Developing a novel catalytic approach for imine formation by using self-replicating catalyst

Fatin Ilyani Nasir, Douglas Philp, Siti Aishah Hasbullah, Nurul Izzaty Hassan

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Abstract

Synthesis of imine compounds usually results in moderate yield due its reversibility characteristic and prone to hydrolysis. Hence, to increase the formation of imine compound, self-replicating catalyst was introduced. The self-replicating catalyst is the imine product itself. The first imine compound, 4-{[4-(3,5-Dimethyl-phenylcarbamoyl)-benzylidene]-amino}-phenyl)-acetic acid has been synthesized from 4-Amino-N-(3,5-dimethyl-phenyl)-benzamide and (4-formyl-phenyl)-acetic acid. Simultaneously, 4-formylbenzoic acid was reacted with thionyl chloride to produce 4-formylbenzoyl chloride, which was then reacted with 2-amino-4,6-dimethylpyridine in the presence of triethylamine to afford N-(4,6-dimethyl-pyridin-2-yl)-4-formyl-benzamide. N-(4,6-dimethyl-pyridin-2-yl)-4-formyl-benzamide formed then reacted with 4-amino-2-methylbenzoic acid to form the second imine derivative, 4-{[4-(4,6-dimethyl-pyridin-2-ylcarbamoyl)-benzylidene]-amino}-2-methyl-benzoic acid. The concentration time profile for the synthesis of self-replicating imine 1 reveals the classic sigmoidal shape characteristics of an autocatalytic process and the rate of the reaction are higher than that observed in the absence of recognition. In order to demonstrate the nature of self-replicating catalyst, a preformed imine 1 was doped into the reaction mixture of amine 1 and the corresponding aldehyde, 4-formylbenzoic acid. The insertion of substoichiometric amounts (15 mol%) of imine 1 at the start of the reaction has accelerated the rate formation of imine 1.

Original languageEnglish (US)
Title of host publication2015 UKM FST Postgraduate Colloquium
Subtitle of host publicationProceedings of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology 2015 Postgraduate Colloquium
EditorsMohd Shahrul Mohd Nadzir, Humaida Banu Samsudin, Marlia Mohd Hanafiah, Asmat Ahmad, Nurul Izzaty Hassan, Izfa Riza Hazmi, Hani Kartini Agustar, Zahari Ibarahim, Noor Baa'yah Ibrahim, Sakhinah Abu Bakar, Mohd Salmi Md Noorani, Nurul Huda Abd Karim, Saiful Irwan Zubairi, Nazlina Ibrahim
PublisherAmerican Institute of Physics Inc.
ISBN (Electronic)9780735413252
DOIs
StatePublished - Sep 25 2015
Event2015 Postgraduate Colloquium of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology, UKM FST 2015 - Selangor, Malaysia
Duration: Apr 15 2015Apr 16 2015

Publication series

NameAIP Conference Proceedings
Volume1678
ISSN (Print)0094-243X
ISSN (Electronic)1551-7616

Other

Other2015 Postgraduate Colloquium of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology, UKM FST 2015
CountryMalaysia
CitySelangor
Period4/15/154/16/15

Keywords

  • autocatalytic
  • imine
  • self-replicating

ASJC Scopus subject areas

  • Physics and Astronomy(all)

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