Preparing Alicyclic Ring Containing Compound Directly By Isomerization Patents (Class 564/444)
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Patent number: 10118888Abstract: A method for isomerizing a bis(aminomethyl)cyclohexane, including isomerizing a bis(aminomethyl)cyclohexane while introducing an inert gas in a reaction solution containing a bis(aminomethyl)cyclohexane, at least one selected from the group consisting of an alkali metal, an alkali metal-containing compound, an alkaline earth metal and an alkaline earth metal-containing compound, and a benzylamine compound.Type: GrantFiled: February 25, 2016Date of Patent: November 6, 2018Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yuko Shimizu, Yoshiaki Yamamoto
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Publication number: 20150148322Abstract: The invention relates to novel piperidino-dihydrothienopyrimidine sulfoxides of formula I, wherein Ring A is a 6-membered aromatic ring which may optionally comprise one or two nitrogen atoms and wherein R is Cl and wherein R may be located either in the para-, meta- or ortho-position of Ring A, wherein S* is a sulphur atom that represents a chiral center, and all pharmaceutically acceptable salts, enantiomers and racemates, hydrates and solvates thereof and the use of these compounds for the treatment of inflammatory or allergic diseases of the respiratory tract such as COPD or asthma.Type: ApplicationFiled: March 15, 2012Publication date: May 28, 2015Applicant: BOEHRINGER INGELHEIM INTERNATIONAL GMBHInventors: Pascale A.J. Pouzet, Peter Nickolaus, Ulrike Werthmann, Rogelio P. Frutos, Bing-Shiou Yang, Soojin Kim, Jason Alan Mulder, Nitinchandra Patel, Chris H. Senanayake, Thomas G. Tampone, Xudong Wei
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Patent number: 7256313Abstract: The invention relates to processes for preparing 3-aminomethyl-3,5,5-trimethylcyclo-hexylamine (isophoronediamine, IPDA) having a high cis/trans isomer ratio. IPDA having a cis/trans isomer ratio in the range from 63/37 to 66/34 can be obtained in any desired cis/trans isomer ratio, irrespective of temperature, by reacting IPDA with H2 and NH3 in the presence of a hydrogenation catalyst. IPDA having a cis/trans isomer ratio of at least 73/27 which is an important starting material for the synthesis of polyurethanes and polyamides can be obtained by combining this isomerization process with distillative processes.Type: GrantFiled: August 6, 2003Date of Patent: August 14, 2007Assignee: BASF AktiengesellschaftInventors: Frank Funke, Thomas Hill, Jobst Rüdiger Von Watzdorf, Wolfgang Mattmann, Wolfgang Harder, Erhard Henkes, Gerd Littmann, Manfred Julius
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Patent number: 6774270Abstract: A method of removing hexafluoropropylene dimers (“HFP dimers”), dimer hydrides and other oligomers from a fluid is described. The method comprises heating the fluid to isomerize the HFP dimers to the thermodynamic isomer, and contacting the fluid with a tertiary amine (or salts thereof) to form a hexafluoropropylene dimer—tertiary amine adduct. The method may further comprise the step of separating the dimer adducts from the reaction mixture.Type: GrantFiled: April 1, 2003Date of Patent: August 10, 2004Assignee: 3M Innovative Properties CompanyInventors: Zhongxing Zhang, Zai-Ming Qiu, Daniel R. Vitcak, Richard M. Flynn
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Patent number: 6756500Abstract: A process for preparing a cyclic compound comprising subjecting a starting material in the presence of a catalyst component to metathesis reaction in the presence of an ionic liquid, wherein the starting material is a &agr;,&ohgr;-diene bearing a &agr; substituent NRR1 in the &agr; position to a double bond, wherein R is hydrogen or an organic substituent, R1 is tert-butyl, P(R)2, P(R2)2, COR, SO2PhR, COOR or CONRR2, R2is alkyl or phenyl, or R and R1 together form and in which &agr;,&ohgr;-dienes optionally bear at least one further substituent R in any other position with the exception of the &agr; position, wherein R is selected from the group consisting of hydrogen, fused or unfused aryl, alkyl, CN, COOR2 or halogen, and wherein the starting material optionally contains a member selected from the group containing at least one further substituent that is inert in the metathesis reaction and a heteroatom selected from the group consisting of branched alkyl radicals, unbranched alkyl radicalType: GrantFiled: February 25, 2000Date of Patent: June 29, 2004Assignee: Bayer AktiengesellschaftInventors: Christoph Gürtler, Manfred Jautelat
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Patent number: 6350910Abstract: The present invention describes a method for stereospecific isomerisation of prochiral allylamines into enamines and chiral imines, by using catalysts of Rh, Ir and Ru having phosphine chiral ligands immobilised on a solid material. The immobilised ligands are derivatives of phosphines of the type bis(diphenylphosphino)biaryl such as, for example, the phosphine known by the name BINAP. The method is particularly suitable for the production of optically active citronellal which may be obtained in optical purities above 95%.Type: GrantFiled: June 7, 2000Date of Patent: February 26, 2002Assignee: Firmenich SAInventor: Christian Chapuis
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Publication number: 20020010360Abstract: The invention relates to a novel process for the preparation of an aminoalcohol of the formula 1Type: ApplicationFiled: January 30, 2001Publication date: January 24, 2002Applicant: Lonza AGInventors: Walter Brieden, Josef Schroer, Christine Bernegger-Egli, Eva Maria Urban, Michael Petersen, Jean-Paul Roduit, Katja Berchtold, Holger Breitbach
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Patent number: 6140540Abstract: This invention relates to an improved hydrogenation and isomerization process wherein aromatic amines are hydrogenated to their ring hydrogenated counterparts and substantially isomerized to their thermodynamic form. These aromatic amines are presented by the formulas: ##STR1## wherein R is hydrogen or C.sub.1-6 alkyl, R1 and R2 are hydrogen or C.sub.1-6 aliphatic, A is C.sub.1-4 or NH; n is 0-2, x is 1-3 and y is 0 to 2 except the sum of the y groups must be at least 1.Type: GrantFiled: April 6, 1993Date of Patent: October 31, 2000Assignee: Air Products and Chemicals, Inc.Inventors: Gamini Ananda Vedage, Richard Scott Myers, John Nelson Armor
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Patent number: 6121493Abstract: This invention relates to an isomerization process wherein hydrogenated aromatic amines are substantially isomerized to their thermodynamic form. These hydrogenated aromatic amines are presented by the formulas: ##STR1## wherein R is hydrogen or C.sub.1-6 aliphatic, R1 and R2 are hydrogen or C.sub.1-6 aliphatic, A is C.sub.1-4 or NH; n is 0-2, x is 1-3 and y is 1 to 2 except the sum of the y groups in Formula I may be 1.The improvement in the process comprises using a catalytic system comprising cobalt preferably in combination with another Group VIII metal selected from rhodium, ruthenium, platinum, and palladium and the metal, copper. Preferably the catalyst comprises cobalt in combination with rhodium or ruthenium wherein the weight ratio of cobalt to rhodium or ruthenium, calculated on metal content, is from about 0.2 to 100 weight parts cobalt per weight part rhodium or ruthenium and the isomerization is carried out in the presence of hydrogen.Type: GrantFiled: March 30, 1993Date of Patent: September 19, 2000Assignee: Air Products and Chemicals, Inc.Inventors: Gamini Ananda Vedage, John Nelson Armor
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Patent number: 6020527Abstract: The present invention describes a stereospecific process for the isomerization of prochiral allyl amines into chiral enamines and imines, using Rh, Ir or Ru catalysts which carry chiral phosphine ligands derived from ferrocenes, which may be immobilized on a solid carrier, or from steroides. The process is in particular appropriate for the production of chiral citronellal, which can be obtained in optical purities of greater than 95%.Type: GrantFiled: March 31, 1999Date of Patent: February 1, 2000Assignee: Firmenich SAInventors: Christian Chapuis, Michel Barthe
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Patent number: 5969187Abstract: Provided a process for producing higher content of trans 1,4-bis(aminomethyl)cyclohexane which is used as the raw material for producing polyamides or polyurethanes having physically and chemically excellent properties from 1,4-bis(aminomethyl)cyclohexane which is generally produced by hydrogenation of p-xylylenediamine.That is, a mixture of cis and trans 1,4-bis(aminomethyl)cyclohexane is isomerized by heating at 120 to 250.degree. C. in the presence of a platinum group catalyst to change to trans isomer. 1,4-bis(aminomethyl)cyclohexane containing more than 80% trans isomer is produced by combining this isomerization technique and crystallization technique.Type: GrantFiled: February 26, 1998Date of Patent: October 19, 1999Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takashi Okawa, Tomoo Tsujimoto, Hideo Ikarashi, Masaharu Doya, Yutaka Kanbara
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Patent number: 5814664Abstract: The present invention relates to advanced glycosylation endproducts, and particularly to the use of novel cyclopentenone aminoreductones, 3-alkylamino-2 -hydroxy-4-hydroxymethyl-2-cyclopenten-1-ones. Such AGEs can be used in various diagnostic and therapeutic methods.Type: GrantFiled: June 23, 1997Date of Patent: September 29, 1998Assignee: Picower Institute for Medical ResearchInventors: Peter C. Ulrich, Xini Zhang
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Patent number: 5744644Abstract: It has been found that certain polyhydroxyalkylamines have a particularly good solubility in water, alcohols and in mixtures of water and alcohols. The concentrated solutions described consist essentially of water, alcohols, preferably C.sub.1 -C.sub.3 -alcohols, or water/alcohol mixtures as solvent and at least one dialkylaminopropylglucamine of the formula 1 belowZ--NH--CH.sub.2 CH.sub.2 CH.sub.2 --NR.sup.1 R.sup.2 ( 1)where R.sup.1 and R.sup.2 are identical or different and are C.sub.1 -C.sub.4 -alkyl or hydroxyalkyl having from 2 to 4 carbon atoms and Z is a linear polyhydroxyhydrocarbon radical having at least three OH groups which may, if desired, be alkoxylated, The concentrated solutions are particularly useful for preparing the corresponding polyhydroxyalkylcarboxamides.Type: GrantFiled: May 23, 1996Date of Patent: April 28, 1998Assignee: Hoechst AktiengesellschaftInventor: Bernd Papenfuhs
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Patent number: 5516943Abstract: A two-step process for the conversion of a trans-1-amino-2-hydroxycycloalkane stereoselectively to a cis-1-amino-2-hydroxycycloalkane is disclosed. The novel step, a one-step hydrolysis with formal inversion, can be used to convert an amide of a trans-1-amino-2-hydroxycycloalkane to a cis-1-amino-2-hydroxycycloalkane. Methods for obtaining the trans-1-amino-2-hydroxycycloalkanes and their amides from alkenes are also disclosed. A preferred process converts indene to cis-1-amino-2-indanol.Type: GrantFiled: September 14, 1993Date of Patent: May 14, 1996Assignee: Sepracor, Inc.Inventors: Yun Gao, Yaping Hong, Xiaoyi Nie, Roger P. Bakale, Richard R. Feinberg, Charles M. Zepp
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Patent number: 5319069Abstract: An electrophotographic photoconductor comprising an electroconductive support and a photoconductive layer formed thereon comprising as an effective component at least one polyether compound represented by formula (I): ##STR1## wherein Ar represents a phenylene group or a biphenylene group; R.sup.1 and R.sup.2 each represent an alkyl group which may have a substituent, or an aryl group which may have a substituent; and n is an integer of 1 to 4. Furthermore, charge transporting material comprising the above polyether compound, polyether compounds having formula (II) for use in the electrophotographic photoconductor and a method of preparing the same are disclosed, ##STR2## wherein m is an integer of 1 or 2.Type: GrantFiled: June 2, 1993Date of Patent: June 7, 1994Assignee: Ricoh Company, Ltd.Inventors: Masaomi Sasaki, Tamotsu Aruga, Tomoyuki Shimada
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Patent number: 4861890Abstract: A process for producing chiral enamines by isomerizing a beta, gamma unsaturated amine with a rhodium-diphosphine complex with the addition of an achiral triarylphosphine and, if desired, hydrolyzing the compound of the enamine I obtained to the corresponding aldehyde.Type: GrantFiled: August 10, 1987Date of Patent: August 29, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Bernd Heiser, Hansjorg Stoller
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Patent number: 4843107Abstract: Polyamines containing primary amino groups are made by a one-shot process for the hydrolysis of prepolymers containing isocyanate end groups and having an isocyanate content of from 0.5 to 40 weight % with 0.75 to 40 mol of water per equivalent of isocyanate groups in the presence of very small quantities of sodium hydroxide in certain organic, polar solvents. The compounds containing isocyanate groups used for this process are isocyanate prepolymers (preferably containing urethane groups). Hydrolysis according to this process leads directly to the polyamines with elimination of carbon dioxide. These polyamines may be isolated by the usual methods and the removal of the small quantities of catalyst may advantageously be omitted. These polyamines are useful for the preparation of polyurethane(urea)s.Type: GrantFiled: March 24, 1988Date of Patent: June 27, 1989Assignee: Bayer AktiengesellschaftInventors: Andreas Ruckes, Werner Rasshofer, Klaus Konig, Richard Kopp
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Patent number: 4843108Abstract: Polyamines are produced by hydrolyzing isocyanate compounds having an NCO content of from 0.5 to 40 wt. % with from 0.75 to 40 moles of water per equivalent of NCO groups in the presence of from 0.021 to 0.099 wt. % sodium hydroxide and at least 10 wt. % water-miscible polar organic solvent containing nitrile, ketone, sulfoxide or ether groups having a boiling point of from 56.degree. to 250.degree. C. The reaction mixture is maintained in a homogeneous phase. The reaction is carried out at 40.degree. to 170.degree. C. These polyamines are useful in the production of polyurethane(urea)s.Type: GrantFiled: March 24, 1988Date of Patent: June 27, 1989Assignee: Bayer AktiengesellschaftInventors: Andreas Ruckes, Werner Rasshofer, Klaus Konig, Richard Kopp
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Patent number: 4665000Abstract: Disclosed for incorporation in imaging members are novel aromatic ether compositions of the formula R--X--R.sub.1, wherein R and R.sub.1 are independently selected from arylamino and substituted arylamino groups, and X is selected from the group consisting of oxygen, sulfur, selenium, and tellurium. Also disclosed are photoresponsive imaging devices containing a photogenerating layer and in contact therewith a hole transport layer comprised of the aromatic ethers illustrated herein.Type: GrantFiled: October 19, 1984Date of Patent: May 12, 1987Assignee: Xerox CorporationInventors: Emery G. Tokoli, Anthony M. Horgan
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Patent number: 4304934Abstract: This invention relates to a method of synthesizing 3-amino-2-hydroxy-2-cyclopentenones possessing an aliphatic substituent in the 4-position which comprises reacting cyanoacetamide with an aliphatic aldehyde to yield the corresponding .beta.-substituted-.alpha.,.alpha.'-dicyanoglutaramide, hydrolyzing the amide to the corresponding .beta.Type: GrantFiled: December 30, 1980Date of Patent: December 8, 1981Assignee: Polaroid CorporationInventors: James R. Bartels-Keith, Eva R. Karger, Jean B. Rogers
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Patent number: 4244890Abstract: Disclosed are novel cyclic terpenoid amines which can be prepared by cyclizing the corresponding acyclic terpenoid amine.CROSS REFERENCE TO RELATED APPLICATIONSThis application is related to applicant's commonly owned copending application Ser. No. 916,966 filed 19 June 1978, now U.S. Pat. No. 4,179,468 dated 18 Dec. 1979 and entitled Cyclic Terpenoid Onium Salts, Their Preparation and Uses.Type: GrantFiled: December 14, 1977Date of Patent: January 13, 1981Assignee: SCM CorporationInventors: Bernard J. Kane, Richard A. Von Genk