公开(公告)号：US11932596B2

公开(公告)日：2024-03-19

申请号：US18091516

申请日：2022-12-30

Applicant: DAIKIN INDUSTRIES, LTD.

Inventor： Naoyuki Hoshiya ,  Akihiro Gotou ,  Yosuke Kishikawa

IPC: C07C43/176 ,  C07C41/16 ,  C07C43/17 ,  C07D209/48 ,  C07D211/22 ,  C07D213/30 ,  C07D317/22 ,  C07D333/16 ,  C07F7/18

CPC classification number: C07C41/16 ,  C07C43/17 ,  C07C43/176 ,  C07D209/48 ,  C07D211/22 ,  C07D213/30 ,  C07D317/22 ,  C07D333/16 ,  C07F7/1804 ,  C07C41/16 ,  C07C43/176 ,  C07C41/16 ,  C07C43/17

Abstract: An object of the present invention is to provide, for example, a novel method for synthesizing a fluorovinyl ether compound from a fluorine-containing vinyl compound. This problem is solved by a method for producing a compound represented by formula (1):




wherein

Ra1 is a hydrogen atom, a halogeno group, an alkyl group, a fluoroalkyl group, or an aromatic group optionally having one or more substituents,

Rf is a fluoro group or a perfluoroalkyl group,

Ra2 is a hydrogen atom, a halogeno group, an alkyl group, a fluoroalkyl group, or an aromatic group optionally having one or more substituents, or

(i) Ra1 and Ra2, (ii) Ra1 and Rf, or (iii) Rf and Ra2 may be linked to each other,

Rb1 is Rs,

Rb2 is a hydrogen atom or Rs,

Rb3 is a hydrogen atom or Rs, or

two or three of Rb1, Rb2, and Rb3, taken together with the adjacent carbon atom, may form a ring optionally having one or more substituents, and

Rs, in each occurrence, is the same or different and represents a hydrocarbon group optionally having one or more substituents, the method comprising

step A of reacting a compound represented by formula (2):





wherein

Rx is a leaving group, and

other symbols are as defined above,

with a compound represented by formula (3):





wherein the symbols in the formula are as defined above,

in the presence of a transition metal catalyst.

公开(公告)号：US11560347B2

公开(公告)日：2023-01-24

申请号：US17255689

申请日：2019-06-26

Applicant: DAIKIN INDUSTRIES, LTD.

Inventor： Naoyuki Hoshiya ,  Akihiro Gotou ,  Yosuke Kishikawa

IPC: C07C41/16

Abstract: A method for synthesizing a fluorovinyl ether compound from a fluorine-containing vinyl compound. Specifically, a method for producing a compound represented by formula (1), comprising step A of reacting a compound represented by formula (2) with a compound represented by formula (3) in the presence of a transition metal catalyst: wherein the substituents are defined in the disclosure.

公开(公告)号：US20250042830A1

公开(公告)日：2025-02-06

申请号：US18919789

申请日：2024-10-18

Applicant: DAIKIN INDUSTRIES, LTD.

Inventor： Michiaki OKADA ,  Asako Yoshiyama ,  Masayuki Kishimoto ,  Yuka Kawakami ,  Yoshichika Kuroki ,  Naoyuki Hoshiya ,  Daichi Mari

IPC: C07C41/44 ,  C07C41/38 ,  C07C53/21

Abstract: There is provided a method for producing a composition containing a purified fluorine-containing ether compound.
A method for producing a composition containing a purified fluorine-containing ether compound, wherein
the fluorine-containing ether compound is represented by CHX1X2CF2OX3  general formula (1): wherein X1 and X2 are the same or different and represent a hydrogen atom, a fluorine atom, or a trifluoromethyl group, and X3 represents an alkyl group having 1 to 6 carbon atoms and optionally containing a fluorine atom, provided that X1 and X2 are not trifluoromethyl groups at the same time, and the method includes: (A) converting, through a reaction between a fluorine-containing olefin compound represented by CX1X2═CF(CF2)nOX3  general formula (2):, wherein n represents 0 or 1, and X1, X2 and X3 are the same as described above, provided that when X1 or X2 is a trifluoromethyl group, n is 0, and X1 and X2 are not trifluoromethyl groups at the same time, and a nitrogen-containing compound in the presence of the fluorine-containing ether compound represented by general formula (1), the fluorine-containing olefin compound represented by general formula (2) into an adduct of the nitrogen-containing compound and/or a fluorine-containing carboxylic acid analogue to obtain a composition containing the fluorine-containing ether compound represented by general formula (1) and the adduct of the nitrogen-containing compound and/or the fluorine-containing carboxylic acid analogue, wherein the nitrogen-containing compound is nitrogen-containing compound A having a structure in which an acyl group is bonded to a nitrogen atom and/or nitrogen-containing compound B that is a tertiary amine compound; and (B) separating the adduct of the nitrogen-containing compound and/or the fluorine-containing carboxylic acid analogue from the composition obtained in step (A) to obtain the composition containing a purified fluorine-containing ether compound.

公开(公告)号：US20230303748A1

公开(公告)日：2023-09-28

申请号：US18320391

申请日：2023-05-19

Applicant: DAIKIN INDUSTRIES, LTD.

Inventor： Asuka NOHARA ,  Shinya Handa ,  Daisuke Ota ,  Yoshinori Nanba ,  Akiyoshi Yamauchi ,  Naoyuki Hoshiya ,  Tsuyoshi Noguchi

IPC: C08F236/20 ,  C08L47/00

CPC classification number: C08F236/20 ,  C08L47/00

Abstract: Provided is a fluoropolymer comprising tetrafluoroethylene unit (1) and a monomer unit (2) derived from a perfluoroalkadlene represented by formula (2):


CF2═CF(CF2)nCF═CF2

where n represents an integer of 2 to 10, wherein a content of tetrafluoroethylene unit (1) is 98.0 to 99.999 mol % or more based on total monomer units constituting the fluoropolymer, and a content of the monomer unit (2) is 0.001 to 2.0 mol % based on total monomer units constituting the fluoropolymer.

公开(公告)号：US11420923B2

公开(公告)日：2022-08-23

申请号：US17253856

申请日：2019-06-21

Applicant: DAIKIN INDUSTRIES, LTD.

Inventor： Akihiro Gotou ,  Yosuke Kishikawa ,  Naoyuki Hoshiya ,  Makoto Matsuura

IPC: C07C51/145 ,  C07C67/36 ,  B01J31/22 ,  B01J31/24

Abstract: An object of the present invention is to provide a novel method for producing an α-fluoroacrylic acid ester compound. This problem is solved by a method for producing a compound represented by formula (1), wherein R1 and R2 are identical or different, and each represents an alkyl group or the like; and R3 is an alkyl group or the like, the method comprising step A of reacting a compound represented by formula (2) with R3—OH (3) and carbon monoxide in the presence of palladium, a double bond-containing compound (α), a diphosphine compound (β), and a base, to obtain the compound represented by formula (1) above.