Chlorination of chitin with sulfuryl chloride under homogeneous conditions

How Tseng, Kensuke Takechi, Ken-ichi Furuhata

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Chitin was chlorinated with sulfuryl chloride under homogeneous conditions in LiCl-N,N-dimethylacetamide. Chlorodeoxychitins were obtained in the reactions at temperatures from −30 to 70 °C. The regioselective replacement of C-6 hydroxyl groups with chlorine atoms occurred in the reaction for 4 h at −20 °C while C-3 hydroxyl groups were also replaced above 0 °C when the molar ratio of sulfuryl chloride to the repeating unit of chitin was 15. The yield of chlorodeoxychitin decreased from 90 to 60% with the rise in reaction temperature from −30 to 60 °C and dropped to 27% at 70 °C. All the chlorodeoxychitin samples were soluble in formic acid.
Original languageEnglish
Pages (from-to)13-18
Number of pages6
JournalCarbohydrate Polymers
Volume33
Issue number1
DOIs
Publication statusPublished - 1997
Externally publishedYes

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Chitin
formic acid
Chlorination
Hydroxyl Radical
Chlorides
Formic acid
Chlorine
Atoms
Temperature
dimethylacetamide

Cite this

Chlorination of chitin with sulfuryl chloride under homogeneous conditions. / Tseng, How; Takechi, Kensuke; Furuhata, Ken-ichi .

In: Carbohydrate Polymers, Vol. 33, No. 1, 1997, p. 13-18.

Research output: Contribution to journalArticle

Tseng, How ; Takechi, Kensuke ; Furuhata, Ken-ichi . / Chlorination of chitin with sulfuryl chloride under homogeneous conditions. In: Carbohydrate Polymers. 1997 ; Vol. 33, No. 1. pp. 13-18.
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