Alkyl Ketene Dimer CAS 144245-85-2 AKD

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Basic Info of Alkyl Ketene Dimer

What is Alkyl Ketene Dimer?

The Chinese name of AKD is AlkylKetene Dimer. In 1956, AKD began to be industrialized and was only used in special paper that needs heavy sizing. In recent years, cultural paper has basically been changed to AKD neutral sizing. more application areas.

Alkyl ketene dimers (akds) are a class of organic compounds based on oxetan-2-one 4-membered ring system. They are also the central structural elements of propanolactone and diene ketones. The oxyheterocyclobutane ring of the alkyl vinyl ketone dimer related to the technology is connected, with a C 12 – C 16 alkyl group at position 3 and a C 13 – C 17 alkylene group at position 4.

Alkylated ketene dimers are mainly used in sizing of paper and paperboard and hydrophobicization of cellulose fibers. Such modified products are known for higher mechanical strength and less penetration of water, ink or printing ink.

AKD has slave β- The propanolactone ring extends to a hydrophobic alkyl group. A specific example comes from the dimerization of vinyl stearate. This vinyl ketone is produced by pyrolysis of stearyl chloride. AKD reacts with hydroxyl groups on cellulose through esterification. Esterification competes with the hydrolysis of AKD. Before the development of AKD, the hydrophobicity was given by adding rosin into the paper.

Related to AKD is alkenyl succinic anhydride (ASA). As for AKD, ASA reacts with the hydroxyl group of cellulose to form ester, which fixes the hydrophobic group on the surface. ASA is prepared by Olefination of unsaturated hydrocarbons with maleic anhydride.

Alkyl Ketene Dimer Uses

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Preparation of Alkyl Ketene Dimer

In 1945, the industrial synthesis patent of alkylated ketene dimer (still called ketene ketone at that time) was obtained from long-chain carboxylic acid chloride with triethylamine as tertiary amine in inert solvent (such as ether or benzene) under anhydrous conditions. The insoluble triethylamine hydrochloride was filtered and the solvent was evaporated to obtain long-chain alkyl dimer with a yield of more than 90%.

硬脂酰氯合成 von C18-AKD

Trialkylamine hydrochloride or other amines, such as N, N, n ‘, n’ – tetramethyl-hexane-1,6-diamine, are more easily separated using other solvents (such as carboxylic acid esters or ketones).

A solvent free method is also described in which the resulting amine hydrochloride is filtered out or extracted with diluted aqueous acid.

A continuous method in which long-chain carboxyacyl chloride and tertiary amines (such as dimethylisopropylamine, dimethylcyclohexylamine or triethylamine) are separately supplied to a tubular reactor, kneader or preferably a twin-screw extruder or planetary roller extruder without solvent, and provide a lactone content of more than 90% in a short reaction time at 90 and 110 ° C. Treatment by phase separation or acid extraction.


  1.  “AKD, Alkylketene Dimer”
  2. US 2627477, W.F. Downey, “Higher alkyl ketene dimer emulsion”, published 1953-02-03, assigned to Hercules Powder Co.
  3.  Lindström, T.; Larsson, T. (2005), STFI-Packfors (ed.), A note on AKD-sizing: an investigation of real and apparent contradictions in literature regarding spreadin/diffusion of AKD on cellulose, Report no. 81 (PDF)

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