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פותח על ידי קלירמאש פתרונות בע"מ -
Cleavable Surfactants: A Comparison between Ester, Amide, and Carbonate as the Weak Bond
Year:
2019
Authors :
צ'והאן, וינאי
;
.
Volume :
22
Co-Authors:

Stjerndahl, M., AkzoNobel Functional Chemistry, Hamnvägen 2, Stenungsund, 444 85, Sweden; Lundberg, D., C.R. Competence, Center for Chemistry and Chemical Engineering, P.O. Box 124, Lund, 221 00, Sweden; Bordes, R., Chalmers University of Technology, Department of Chemistry and Chemical Engineering, Gothenburg, 412 96, Sweden; Holmberg, K., Chalmers University of Technology, Department of Chemistry and Chemical Engineering, Gothenburg, 412 96, Sweden

Facilitators :
From page:
1139
To page:
1145
(
Total pages:
7
)
Abstract:

Cleavable surfactants, i.e., surfactants in which a weak bond has deliberately been inserted into the molecule, are of interest when remaining surface-active material at a surface can cause problems. Ester and amide bonds are established as week linkages in surfactants but these generate an acid when they hydrolyze. For some applications, acidic degradation products are unwanted. Surfactants with a carbonate bond between the polar headgroup and the hydrophobic tail are of interest for such purposes. In this article, we compare the physical–chemical properties of nonionic carbonate surfactants with those of the corresponding ester and amide surfactants. The half-lives of the different cleavable surfactants are also compared and it was found that a carbonate bond is slightly more stable to alkaline hydrolysis than an ester bond when present in otherwise identical structures. A nonionic Gemini surfactant with a carbonate bond in the spacer, which on hydrolysis decomposes into two identical single-tailed nonionic amphiphiles, is also presented. The hydrolysis kinetics for this surfactant was studied in some detail and it was found that it degrades much faster at low temperature than at higher temperature. This anti-Arrhenius type of hydrolysis kinetics is proposed to be due to the reverse solubility versus temperature behavior of ethoxylated surfactants. © 2019 AOCS

Note:
Related Files :
Amides
carbonate
Carbonates
Carbonation
Degradation
Esters
Hydrolysis
Surfactants
temperature
עוד תגיות
תוכן קשור
More details
DOI :
10.1002/jsde.12247
Article number:
0
Affiliations:
Database:
סקופוס
Publication Type:
מאמר
;
.
Language:
אנגלית
Editors' remarks:
ID:
39418
Last updated date:
02/03/2022 17:27
Creation date:
26/02/2019 11:12
Scientific Publication
Cleavable Surfactants: A Comparison between Ester, Amide, and Carbonate as the Weak Bond
22

Stjerndahl, M., AkzoNobel Functional Chemistry, Hamnvägen 2, Stenungsund, 444 85, Sweden; Lundberg, D., C.R. Competence, Center for Chemistry and Chemical Engineering, P.O. Box 124, Lund, 221 00, Sweden; Bordes, R., Chalmers University of Technology, Department of Chemistry and Chemical Engineering, Gothenburg, 412 96, Sweden; Holmberg, K., Chalmers University of Technology, Department of Chemistry and Chemical Engineering, Gothenburg, 412 96, Sweden

Cleavable Surfactants: A Comparison between Ester, Amide, and Carbonate as the Weak Bond

Cleavable surfactants, i.e., surfactants in which a weak bond has deliberately been inserted into the molecule, are of interest when remaining surface-active material at a surface can cause problems. Ester and amide bonds are established as week linkages in surfactants but these generate an acid when they hydrolyze. For some applications, acidic degradation products are unwanted. Surfactants with a carbonate bond between the polar headgroup and the hydrophobic tail are of interest for such purposes. In this article, we compare the physical–chemical properties of nonionic carbonate surfactants with those of the corresponding ester and amide surfactants. The half-lives of the different cleavable surfactants are also compared and it was found that a carbonate bond is slightly more stable to alkaline hydrolysis than an ester bond when present in otherwise identical structures. A nonionic Gemini surfactant with a carbonate bond in the spacer, which on hydrolysis decomposes into two identical single-tailed nonionic amphiphiles, is also presented. The hydrolysis kinetics for this surfactant was studied in some detail and it was found that it degrades much faster at low temperature than at higher temperature. This anti-Arrhenius type of hydrolysis kinetics is proposed to be due to the reverse solubility versus temperature behavior of ethoxylated surfactants. © 2019 AOCS

Scientific Publication
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