Startseite Solvent-Free Acetalization of Glycerol with n-Octanal using Combined Brønsted Acid-Surfactant Catalyst
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Solvent-Free Acetalization of Glycerol with n-Octanal using Combined Brønsted Acid-Surfactant Catalyst

  • Xu Li , Lan Wu , Qiong Tang und Jinxiang Dong
Veröffentlicht/Copyright: 6. Januar 2017
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Tenside Surfactants Detergents
Aus der Zeitschrift Tenside Surfactants Detergents Band 54 Heft 1

Abstract

Glycerol, derived from biodiesel production, is a renewable feedstock for the production of value-added chemicals. Herein, we report an investigation of the acetalization of glycerol with n-octanal by homogeneous acid catalysis in the absence of a solvent, using p-dodecylbenzenesulfonic acid, p-toluenesulfonic acid, and sulfuric acid, respectively, as catalysts. p-Dodecylbenzenesulfonic acid, a surfactant-type Brønsted acid, proved to be an excellent catalyst capable of efficiently promoting the reaction under solvent-free conditions, and the yields of glycerol acetals reached 99% under the optimal conditions. The distribution of five- and six-membered cyclic acetal regioisomers varied depending on the reaction time and temperature. Moreover, the amphiphilic properties of the products, with different ratios of five- to six-membered cyclic acetals, have been evaluated by surface tension measurements.

Kurzfassung

Das aus der Biodieselproduktion gewonnene Glycerin ist ein nachwachsender Rohstoff für die Herstellung von Chemikalien mit Zusatznutzen. In diesem Beitrag berichten wir über die Acetalisierung von Glycerol mit n-Octanal in einer homogenen und sauren Katalysereaktion unter Verwendung von p-Dodecylbenzenesulfonsäure, p-Toluolsulfonsäure und Schwefelsäure als Katalysatoren und bei Abwesenheit eines Lösemittels. p-Dodecylbenzenesulfonsäure, eine tensidische Brønstedtsäure erwies sich als ein ausgezeichneter Katalysator, der in der Lage ist, die Reaktion unter lösungsmittelfreien Bedingungen effizient zu beschleunigen. Die Ausbeuten an Glycerinacetalen erreichten unter optimalen Bedingungen 99%. Die Verteilung der fünf- und sechsgliedrigen cyclischen Acetalregioisomere variierte in Abhängigkeit von der Reaktionszeit und der Temperatur. Darüber hinaus wurden die amphiphilen Eigenschaften der Produkte mit unterschiedlichen Verhältnissen von fünf- bis sechsgliedrigen cyclischen Acetalen durch Oberflächenspannungsmessungen bewertet.

Key words: Glycerol acetals; biodiesel; solvent-free reaction; surfactant-type brønsted acid; homogeneous acid catalysis
Stichwörter: Gylcerinacetale; Biodiesel; Lösemittelfreie Reaktion; tensidische Brønstedtsäure; homogene saure Katalyse
*Correspondence address, Mr. Jinxiang Dong, Research Institute of Special Chemicals, College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Yingze West Street No. 79, Taiyuan 030024, Shanxi, P.R. China, Tel.: +86-351-6111178, Fax: +86-351-6111178, E-Mail:

Xu Li, Lan Wu, Qiong Tang, Jinxiang Dong: Research Institute of Special Chemicals, College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan, Shanxi, P.R. China

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Received: 2016-07-18
Accepted: 2016-09-28
Published Online: 2017-01-06
Published in Print: 2017-01-20

© 2017, Carl Hanser Publisher, Munich

Artikel in diesem Heft

  1. Contents/Inhalt
  2. Contents
  3. Editorial
  4. Review of the Year 2016
  5. Review
  6. Reaction Principle of Alcohol Ether Sulfonates by Sulfonated Alkylation Method – A Review
  7. Biosurfactants/Novel Surfactants
  8. Distribution Coefficients of Lipopeptide Biosurfactant in Different Solvents and its Separation from a Surfactant/Polymer Mixture in Aqueous Solutions
  9. Synthesis and Surface Properties of Anionic Vinylguaiacol Based Surfactants
  10. Novel Mesoporous ZSM-5 Zeolite with Disparate Morphologies Synthesized by a Double Long-alkyl-chain Organosilane Template
  11. Environmental Chemistry
  12. Preparation and Characterization of Glauber's Salt Microcapsules for Thermal Energy Storage
  13. Physical Chemistry
  14. Preparation and Characterization of a Humate Surfactant with Hydroxymethylation and Esterification Modification of Lignite
  15. Properties of Cationic Choline-Derived Surfactant with Photolabile Cinnamate Counterion
  16. Micellar Catalysis
  17. Solvent-Free Acetalization of Glycerol with n-Octanal using Combined Brønsted Acid-Surfactant Catalyst
  18. Synthesis
  19. Purification, Analysis and Surfactant Synthesis of Waste Cooking Oil
  20. Application
  21. Preparation and Properties of Novel Asymmetric Gemini Alkyl Polyglycosides
  22. Synthesis and Properties of Esterquats as Antibacterial Agent and Fabric Softener
https://doi.org/10.3139/113.110480
Schlagwörter für diesen Artikel
Glycerol acetals; biodiesel; solvent-free reaction; surfactant-type brønsted acid; homogeneous acid catalysis

Artikel in diesem Heft

  1. Contents/Inhalt
  2. Contents
  3. Editorial
  4. Review of the Year 2016
  5. Review
  6. Reaction Principle of Alcohol Ether Sulfonates by Sulfonated Alkylation Method – A Review
  7. Biosurfactants/Novel Surfactants
  8. Distribution Coefficients of Lipopeptide Biosurfactant in Different Solvents and its Separation from a Surfactant/Polymer Mixture in Aqueous Solutions
  9. Synthesis and Surface Properties of Anionic Vinylguaiacol Based Surfactants
  10. Novel Mesoporous ZSM-5 Zeolite with Disparate Morphologies Synthesized by a Double Long-alkyl-chain Organosilane Template
  11. Environmental Chemistry
  12. Preparation and Characterization of Glauber's Salt Microcapsules for Thermal Energy Storage
  13. Physical Chemistry
  14. Preparation and Characterization of a Humate Surfactant with Hydroxymethylation and Esterification Modification of Lignite
  15. Properties of Cationic Choline-Derived Surfactant with Photolabile Cinnamate Counterion
  16. Micellar Catalysis
  17. Solvent-Free Acetalization of Glycerol with n-Octanal using Combined Brønsted Acid-Surfactant Catalyst
  18. Synthesis
  19. Purification, Analysis and Surfactant Synthesis of Waste Cooking Oil
  20. Application
  21. Preparation and Properties of Novel Asymmetric Gemini Alkyl Polyglycosides
  22. Synthesis and Properties of Esterquats as Antibacterial Agent and Fabric Softener
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