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

Nerea Rodriguez Rodriguez; Adriaan van den Bruinhorst; Laura J.B.M. Kollau; Maaike C. Kroon; Koen Binnemans

doi:10.1021/acssuschemeng.9b01378

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

Onderzoeksoutput: Bijdrage aan tijdschrift › Tijdschriftartikel › Academic › peer review

294 Citaten (Scopus)

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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 (x_ChCl = 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.

Originele taal-2	Engels
Pagina's (van-tot)	11521-11528
Aantal pagina's	8
Tijdschrift	ACS Sustainable Chemistry & Engineering
Volume	7
Nummer van het tijdschrift	13
DOI's	https://doi.org/10.1021/acssuschemeng.9b01378
Status	Gepubliceerd - 28 mei 2019

Financiering

This research was financially supported by the Strategic Initiative Materials in Flanders (SIM), in the context of the Strategic Basic Research (SBO) program, SBO-SMART, Sustainable Metal Extraction from Tailings, with grant no. HBC.2016.0456. The Dutch Organization for Scientific Research (NWO) is acknowledged for the financial support (grant number: ECHO.11.TD.006).

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@article{b4701f3ed2d24514a1daf43823778053,

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.",

keywords = "Carboxylic acid, Choline chloride, Decomposition, Deep-eutectic solvent, Esterification, Malonic acid",

author = "\{Rodriguez Rodriguez\}, Nerea and \{van den Bruinhorst\}, Adriaan and Kollau, \{Laura J.B.M.\} and Kroon, \{Maaike C.\} and Koen Binnemans",

year = "2019",

month = may,

day = "28",

doi = "10.1021/acssuschemeng.9b01378",

language = "English",

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journal = "ACS Sustainable Chemistry \& Engineering",

issn = "2168-0485",

publisher = "American Chemical Society",

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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. et al.
In: ACS Sustainable Chemistry & Engineering, Vol. 7, Nr. 13, 28.05.2019, blz. 11521-11528.

Onderzoeksoutput: Bijdrage aan tijdschrift › Tijdschriftartikel › Academic › peer 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

PY - 2019/5/28

Y1 - 2019/5/28

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.

KW - Carboxylic acid

KW - Choline chloride

KW - Decomposition

KW - Deep-eutectic solvent

KW - Esterification

KW - Malonic acid

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DO - 10.1021/acssuschemeng.9b01378

M3 - Article

AN - SCOPUS:85070217848

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VL - 7

SP - 11521

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JO - ACS Sustainable Chemistry & Engineering

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ER -

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

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