Abstract
Abstract: Novel optically active carbonate-type cationics were designed and synthesized via a green method. A series of w-alkyl 7V,7V-dimethylaminoalkyl carbonates was prepared via a two-step successive carbonate exchange reaction of diphenyl carbonate with 1-alkanol followed by the reaction of the optically active or racemic amino alcohol in the presence of triethylamine. The quaternarization of the 7V,7V-dimethylamino group was carried out using methyl iodide. Furthermore, optically active cationics were prepared by the lipase-catalyzed enantioselective hydrolysis of the racemic cationics. Carbonate-type cationics having an isopropylene linkage showed high hydrolytic stability. They exhibited surfactant properties similar to those of the corresponding racemic cationics. Although no significant differences in the antimicrobial activities were observed owing to the stereochemistry of the cationics, the biodegradability was strongly influenced by the stereochemistry. Some optically active cationics were rapidly biodegraded by activated sludge.
| Original language | English |
|---|---|
| Pages (from-to) | 185-195 |
| Number of pages | 11 |
| Journal | Journal of Oleo Science |
| Volume | 60 |
| Issue number | 4 |
| Publication status | Published - 2011 |
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Keywords
- Biodegradability
- Carbonate linkage
- Lipase
- Quaternary ammonium-type cationics
- Stereochemistry
ASJC Scopus subject areas
- Chemical Engineering(all)
- Chemistry(all)
Cite this
Chemo-enzymatic Synthesis and Properties of Novel Optically Active Cationics Containing Carbonate Linkages. / Banno, Taisuke; Kawada, Kazuo; Matsumura, Shuichi.
In: Journal of Oleo Science, Vol. 60, No. 4, 2011, p. 185-195.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Chemo-enzymatic Synthesis and Properties of Novel Optically Active Cationics Containing Carbonate Linkages
AU - Banno, Taisuke
AU - Kawada, Kazuo
AU - Matsumura, Shuichi
PY - 2011
Y1 - 2011
N2 - Abstract: Novel optically active carbonate-type cationics were designed and synthesized via a green method. A series of w-alkyl 7V,7V-dimethylaminoalkyl carbonates was prepared via a two-step successive carbonate exchange reaction of diphenyl carbonate with 1-alkanol followed by the reaction of the optically active or racemic amino alcohol in the presence of triethylamine. The quaternarization of the 7V,7V-dimethylamino group was carried out using methyl iodide. Furthermore, optically active cationics were prepared by the lipase-catalyzed enantioselective hydrolysis of the racemic cationics. Carbonate-type cationics having an isopropylene linkage showed high hydrolytic stability. They exhibited surfactant properties similar to those of the corresponding racemic cationics. Although no significant differences in the antimicrobial activities were observed owing to the stereochemistry of the cationics, the biodegradability was strongly influenced by the stereochemistry. Some optically active cationics were rapidly biodegraded by activated sludge.
AB - Abstract: Novel optically active carbonate-type cationics were designed and synthesized via a green method. A series of w-alkyl 7V,7V-dimethylaminoalkyl carbonates was prepared via a two-step successive carbonate exchange reaction of diphenyl carbonate with 1-alkanol followed by the reaction of the optically active or racemic amino alcohol in the presence of triethylamine. The quaternarization of the 7V,7V-dimethylamino group was carried out using methyl iodide. Furthermore, optically active cationics were prepared by the lipase-catalyzed enantioselective hydrolysis of the racemic cationics. Carbonate-type cationics having an isopropylene linkage showed high hydrolytic stability. They exhibited surfactant properties similar to those of the corresponding racemic cationics. Although no significant differences in the antimicrobial activities were observed owing to the stereochemistry of the cationics, the biodegradability was strongly influenced by the stereochemistry. Some optically active cationics were rapidly biodegraded by activated sludge.
KW - Biodegradability
KW - Carbonate linkage
KW - Lipase
KW - Quaternary ammonium-type cationics
KW - Stereochemistry
UR - http://www.scopus.com/inward/record.url?scp=79953070444&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=79953070444&partnerID=8YFLogxK
M3 - Article
C2 - 21427515
AN - SCOPUS:79953070444
VL - 60
SP - 185
EP - 195
JO - Journal of Oleo Science
JF - Journal of Oleo Science
SN - 1345-8957
IS - 4
ER -