Carbon To Carbon Unsaturation Containing Patents (Class 568/596)
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Patent number: 9051254Abstract: 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: GrantFiled: June 11, 2012Date of Patent: June 9, 2015Assignees: HANGZHOU NORMAL UNIVERSITY, UNIVERSITY OF SHAOXINGInventors: Pengfei Zhang, Chao Shen, Runpu Shen, Wei Liu, Chunlei Wu
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Patent number: 8940944Abstract: 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: GrantFiled: March 22, 2012Date of Patent: January 27, 2015Assignee: Solvay Solexis S.p.A.Inventors: Marco Apostolo, Francesco Triulzi, Vito Tortelli, Marco Galimberti
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Patent number: 8846968Abstract: 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: GrantFiled: December 3, 2012Date of Patent: September 30, 2014Assignees: Shaoxing University, Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical FactoryInventors: Runpu Shen, Chunlei Lv, Xiaoyue Jiang, Xuejun Lao, Weidong Ye, Luo Liu, Xiaohua Song, Chunlei Wu
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Publication number: 20140005434Abstract: 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: ApplicationFiled: December 3, 2012Publication date: January 2, 2014Applicants: Shaoxing University, Zhejiang Medicine Co., Ltd. XinchangInventors: Runpu Shen, Chunlei LV, Xiaoyue Jiang, Xuejun Lao, Weidong Ye, Luo Liu, Xiaohua Song, Chunlei Wu
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Patent number: 8563780Abstract: 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: GrantFiled: May 12, 2009Date of Patent: October 22, 2013Assignee: DSM IP Assets B.V.Inventors: Werner Bonrath, Rolf Kuenzi
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Publication number: 20130096209Abstract: 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: ApplicationFiled: April 15, 2011Publication date: April 18, 2013Applicants: Kraft Foods Global Brands LLC, Chromocell CorporationInventors: David Hayashi, William P. Jones, Jane V. Leland, Peter H. Brown, Joseph Gunnet, Daniel Lavery, Louise Slade, Kambiz Shekdar, Jessica Langer
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Publication number: 20120316366Abstract: 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: ApplicationFiled: June 11, 2012Publication date: December 13, 2012Applicants: UNIVERSITY OF SHAOXING, HANGZHOU NORMAL UNIVERSITYInventors: PENGFEI ZHANG, CHAO SHEN, RUNPU SHEN, WEI LIU, CHUNLEI WU
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Publication number: 20120226077Abstract: 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: ApplicationFiled: March 22, 2012Publication date: September 6, 2012Applicant: SOLVAY S.A.Inventors: Marco Apostolo, Francesco Triulzi, Vito Tortelli, Marco Galimberti
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Patent number: 8217192Abstract: 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: GrantFiled: January 16, 2009Date of Patent: July 10, 2012Assignee: Takasago International CorporationInventors: Shigeru Tanaka, Kenji Yagi, Hideo Ujihara, Kenya Ishida
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Publication number: 20120029240Abstract: 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: ApplicationFiled: May 12, 2009Publication date: February 2, 2012Inventors: Werner Bonrath, Rolf Kuenzi
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Publication number: 20110105773Abstract: 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: ApplicationFiled: January 16, 2009Publication date: May 5, 2011Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Shigeru Tanaka, Kenji Yagi, Hideo Ujihara, Kenya Ishida
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Patent number: 7700814Abstract: 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: GrantFiled: March 27, 2007Date of Patent: April 20, 2010Assignee: ExxonMobil Chemical Patents Inc.Inventors: Ronald D. Garton, Corey W. Reed, Krishna K. Rao, Bruce D. Lilly
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Patent number: 7605286Abstract: 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: GrantFiled: June 23, 2004Date of Patent: October 20, 2009Assignee: Sumitomo Chemical Company, LimitedInventors: Tetsuya Ikemoto, Yosuke Watanabe
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Patent number: 7501545Abstract: 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: GrantFiled: March 13, 2007Date of Patent: March 10, 2009Assignee: FUJIFILM CorporationInventors: Yushi Kaneko, Naoyuki Hanaki
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Patent number: 7488851Abstract: 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: GrantFiled: May 17, 2005Date of Patent: February 10, 2009Assignee: Universidade Do PortoInventors: Alírio Egídio Rodrigues, Viviana Manuela Tenedório Matos Da Silva
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Patent number: 7271296Abstract: 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: GrantFiled: October 15, 2004Date of Patent: September 18, 2007Assignee: BASF AktiengesellschaftInventors: Hansgeorg Ernst, Klaus Henrich
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Patent number: 7232639Abstract: 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: GrantFiled: February 25, 2003Date of Patent: June 19, 2007Assignee: NEC CorporationInventors: Katsumi Maeda, Kaichiro Nakano
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Patent number: 7022665Abstract: 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: GrantFiled: June 21, 2004Date of Patent: April 4, 2006Assignee: Firmenich SAInventors: René Decorzant, Ferdinand Naef
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Patent number: 6919480Abstract: The present invention provides novel processes for preparing a fluorinated acyl fluoride and a fluorinated vinyl ether.Type: GrantFiled: December 5, 2003Date of Patent: July 19, 2005Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu
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Patent number: 6858761Abstract: 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: GrantFiled: March 18, 2002Date of Patent: February 22, 2005Assignee: Nippon Shokubai Co., Ltd.Inventors: Yukihiro Yoneda, Tokumasa Ishida, Masahiro Uemura
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Patent number: 6747174Abstract: The present invention provides novel processes for preparing a fluorinated acyl fluoride and a fluorinated vinyl ether.Type: GrantFiled: January 28, 2003Date of Patent: June 8, 2004Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu
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Patent number: 6610892Abstract: 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: GrantFiled: March 12, 2002Date of Patent: August 26, 2003Assignee: BASF AktiengesellschaftInventors: Hansgeorg Ernst, Klaus Henrich
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Patent number: 6518464Abstract: 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: GrantFiled: September 5, 2001Date of Patent: February 11, 2003Assignee: BASF AktiengesellschaftInventors: Jörg Therre, Gerd Kaibel, Werner Aquila, Günter Wegner, Hartwig Fuchs
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Publication number: 20020035298Abstract: 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: ApplicationFiled: September 5, 2001Publication date: March 21, 2002Inventors: Jorg Therre, Gerd Kaibel, Werner Aquila, Gunter Wegner, Hartwig Fuchs
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Patent number: 6313322Abstract: 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: GrantFiled: February 1, 2000Date of Patent: November 6, 2001Assignee: BASF AktiengesellschaftInventors: Gisela Hieber, Klaus Ebel
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Patent number: 6291719Abstract: 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: GrantFiled: August 29, 2000Date of Patent: September 18, 2001Assignees: China Petro-Chemical Corporation, Qilu Petro-Chemical Corporation SinopecInventors: Buliang Gao, Jinyong Zhang, Jinshan Wang, Xingren Hao, Zaiqun Yu, Wei Wang
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Patent number: 6255535Abstract: 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: GrantFiled: December 22, 1999Date of Patent: July 3, 2001Assignees: Dyneon LLC, 3M Innovative Properties CompanyInventors: Jay F. Schulz, George G. I. Moore, Werner Schwertfeger, Klaus Hintzer, Zai-Ming Qiu, Miguel A. Guerra, Erik D. Hare, Allan T. Worm
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Patent number: 6046367Abstract: 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: GrantFiled: October 7, 1994Date of Patent: April 4, 2000Assignee: E. I. du Pont de Nemours and CompanyInventor: Zhen-Yu Yang
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Patent number: 5986113Abstract: 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: GrantFiled: March 26, 1998Date of Patent: November 16, 1999Assignee: Roche Vitamins IncInventor: August Ruttimann
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Patent number: 5739394Abstract: 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: GrantFiled: December 16, 1996Date of Patent: April 14, 1998Assignee: Bayer AktiengesellschaftInventor: Norbert Lui
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Patent number: 5731475Abstract: 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: GrantFiled: April 4, 1997Date of Patent: March 24, 1998Assignee: Zeneca LimitedInventors: Martin Charles Bowden, Michael Drysdale Turnbull
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Patent number: 5710345Abstract: 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: GrantFiled: November 15, 1996Date of Patent: January 20, 1998Assignee: Ausimont, S.P.AInventors: Walter Navarrini, Vito Tortelli, Alessandro Zedda
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Patent number: 5599848Abstract: 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: GrantFiled: August 7, 1995Date of Patent: February 4, 1997Assignee: BASF AktiengesellschaftInventors: Ulrich Klein, Ulrich Neumann, Wolfgang Mackenroth, Guenter Renz, Wolfgang Krieg, Christiane Mackenroth, Ernst Buschmann, Jacobus J. DeKramer, Roland Milli
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Patent number: 5600015Abstract: 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: GrantFiled: May 19, 1995Date of Patent: February 4, 1997Assignee: Hoffmann-La Roche Inc.Inventors: Emil A. Broger, Robert K. M uller
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Patent number: 5455361Abstract: 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: GrantFiled: September 13, 1993Date of Patent: October 3, 1995Assignee: Wacker-Chemie GmbHInventors: Gerald Fleischmann, Herbert Eck, Hermann Petersen, Siegfried Pflaum
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Patent number: 5393867Abstract: 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: GrantFiled: January 18, 1994Date of Patent: February 28, 1995Assignee: Eastman Chemical CompanyInventors: James C. Matayabas, Jr., Falling: Stephen N.
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Patent number: 5338888Abstract: 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: GrantFiled: July 6, 1993Date of Patent: August 16, 1994Assignee: BASF AktiengesellschaftInventors: Joachim Paust, Wolfgang Krause
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Patent number: 5149843Abstract: 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: GrantFiled: June 7, 1991Date of Patent: September 22, 1992Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 4983748Abstract: 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: GrantFiled: December 28, 1988Date of Patent: January 8, 1991Assignee: National Starch and Chemical Investment Holding CorporationInventors: John J. Tsai, Patrick G. Jobe, Diane J. Lamb, Robert L. Billmrs, Martin M. Tessler
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Patent number: 4948781Abstract: 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: GrantFiled: January 26, 1983Date of Patent: August 14, 1990Assignee: Givaudan CorporationInventors: Roman Kaiser, Dietmar Lamparsky
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Patent number: 4876370Abstract: 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: GrantFiled: September 19, 1988Date of Patent: October 24, 1989Assignee: Rhone-Poulenc SanteInventors: Lucette Duhamel, Pierre Duhamel
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Patent number: 4827004Abstract: 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: GrantFiled: August 24, 1987Date of Patent: May 2, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Albert Fischli, Max Schmid, Rudolf Schmid
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Patent number: 4642390Abstract: 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: GrantFiled: May 30, 1986Date of Patent: February 10, 1987Assignee: National Starch and Chemical CorporationInventor: Dennis Neigel
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Patent number: 4634778Abstract: 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: GrantFiled: November 16, 1984Date of Patent: January 6, 1987Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel, Pierre Chabardes
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Patent number: 4631146Abstract: 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: GrantFiled: February 19, 1986Date of Patent: December 23, 1986Assignee: Consortium fur elektrochemische Industrie GmbHInventors: Helmut Gebauer, Marlies Regiert
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Patent number: 4616095Abstract: 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: GrantFiled: August 13, 1985Date of Patent: October 7, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
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Patent number: 4613706Abstract: 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: GrantFiled: August 13, 1985Date of Patent: September 23, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
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Patent number: 4579979Abstract: 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: GrantFiled: January 24, 1985Date of Patent: April 1, 1986Assignee: Degussa AktiengesellschaftInventors: Juan Andrade, Dietrich Arntz, Michael Kraft, Gunter Prescher
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Patent number: 4570018Abstract: 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: GrantFiled: May 16, 1984Date of Patent: February 11, 1986Assignee: Shionogi & Co., Ltd.Inventors: Tsutomu Aoki, Hiromi Takahashi, Toshiro Konoike, Teruji Tsuji, Wataru Nagata
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Patent number: 4532335Abstract: 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: GrantFiled: March 7, 1983Date of Patent: July 30, 1985Assignee: SRI InternationalInventor: Robert F. Helwing