1,1-dimethoxy-2,5-dimethyl-2-vinyl-4-hexene, 1,1-dimethoxy-2,2,5-trimethyl-4-hexene, and 1,1-dimethoxy-2,2-dimethyl-3-phenyl-propane. The invention also relates to the production of these compounds and their use as fragrant substances in the cosmetics, detergent and perfume industries.
    Type: Grant
    Filed: February 19, 1986
    Date of Patent: December 23, 1986
    Assignee: Consortium fur elektrochemische Industrie GmbH
    Inventors: Helmut Gebauer, Marlies Regiert
  • Patent number: 4616095
    Abstract: Described is an isomer-directed process for producing asymmetric ketones defined according to the generic structure: ##STR1## wherein one of Z.sub.1 or Z.sub.2 is the moiety: ##STR2## and the other of Z.sub.1 or Z.sub.2 is hydrogen; wherein R.sub.11 and R.sub.21 represent hydrogen or the same or different alkyl or alkenyl with the proviso that R.sub.11 and R.sub.21 are not both hydrogen or wherein R.sub.11 and R.sub.21 taken together:(i) complete a cycloalkyl, cycloalkenyl, bicycloalkyl, mono or polyalkyl cycloakyl or mono or polyalkyl cycloalkenyl ring, or(ii) represent alkylidene, cycloalkenyl alkylidene, aralkylidene, mono or polyalkyl cycloalkenyl alkylidene or mono or polyalkyl aralkylidene;and wherein R.sub.6, R.sub.7 and R.sub.
    Type: Grant
    Filed: August 13, 1985
    Date of Patent: October 7, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
  • Patent number: 4613706
    Abstract: Described is an isomer-directed process for producing asymmetric ketones defined according to the generic structure: ##STR1## wherein one of Z.sub.1 or Z.sub.2 is the moiety: ##STR2## and the other of Z.sub.1 or Z.sub.2 is hydrogen; wherein R.sub.11 and R.sub.21 represent hydrogen or the same or different alkyl or alkenyl with the proviso that R.sub.11 and R.sub.21 are not both hydrogen or wherein R.sub.11 and R.sub.21 taken together:(i) complete a cycloalkyl, cycloalkenyl, bicycloalkyl, mono or polyalkyl cycloalkyl or mono or polyalkyl cycloalkenyl ring, or(ii) represent alkylidene, cycloalkenyl alkylidene, aralkylidene, mono or polyalkyl cycloalkenyl alkylidene or mono or polyalkyl aralkylidene;and wherein R.sub.6, R.sub.7 and R.sub.
    Type: Grant
    Filed: August 13, 1985
    Date of Patent: September 23, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
  • Patent number: 4579979
    Abstract: A method of preparation for acetals utilizing saturated or unsaturated aldehydes, in particular, the preparation of dimethylacetals of acetaldehyde, acrolein and methacrolein. The production of the acetal takes place in a liquid phase in the presence of a solid acid catalyst, such as a strongly acidic ion exchange resin or zeolite. The conversion mixture is extracted by means of water and by means of water insoluble organic solvents. There is obtained not only the desired acetals, but in addition also the unconverted initial quantities of the starting materials by a simple method and with very good yields.
    Type: Grant
    Filed: January 24, 1985
    Date of Patent: April 1, 1986
    Assignee: Degussa Aktiengesellschaft
    Inventors: Juan Andrade, Dietrich Arntz, Michael Kraft, Gunter Prescher
  • Patent number: 4570018
    Abstract: A novel chemical, fluorochlorocyclopropane (I) of the following formula: ##STR1## is prepared by the addition of fluorochlorocarbene to the corresponding olefin (II) of the following formula:CH.sub.2 .dbd.CR.sup.1 -R.sup.2The compound is a useful intermediate for synthesizing some chemicals, e.g., some cephalosporins.(wherein R.sup.1 is hydrogen, halogen, 1 to 8C alkylamino, alkoxy, or alkylthio andR.sup.2 is halogen, 1 to 8C alkylamino, alkoxy, or alkylthio).
    Type: Grant
    Filed: May 16, 1984
    Date of Patent: February 11, 1986
    Assignee: Shionogi & Co., Ltd.
    Inventors: Tsutomu Aoki, Hiromi Takahashi, Toshiro Konoike, Teruji Tsuji, Wataru Nagata
  • Patent number: 4532335
    Abstract: Allyl acetals and substituted allyl acetals are rearranged to produce ketene acetals by heating the acetals in a solution of an alkali metal alkoxide in an ethylene amine.
    Type: Grant
    Filed: March 7, 1983
    Date of Patent: July 30, 1985
    Assignee: SRI International
    Inventor: Robert F. Helwing