Isolation and purification of cardanol from cashew (Anarcadium occidentale, L.) nut shell liquid and synthesis of cardanyloxyacetic acid

Date

4-2009

Degree

Bachelor of Science in Chemistry

College

College of Arts and Sciences (CAS)

Adviser/Committee Chair

Hidelisa P. Hernandez

Abstract

ABSTRACT

NATIVIDAD, JAMES THOMAS G. College of Arts and Sciences, University of the Philippines Los Banos, April 2009. Isolation and Purification of Cardanol from Cashew (Anacardium occidentale L) Nut Shell Liquid and Synthesis of Cardanyloxyacetic Acid

Adviser: HIDELISA P. HERNANDEZ, Ph. D.

Natural cashew nut shell liquid (CNSL) was extracted from dried cashew nut shells through mechanical expulsion and Soxhlet extraction. The CNSL obtained from the mechanical oil expeller was dark brown and highly viscous with percentage yield of 24.97%, (g/g) whereas, that extracted through Soxhlet extraction was dark red brown and slightly viscous with percentage yield of 26.708 % (g/g). Natural CNSL was subjected to thin layer chromatography (TLC) to establish the retardation properties of the major phenolic components, namely, anacardic acid, cardanol, and cardol.

Technical CNSL was prepared by heating the natural CNSL with calcium hydroxide at 160-180°C for 100 minutes. The percentage yield for this procedure was found to be 84.71%. The decarboxylation of anacardic acid was confirmed by TLC and Fourier Transform-Infrared (FT-IR) analysis.

Cardanol and cardol were separated extracting cardol with aqueous ammonia. The violet viscous crude cardanol isolate was subjected to column chromatography producing a translucent dark red orange and slightly viscous cardanol. Yield was 81. 44 % based on mass/mass technical CNSL. The purity and identity of cardanol was confirmed by TLC, FT-IR and NMR spectroscopic analyses.

The aryloxyacetic acid derivative of cardanol was prepared by the Williamson ether synthesis from chloroacetic acid. The percentage yield for the synthesis of cardanyloxyacetic acid was 78.19% based on mass/ mass cardanol. The crude product was subjected to column • chromatography and the percent recovery was 87.56% based on mass/mass crude product. Thin layer chromatography of the purified compound resulted in a chromatogram with a single spot lower than that of cardanol. The purified compound was also subjected to ER, IH and "C NMR spectroscopic analyses, wherein, peaks corresponding to carbonyl group and aromatic ether were confirmed to be present, thus, proving that cardanyloxyacetic acid was indeed synthesized. An attempt to synthesize aryloxypropionic acid derivative of cardanol was also done through Williamson ether reaction using 3-chloropropionic acid and subjected to IR, ill and "C NMR spectroscopic analyses; however, no peaks in the spectra corresponded to those of carbonyl group and aromatic ether, therefore, confirming that the derivative was not synthesized successfully.

Language

English

Location

UPLB Main Library Special Collections Section (USCS)

Call Number

LG 993.5 2009 C4 N38

Document Type

Thesis

This document is currently not available here.

Share

COinS