A sonoelectrochemical Fenton process for efficient synthesis of tetramethyladipic acid from pivalic acid

David H. Bremner, Arthur E. Burgess, Feng-Bin Li

Research output: Contribution to journalArticle

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Abstract

Tetramethyladipic acid (TMAA), a starting monomer for several technically important polymers (polyester resins and polyamide fibres) is synthesised by direct carbon–carbon bond formation between the saturated primary carbon atoms of pivalic acid (PA) using a sonoelectrochemical Fenton process. Through controlled electrochemical dissolution assisted by ultrasound radiation, Fe2+ ions are produced in situ from metallic iron in the reaction mixture. The effects of ultrasound with electrolysis, temperature, amount of substrate present, reagent concentration, solution acidity and quantity of electric charge have been examined. Under suitable conditions, the synthesis yield based on initial PA present, hydrogen peroxide used and amount of iron dissolved reached 34, 40 and 75%, respectively and less by-product was observed. These results show significant improvement in terms of direct cost savings by omission of separate preparation of a ferrous salt, fewer side reactions during the dimerisation process, less waste, easier purification; increased efficiency due to recycling of iron ions and improved reactivity of fresh Fe2+ ions. All of these advantages make this sonoelectrochemical approach a much more efficient and environmentally cleaner option.
Original languageEnglish
Pages (from-to)126-130
Number of pages5
JournalGreen Chemistry
Issue number3
DOIs
StatePublished - Apr 2001

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Cite this

Bremner, David H.; Burgess, Arthur E.; Li, Feng-Bin / A sonoelectrochemical Fenton process for efficient synthesis of tetramethyladipic acid from pivalic acid.

In: Green Chemistry, No. 3, 04.2001, p. 126-130.

Research output: Contribution to journalArticle

@article{19be5469483c4b89a12efb210a27d6bd,
title = "A sonoelectrochemical Fenton process for efficient synthesis of tetramethyladipic acid from pivalic acid",
abstract = "Tetramethyladipic acid (TMAA), a starting monomer for several technically important polymers (polyester resins and polyamide fibres) is synthesised by direct carbon–carbon bond formation between the saturated primary carbon atoms of pivalic acid (PA) using a sonoelectrochemical Fenton process. Through controlled electrochemical dissolution assisted by ultrasound radiation, Fe2+ ions are produced in situ from metallic iron in the reaction mixture. The effects of ultrasound with electrolysis, temperature, amount of substrate present, reagent concentration, solution acidity and quantity of electric charge have been examined. Under suitable conditions, the synthesis yield based on initial PA present, hydrogen peroxide used and amount of iron dissolved reached 34, 40 and 75%, respectively and less by-product was observed. These results show significant improvement in terms of direct cost savings by omission of separate preparation of a ferrous salt, fewer side reactions during the dimerisation process, less waste, easier purification; increased efficiency due to recycling of iron ions and improved reactivity of fresh Fe2+ ions. All of these advantages make this sonoelectrochemical approach a much more efficient and environmentally cleaner option.",
author = "Bremner, {David H.} and Burgess, {Arthur E.} and Feng-Bin Li",
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A sonoelectrochemical Fenton process for efficient synthesis of tetramethyladipic acid from pivalic acid. / Bremner, David H.; Burgess, Arthur E.; Li, Feng-Bin.

In: Green Chemistry, No. 3, 04.2001, p. 126-130.

Research output: Contribution to journalArticle

TY - JOUR

T1 - A sonoelectrochemical Fenton process for efficient synthesis of tetramethyladipic acid from pivalic acid

AU - Bremner,David H.

AU - Burgess,Arthur E.

AU - Li,Feng-Bin

PY - 2001/4

Y1 - 2001/4

N2 - Tetramethyladipic acid (TMAA), a starting monomer for several technically important polymers (polyester resins and polyamide fibres) is synthesised by direct carbon–carbon bond formation between the saturated primary carbon atoms of pivalic acid (PA) using a sonoelectrochemical Fenton process. Through controlled electrochemical dissolution assisted by ultrasound radiation, Fe2+ ions are produced in situ from metallic iron in the reaction mixture. The effects of ultrasound with electrolysis, temperature, amount of substrate present, reagent concentration, solution acidity and quantity of electric charge have been examined. Under suitable conditions, the synthesis yield based on initial PA present, hydrogen peroxide used and amount of iron dissolved reached 34, 40 and 75%, respectively and less by-product was observed. These results show significant improvement in terms of direct cost savings by omission of separate preparation of a ferrous salt, fewer side reactions during the dimerisation process, less waste, easier purification; increased efficiency due to recycling of iron ions and improved reactivity of fresh Fe2+ ions. All of these advantages make this sonoelectrochemical approach a much more efficient and environmentally cleaner option.

AB - Tetramethyladipic acid (TMAA), a starting monomer for several technically important polymers (polyester resins and polyamide fibres) is synthesised by direct carbon–carbon bond formation between the saturated primary carbon atoms of pivalic acid (PA) using a sonoelectrochemical Fenton process. Through controlled electrochemical dissolution assisted by ultrasound radiation, Fe2+ ions are produced in situ from metallic iron in the reaction mixture. The effects of ultrasound with electrolysis, temperature, amount of substrate present, reagent concentration, solution acidity and quantity of electric charge have been examined. Under suitable conditions, the synthesis yield based on initial PA present, hydrogen peroxide used and amount of iron dissolved reached 34, 40 and 75%, respectively and less by-product was observed. These results show significant improvement in terms of direct cost savings by omission of separate preparation of a ferrous salt, fewer side reactions during the dimerisation process, less waste, easier purification; increased efficiency due to recycling of iron ions and improved reactivity of fresh Fe2+ ions. All of these advantages make this sonoelectrochemical approach a much more efficient and environmentally cleaner option.

U2 - 10.1039/b010123k

DO - 10.1039/b010123k

M3 - Article

SP - 126

EP - 130

JO - Green Chemistry

T2 - Green Chemistry

JF - Green Chemistry

SN - 1463-9262

IS - 3

ER -