# US 5,344,943 A · Long-chain ketene dimers > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,344,943 A - Document ID: US5344943A - Status: Granted - Kind: A - Application number: 07/998,810 - Filed: 1992-12-29 - Granted: 1994-09-06 - Earliest claimed: 1991-12-30 - Assignees: Akzo Nobel N.V. - Inventors: Nils Brolund - Web page: https://patentgrep.com/patent/US5344943A ## CPC - C07C 45/89: from carboxylic acids, their anhydrides, esters or halides - C07C 49/88: Ketenes; Dimeric ketenes - D21H 17/17: Ketenes, e.g. ketene dimers - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - D21H: PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR ## Abstract Long-chain ketene dimers are prepared in a process in which in the absence of an organic solvent, carboxylic acid chloride is fed, with intensive mixing, into a recipient of triethyl amine at a rate of not more than 3 moles/hour per mole of present triethyl amine, and the mixing rate, feed rate, and heat exchange are so attuned to each other that the viscosity of the mixture always is less than 250 mPa.s, measured at 60.degree. C. (rate of shear higher than 100 l/sec). The process is characterized in that the molar ratio of the total amount of carboxylic acid chloride fed in to the recipient amount of amine is 1:1.025 to 1:2, and, after the conversion, the reaction mixture containing the ketene dimer is treated with diluted aqueous hydrochloric acid or an aqueous solution of triethyl amine hydrochloride and hydrochloric acid, and the ketene dimer is separated. The ketenes prepared in accordance with the present invention are highly suitable for use in paper sizing. ## Claims ### Claim 1 A process for the preparation of long-chain ketene dimers which comprises reacting carboxylic acid chlorides of the formula: RCH.sub.2 COCl wherein R is a saturated or unsaturated hydrocarbon group having 6-30 carbon atoms, with triethyl amine to obtain a amine hydrochloride-containing reaction mixture containing ketene dimer, and treating said mixture with dilute aqueous hydrochloric acid or an aqueous solution of triethyl amine hydrochloride and hydrochloride acid to separate out the ketene dimer product, wherein the process is characterized in that said acid chloride is fed, in the absence of an organic solvent into said triethyl amine under intensive mixing at a rate of not more than 3 moles/hour per mole of triethyl amine, and mixing, feed rate and heat exchange are controlled such that the viscosity of the mixture is maintained at less than about 250 mPa.s, measured at 60.degree. C. (rate of shear higher than 100 1/sec) and the molar ratio of the total amount of carboxylic acid chloride fed into the triethyl amine is 1:1.025 to 1:2. ### Claim 2 (depends on 1) The process according to claim 1, wherein the carboxylic acid chloride is fed into the triethyl amine at a rate of not more than about 1 mole/hour per mole of present triethyl amine. ### Claim 3 (depends on 1) The process according to claim 1, wherein upon conclusion of feeding said acid chloride into said triethyl amine the mixture containing ketene dimer product is allowed to stand for 5-30 minutes. ### Claim 4 (depends on 1) The process according to claim 1, wherein the conversion is carried out at a temperature range of from about 50.degree. to 100.degree. C. ### Claim 5 (depends on 1) The process according to claim 1, wherein said treatment of the reaction mixture is carried out with an aqueous solution containing 0-50 wt. % of triethyl amine hydrochloride and 3-32 wt. % of hydrochloric acid. ### Claim 6 (depends on 1) The process according to claim 1, wherein the reaction of said organic fatty acid chlorides and triethyl amines is conducted in an agitator vessel in batch operation, and the separation of the ketene dimer product is carried out in batch operation, semi-continuous operation or continuous operation. ### Claim 7 (depends on 1) The process according to claim 1, wherein the reaction of said organic fatty acid chlorides and triethyl amines is conducted in an agitator vessel cascade in continuous operation, and the separation of the ketene dimer product is carried out in batch operation, semi-continuous operation or continuous operation. ### Claim 8 (depends on 1) The process according to claim 1, wherein the reaction of said organic fatty acid chlorides and triethyl amines is conducted in a combination of an agitator vessel and a tubular reactor in continuous operation, and the separation of the ketene dimer product is carried out in batch operation, semi-continuous operation or continuous operation. ### Claim 9 (depends on 1) The process according to claim 1, wherein the reaction of said organic fatty acid chlorides and triethyl amines is conducted in a combination of a loop reactor and a tubular reactor in continuous operation, and the separation of the ketene dimer product is carried out in batch operation, semi-continuous operation or continuous operation. ### Claim 10 (depends on 3) The process of claim 3 wherein said mixture is allowed to stand for about 10-20 minutes. ### Claim 11 (depends on 4) The process of claim 4 wherein said conversion is carried out at a temperature of from about 55.degree. C. to 65.degree. C.