Synthesis of maleic and succinic acid monoesters of cardanol from cashew (Anarcadium occidentale L.) nut shell liquid

Date

4-2010

Degree

Bachelor of Science in Chemistry

College

College of Arts and Sciences (CAS)

Adviser/Committee Chair

Hidelisa P. Hernandez

Abstract

A dark brown viscous natural CNSL was extracted using screw-type mechanical oil expeller. The TLC analysis showed three spots corresponding to cardol, anacardic acid, and cardanol. Technical CNSL was prepared by heating the mixture of natural CNSL and Ca(01-1)2 at 140 °C - 150 °C for three hours. Treatments such as technical isopropyl alcohol extraction and calcium anacardate precipitation were done to remove the polymeric materials and the unconverted anacardic acid components. The TLC analysis of the alcoholic technical CNSL showed two spots corresponding to cardanol and cardol. Cardanol was isolated from technical CNSL using a modified procedure of Kumar et al. (2002). Alcoholic technical CNSL was reacted 28% ammonium hydroxide, extracted with DCM. and acidified obtaining the orange crude cardanol. The TLC analysis of crude cardanol showed spots corresponding to cardanol and polymeric materials. The crude cardanol was purified through VLC obtaining yellow eluates. The NMR and '3C NMR analysis confirmed that the pure isolate was cardanol with saturated, monoene, diene, and triene pentadecyl side chain. Cardanol monoesters of maleic (MAM) and succinic acids (SAMH) were prepared via nucleophilic acyl substitution reaction maintained at low-water and low-temperature conditions. Acidification step for MAM formation was not performed to prevent the geometric isomerization of the maleic acid moiety. Each of the crude SAMH and MAM were purified through VLC by gradient elution. The TLC analysis of pure SAMH and MAM showed spots corresponding to SAMH and MAM which confimied the formation and isolation of SAMH and MAM. The IH NMR and '3C NMR analysis confirmed the presence of cardanol monoesters of maleic and succinic acids. However, traces of cardanol and other impurities in SAMII and MAM were also confirmed.

Language

Filipino

Location

UPLB Main Library Special Collections Section (USCS)

Call Number

Thesis

Document Type

Thesis

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