公开(公告)号：US11167278B2

公开(公告)日：2021-11-09

申请号：US16466413

申请日：2017-12-06

Applicant: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY ,  N.E. CHEMCAT CORPORATION

Inventor： Junchul Choi ,  Norihisa Fukaya ,  Shunya Onozawa ,  Kazuhiko Sato ,  Hiroyuki Yasuda ,  Tomoteru Mizusaki ,  Yukio Takagi

IPC: B01J31/22

Abstract: An organometallic complex catalyst that makes it possible to obtain a higher yield of a desired product than conventional catalysts in a cross-coupling reaction. The organometallic complex catalyst has a structure represented by formula (1) and is for use in a cross-coupling reaction. In formula (1), M is the coordination center and represents a metal atom such as Pd or an ion thereof. R1, R2, and R3 may be the same or different and are a substituent such as a hydrogen atom. R4, R5, R6, and R7 may be the same or different and are a substituent such as a hydrogen atom. X represents a halogen atom. R8 represents a substituent that has a π bond and 3-20 carbon atoms. With regard to the electron-donating properties of R1-R7 with respect to the coordination center M of the ligand containing R1-R7 that is indicated in formula (2), R1-R7 are arranged in combination such that the TEP value obtained from infrared spectroscopy shifts toward the low frequency side compared to the TEP value of the ligand of formula (2-1).

公开(公告)号：US10029241B2

公开(公告)日：2018-07-24

申请号：US14786326

申请日：2014-04-22

Applicant: MARUZEN PETROCHEMICAL CO., LTD. ,  NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY

Inventor： Takashi Naniki ,  Toshikazu Takahashi ,  Hiroyuki Yasuda ,  Shouji Yamamoto

IPC: B01J31/02 ,  C07D317/36 ,  C07D317/38 ,  B01J21/08 ,  B01J27/08 ,  B01J27/16 ,  B01J27/182 ,  B01J35/10 ,  B01J31/26 ,  B01J31/06

Abstract: A method for easily producing a heterogeneous catalyst having excellent catalytic activity at a low cost is provided. The heterogeneous catalyst is used for the purpose of synthesizing a cyclic carbonate by reacting an epoxide and carbon dioxide. A catalyst obtained by this production method and a method for synthesizing a cyclic carbonate with use of this catalyst are also provided.

公开(公告)号：US10000514B2

公开(公告)日：2018-06-19

申请号：US15309900

申请日：2015-04-30

Applicant: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY

Inventor： Norihisa Fukaya ,  Seong-Jib Choi ,  Jun-Chul Choi ,  Toshio Horikoshi ,  Kazuhiko Sato ,  Hiroyuki Yasuda

IPC: C07F7/04

CPC classification number: C07F7/045 ,  C07F7/04

Abstract: An object of the present invention is to provide a method for producing tetraalkoxysilane while saving energy at a high yield. Tetraalkoxysilane can be produced while saving energy at a high yield by the method including a first step of reacting alcohol with carbon dioxide in the presence of a dehydrating agent and/or in a reactor provided with a dehydrating means, and a second step of reacting a reaction mixture obtained in the first step with silicon oxide.

公开(公告)号：US20220008905A1

公开(公告)日：2022-01-13

申请号：US17487333

申请日：2021-09-28

Applicant: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY ,  N.E. CHEMCAT CORPORATION

Inventor： Junchul Choi ,  Norihisa Fukaya ,  Shunya Onozawa ,  Kazuhiko Sato ,  Hiroyuki Yasuda ,  Tomoteru Mizusaki ,  Yukio Takagi

IPC: B01J31/22

Abstract: An organometallic complex catalyst is disclosed for use in a cross-coupling reaction. In formula (1), M is the coordination center and represents a metal atom such as Pd or an ion thereof. R1, R2, and R3 may be the same or different and are a substituent such as a hydrogen atom. R4, R5, R6, and R7 may be the same or different and are a substituent such as a hydrogen atom. X represents a halogen atom. R8 represents a substituent that has a n bond and 3-20 carbon atoms. With regard to the electron-donating properties of R1-R7 with respect to the coordination center M of the ligand containing R1-R7 that is indicated in formula (2), R1-R7 are arranged in combination such that the TEP value obtained from infrared spectroscopy shifts toward the high frequency side compared to the TEP value of the ligand of formula (2-1).

公开(公告)号：US10752579B2

公开(公告)日：2020-08-25

申请号：US16328530

申请日：2017-08-31

Applicant: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY

Inventor： Jun-Chul Choi ,  Norihisa Fukaya ,  Qiao Zhang ,  Hiroyuki Yasuda

IPC: C07C269/04 ,  C07C271/28 ,  C07B61/00

Abstract: A method of production of carbamic acid ester has a high yield and high selectivity and is superior in economy. The method of production of a carbamic acid ester includes reacting an amine, carbon dioxide, and an alkoxysilane compound in the presence of a catalyst containing a zinc compound or an alkali metal compound or in the presence of an ionic liquid. A carbamic acid ester is produced, for example by reacting aniline, carbon dioxide, and tetramethoxysilane at a temperature of 150 to 180° C. in the presence of zinc acetate and 2,2′-bipyridine.

公开(公告)号：US10011621B2

公开(公告)日：2018-07-03

申请号：US14786455

申请日：2014-04-22

Applicant: MARUZEN PETROCHEMICAL CO., LTD. ,  NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY

Inventor： Masuo Yamazaki ,  Takashi Naniki ,  Toshikazu Takahashi ,  Hiroyuki Yasuda ,  Shouji Yamamoto

IPC: B01J31/06 ,  B01J31/02 ,  C07F9/54 ,  C07D317/36 ,  C07D317/38 ,  B01J21/08 ,  B01J27/08 ,  B01J27/182 ,  B01J35/10

CPC classification number: C07F9/5414 ,  B01J21/08 ,  B01J27/08 ,  B01J27/182 ,  B01J31/0268 ,  B01J31/0269 ,  B01J31/0274 ,  B01J31/0275 ,  B01J31/069 ,  B01J35/1019 ,  B01J35/1023 ,  B01J35/1061 ,  B01J2231/341 ,  C07D317/36 ,  C07D317/38

Abstract: Disclosed herein is a method for producing silica gel-immobilized phosphonium salt catalysts including the steps of (a) reacting a silane compound with a silica gel in the presence of xylene, to obtain a catalyst precursor having a haloalkyl group or a haloaryl group, wherein the silane compound has a haloalkyl group or a haloaryl group, and a proportion of the silane compound is from 0.001 to 0.06 mol relative to 1 mol of the silica gel, and (b) reacting the catalyst precursor with a tertiary phosphine in xylene, to obtain a catalyst for synthesizing a cyclic carbonate, in which the silane compound is represented by formula (1), and the tertiary phosphine is represented by formula (2): X—R1—Si(OR2)3  (1)

公开(公告)号：US09834536B2

公开(公告)日：2017-12-05

申请号：US14786334

申请日：2014-04-22

Applicant: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY ,  MARUZEN PETROCHEMICAL CO., LTD.

Inventor： Toshikazu Takahashi ,  Hiroyuki Yasuda ,  Toshiyasu Sakakura ,  Shouji Yamamoto ,  Takashi Naniki ,  Takuro Furukawa

IPC: B01J21/08 ,  B01J27/08 ,  B01J27/182 ,  B01J31/02 ,  B01J31/06 ,  B01J35/10 ,  C07D317/36 ,  C07D317/38

CPC classification number: C07D317/38 ,  B01J21/08 ,  B01J27/08 ,  B01J27/182 ,  B01J31/0231 ,  B01J31/0267 ,  B01J31/0268 ,  B01J31/0269 ,  B01J31/0271 ,  B01J31/069 ,  B01J35/1019 ,  B01J35/1023 ,  B01J35/1061 ,  B01J2231/341 ,  C07D317/36

Abstract: A method for producing a heterogeneous catalyst for use of synthesizing cyclic carbonates by reacting an epoxide and carbon dioxide in the presence of the catalyst. A method for making a catalyst that includes forming a catalyst precursor then reacting the catalyst precursor with a tertiary phosphine.

公开(公告)号：US20170225156A1

公开(公告)日：2017-08-10

申请号：US15448128

申请日：2017-03-02

Applicant: National Institute of Advanced Industrial Science and Technology

Inventor： Jun-Chul Choi ,  Norihisa Fukaya ,  Hiroyuki Yasuda

IPC: B01J31/16 ,  B01J31/24 ,  C07F15/00 ,  B01J31/22

CPC classification number: B01J31/1608 ,  B01J23/42 ,  B01J23/44 ,  B01J29/0325 ,  B01J29/74 ,  B01J31/1633 ,  B01J31/1805 ,  B01J31/20 ,  B01J31/223 ,  B01J31/2273 ,  B01J31/2295 ,  B01J31/24 ,  B01J35/002 ,  B01J35/006 ,  B01J37/08 ,  B01J37/086 ,  B01J2231/323 ,  B01J2231/645 ,  B01J2531/824 ,  B01J2531/828 ,  C01B33/20 ,  C01B39/46 ,  C07C5/03 ,  C07C2531/22 ,  C07C2601/18 ,  C07F15/006 ,  C07F15/0066 ,  C07F15/0086 ,  C07F15/0093 ,  Y02P20/588 ,  C07C13/26

Abstract: A metal complex represented by the following Formula (1): (wherein M represents palladium or platinum; L represents a ligand selected from carbon monoxide, an olefin compound, an amine compound, a phosphine compound, an N-heterocyclic carbene compound, a nitrile compound and an isocyanide compound; n represents an integer of 0 to 2 showing the number of the ligand; and each of R1 to R4 represents an organic group). The metal complex described above can be fixed on an inorganic oxide while maintaining a skeletal structure thereof to obtain a supported metal complex, and this makes it possible to allow the supported metal complex to maintain the same catalytic activity as that of the original metal complex.Also, calcining the supported metal complex obtained in the manner described above makes it possible to obtain a supported metal catalyst which is improved in catalytic activity to a greater extent than conventional supported metal catalysts.