Four-membered Alicyclic Ring Containing Patents (Class 568/839)
  • Patent number: 11623904
    Abstract: Provided is a process in which a cyclobutanediol compound having a high cis:trans ratio can be stably obtained. The cyclobutanediol compound having a cis:trans ratio of 1.5:1 to 5000:1 is produced by using at least one compound selected from a group consisting of a cyclobutanedione compound, a cyclobutane ketol compound, and a cyclobutanediol compound as a raw material, and performing a catalytic hydrogenation reaction and an isomerization reaction in the cyclobutanediol compound in a solid phase state in the presence of a metal catalyst without adding a solvent.
    Type: Grant
    Filed: March 17, 2021
    Date of Patent: April 11, 2023
    Assignee: JNC CORPORATION
    Inventors: Shinichi Furusato, Toshiyuki Kawanabe, Kaori Tsuruoka, Hironao Sajiki, Tsuyoshi Yamada, Kwihwan Park
  • Patent number: 9238602
    Abstract: This invention is generally directed to a process for the preparation of cis-2,2,4,4-tetramethylcyclobutane-1,3-diol comprising: treatment of at least one monomer selected from 2,2,4,4-tetramethylcyclobutane-1,3-dione, 3-hydroxy-2,2,4,4-tetramethylcyclobutanone, and 2,2,4,4-tetramethylcyclobutane-1,3-diol said diol having a starting cis:trans molar ratio of 0:1 to about 2:1, or mixtures thereof by contacting said monomer(s) with hydrogen in the presence of a reaction solvent in which the resulting cis-2,2,4,4-tetramethylcyclobutane-1,3-diol is partially soluble and further in the presence of a catalyst comprising about 0.1 to about 10 weight percent ruthenium, based on the total weight of the catalyst, deposited on a support material, under reaction conditions sufficient to produce a cis-2,2,4,4-tetramethylcyclobutane-1,3-diol having a final cis:trans molar ratio of from 2:1 to about 25:1.
    Type: Grant
    Filed: December 10, 2014
    Date of Patent: January 19, 2016
    Assignee: Eastman Chemical Company
    Inventors: Jerome Leonard Stavinoha, Jr., Carey Dan Ashcroft, Kelmara Khadene Kelly, Craig Alan Hoyme
  • Patent number: 9238603
    Abstract: This invention is generally directed to a batch process for the preparation of cis-2,2,4,4-tetramethylcyclobutane-1,3-diol comprising: (A) treatment of at least one monomer selected from 2,2,4,4-tetramethylcyclobutane-1,3-dione, 3-hydroxy-2,2,4,4-tetramethylcyclobutanone, and 2,2,4,4-tetramethylcyclobutane-1,3-diol said diol having a starting cis:trans molar ratio of 0:1 to about 2:1, or mixtures thereof by contacting said monomer(s) with hydrogen in the presence of a reaction solvent in which the resulting cis-2,2,4,4-tetramethylcyclobutane-1,3-diol is partially soluble and further in the presence of a catalyst comprising about 0.
    Type: Grant
    Filed: December 10, 2014
    Date of Patent: January 19, 2016
    Assignee: Eastman Chemical Company
    Inventors: Jerome Leonard Stavinoha, Jr., Carey Dan Ashcroft, Craig Alan Hoyme, Kelmara Khadene Kelly
  • Patent number: 9156759
    Abstract: A method for isolating 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) solids from an isolated feed slurry formed in a TMCD process comprising TMCD, a liquid phase, and impurities by (a) treating the isolated feed slurry in a product isolation zone to produce an isolated TMCD product wet cake, a mother liquor, and impurities; wherein the product isolation zone can comprise at least one rotary pressure drum filter.
    Type: Grant
    Filed: May 1, 2015
    Date of Patent: October 13, 2015
    Assignee: EASTMAN CHEMICAL COMPANY
    Inventors: Kenny Randolph Parker, Craig Alan Hoyme
  • Patent number: 9024080
    Abstract: A method for isolating 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) solids from an isolated feed slurry formed in a TMCD process comprising TMCD, a liquid phase, and impurities by (a) treating the isolated feed slurry in a product isolation zone to produce an isolated TMCD product wet cake, a mother liquor, and impurities; wherein the product isolation zone can comprise at least one rotary pressure drum filter.
    Type: Grant
    Filed: September 15, 2014
    Date of Patent: May 5, 2015
    Assignee: Eastman Chemical Company
    Inventors: Kenny Parker, Craig Hoyme
  • Publication number: 20140378716
    Abstract: A method for isolating 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) solids from an isolated feed slurry formed in a TMCD process comprising TMCD, a liquid phase, and impurities by (a) treating the isolated feed slurry in a product isolation zone to produce an isolated TMCD product wet cake, a mother liquor, and impurities; wherein the product isolation zone can comprise at least one rotary pressure drum filter.
    Type: Application
    Filed: September 15, 2014
    Publication date: December 25, 2014
    Applicant: Eastman Chemical Company
    Inventors: Kenny Parker, Craig Hoyme
  • Patent number: 8859825
    Abstract: A method for isolating 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) solids from an isolated feed slurry formed in a TMCD process comprising TMCD, a liquid phase, and impurities by (a) treating the isolated feed slurry in a product isolation zone to produce an isolated TMCD product wet cake, a mother liquor, and impurities; wherein the product isolation zone can comprise at least one rotary pressure drum filter.
    Type: Grant
    Filed: December 19, 2011
    Date of Patent: October 14, 2014
    Assignee: Eastman Specialties Holdings Corporation
    Inventors: Kenny Randolph Parker, Craig Alan Hoyme
  • Patent number: 8716535
    Abstract: The invention provides alkene fluoroalkanol and fluorinated polyol precursors to fluoroalkanol-substituted ?,?-unsaturated esters. The fluoroalkanol-substituted ?,?-unsaturated esters are olefins that can be readily polymerized to provide fluoroalkanol-substituted polymers useful in lithographic photoresist compositions. Also provided are methods for synthesizing the alkene fluoroalkanol and fluorinated polyol precursors.
    Type: Grant
    Filed: October 16, 2008
    Date of Patent: May 6, 2014
    Assignee: International Business Machines Corporation
    Inventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
  • Patent number: 8716534
    Abstract: The invention provides alkene fluoroalkanol and fluorinated polyol precursors to fluoroalkanol-substituted ?,?-unsaturated esters. The fluoroalkanol-substituted ?,?-unsaturated esters are olefins that can be readily polymerized to provide fluoroalkanol-substituted polymers useful in lithographic photoresist compositions. Also provided are methods for synthesizing the alkene fluoroalkanol and fluorinated polyol precursors.
    Type: Grant
    Filed: October 16, 2008
    Date of Patent: May 6, 2014
    Assignee: International Business Machines Corporation
    Inventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
  • Patent number: 8420869
    Abstract: Disclosed is a process for the preparation of a 2,2,4,4-tetraalkylcyclobutane-1,3-diol by hydrogenation of the corresponding 2,2,4,4-tetraalkylcyclobutane-1,3-dione in the vapor phase in the presence of a supported catalyst. The process is useful for the preparation of 2,2,4,4-tetramethylcyclobutane-1,3-diol from 2,2,4,4-tetramethylcyclobutane-1,3-dione. The process can produce a 2,2,4,4-tetraalkylcyclobutane-1,3-diol product having a cis:trans isomer ratio of 1:1 or greater.
    Type: Grant
    Filed: December 9, 2010
    Date of Patent: April 16, 2013
    Assignee: Eastman Chemical Company
    Inventors: Zhidong Zhu, Gerald Charles Tustin, Philip Conrad Heidt, Zhufang Liu
  • Patent number: 8420868
    Abstract: Disclosed is a process for the preparation of a 2,2,4,4-tetraalkylcyclobutane-1,3-diols by hydrogenation of a 2,2,4,4-tetraalkylcyclobutane-1,3-dione in the presence of a catalyst comprising ruthenium deposited on a carbon nanotube support. The process is useful for the preparation of 2,2,4,4-tetramethylcyclobutane-1,3-diol. The process may be carried out in the presence or absence of a solvent and in the liquid or vapor phase. Also disclosed is a process for modifying the cis:trans ratio of the 2,2,4,4-tetramethylcyclobutane-1,3-diol hydrogenation product by contacting the diol with hydrogen in the presence of a supported ruthenium catalyst.
    Type: Grant
    Filed: December 9, 2010
    Date of Patent: April 16, 2013
    Assignee: Eastman Chemical Company
    Inventors: Zhufang Liu, Lori Cooke Ensor, Guy Ralph Steinmetz, Jerome Leonard Stavinoha, Jr.
  • Patent number: 8394997
    Abstract: Disclosed is a process for the isomerization of 2,2,4,4-tetraalkylcyclobutane-1,3-diols, such as 2,2,4,4-tetramethylcyclobutane-1,3-diol, by contacting the diol with a supported ruthenium catalyst in the presence of hydrogen at elevated pressures and temperatures. The process is carried under conditions in which there is no net production of 2,2,4,4-tetraalkylcyclobutane-1,3-diol. The process may be carried out in the presence or absence of a solvent and in the liquid or vapor phase.
    Type: Grant
    Filed: December 9, 2010
    Date of Patent: March 12, 2013
    Assignee: Eastman Chemical Company
    Inventors: Zhufang Liu, Lori Cooke Ensor, Kelmara Khadene Kelly, Jerome Leonard Stavinoha, Jr., Kim Steven Chamberlin, Charles Everette Kelly, Carey Dan Ashcroft, Charles Edwan Sumner, Jr.
  • Publication number: 20130012422
    Abstract: The present application relates to perfume raw materials, perfume delivery systems and consumer products comprising such perfume raw materials and/or such perfume delivery systems, as well as processes for making and using such perfume raw materials, perfume delivery systems and consumer products. Such perfume raw materials and compositions, including the delivery systems, disclosed herein expand the perfume communities options as such perfume raw materials can provide variations on character and such compositions can provide desired odor profiles.
    Type: Application
    Filed: September 14, 2012
    Publication date: January 10, 2013
    Inventors: Johan SMETS, Hugo Robert Germain Denutte, An Pintens, David Thomas Stanton, Koen Van Aken, Inge Helena Hubert Laureyn, Bram Denolf, Freek Annie Camiel Vrielynck
  • Publication number: 20120189546
    Abstract: This invention relates to novel cyclo alkyl compounds suitable for labeling by 18F, methods of preparing such a compound, compositions comprising such compounds, kits comprising such compounds or compositions and uses of such compounds, compositions or kits for diagnostic imaging by positron emission tomography (PET).
    Type: Application
    Filed: July 9, 2010
    Publication date: July 26, 2012
    Applicant: BAYER PHARMA AKTIENGESELLSCHAFT
    Inventors: Keith Graham, Heribert Schmitt-Willich, Dominic Franck
  • Publication number: 20120157720
    Abstract: A method for isolating 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) solids from an isolated feed slurry formed in a TMCD process comprising TMCD, a liquid phase, and impurities by (a) treating the isolated feed slurry in a product isolation zone to produce an isolated TMCD product wet cake, a mother liquor, and impurities; wherein the product isolation zone can comprise at least one rotary pressure drum filter.
    Type: Application
    Filed: December 19, 2011
    Publication date: June 21, 2012
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Kenny Randolph Parker, Craig Alan Hoyme
  • Publication number: 20120149948
    Abstract: Disclosed is a process for the isomerization of 2,2,4,4-tetraalkylcyclobutane-1,3-diols, such as 2,2,4,4-tetramethylcyclobutane-1,3-diol, by contacting the diol with a supported ruthenium catalyst in the presence of hydrogen at elevated pressures and temperatures. The process is carried under conditions in which there is no net production of 2,2,4,4-tetraalkylcyclobutane-1,3-diol. The process may be carried out in the presence or absence of a solvent and in the liquid or vapor phase.
    Type: Application
    Filed: December 9, 2010
    Publication date: June 14, 2012
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Zhufang Liu, Lori Cooke Ensor, Kelmara Khadene Kelly, Jerome Leonard Stavinoha, JR., Kim Steven Chamberlin, Charles Everette Kelly, Carey Dan Ashcroft, Charles Edwan Sumner, JR.
  • Publication number: 20120149946
    Abstract: Disclosed is a process for the preparation of a 2,2,4,4-tetraalkylcyclobutane-1,3-diols by hydrogenation of a 2,2,4,4-tetraalkylcyclobutane-1,3-dione in the presence of a catalyst comprising ruthenium deposited on a carbon nanotube support. The process is useful for the preparation of 2,2,4,4-tetramethylcyclobutane-1,3-diol. The process may be carried out in the presence or absence of a solvent and in the liquid or vapor phase. Also disclosed is a process for modifying the cis:trans ratio of the 2,2,4,4-tetramethylcyclo-butane-1,3-diol hydrogenation product by contacting the diol with hydrogen in the presence of a supported ruthenium catalyst.
    Type: Application
    Filed: December 9, 2010
    Publication date: June 14, 2012
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Zhufang Liu, Lori Cooke Ensor, Guy Ralph Steinmetz, Jerome Leonard Stavinoha, JR.
  • Publication number: 20120149947
    Abstract: Disclosed is a process for the preparation of a 2,2,4,4-tetraalkylcyclobutane-1,3-diol by hydrogenation of the corresponding 2,2,4,4-tetraalkylcyclobutane-1,3-dione in the vapor phase in the presence of a supported catalyst. The process is useful for the preparation of 2,2,4,4-tetramethylcyclobutane-1,3-diol from 2,2,4,4-tetramethylcyclobutane-1,3-dione. The process can produce a 2,2,4,4-tetraalkylcyclobutane-1,3-diol product having a cis:trans isomer ratio of 1:1 or greater.
    Type: Application
    Filed: December 9, 2010
    Publication date: June 14, 2012
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Zhidong Zhu, Gerald Charles Tustin, Philip Conrad Heidt, Zhufang Liu
  • Publication number: 20110282105
    Abstract: Disclosed is a novel process for the continuous crystallization of a mixture of cis-2,2,4,4-tetramethylcyclobutanediol and trans-2,2,4,4-tetramethylcyclobutanediol dissolved in a solvent.
    Type: Application
    Filed: May 16, 2011
    Publication date: November 17, 2011
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventor: Ruairi Seosamh O'meadhra
  • Patent number: 7989667
    Abstract: Disclosed is a novel process for the continuous crystallization of a mixture of cis-2,2,4,4-tetramethylcyclobutanediol and trans-2,2,4,4-tetramethylcyclobutanediol dissolved in a solvent.
    Type: Grant
    Filed: September 4, 2009
    Date of Patent: August 2, 2011
    Assignee: Eastman Chemical Company
    Inventor: Ruairi Seosamh O'meadhra
  • Patent number: 7838707
    Abstract: The present disclosure relates to the production of a 2,2,4,4-tetraalkylcyclobutane-1,3-diol. In one embodiment, the present invention relates to the production of a 2,2,4,4-tetraalkylcyclobutane-1,3-diol by hydrogenation of a 2,2,4,4-tetraalkylcyclobutane-1,3-dione in the presence of a ruthenium-promoted cobalt-based catalyst.
    Type: Grant
    Filed: November 30, 2007
    Date of Patent: November 23, 2010
    Assignee: Eastman Chemical Company
    Inventors: Jennifer Ellen McCusker-Orth, Jerome Leonard Stavinoha, Jr., Anthony Dominick Messina, Steven Thomas Perri, Zhufang Liu, Philip Conrad Heidt, Brent Alan Tennant
  • Publication number: 20100137178
    Abstract: The present application relates to perfume raw materials, perfume delivery systems and consumer products comprising such perfume raw materials and/or such perfume delivery systems, as well as processes for making and using such perfume raw materials, perfume delivery systems and consumer products. Such perfume raw materials and compositions, including the delivery systems, disclosed herein expand the perfume communities options as such perfume raw materials can provide variations on character and such compositions can provide desired odor profiles.
    Type: Application
    Filed: December 1, 2009
    Publication date: June 3, 2010
    Inventors: Johan Smets, Hugo Robert Germain Denutte, An Pintens, David Thomas Stanton, Koen Van Aken, Inge Helena Hubert Laureyn, Bram Denolf, Freek Annie Camiel Vrielynck
  • Patent number: 7723551
    Abstract: The present disclosure pertains to processes for the simultaneous co-production of 2,2,4,4-tetramethylcyclobutane-1,3-diol and 1,4-cyclohexanedimethanol by hydrogenation 2,2,4,4-tetramethylcyclobutane-1,3-dione and dimethylcyclohexane-1,4-dicarboxylate, respectively, under hydrogenation conditions of temperature and pressure.
    Type: Grant
    Filed: November 30, 2007
    Date of Patent: May 25, 2010
    Assignee: Eastman Chemical Company
    Inventors: Jennifer Ellen McCusker, Jerome Leonard Stavinoha, Jr., Christopher Fletcher Tomlin, Michael Wayne Salyer
  • Patent number: 7691456
    Abstract: The invention relates to novel dioxane derivatives of the formula R1-(A1-Z1)m-G-(Z2-A2)n-R2, in which G denotes (I) or (II), and in which R1, R2, A1, A2, Z1, Z2, m and n have the meanings indicated in claim 1, to the use thereof as component(s) of liquid-crystalline media, and to liquid-crystal and electro-optical display elements which contain the liquid-crystalline media according to the invention.
    Type: Grant
    Filed: October 11, 2006
    Date of Patent: April 6, 2010
    Assignee: Merck Patent Gesellschaft
    Inventors: Lars Lietzau, Werner Binder, Melanie Klasen-Memmer, Eike Poetsch, Markus Czanta
  • Publication number: 20100063331
    Abstract: Disclosed is a novel process for the continuous crystallization of a mixture of cis-2,2,4,4-tetramethylcyclobutanediol and trans-2,2,4,4-tetramethylcyclobutanediol dissolved in a solvent.
    Type: Application
    Filed: September 4, 2009
    Publication date: March 11, 2010
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventor: Ruairi Seosamh O'Meadhra
  • Patent number: 7582804
    Abstract: The present disclosure relates to the production of 2,2,4,4-tetraalkylcyclobutane-1,3-diol. In one embodiment, the present invention relates to the production of 2,2,4,4-tetraalkylcyclobutane-1,3-diol by hydrogenation of 2,2,4,4-tetraalkylcyclobutane-1,3-dione in the presence of a promoted copper-based catalyst.
    Type: Grant
    Filed: November 30, 2007
    Date of Patent: September 1, 2009
    Assignee: Eastman Chemical Company
    Inventors: Jennifer Ellen McCusker-Orth, Jerome Leonard Stavinoha, Jr., Anthony Dominick Messina, Steven Thomas Perri, Zhufang Liu, Philip Conrad Heidt, Brent Alan Tennant
  • Patent number: 7560600
    Abstract: The present invention relates to the production of a 2,2,4,4-tetraalkylcyclobutane-1,3-diol. In one embodiment, the present invention relates to the production of a 2,2,4,4-tetraalkylcyclobutane-1,3-diol by hydrogenation of a 2,2,4,4-tetraalkylcyclobutane-1,3-dione in the presence of a promoted nickel-based catalyst.
    Type: Grant
    Filed: November 30, 2007
    Date of Patent: July 14, 2009
    Assignee: Eastman Chemical Company
    Inventors: Jennifer Ellen McCusker-Orth, Michael Wayne Salyer
  • Patent number: 7524994
    Abstract: The present disclosure relates to the production of a 2,2,4,4-tetraalkylcyclobutane-1,3-diol. In one embodiment, the present invention relates to the production of a 2,2,4,4-tetraalkylcyclobutane-1,3-diol by hydrogenation of a 2,2,4,4-tetraalkylcyclobutane-1,3-dione in the presence of an iridium-promoted cobalt-based catalyst.
    Type: Grant
    Filed: November 30, 2007
    Date of Patent: April 28, 2009
    Assignee: Eastman Chemical Company
    Inventors: Jennifer Ellen McCusker-Orth, Jerome Leonard Stavinoha, Jr., Anthony Dominick Messina, Steven Thomas Perri, Zhufang Liu, Philip Conrad Heidt, Brent Alan Tennant
  • Patent number: 7521583
    Abstract: The present invention relates to the production of 2,2,4,4-tetramethylcyclobutane-1,3-diol. In one embodiment, the present invention relates to the production of 2,2,4,4-tetramethylcyclobutane-1,3-diol by hydrogenation of 2,2,4,4-tetramethylcyclobutane-1,3-dione in the presence of a cobalt-based catalyst.
    Type: Grant
    Filed: November 30, 2007
    Date of Patent: April 21, 2009
    Assignee: Eastman Chemical Company
    Inventors: Jennifer Ellen McCusker-Orth, Jerome Leonard Stavinoha, Jr., Anthony Dominick Messina, Steven Thomas Perri, Zhufang Liu, Philip Conrad Heidt, Brent Alan Tennant
  • Publication number: 20080154069
    Abstract: The present disclosure relates to the production of a 2,2,4,4-tetraalkylcyclobutane-1,3-diol. In one embodiment, the present invention relates to the production of a 2,2,4,4-tetraalkylcyclobutane-1,3-diol by hydrogenation of a 2,2,4,4-tetraalkylcyclobutane-1,3-dione in the presence of a ruthenium-promoted cobalt-based catalyst.
    Type: Application
    Filed: November 30, 2007
    Publication date: June 26, 2008
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Jennifer Ellen McCusker-Orth, Jerome Leonard Stavinoha, Anthony Dominick Messina, Steven Thomas Perri, Zhufang Liu, Philip Conrad Heidt, Brent Alan Tennant
  • Publication number: 20080132738
    Abstract: The present invention relates to the production of a 2,2,4,4-tetraalkylcyclobutane-1,3-diol. In one embodiment, the present invention relates to the production of a 2,2,4,4-tetraalkylcyclobutane-1,3-diol by hydrogenation of a 2,2,4,4-tetraalkylcyclobutane-1,3-dione in the presence of a promoted nickel-based catalyst.
    Type: Application
    Filed: November 30, 2007
    Publication date: June 5, 2008
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Jennifer Ellen McCusker-Orth, Michael Wayne Salyer
  • Publication number: 20080132737
    Abstract: The present disclosure relates to the production of a 2,2,4,4-tetraalkylcyclobutane-1,3-diol. In one embodiment, the present invention relates to the production of a 2,2,4,4-tetraalkylcyclobutane-1,3-diol by hydrogenation of a 2,2,4,4-tetraalkylcyclobutane-1,3-dione in the presence of an iridium-promoted cobalt-based catalyst.
    Type: Application
    Filed: November 30, 2007
    Publication date: June 5, 2008
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Jennifer Ellen McCusker-Orth, Jerome Leonard Stavinoha, Anthony Dominick Messina, Steven Thomas Perri, Zhufang Liu, Philip Conrad Heidt, Brent Alan Tennant
  • Publication number: 20080132739
    Abstract: The present invention relates to the production of 2,2,4,4-tetramethylcyclobutane-1,3-diol. In one embodiment, the present invention relates to the production of 2,2,4,4-tetramethylcyclobutane-1,3-diol by hydrogenation of 2,2,4,4-tetramethylcyclobutane-1,3-dione in the presence of a cobalt-based catalyst.
    Type: Application
    Filed: November 30, 2007
    Publication date: June 5, 2008
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Jennifer Ellen McCusker-Orth, Jerome Leonard Stavinoha, Anthony Dominick Messina, Steven Thomas Perri, Zhufang Liu, Philip Conrad Heidt, Brent Alan Tennant
  • Publication number: 20080076946
    Abstract: The object of the present invention is to provide a process capable of producing cycloalkanol and/or cycloalkanone in excellent selectivity by oxidizing cycloalkane in a good degree of conversion. The present invention relates to a process for producing cycloalkanol and/or cycloalkanone, which comprises oxidizing cycloalkane with oxygen at 25 to 140° C. in the presence of mesoporous silica containing the group 8 and/or 9 element in the periodic table, wherein the content of phosphorus atom in the mesoporous silica is 0 to 4 mol % based on silicon atom. Said element is preferably cobalt and said mesoporous silica is preferably MCM-41.
    Type: Application
    Filed: September 6, 2007
    Publication date: March 27, 2008
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Masahiro HOSHINO, Hajime Ishida, Tatsuya Suzuki
  • Patent number: 6894198
    Abstract: An alkali metal alkoxide or alkaline earth metal alkoxide in granular form.
    Type: Grant
    Filed: October 15, 2002
    Date of Patent: May 17, 2005
    Assignee: Degussa AG
    Inventors: Andreas Harthun, Christoph Theis, André Noppe, Josef Metz
  • Publication number: 20040014633
    Abstract: An alkyl gycol ether having the following formula 1
    Type: Application
    Filed: July 10, 2002
    Publication date: January 22, 2004
    Applicant: Takasago International Corporation
    Inventors: Takashi Aida, Andrew T. Lupo, Hiroyuki Matsuda
  • Patent number: 6646170
    Abstract: The present invention relates to novel ether compounds, compositions comprising ether compounds, and methods useful for treating and preventing cardiovascular diseases, dyslipidemias, dysproteinemias, and glucose metabolism disorders comprising administering a composition comprising an ether compound. The compounds, compositions, and methods of the invention are also useful for treating and preventing Alzheimer's Disease, Syndrome X, peroxisome proliferator activated receptor-related disorders, septicemia, thrombotic disorders, obesity, pancreatitis, hypertension, renal disease, cancer, inflammation, and impotence. In certain embodiments, the compounds, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.
    Type: Grant
    Filed: April 26, 2002
    Date of Patent: November 11, 2003
    Assignee: Esperion Therapeutics, Inc.
    Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
  • Patent number: 5498734
    Abstract: The magnesium complexes of cyclic hydrocarbons containing conjugated dienes, such as 1,2-dimethylenecycloalkanes, and 1,3-butadienes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4 diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, alkylditriflates, bromoalkylnitriles, esters, or amides serve as a convenient method for synthesizing carbocyclic systems. Significantly, carbocycles prepared by this method contain functional groups such as the exocyclic double bond or a keto group in one of the rings which could be used for further elaboration of these molecules. Furthermore, fused bicyclic systems containing a substituted five-membered ring can be conveniently prepared at high temperatures by the reactions of (2-butene-1,4-diyl)magnesium complexes with carboxylic esters or acid halides whereas low temperatures lead to regioselective synthesis of .beta.,.gamma.-unsaturated ketones. Additionally, .gamma.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: March 12, 1996
    Assignee: University of Nebraska
    Inventor: Reuben D. Rieke
  • Patent number: 5475151
    Abstract: Disclosed is a process for the preparation of cyclopropylmethanol(hydroxymethylcyclopropane) by the hydrogenation of cyclopropanecarboxaldehyde in the presence of a cobalt or nickel catalyst.
    Type: Grant
    Filed: November 28, 1994
    Date of Patent: December 12, 1995
    Inventors: Shaowo Liang, Timothy W. Price
  • Patent number: 5449840
    Abstract: A cyclopropane derivative of formula (I) ##STR1## wherein B.sup.1 is a purine or pyrimidine residue, R.sup.1 and R.sup.2 are, independently, hydrogen or a protecting group for hydroxyl and each of k, m and n represents, independently, an integer of 1 or 2 is useful for its antiviral effect.
    Type: Grant
    Filed: December 16, 1994
    Date of Patent: September 12, 1995
    Assignee: Ajinomoto Co., Inc.
    Inventors: Satoshi Hatsuya, Takaaki Sekiyama, Takashi Tsuji, Satoshi Iwayama, Masahiko Okunishi
  • Patent number: 5412134
    Abstract: The protected cyclobutanone of the formula ##STR1## is treated with a dialkylaluminum chloride, an alkylaluminum dichloride, a trialkylaluminum compound, diphenylsilane in the presence of tris(triphenylphosphine) rhodium (I) chloride, or iridium tetrachloride to yield the corresponding diprotected cyclobutanol. This compound is useful as an intermediate in the preparation of antiviral agents.
    Type: Grant
    Filed: May 26, 1992
    Date of Patent: May 2, 1995
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Janak Singh, Gregory S. Bisacchi, Richard H. Mueller
  • Patent number: 5258556
    Abstract: Disclosed is a novel process for the manufacture of 2,2,4,4 tetramethylcyclobutane 1,3 diol commencing with the pyrolysis of isobutyric anhydride to produce dimethylketene. Dimethylketene is absorbed into 2,2,4,4 tetramethylcyclobutane 1,3 dione which function as the process solvents for subsequent dimerization of the dimethylketene to 2,2,4,4-tetramethylcyclobutane-1,3 -dione followed by the catalytic hydrogenation of the dione to the diol product.
    Type: Grant
    Filed: February 1, 1993
    Date of Patent: November 2, 1993
    Assignee: Eastman Kodak Company
    Inventors: Charles E. Sumner, Jr., Bruce L. Gustafson, Jennifer R. Knight
  • Patent number: 5210265
    Abstract: Novel compounds have at least one perfluorocyclobutane ring and at least two functional groups suitable for forming condensation polymers. Preferably the compounds have a structures represented by Formula II: ##STR1## wherein R and R' independently represent optionally inertly substituted groups: X and X' represent any molecular structures which link R and R' with the perfluorocyclobutane ring; n and n' are the number of G and G' groups, respectively: and G and G' independently represent any reactive functional groups or any groups convertible into reactive functional groups. The compounds are preferably prepared by a process of thermally dimerizing trifluorovinyl compound to form a compounds of Formula IG.sub.n -R-X-CF.dbd.CF.sub.2wherein G represents G or G' in Formula II: X represents X or X' of Formula II: and n represents n or n' of Formula II, to form a compound having a perfluorocyclobutane group.
    Type: Grant
    Filed: March 12, 1991
    Date of Patent: May 11, 1993
    Assignee: The Dow Chemical Company
    Inventors: Katherine S. Clement, David A. Babb, Bobby R. Ezzell
  • Patent number: 5169994
    Abstract: Disclosed is a novel process for the manufacture of 2,2,4,4-tetramethylcyclobutanediol commencing with the pyrolysis of isobutyric anhydride to produce dimethylketene. Dimethylketene is absorbed into certain carboxylate ester solvents which function as the process solvents for subsequent dimerization of the dimethylketene to 2,2,4,4-tetramethylcyclobutanedione followed by the catalytic hydrogenation of the dione to the diol product.
    Type: Grant
    Filed: August 20, 1991
    Date of Patent: December 8, 1992
    Assignee: Eastman Kodak Company
    Inventors: Charles E. Sumner, Jr., Bruce L. Gustafson, Jennifer R. Knight
  • Patent number: 5149889
    Abstract: A process is disclosed for the preparation of tertiary alcohols, alpha-alkyl substituted nitriles, alkyl-substituted imines or tertiary amines by alkylation of a starting material that is a carbonyl compound or a nitrile followed by hydrolysis wherein the alkylation is carried out with the aid of a reaction system formed by suspending a mixture of:substantially 15 to 25% by weight of methyllithium or ethyllithium;substantially 35 to 45% by weight of an inorganic compound selected from the group which consists of at least one metal oxide selected from the group which consists of SiO.sub.2, Al.sub.2 O.sub.3, and CaO, and synthetic anhydrous aluminum silicate; andsubstantially 35 to 45% by weight of a paraffin oil or wax; in an organic solvent selected from the group which consists of:C.sub.5 to C.sub.10 saturated aliphatic hydrocarbons, C.sub.5 to C.sub.
    Type: Grant
    Filed: October 30, 1990
    Date of Patent: September 22, 1992
    Assignee: Metallgesellschaft Aktiengesellschaft
    Inventors: Jurgen Deberitz, Wilfried Weiss
  • Patent number: 5126345
    Abstract: Antiviral activity is exhibited by compounds having the formula ##STR1## and its pharmaceutically acceptable salts wherein R.sub.1 is ##STR2## R.sub.6 is hydrogen, alkyl, substituted alkyl, or aryl; and R.sub.7 and R.sub.
    Type: Grant
    Filed: February 8, 1991
    Date of Patent: June 30, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: William A. Slusarchyk, Robert Zahler
  • Patent number: 5087775
    Abstract: A process for the preparation of partially fluorinated alcohols starting from halogen-containing alkenes, and 2,2,3,3,4,4-hexafluorocyclopentanol as a new partially fluorinated alcohol.
    Type: Grant
    Filed: October 24, 1990
    Date of Patent: February 11, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Dietmar Bielefeldt, Michael Negele, Heinz Ziemann
  • Patent number: 5004843
    Abstract: Process for preparing predominantly Z-substituted allylic alcohols of the formula: ##STR1## wherein R.sup.1 is a straight or branched C.sub.1 -C.sub.25 alkyl group optionally bearing at least one substituent and/or at least one unsaturated linkage and R.sup.2 is a hydrogen atom or a methyl group, which comprises reacting a vinyl epoxide of the formula: ##STR2## wherein R.sup.2 is as defined above with an organolithium compound of the formula above. More particularly, there is disclosed a process for R.sup.1 --Li wherein R.sup.1 is as defined above; particularly, process for preparing .alpha.-santalol of the formula: ##STR3## which comprises reacting 3-methyl-3,4-epoxybutene-1 with lithiomethyl-2,3-dimethyltricyclo[2.2.1.0.sup.2,6 ]heptane.
    Type: Grant
    Filed: May 29, 1990
    Date of Patent: April 2, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mitsuhisa Tamura, Gohu Suzukamo, Ken-ichi Hirose
  • Patent number: 4999454
    Abstract: The invention is directed to a new process for the preparation of carbinols of the general formula I ##STR1## by reaction chloral and olefins of the general formula ##STR2## and by optional acylation of the product comprising dissolving a catalyst of the general formula IIIFe.sub.n (NH.sub.4).sub.x Y.sub.m .multidot.A.sub.p IIIin chloral, then adding the olefin of the general formula II in order to produce a complex of the general formula IV ##STR3## from which a complex of the general formula V ##STR4## is formed, and from the reaction mixture a compound of the general formula I is obtained whereafter(a) the residual complex of the general formula V dissolved in the product is decomposed with an acidic solution and if desired the obtained product is distilled or(b) the product in the reaction mixture is acylated.The compounds prepared according to the invention can be utilized as intermediates when preparing e.g., permethrin and other pyrethroid insecticides.
    Type: Grant
    Filed: October 3, 1985
    Date of Patent: March 12, 1991
    Assignee: Chinoin Gyogyszer ES Vegyeszeti Termekek Gyara RT.
    Inventors: Rudolf Soos, Jozsef Nemes, Miklos Szelestei, Istvan Schler, Laszlo Vidra, Istvan Szekely
  • Patent number: 4990693
    Abstract: Novel physiologically active substances KS-504a, KS-504b and KS-504d having a vasodilative activity and a novel physiologically active substance KS-504e having an activity to inhibit histamine secretion are produced by culturing a microorganism of the genus Mollisia.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: February 5, 1991
    Assignee: Kyowa Hakko Kogyo Co. Ltd.
    Inventors: Satoshi Nakanishi, Koji Yamada, Katsuhiko Ando, Isao Kawamoto, Toru Yasuzawa, Hiroshi Sano, Noriaki Hirayama, Hiroshi Kase, Joji Goto, Etsuyo Shimizu