# US 2019/0169107 A1 · Preparation process of perfluoroalkyl compound with monohydroperfluoroalkane as starting material > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2019/0169107 A1 - Document ID: US20190169107A1 - Status: Published application - Kind: A1 - Application number: 16/323,299 - Filed: 2017-02-16 - Published: 2019-06-06 - Earliest claimed: 2016-08-05 - Assignees: Kanto Denka Kogyo Co., Ltd.; National University Corporation Gunma University - Applicants: Kanto Denka Kogyo Co., Ltd.; National University Corporation Gunma University - Inventors: Hideki AMII; Kazuki KOMODA; Masafumi KOBAYASHI; Yutaka NAKAMURA; Ryusuke OBINATA; Akinori HARADA - Web page: https://patentgrep.com/patent/US20190169107A1 ## CPC - C07C 29/38: by reaction with aldehydes or ketones - C07C 31/125: containing five to twenty-two carbon atoms - C07C 33/46: containing only six-membered aromatic rings as cyclic parts - C07C 35/48: Halogenated derivatives - C07C 41/26: by introduction of hydroxy or O-metal groups - C07C 41/30: by increasing the number of carbon atoms, e.g. by oligomerisation - C07C 43/23: containing hydroxy or O-metal groups - C07C 209/68: from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton - C07C 209/78: from carbonyl compounds, e.g. from formaldehyde, and amines having amino groups bound to carbon atoms of six-membered aromatic rings, with formation of methylene-diarylamines - C07C 211/48: N-alkylated amines - C07C 231/12: by reactions not involving the formation of carboxamide groups - C07C 233/15: with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring - C07C 2601/14: The ring being saturated - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract A simple production process is provided of a perfluoroalkyl compound that uses monohydroperfluoroalkane as a starting material, the perfluoroalkyl compound being an important intermediate of organic electronic materials, medicine, agricultural chemicals, functional polymer materials and the like. With monohydroperfluoroalkane is reacted a base and then a carbonyl compound to produce an alcohol having a perfluoroalkyl group. For example, potassium hydroxide is made to interact with trifluoromethane, and a reaction with a carbonyl compound is induced to produce an alcohol having a trifluoromethyl group. ## Claims ### Claim 1 A production process of alcohol having a perfluoroalkyl group represented by General Formula [4]: wherein, RF is a perfluoroalkyl group which is an alkyl group that may have a straight chain of 1 to 2 carbons, or a straight chain, branched chain or ring structure of 3 to 10 carbons, and which has all hydrogens on carbon substituted with fluorine; and R1 and R2 are each independently a hydrogen atom or an alkyl group, aryl group, heteroaryl group, aralkyl group, alkenyl group, or alkynyl group that may have a straight chain of 1 to 2 carbons, or a straight chain, branched chain or ring structure of 3 to 10 carbons, and that may have a substituent; and R1 and R2 may be merged to form a ring; the production process comprising: reacting in an organic solvent a carbonyl compound represented by General Formula [1]: wherein, R1 and R2 are each independently a hydrogen atom or an alkyl group, aryl group, heteroaryl group, aralkyl group, alkenyl group, or alkynyl group that may have a straight chain of 1 to 2 carbons, or a straight chain, branched chain or ring structure of 3 to 10 carbons, and that may have a substituent; and R1 and R2 may be merged to form a ring; a hydroxide represented by General Formula [2]: M(OH)x [2] wherein, M is a metal belonging to Group I, Group II, Group III, Group IV, Group V, Group VI, Group VII, Group VIII, Group IX, Group X, Group XI, Group XII, and Group XIII in a periodic table of elements or ammonium that may be unsubstituted or that may have an alkyl group of 1 to 10 carbons as a substituent, which may be used alone or in a mixture of multiple substances, and x is equal to an oxidation number of a substance represented by M; and monohydroperfluoroalkane represented by General Formula [3]: RFH [3] wherein, RF is a perfluoroalkyl group which is an alkyl group that may have a straight chain of 1 to 2 carbons, or a straight chain, branched chain or ring structure of 3 to 10 carbons, and which has all hydrogens on carbon substituted with fluorine. ### Claim 2 (depends on 1) The process according to claim 1, wherein RFH represented by General Formula [3] is trifluoromethane. ### Claim 3 (depends on 1) The process according to claim 1, wherein RFH represented by General Formula [3] is pentafluoroethane. ### Claim 4 (depends on 1) The process according to claim 1, wherein M(OH)x represented by General Formula [2] is potassium hydroxide. ### Claim 5 (depends on 1) The process according to claim 1, wherein M(OH)x represented by General Formula [2] is sodium hydroxide. ### Claim 6 (depends on 1) The process according to claim 1, wherein M(OH), represented by General Formula [2] is tetramethylammonium or a hydrate thereof. ### Claim 7 (depends on 1) The process according to claim 1, wherein M(OH)x represented by General Formula [2] is added to a reaction system as a powder. ### Claim 8 (depends on 1) The process according to claim 1, wherein the organic solvent is dimethyl sulfoxide, dimethyl formamide, N-methylpyrrolidone, tetrahydrofuran, diglyme, acetonitrile, or a combination thereof. ### Claim 9 (depends on 1) The process according to claim 1, wherein monohydroperfluoroalkane is in a gas state when it comes in contact with a reaction solution. ### Claim 10 (depends on 1) The process according to claim 1, wherein monohydroperfluoroalkane is in a liquid or solid state when it is mixed with a reaction solution.