# US 2022/0033348 A1 · Preparation of cationic surfactants > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2022/0033348 A1 - Document ID: US20220033348A1 - Status: Published application - Kind: A1 - Application number: 16/942,565 - Filed: 2020-07-29 - Published: 2022-02-03 - Earliest claimed: 2020-07-29 - Assignees: Saudi Arabian Oil Company - Applicants: Saudi Arabian Oil Company - Inventors: Xuan Zhang; Ming Han; Jinxun Wang - Web page: https://patentgrep.com/patent/US20220033348A1 ## CPC - C07C 237/52: having the nitrogen atom of at least one of the carboxamide groups further acylated - C07C 231/02: from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines - C07C 231/12: by reactions not involving the formation of carboxamide groups - C07C 233/36: having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton - C07C 233/38: having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton - C09K 8/584: characterised by the use of specific surfactants - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## Abstract Compositions that include cationic surfactants and methods of synthesizing compositions that include cationic surfactants. The surfactants include a quaternary amine and a saturated or unsaturated alkyl chain with 4 to 28 carbons. The surfactants can be generated by reacting a fatty acid modified with an amino alkyl group and an epihalohydrin in the presence of a base. The cationic surfactants can be generated by reacting a fatty acid modified with an amino alkyl group, an epihalohydrin, and a carboxylic acid. The cationic surfactants can be generated by reacting a carboxylic acid, an epihalohydrin, and a catalyst to afford a halo-substituted alkyl ester, followed by reacting the halo-substituted alky ester with a fatty acid modified with an amino alkyl group. ## Claims ### Claim 1 A compound of Formula I: wherein X is halide, R1 is a saturated or unsaturated alkyl with 4 to 28 carbons, R2 is alkyl, R3 is methyl, and R4 is selected from the group consisting of ### Claim 2 (depends on 1) The compound of claim 1, wherein R2 is propyl. ### Claim 3 (depends on 1) The compound of claim 1, wherein R1 is a monounsaturated alkyl chain with 21 carbons. ### Claim 4 (depends on 3) The compound of claim 3, wherein R1 is ### Claim 5 (depends on 1) The compound of claim 1, wherein R4 is ### Claim 6 (depends on 1) The compound of claim 1, wherein R4 is ### Claim 7 (depends on 1) The compound of claim 1, wherein R4 is ### Claim 8 A compound of Formula II: wherein R is selected from the group consisting of: and wherein X is halide. ### Claim 9 (depends on 8) The compound of claim 8, wherein R is ### Claim 10 (depends on 8) The compound of claim 8, wherein R is ### Claim 11 (depends on 8) The compound of claim 8, wherein R is ### Claim 12 A process comprising reacting: a fatty acid modified with an amino alkyl group; and an epihalohydrin, in a presence of a base, to afford a cationic surfactant. ### Claim 13 (depends on 12) The process of claim 12, wherein reacting the fatty acid modified with an amino alkyl group comprises reacting N, N-dimethyl-erucyl-1,3-propylenediamine. ### Claim 14 (depends on 12) The process of claim 12, wherein reacting the epihalohydrin comprises reacting epichlorohydrin. ### Claim 15 (depends on 12) The process of claim 12, wherein reacting in the presence of a base comprises reacting in a presence of sodium hydroxide. ### Claim 16 A process comprising reacting: a fatty acid modified with an amino alkyl group; an epihalohydrin; and a carboxylic acid to afford a cationic surfactant. ### Claim 17 (depends on 16) The process of claim 16, wherein reacting a fatty acid modified with an amino alkyl group comprises reacting N,N-dimethyl-erucyl-1,3-propylenediamine. ### Claim 18 (depends on 16) The process of claim 16, wherein reacting an epihalohydrin comprises reacting epichlorohydrin. ### Claim 19 (depends on 16) The process of claim 16, wherein reacting a carboxylic acid comprises reacting a carboxylic acid selected from the group consisting of: acetic acid; propionic acid; and trifluoroacetic acid. ### Claim 20 (depends on 16) The process of claim 16, wherein reacting a carboxylic acid comprises reacting acetic acid. ### Claim 21 (depends on 16) The process of claim 16, wherein reacting a carboxylic acid comprises reacting propionic acid. ### Claim 22 (depends on 16) The process of claim 16, wherein reacting a carboxylic acid comprises reacting trifluoroacetic acid. ### Claim 23 A process, comprising: reacting: a carboxylic acid; an epihalohydrin; and a catalyst to afford a halo-substituted alkyl ester; and reacting the halo-substituted alkyl ester with a fatty acid modified with an amino alkyl group to afford a cationic surfactant. ### Claim 24 (depends on 23) The process of claim 23, wherein reacting a catalyst comprises reacting tetrabutylammonium bromide. ### Claim 25 (depends on 23) The process of claim 23, wherein reacting an epihalohydrin comprises reacting epichlorohydrin. ### Claim 26 (depends on 23) The process of claim 23, wherein reacting a carboxylic acid comprises reacting a carboxylic acid selected from the group consisting of: acetic acid; propionic acid; and trifluoroacetic acid. ### Claim 27 (depends on 23) The process of claim 23, wherein reacting a carboxylic acid comprises reacting acetic acid. ### Claim 28 (depends on 23) The process of claim 23, wherein reacting a carboxylic acid comprises reacting propionic acid. ### Claim 29 (depends on 23) The process of claim 23, wherein reacting a carboxylic acid comprises reacting trifluoroacetic acid. ### Claim 30 (depends on 23) The process of claim 23, wherein reacting a fatty acid modified with an amino alkyl group comprises reacting N, N-dimethyl-erucyl-1,3-propylenediamine.