Synthesis of symmetric ethers using monocationic and dicationic acidic ionic liquids

Ance Eglite; Linda Pudnika; Marta Anda Balode; Anda Prikšane

doi:10.4028/www.scientific.net/KEM.762.104

Synthesis of symmetric ethers using monocationic and dicationic acidic ionic liquids

Ance Eglite^*
, Linda Pudnika
, Marta Anda Balode
, Anda Prikšane

^*Corresponding author for this work

Department of Chemistry

University of Latvia

Research output: Chapter in Book/Report/Conference proceeding › Conference paper › Research › peer-review

Abstract

A series of monocationic and dicationic-SO₃H functionalized Brønsted acidic ionic liquids (BAILs) were synthesized using different amines int. al., N,N,N',N'-tetramethylethylenediamine, 1-methylimidazole, pyridine, and alkylating agents: 1,3-propane- and 1,4-butanesultones. The Hammett acidity (H₀) and thermal properties by TG-DSC techniques are investigated. These ionic liquids have been applied to catalyze the dehydration reaction of aliphatic long chain alcohols (1-heptanol, 1-octanol, 1-decanol) at 195 °C. The optimization of reaction conditions and the use of dicationic ionic liquids allow to reach rather high yields of symmetric diheptyl ether and dioctyl ether. The reusability of ionic liquids is evaluated using monocationic [PyPS][HSO₄], dicationic [TMEDAPS][HSO₄] ionic liquids, and 1-heptanol.

Original language	English
Title of host publication	Materials Science and Applied Chemistry - 58th International Conference of Materials Science and Applied Chemistry, MSAC 2017
Editors	Valdis Kokars
Publisher	Trans Tech Publications Ltd
Pages	104-108
Number of pages	5
ISBN (Print)	9783035712384
DOIs	https://doi.org/10.4028/www.scientific.net/KEM.762.104
Publication status	Published - 2018
Event	58th International Conference of Materials Science and Applied Chemistry, MSAC 2017 - Riga, Latvia Duration: 20 Oct 2017 → 20 Oct 2017

Publication series

Name	Key Engineering Materials
Volume	762
ISSN (Print)	1013-9826
ISSN (Electronic)	1662-9795

Conference

Conference	58th International Conference of Materials Science and Applied Chemistry, MSAC 2017
Country/Territory	Latvia
City	Riga
Period	20/10/17 → 20/10/17

Keywords

Aliphatic alcohols
Brønsted acidic catalyst
Dehydration reactions
Dicationic ionic liquids
Monocationic ionic liquids

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10.4028/www.scientific.net/KEM.762.104

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Eglite, A., Pudnika, L., Balode, M. A., & Prikšane, A. (2018). Synthesis of symmetric ethers using monocationic and dicationic acidic ionic liquids. In V. Kokars (Ed.), Materials Science and Applied Chemistry - 58th International Conference of Materials Science and Applied Chemistry, MSAC 2017 (pp. 104-108). (Key Engineering Materials; Vol. 762). Trans Tech Publications Ltd. https://doi.org/10.4028/www.scientific.net/KEM.762.104

Eglite, Ance ; Pudnika, Linda ; Balode, Marta Anda et al. / Synthesis of symmetric ethers using monocationic and dicationic acidic ionic liquids. Materials Science and Applied Chemistry - 58th International Conference of Materials Science and Applied Chemistry, MSAC 2017. editor / Valdis Kokars. Trans Tech Publications Ltd, 2018. pp. 104-108 (Key Engineering Materials).

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title = "Synthesis of symmetric ethers using monocationic and dicationic acidic ionic liquids",

abstract = "A series of monocationic and dicationic-SO3H functionalized Br{\o}nsted acidic ionic liquids (BAILs) were synthesized using different amines int. al., N,N,N',N'-tetramethylethylenediamine, 1-methylimidazole, pyridine, and alkylating agents: 1,3-propane- and 1,4-butanesultones. The Hammett acidity (H0) and thermal properties by TG-DSC techniques are investigated. These ionic liquids have been applied to catalyze the dehydration reaction of aliphatic long chain alcohols (1-heptanol, 1-octanol, 1-decanol) at 195 °C. The optimization of reaction conditions and the use of dicationic ionic liquids allow to reach rather high yields of symmetric diheptyl ether and dioctyl ether. The reusability of ionic liquids is evaluated using monocationic [PyPS][HSO4], dicationic [TMEDAPS][HSO4] ionic liquids, and 1-heptanol.",

keywords = "Aliphatic alcohols, Br{\o}nsted acidic catalyst, Dehydration reactions, Dicationic ionic liquids, Monocationic ionic liquids",

author = "Ance Eglite and Linda Pudnika and Balode, \{Marta Anda\} and Anda Prik{\v s}ane",

note = "Publisher Copyright: {\textcopyright} 2018 Trans Tech Publications, Switzerland.; 58th International Conference of Materials Science and Applied Chemistry, MSAC 2017 ; Conference date: 20-10-2017 Through 20-10-2017",

year = "2018",

doi = "10.4028/www.scientific.net/KEM.762.104",

language = "English",

isbn = "9783035712384",

series = "Key Engineering Materials",

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Eglite, A, Pudnika, L, Balode, MA & Prikšane, A 2018, Synthesis of symmetric ethers using monocationic and dicationic acidic ionic liquids. in V Kokars (ed.), Materials Science and Applied Chemistry - 58th International Conference of Materials Science and Applied Chemistry, MSAC 2017. Key Engineering Materials, vol. 762, Trans Tech Publications Ltd, pp. 104-108, 58th International Conference of Materials Science and Applied Chemistry, MSAC 2017, Riga, Latvia, 20/10/17. https://doi.org/10.4028/www.scientific.net/KEM.762.104

Synthesis of symmetric ethers using monocationic and dicationic acidic ionic liquids. / Eglite, Ance; Pudnika, Linda; Balode, Marta Anda et al.
Materials Science and Applied Chemistry - 58th International Conference of Materials Science and Applied Chemistry, MSAC 2017. ed. / Valdis Kokars. Trans Tech Publications Ltd, 2018. p. 104-108 (Key Engineering Materials; Vol. 762).

Research output: Chapter in Book/Report/Conference proceeding › Conference paper › Research › peer-review

TY - GEN

T1 - Synthesis of symmetric ethers using monocationic and dicationic acidic ionic liquids

AU - Eglite, Ance

AU - Pudnika, Linda

AU - Balode, Marta Anda

AU - Prikšane, Anda

PY - 2018

Y1 - 2018

N2 - A series of monocationic and dicationic-SO3H functionalized Brønsted acidic ionic liquids (BAILs) were synthesized using different amines int. al., N,N,N',N'-tetramethylethylenediamine, 1-methylimidazole, pyridine, and alkylating agents: 1,3-propane- and 1,4-butanesultones. The Hammett acidity (H0) and thermal properties by TG-DSC techniques are investigated. These ionic liquids have been applied to catalyze the dehydration reaction of aliphatic long chain alcohols (1-heptanol, 1-octanol, 1-decanol) at 195 °C. The optimization of reaction conditions and the use of dicationic ionic liquids allow to reach rather high yields of symmetric diheptyl ether and dioctyl ether. The reusability of ionic liquids is evaluated using monocationic [PyPS][HSO4], dicationic [TMEDAPS][HSO4] ionic liquids, and 1-heptanol.

AB - A series of monocationic and dicationic-SO3H functionalized Brønsted acidic ionic liquids (BAILs) were synthesized using different amines int. al., N,N,N',N'-tetramethylethylenediamine, 1-methylimidazole, pyridine, and alkylating agents: 1,3-propane- and 1,4-butanesultones. The Hammett acidity (H0) and thermal properties by TG-DSC techniques are investigated. These ionic liquids have been applied to catalyze the dehydration reaction of aliphatic long chain alcohols (1-heptanol, 1-octanol, 1-decanol) at 195 °C. The optimization of reaction conditions and the use of dicationic ionic liquids allow to reach rather high yields of symmetric diheptyl ether and dioctyl ether. The reusability of ionic liquids is evaluated using monocationic [PyPS][HSO4], dicationic [TMEDAPS][HSO4] ionic liquids, and 1-heptanol.

KW - Aliphatic alcohols

KW - Brønsted acidic catalyst

KW - Dehydration reactions

KW - Dicationic ionic liquids

KW - Monocationic ionic liquids

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DO - 10.4028/www.scientific.net/KEM.762.104

M3 - Conference paper

AN - SCOPUS:85043589961

SN - 9783035712384

T3 - Key Engineering Materials

SP - 104

EP - 108

BT - Materials Science and Applied Chemistry - 58th International Conference of Materials Science and Applied Chemistry, MSAC 2017

A2 - Kokars, Valdis

PB - Trans Tech Publications Ltd

T2 - 58th International Conference of Materials Science and Applied Chemistry, MSAC 2017

Y2 - 20 October 2017 through 20 October 2017

ER -

Eglite A, Pudnika L, Balode MA, Prikšane A. Synthesis of symmetric ethers using monocationic and dicationic acidic ionic liquids. In Kokars V, editor, Materials Science and Applied Chemistry - 58th International Conference of Materials Science and Applied Chemistry, MSAC 2017. Trans Tech Publications Ltd. 2018. p. 104-108. (Key Engineering Materials). doi: 10.4028/www.scientific.net/KEM.762.104

Synthesis of symmetric ethers using monocationic and dicationic acidic ionic liquids

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Keywords

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