Cited by 401Chemical Synthesis and ReactionsMulticomponent Synthesis of HeterocyclesSurfactants and Colloidal Systems

Dehydration Reactions in Water. Brønsted Acid−Surfactant-Combined Catalyst for Ester, Ether, Thioether, and Dithioacetal Formation in Water

Manabe, Kei, Iimura, Shinya, Sun, Xiang-Min, Kobayashi, Shū·2002·Journal of the American Chemical Society

Abstract

Dehydration reactions in water have been realized by a surfactant-type catalyst, dodecylbenzenesulfonic acid (DBSA). These reactions include dehydrative esterification, etherification, thioetherification, and dithioacetalization. In these reactions, DBSA and substrates form emulsion droplets whose interior is hydrophobic enough to exclude water molecules generated during the reactions. Detailed studies on the esterification revealed that the yields of esters were affected by temperature, amounts of DBSA used, and the substrates. Esters were obtained in high yields for highly hydrophobic substrates. On the basis of the difference in hydrophobicity of the substrates, unique selective esterification and etherification in water were attained. Furthermore, chemospecific, three-component reactions under DBSA-catalyzed conditions were also found to proceed smoothly. This work not only may lead to environmentally benign systems but also will provide a new aspect of organic chemistry in water.

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Crossref · 10.1021/ja026241j

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  • Kobayashi developed a unique catalytic system using a surfactant-like acid, DBSA, to mediate the emulsion polycondensation of aliphatic carboxylic acids and alcohols in water.

    “Kobayashi developed a unique catalytic system [250][251][252] using a surfactant-like acid, such as dodecylbenzenesulfonic acid (DBSA), to mediate the emulsion polycondensation of aliphatic carboxylic acids and alcohols in water.”

    From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [251]

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Authors
Manabe, K., Iimura, S., Sun, X.-M., & Kobayashi, S.
Affiliations
The University of Tokyo (JP)
Corresponding author
Kobayashi, Shū
Venue
Journal of the American Chemical Society
Published
2002-09-13
Volume
124
Issue
40
Pages
11971-11978
ISSN
  • 0002-7863 (ISSN-L)
  • 1520-5126
OpenAlex
W1982368556
Cited by
401
References
56
Citations by year
2026: 8 · 2025: 15 · 2024: 12 · 2023: 13 · 2022: 15 · 2021: 15 · 2020: 18 · 2019: 12 · 2018: 20 · 2017: 20 · 2016: 11 · 2015: 19 · 2014: 27 · 2013: 36 · 2012: 23
FWCI
8.36
Type
journal article
Language
en
Open access
closed
Locations
  • Journal of the American Chemical Society (publishedVersion)
  • PubMed (publishedVersion)
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Chemical Synthesis and Reactions
  • Physical Sciences › Chemistry › Organic Chemistry › Multicomponent Synthesis of Heterocycles
  • Physical Sciences › Chemistry › Organic Chemistry › Surfactants and Colloidal Systems
Keywords
dodecylbenzenesulfonic acid, Brønsted acid catalysis, thioetherification, emulsion droplets, hydrophobicity, selective esterification, three-component reaction, green chemistry

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