Formation of citraconic anhydride via condensation of dialkyl succinates and formaldehyde

Dushyant Shekhawat, Kirthivasan Nagarajan, James E. Jackson, Dennis J. Miller

Research output: Contribution to journalArticle

  • 8 Citations

Abstract

The formation of citraconic anhydride (CAN) from the condensation of succinic acid and its derivatives with formaldehyde over oxide catalysts is described. Alumina and aluminum phosphate are active catalysts that give selectivity to citraconic anhydride as high as 75% in an integral fixed bed reactor. Weakly acidic sites on the catalyst surface, particularly Lewis acid sites, are responsible for activating the desired reaction pathway. Strongly acidic sites lead to cracking and coking, while basic sites facilitate the Cannizzaro reaction of formaldehyde to carbon dioxide and methanol. Catalyst deactivation via coking occurs over the course of reaction, but activity is easily restored by regeneration in air at elevated temperatures. The reaction system under investigation is part of an overall process to produce itaconic acid from renewable resource-based succinic acid.

LanguageEnglish (US)
Pages261-273
Number of pages13
JournalApplied Catalysis A: General
Volume223
Issue number1-2
DOIs
StatePublished - 2002

Profile

Succinates
Formaldehyde
Condensation
Coking
Succinic Acid
Catalysts
Acids
Lewis Acids
Catalyst deactivation
Catalyst selectivity
Aluminum Oxide
Carbon Dioxide
Oxides
Methanol
Derivatives
Carbon dioxide
Phosphates
Alumina
Air
Aluminum

Keywords

  • Alumina
  • Aluminum phosphate
  • Citraconate
  • Citraconic anhydride
  • Formaldehyde
  • Itaconate
  • Itaconic acid
  • Stobbe condensation
  • Succinic acid

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology

Cite this

Formation of citraconic anhydride via condensation of dialkyl succinates and formaldehyde. / Shekhawat, Dushyant; Nagarajan, Kirthivasan; Jackson, James E.; Miller, Dennis J.

In: Applied Catalysis A: General, Vol. 223, No. 1-2, 2002, p. 261-273.

Research output: Contribution to journalArticle

@article{87dfb3de640c4b7bbe1671e243a25822,
title = "Formation of citraconic anhydride via condensation of dialkyl succinates and formaldehyde",
abstract = "The formation of citraconic anhydride (CAN) from the condensation of succinic acid and its derivatives with formaldehyde over oxide catalysts is described. Alumina and aluminum phosphate are active catalysts that give selectivity to citraconic anhydride as high as 75{\%} in an integral fixed bed reactor. Weakly acidic sites on the catalyst surface, particularly Lewis acid sites, are responsible for activating the desired reaction pathway. Strongly acidic sites lead to cracking and coking, while basic sites facilitate the Cannizzaro reaction of formaldehyde to carbon dioxide and methanol. Catalyst deactivation via coking occurs over the course of reaction, but activity is easily restored by regeneration in air at elevated temperatures. The reaction system under investigation is part of an overall process to produce itaconic acid from renewable resource-based succinic acid.",
keywords = "Alumina, Aluminum phosphate, Citraconate, Citraconic anhydride, Formaldehyde, Itaconate, Itaconic acid, Stobbe condensation, Succinic acid",
author = "Dushyant Shekhawat and Kirthivasan Nagarajan and Jackson, {James E.} and Miller, {Dennis J.}",
year = "2002",
doi = "10.1016/S0926-860X(01)00762-1",
language = "English (US)",
volume = "223",
pages = "261--273",
journal = "Applied Catalysis A: General",
issn = "0926-860X",
publisher = "Elsevier",
number = "1-2",

}

TY - JOUR

T1 - Formation of citraconic anhydride via condensation of dialkyl succinates and formaldehyde

AU - Shekhawat,Dushyant

AU - Nagarajan,Kirthivasan

AU - Jackson,James E.

AU - Miller,Dennis J.

PY - 2002

Y1 - 2002

N2 - The formation of citraconic anhydride (CAN) from the condensation of succinic acid and its derivatives with formaldehyde over oxide catalysts is described. Alumina and aluminum phosphate are active catalysts that give selectivity to citraconic anhydride as high as 75% in an integral fixed bed reactor. Weakly acidic sites on the catalyst surface, particularly Lewis acid sites, are responsible for activating the desired reaction pathway. Strongly acidic sites lead to cracking and coking, while basic sites facilitate the Cannizzaro reaction of formaldehyde to carbon dioxide and methanol. Catalyst deactivation via coking occurs over the course of reaction, but activity is easily restored by regeneration in air at elevated temperatures. The reaction system under investigation is part of an overall process to produce itaconic acid from renewable resource-based succinic acid.

AB - The formation of citraconic anhydride (CAN) from the condensation of succinic acid and its derivatives with formaldehyde over oxide catalysts is described. Alumina and aluminum phosphate are active catalysts that give selectivity to citraconic anhydride as high as 75% in an integral fixed bed reactor. Weakly acidic sites on the catalyst surface, particularly Lewis acid sites, are responsible for activating the desired reaction pathway. Strongly acidic sites lead to cracking and coking, while basic sites facilitate the Cannizzaro reaction of formaldehyde to carbon dioxide and methanol. Catalyst deactivation via coking occurs over the course of reaction, but activity is easily restored by regeneration in air at elevated temperatures. The reaction system under investigation is part of an overall process to produce itaconic acid from renewable resource-based succinic acid.

KW - Alumina

KW - Aluminum phosphate

KW - Citraconate

KW - Citraconic anhydride

KW - Formaldehyde

KW - Itaconate

KW - Itaconic acid

KW - Stobbe condensation

KW - Succinic acid

UR - http://www.scopus.com/inward/record.url?scp=0037050135&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037050135&partnerID=8YFLogxK

U2 - 10.1016/S0926-860X(01)00762-1

DO - 10.1016/S0926-860X(01)00762-1

M3 - Article

VL - 223

SP - 261

EP - 273

JO - Applied Catalysis A: General

T2 - Applied Catalysis A: General

JF - Applied Catalysis A: General

SN - 0926-860X

IS - 1-2

ER -