Preparing Alicyclic Ring Containing Compound Directly By Isomerization Patents (Class 564/444)
  • Patent number: 10118888
    Abstract: 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: Grant
    Filed: February 25, 2016
    Date of Patent: November 6, 2018
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Yuko Shimizu, Yoshiaki Yamamoto
  • Publication number: 20150148322
    Abstract: 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: Application
    Filed: March 15, 2012
    Publication date: May 28, 2015
    Applicant: BOEHRINGER INGELHEIM INTERNATIONAL GMBH
    Inventors: 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
  • Patent number: 7256313
    Abstract: 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: Grant
    Filed: August 6, 2003
    Date of Patent: August 14, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Frank Funke, Thomas Hill, Jobst Rüdiger Von Watzdorf, Wolfgang Mattmann, Wolfgang Harder, Erhard Henkes, Gerd Littmann, Manfred Julius
  • Patent number: 6774270
    Abstract: 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: Grant
    Filed: April 1, 2003
    Date of Patent: August 10, 2004
    Assignee: 3M Innovative Properties Company
    Inventors: Zhongxing Zhang, Zai-Ming Qiu, Daniel R. Vitcak, Richard M. Flynn
  • Patent number: 6756500
    Abstract: 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 radical
    Type: Grant
    Filed: February 25, 2000
    Date of Patent: June 29, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christoph Gürtler, Manfred Jautelat
  • Patent number: 6350910
    Abstract: 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: Grant
    Filed: June 7, 2000
    Date of Patent: February 26, 2002
    Assignee: Firmenich SA
    Inventor: Christian Chapuis
  • Publication number: 20020010360
    Abstract: The invention relates to a novel process for the preparation of an aminoalcohol of the formula 1
    Type: Application
    Filed: January 30, 2001
    Publication date: January 24, 2002
    Applicant: Lonza AG
    Inventors: Walter Brieden, Josef Schroer, Christine Bernegger-Egli, Eva Maria Urban, Michael Petersen, Jean-Paul Roduit, Katja Berchtold, Holger Breitbach
  • Patent number: 6140540
    Abstract: 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: Grant
    Filed: April 6, 1993
    Date of Patent: October 31, 2000
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gamini Ananda Vedage, Richard Scott Myers, John Nelson Armor
  • Patent number: 6121493
    Abstract: 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: Grant
    Filed: March 30, 1993
    Date of Patent: September 19, 2000
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gamini Ananda Vedage, John Nelson Armor
  • Patent number: 6020527
    Abstract: 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: Grant
    Filed: March 31, 1999
    Date of Patent: February 1, 2000
    Assignee: Firmenich SA
    Inventors: Christian Chapuis, Michel Barthe
  • Patent number: 5969187
    Abstract: 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: Grant
    Filed: February 26, 1998
    Date of Patent: October 19, 1999
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takashi Okawa, Tomoo Tsujimoto, Hideo Ikarashi, Masaharu Doya, Yutaka Kanbara
  • Patent number: 5814664
    Abstract: 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: Grant
    Filed: June 23, 1997
    Date of Patent: September 29, 1998
    Assignee: Picower Institute for Medical Research
    Inventors: Peter C. Ulrich, Xini Zhang
  • Patent number: 5744644
    Abstract: 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: Grant
    Filed: May 23, 1996
    Date of Patent: April 28, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Bernd Papenfuhs
  • Patent number: 5516943
    Abstract: 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: Grant
    Filed: September 14, 1993
    Date of Patent: May 14, 1996
    Assignee: Sepracor, Inc.
    Inventors: Yun Gao, Yaping Hong, Xiaoyi Nie, Roger P. Bakale, Richard R. Feinberg, Charles M. Zepp
  • Patent number: 5319069
    Abstract: 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: Grant
    Filed: June 2, 1993
    Date of Patent: June 7, 1994
    Assignee: Ricoh Company, Ltd.
    Inventors: Masaomi Sasaki, Tamotsu Aruga, Tomoyuki Shimada
  • Patent number: 4861890
    Abstract: 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: Grant
    Filed: August 10, 1987
    Date of Patent: August 29, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Bernd Heiser, Hansjorg Stoller
  • Patent number: 4843107
    Abstract: 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: Grant
    Filed: March 24, 1988
    Date of Patent: June 27, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Andreas Ruckes, Werner Rasshofer, Klaus Konig, Richard Kopp
  • Patent number: 4843108
    Abstract: 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: Grant
    Filed: March 24, 1988
    Date of Patent: June 27, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Andreas Ruckes, Werner Rasshofer, Klaus Konig, Richard Kopp
  • Patent number: 4665000
    Abstract: 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: Grant
    Filed: October 19, 1984
    Date of Patent: May 12, 1987
    Assignee: Xerox Corporation
    Inventors: Emery G. Tokoli, Anthony M. Horgan
  • Patent number: 4304934
    Abstract: 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: Grant
    Filed: December 30, 1980
    Date of Patent: December 8, 1981
    Assignee: Polaroid Corporation
    Inventors: James R. Bartels-Keith, Eva R. Karger, Jean B. Rogers
  • Patent number: 4244890
    Abstract: 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: Grant
    Filed: December 14, 1977
    Date of Patent: January 13, 1981
    Assignee: SCM Corporation
    Inventors: Bernard J. Kane, Richard A. Von Genk