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Hardjono Sastrohamidjojo
Chemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta
Chemical Engineering, Chemistry & Bioengineering Chemistry

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STUDY OF CATALYTIC CYCLISATION OF (+)-CITRONELLAL WITH Zn/γ-ALUMINA AS CATALYST Elvina Dhiaul Iftitah; Hardjono Sastrohamidjojo; M. Muchalal
Indonesian Journal of Chemistry Vol 4, No 3 (2004)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (251.006 KB) | DOI: 10.22146/ijc.21852

Abstract

The reaction of catalytic cyclisation of (+)-citronellal has been done using g-alumina and Zn/γ-alumina as catalysts. Zn/γ-alumina catalyst was prepared by impregnation of ZnBr2 into solid of γ-alumina in methanol as a solvent. The calcination process is performed on Muchalal reactor at 400 oC. The reactions were carried out under nitrogen gas atmosphere by mixing 5 mL sample and 1.0 g catalyst at 90-95 oC for 3 hours. The product of reaction was analyzed using GC, FT-IR and GC-MS. The reaction of cyclization of (+)-citronellal with γ-alumina catalyst did not give targeted product as well as reaction with Zn/g-alumina catalyst. Whereas, the reactions with Zn/γ-alumina catalyst gave four compounds of isopulegol stereoisomer. Conversion of (-)-Isopulegol, (+)-Neoisopulegol, (+)-Isoisopulegol and (+)-Neoisoisopulegol  were 64,29%, 18,80%, 9,20% and 3,32% respectively. For that reason, the transformation of (+)-sitronelal using Zn/γ-alumina was considered to be the best catalyst. A reaction mechanism is proposed where the (+)-citronellal molecule binds to a catalyst Lewis acid site via the aldehyde oxygen and the π-electrons of the double bond. Subsequent protonation of the aldehyde via a neighbouring Bronsted acid site initiates the cyclisation to isopulegol.
SYNTHESIS OF SAFRYL KETONE FROM SAFROLE Hanoch J Sohilait; Hardjono Sastrohamidjojo; Sabirin Matsjeh; J Stuart Grossert
Indonesian Journal of Chemistry Vol 4, No 1 (2004)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (45.071 KB) | DOI: 10.22146/ijc.21874

Abstract

Synthesis of safryl ketone from safrole has been achieved through conversion of allyl group to secondary alcohol, followed by oxidation with PCC-Al2O3. The oxymecuration-demercuration reaction of safrole with HgSO4-NaBH4 yields safryl alcohol (66.38%) and the oxidation of safryl alcohol with PCC-Al2O3 yields safryl ketone (62.92%). The structure elucidation of these products was conducted using Fourier Transformed Infra Red Spectroscopy (FTIR), Proton-Nuclear Magnetic Resonance (1H-NMR) and Mass Spectroscopy (MS).
SYNTHESIS OF SECONDARY ALCOHOL COMPOUNDS FROM SAFROLE AND METHYLEUGENOL Hanoch J Sohilait; Hardjono Sastrohamidjojo; Sabirin Matsjeh
Indonesian Journal of Chemistry Vol 3, No 3 (2003)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (41.974 KB) | DOI: 10.22146/ijc.21885

Abstract

Synthesis of secondary alcohols compound from safrole and methyleugenol has been achieved through conversion of allyl group to alcohol.The reaction of safrole and methyleugenol with mercuric acetate in aqueous tetrahydrofuran, followed by in situ reduction of the mercurial intermediate by alkaline sodium borohydride produced secondary alcohol namely safryl alcohol (71.25%) and methyleugenil alcohol (65.56%). The structure elucidation of these products were analyzed by FTIR, 1H-NMR, 13C-NMR and MS.
Co-Authors Elvina Dhiaul Iftitah Hanoch J Sohilait J Stuart Grossert M. Muchalal Sabirin Matsjeh