Degradation of deep-eutectic solvents based on choline chloride and carboxylic acids

Nerea Rodriguez Rodriguez (Corresponding author), Adriaan van den Bruinhorst, Laura J.B.M. Kollau, Maaike C. Kroon, Koen Binnemans

Research output: Contribution to journalArticleAcademicpeer-review

5 Citations (Scopus)

Abstract

Mixtures of carboxylic acids and choline chloride are one of the most commonly used families of deep-eutectic solvents. The thermal and long-term stability of carboxylic acid-choline chloride (ChCl) deep-eutectic solvents was investigated. This family of DESs was found to degrade due to an esterification reaction, mainly between the carboxylic acid and the alcohol moiety of ChCl. The esterification reaction occurs even at room temperature over extended periods of time and is promoted at elevated temperatures. The esterification reaction takes place independently of the preparation method used. Moreover, the deep-eutectic solvent malonic acid-ChCl (xChCl = 0.50) was found to decompose into acetic acid and carbon dioxide when prepared via the heating method, or when heated after preparation at room temperature. Therefore, the applicability of carboxylic acid-ChCl-based solvents is compromised.

Original languageEnglish
Pages (from-to)11521-11528
Number of pages8
JournalACS Sustainable Chemistry & Engineering
Volume7
Issue number13
DOIs
Publication statusPublished - 28 May 2019

Fingerprint

carboxylic acid
Carboxylic Acids
Choline
Carboxylic acids
Eutectics
chloride
Esterification
Degradation
degradation
temperature
Acetic acid
Carbon Dioxide
Acetic Acid
acetic acid
Temperature
alcohol
Carbon dioxide
Alcohols
carbon dioxide
heating

Keywords

  • Carboxylic acid
  • Choline chloride
  • Decomposition
  • Deep-eutectic solvent
  • Esterification
  • Malonic acid

Cite this

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title = "Degradation of deep-eutectic solvents based on choline chloride and carboxylic acids",
abstract = "Mixtures of carboxylic acids and choline chloride are one of the most commonly used families of deep-eutectic solvents. The thermal and long-term stability of carboxylic acid-choline chloride (ChCl) deep-eutectic solvents was investigated. This family of DESs was found to degrade due to an esterification reaction, mainly between the carboxylic acid and the alcohol moiety of ChCl. The esterification reaction occurs even at room temperature over extended periods of time and is promoted at elevated temperatures. The esterification reaction takes place independently of the preparation method used. Moreover, the deep-eutectic solvent malonic acid-ChCl (xChCl = 0.50) was found to decompose into acetic acid and carbon dioxide when prepared via the heating method, or when heated after preparation at room temperature. Therefore, the applicability of carboxylic acid-ChCl-based solvents is compromised.",
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Degradation of deep-eutectic solvents based on choline chloride and carboxylic acids. / Rodriguez Rodriguez, Nerea (Corresponding author); van den Bruinhorst, Adriaan; Kollau, Laura J.B.M.; Kroon, Maaike C.; Binnemans, Koen.

In: ACS Sustainable Chemistry & Engineering, Vol. 7, No. 13, 28.05.2019, p. 11521-11528.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Degradation of deep-eutectic solvents based on choline chloride and carboxylic acids

AU - Rodriguez Rodriguez, Nerea

AU - van den Bruinhorst, Adriaan

AU - Kollau, Laura J.B.M.

AU - Kroon, Maaike C.

AU - Binnemans, Koen

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N2 - Mixtures of carboxylic acids and choline chloride are one of the most commonly used families of deep-eutectic solvents. The thermal and long-term stability of carboxylic acid-choline chloride (ChCl) deep-eutectic solvents was investigated. This family of DESs was found to degrade due to an esterification reaction, mainly between the carboxylic acid and the alcohol moiety of ChCl. The esterification reaction occurs even at room temperature over extended periods of time and is promoted at elevated temperatures. The esterification reaction takes place independently of the preparation method used. Moreover, the deep-eutectic solvent malonic acid-ChCl (xChCl = 0.50) was found to decompose into acetic acid and carbon dioxide when prepared via the heating method, or when heated after preparation at room temperature. Therefore, the applicability of carboxylic acid-ChCl-based solvents is compromised.

AB - Mixtures of carboxylic acids and choline chloride are one of the most commonly used families of deep-eutectic solvents. The thermal and long-term stability of carboxylic acid-choline chloride (ChCl) deep-eutectic solvents was investigated. This family of DESs was found to degrade due to an esterification reaction, mainly between the carboxylic acid and the alcohol moiety of ChCl. The esterification reaction occurs even at room temperature over extended periods of time and is promoted at elevated temperatures. The esterification reaction takes place independently of the preparation method used. Moreover, the deep-eutectic solvent malonic acid-ChCl (xChCl = 0.50) was found to decompose into acetic acid and carbon dioxide when prepared via the heating method, or when heated after preparation at room temperature. Therefore, the applicability of carboxylic acid-ChCl-based solvents is compromised.

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