Patents by Inventor Kazuhiko Yao

Kazuhiko Yao has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 6992227
    Abstract: A process for production of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane which comprises reacting phenol with 3,3,5-trimethylcyclohexanone in the presence of an acid catalyst, separating the resulting phenol adduct crystals of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane from the resulting reaction mixture, and removing the phenol from the phenol adduct crystals, wherein the phenol adduct crystals are dissolved in a crystallization solvent comprising an aromatic hydrocarbon solvent and water, crystallizing the crystals of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane out of the crystallization solvent, and collecting the crystals by filtration at a temperature of 40–60° C.
    Type: Grant
    Filed: September 11, 2000
    Date of Patent: January 31, 2006
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Kazuhiko Yao, Kenji Ekawa, Yoichiro Isota, Toru Nakaguchi
  • Patent number: 6972344
    Abstract: A method of producing 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane comprising: crystallizing a phenol adduct of 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane from a solution comprising 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane and phenol; washing the phenol adduct with a washing solution comprising phenol and water; decomposing by heating the washed phenol adduct in an aqueous solvent to remove phenol from the phenol adduct, thereby obtaining pure 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane.
    Type: Grant
    Filed: December 16, 2004
    Date of Patent: December 6, 2005
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Kazuhiko Yao, Kenji Ekawa
  • Publication number: 20050165258
    Abstract: A method of producing 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane comprising: crystallizing a phenol adduct of 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane from a solution comprising 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane and phenol; washing the phenol adduct with a washing solution comprising phenol and water; decomposing by heating the washed phenol adduct in an aqueous solvent to remove phenol from the phenol adduct, thereby obtaining pure 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane.
    Type: Application
    Filed: December 16, 2004
    Publication date: July 28, 2005
    Inventors: Kazuhiko Yao, Kenji Ekawa
  • Patent number: 6875896
    Abstract: A method for producing a high purity 1,1-bis(4-hydroxyphenyl)cyclohexane represented by the general formula (II), wherein R is a hydrogen atom or alkyl group, comprising the steps of: reacting cyclohexanone and a phenol represented by the general formula (I) in the presence of an acid catalyst; wherein R is the same as defined above, neutralizing the resultant reaction mixture with an alkali; primarily crystallizing and filtering a 1,1-bis(4-hydroxyphenyl)cyclohexane produced to obtain a primary crystallization filtrate; dissolving 100 parts by weight of the primary crystallization filtrate in a mixed solvent, which comprises 5 to 10 parts by weight of water and 100 to 200 parts by weight of a lower aliphatic ketone solvent, or 200 to 400 parts by weight of a lower aliphatic alcohol solvent; filtering the resulting solution through a zeta potential filter; and secondarily crystallizing and filtering the 1,1-bis(4-hydroxyphenyl)cyclohexane from the resulting filtrate in the presence of water.
    Type: Grant
    Filed: June 29, 2004
    Date of Patent: April 5, 2005
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Kazuhiko Yao, Tooru Nakaguchi, Kenji Ekawa
  • Publication number: 20050004405
    Abstract: A method for producing a high purity 1,1-bis(4-hydroxyphenyl)cyclohexane represented by the general formula (II), wherein R is a hydrogen atom or alkyl group, comprising the steps of: reacting cyclohexanone and a phenol represented by the general formula (I) in the presence of an acid catalyst; wherein R is the same as defined above, neutralizing the resultant reaction mixture with an alkali; primarily crystallizing and filtering a 1,1-bis(4-hydroxyphenyl)cyclohexane produced to obtain a primary crystallization filtrate; dissolving 100 parts by weight of the primary crystallization filtrate in a mixed solvent, which comprises 5 to 10 parts by weight of water and 100 to 200 parts by weight of a lower aliphatic ketone solvent, or 200 to 400 parts by weight of a lower aliphatic alcohol solvent; filtering the resulting solution through a zeta potential filter; and secondarily crystallizing and filtering the 1,1-bis(4-hydroxyphenyl)cyclohexane from the resulting filtrate in the presence of water.
    Type: Application
    Filed: June 29, 2004
    Publication date: January 6, 2005
    Inventors: Kazuhiko Yao, Tooru Nakaguchi, Kenji Ekawa
  • Patent number: 6720460
    Abstract: Hydroxyphenyl adamantanes are represented by the general formula (1): wherein R is an alkyl group, cycloalkyl group or phenyl group; m is 0 or an integer 1 or 2; l is 0 or 1; when l is 1, hydroxy groups of substituted hydroxyphenyl groups at positions 1 and 3 are together in para-position; n is 0 or an integer 1, 2 or 3; and when l is 0, n is an integer 1, 2 or 3.
    Type: Grant
    Filed: February 7, 2003
    Date of Patent: April 13, 2004
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Akira Yoshikawa, Kenji Ekawa, Kentaro Watanabe, Kazuhiko Yao, Miwa Hazama
  • Patent number: 6673974
    Abstract: A process for production of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane which comprises reacting phenol with 3,3,5-trimethylcyclohexanone in the presence of an acid catalyst wherein the reaction of phenol with 3,3,5-trimethylcyclohexanone is started in a slurry comprising phenol adduct crystals of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane and hydrated phenol in the presence of an acid catalyst, and then the reaction is continued in the slurry.
    Type: Grant
    Filed: March 6, 2003
    Date of Patent: January 6, 2004
    Assignee: Honshu Chemical Industry Co. Ltd.
    Inventors: Kazuhiko Yao, Kenji Ekawa, Yoichiro Isota, Toru Nakaguchi
  • Patent number: 6673975
    Abstract: The invention provides a process for production of high purity 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (BPTMC) which comprises: (a) a reaction step wherein phenol is reacted with 3,3,5-trimethylcyclohexanone (TMC) in a slurry containing phenol adduct crystals of BPTMC in the presence of an acid catalyst; (b) a neutralization step wherein after the reaction, the resulting reaction mixture in the form of slurry is neutralized with an alkali while heating to convert the slurry to a solution; (c) a primary crystallization and filtration step wherein the resulting solution is cooled and the resulting phenol adduct crystals of BPTMC are collected by filtration; (d) a secondary crystallization and filtration step wherein the adduct crystals obtained in the primary crystallization and filtration step are heated in a crystallization solvent to dissolve the crystals therein to prepare a solution and then the solution is cooled to crystallize BPTMC out of the solution, followed by collecting the crystals of
    Type: Grant
    Filed: March 7, 2003
    Date of Patent: January 6, 2004
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Kazuhiko Yao, Kenji Ekawa, Yoichiro Isota, Toru Nakaguchi
  • Patent number: 6673973
    Abstract: A process for production of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane which comprises reacting phenol with 3,3,5-trimethylcyclohexanone in the presence of an acid catalyst, adding an aqueous solution of an alkali to the resulting reaction mixture to neutralize it, removing a water phase from the thus neutralized reaction mixture, cooling the resulting oil phase to crystallize phenol adduct crystals of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane while obtaining a primary crystallization filtrate, wherein the primary crystallization filtrate is heated to a temperature of 150-250° C. in the presence of an alkali catalyst in an inert gas atmosphere under a reduced pressure to thermally decompose 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane in the primary crystallization filtrate.
    Type: Grant
    Filed: March 6, 2003
    Date of Patent: January 6, 2004
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Kazuhiko Yao, Kenji Ekawa, Yoichiro Isota, Toru Nakaguchi
  • Publication number: 20030187307
    Abstract: Hydroxyphenyl adamantanes are represented by the general formula (1): 1
    Type: Application
    Filed: February 7, 2003
    Publication date: October 2, 2003
    Inventors: Akira Yoshikawa, Kenji Ekawa, Kentaro Watanabe, Kazuhiko Yao, Miwa Hazama
  • Patent number: 6512149
    Abstract: By bringing a p-butylphenol compound or m-butylphenol compound in the gas phase into contact with a solid acid catalyst, i.e., a silica-alumina catalyst or alumina catalyst while heating, butyl groups are removed from the butylphenol compound and at the same time, highly purified isobutylene is recovered.
    Type: Grant
    Filed: April 13, 2001
    Date of Patent: January 28, 2003
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Kazuhiko Yao, Mitsuhiro Higashi, Kenji Ekawa
  • Publication number: 20020007092
    Abstract: By bringing a p-butylphenol compound or m-butylphenol compound in the gas phase into contact with a solid acid catalyst, i.e., a silica-alumina catalyst or alumina catalyst while heating, butyl groups are removed from the butylphenol compound and at the same time, highly purified isobutylene is recovered.
    Type: Application
    Filed: April 13, 2001
    Publication date: January 17, 2002
    Inventors: Kazuhiko Yao, Mitsuhiro Higashi, Kenji Ekawa
  • Patent number: 6284931
    Abstract: A process for producing a 3,3,5-trimethylcyclohexylidenebisphenol, comprising pre-reacting a phenol (A), i.e., phenol whose 2- and 6-positions may be monosubstituted or disubstituted with an alkyl group having 1 to 4 carbon atoms, with 3,3,5-trimethylcyclohexanone (B) at a molar ratio ((A)/(B)) of 3 to 7 in the presence of an acid catalyst until 3,3,5-trimethylcyclohexanone (B) exhibits a degree of conversion of at least 90 mol %; adding the phenol (A) and/or an aromatic hydrocarbon (C) to the thus obtained reaction mixture; and post-reacting the resultant mixture. This process enables not only suppressing a rise of the viscosity of the reaction mixture but also obtaining the desired product at high yield. Therefore, this process is applicable to not only the productivity enhancement in batch processing but also a continuous reaction processing which has been regarded as being difficult.
    Type: Grant
    Filed: October 20, 1999
    Date of Patent: September 4, 2001
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Yoichiro Isota, Toru Nakaguchi, Hiroshi Takenaka, Kazuhiko Yao
  • Patent number: 6118029
    Abstract: A batch or continuous process produces highly pure 3,3',5,5'-tetra-t-butylbiphenol suitable as a starting material for the synthesis of 4,4'-biphenol. The process for producing 3,3',5,5'-tetra-t-butylbiphenol comprises conducting an oxidation coupling of purified 2,6-di-t-butylphenol(i) or crude 2,6-di-t-butylbiphenol(ii), said crude 2,6-di-t-butylphenol being obtained by reacting isobutylene with phenol in the presence of an aluminum catalyst, and removing the aluminum catalyst. The 2,6-di-t-butylphenol is oxidatively coupled in an alkali metal catalyst mixture comprising (1) an alkali metal catalyst and alkylphenols, or (2) alkali metal catalyst, alkylphenols and phenol to produce 3,3',5,5'-tetra-t-butylbiphenol. The oxidative coupling is conducted together with 10-30% by weight of phenol and/or t-butylphenol per 100% by weight of 2,6-di-t-butylphenol in the presence of an alkali metal catalyst.
    Type: Grant
    Filed: January 30, 1998
    Date of Patent: September 12, 2000
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Yoichiro Isota, Kazuhiko Yao, Mikio Kawahara