M. Muchalal
Faculty of Mathematics and Natural Sciences Universitas Gadjah Mada Yogyakarta

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THE KINETIC OF CYCLIZATION-ACETYLATION (R)-(+)-CITRONELLAL WITH ANHYDRIDE ACETIC ACID WHICH CATALYZED OF Zn2+-NATURAL ZEOLITE Cahyono, Edy; Muchalal, M.; Triyono, Triyono; Pranowo, Harno Dwi
Jurnal Zeolit Indonesia Vol 8, No 1 (2009)
Publisher : Jurnal Zeolit Indonesia

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (131.024 KB)

Abstract

Reaction kinetic of acetylation-cyclization (R)- (+)-citronellal with acetic acid anhydride which catalyzed Zn2+-zeolite (Zn2+-Za) was analyzed by Langmuir- Hinshelwood Models. (R)-(+)-citronellal isolated from lemongrass oil with fractionation distillation reduced pressure and analyzed anantiomer ratio with GC chiral column β- DEX 225. Catalyst preparation of Zn2+-Za conducted by acid activation on natural zeolite Malang 100 mesh using 1% HF and 6 M HCl, then soaked on 0,1 M NH4Cl. Calcination was done at 450oC during 1 hour with N2 flow to achieved H-natural zeolite (HZa). Cation exchange H-Za with 0,1 M ZnCl2 conducted to obtain Zn2+-natural zeolit (Zn2+-Za). Reactions of Cyclization-acetylation (R )-(+)- citronellal using a catalyst of Zn2+-Za was done by varying molar ratio of (R )-(+)- citronellal with acetic acid anhydride, namely 0.25, 0.5, 1.0; 1 , 25; 1.5. During the reaction, into system, samples were taken each 1 mL of reaction with duration 10, 20, 30, 60, 120, 180 minutes. Reaction product was extracted with n-hexana. Structure elucidation was done by GC-MS, FTIR spectrophotometer, and 1H-NMR spectrometer. The result showed a greater molar ratio (R)-(+)-citronellal against quantity of acetic acid anhydride acetic, pulegil total was decline. Acetylation-cyclization catalyzed with Zn2+-Za on duration of 30 minutes and 80°C has k of 30.964 to 47.619 mmol (minute.gram catalyst)-1 and KSIT/KAA of 7.09.
Ibuprofen salt production and its application in tablet dosage form Hadisoewignyo, Lannie; Fudholi, Achmad; Muchalal, M.
INDONESIAN JOURNAL OF PHARMACY Vol 20 No 3, 2009
Publisher : Faculty of Pharmacy Universitas Gadjah Mada, Yogyakarta, Skip Utara, 55281, Indonesia

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (664.59 KB) | DOI: 10.14499/indonesianjpharm0iss0pp141-150

Abstract

Ibuprofen is an anti-inflammatory drug and is practically insoluble in water. The low melting point and the poor flowability of ibuprofen can lead to process difficulty in tablets production. The purpose of this research was to make the sodium salt form of ibuprofen which has better solubility in water.Sodium ibuprofen salt was prepared by reacting the ibuprofen and sodium hydroxide, then characterized using TG/DTA, DSC, spectrophotometer UV-VIS, spectrophotometer IR, X-ray diffraction, and SEM. Tablets were prepared by wet granulation method.The characterization result showed that sodium ibuprofen result of the synthesis was dehydrate form with melting point of 199.9 °C. Granules of sodium ibuprofen result of the synthesis had better flowability and bigger density than ibuprofen granules. The physical characterization of the tablet showed that the formula of sodium ibuprofen resulted from the. Sodium ibuprofen showed the higher release rate than ibuprofen so can give quicker onset of action.Key words: sodium ibuprofen, ibuprofen, dissolution.
Sintesis Ester Sorbitol Oleat Menggunakan Lipase dari Getah Pepaya, Candida rugosa dan Rhizopus arrhizus ( Suhardi, Suhardi; Tranggono, Tranggono; Hastuti, Pudji; Muchalal, M.
Agritech Vol 26, No 3 (2006)
Publisher : Faculty of Agricultural Technology, Universitas Gadjah Mada, Yogyakarta, Indonesia

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22146/agritech.9591

Abstract

The ability of  lipase from Carica papaya latex, Candida rugosa and Rhizopus arrhizus to catalyze esterification of sorbitol and oleic acid to produce Sorbitol Oleat Esters (SOE) was investigated in this study. Response Surface Methodology (RSM) was employed to evaluate the effects of temperature (x1 =40-50oC), reaction time (x2=24-72 hours), concentration of enzyme (x3=25-75 units),  on percentage molar conversion as well as to determine the optimum condition of this reaction in term of this factors. Based on RSM analysis using  lipase from Carica papaya latex, the optimum synthesis conditions that giving 58.31% molar conversion, were : temperature of 45.15oC, reaction time  51.73  hours, concentration of enzyme 37 units. Using lipase from Candida rugosa , the optimum synthesis conditions that giving 59.49 % molar conversion, were : temperature of 45.08oC, reaction time  53.42 hours, concentration of enzyme 75 units.  Using lipase from Rhizopus arrhizus, the optimum synthesis conditions that giving 61.89 % molar conversion, were : temperature of 45.01oC, reaction time  61.68 hours, concentration of enzyme 66 units.  The characteristics of SOE products using lipase from Carica papaya latex and Rhizopus arrhizus were degree of esterification (DE) 1 and (DE) 2,  hydrophilic lypophilic balance 7.5-8.0, and surface tension  34.8-35.1 dyne/cm. SOE products using lipase from Candida rugosa were DE 1, DE 2, and DE 3, hydrophilic lypophilic balance 3-6, and surface tension  31.18-31.83 dyne/cm. and capable to maintain emulsion of water in oil.
Sintetis secara Semi Kontinyu Biosurfaktan Ester Sorbitol Oleat Menggunakan Lipase Getah Pepaya Imobil Suhardi, Suhardi; Tranggono, Tranggono; Hastuti, Pudji; Muchalal, M.
Agritech Vol 26, No 1 (2006)
Publisher : Faculty of Agricultural Technology, Universitas Gadjah Mada, Yogyakarta, Indonesia

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22146/agritech.9466

Abstract

Study on synthesis of sorbitol oleiate ester biosurfactan using Carica papaya latex immobilized-hpase as catalyst was caned out using oleic acid as a raw material. In the first step, process optimization for biosurfactan production was done with Carica papaya latex immobilized-lipase as acatalyst using a semi continuous methods. Lipase from Carica papaya latex was extracted using phosphate buffer pH 7.3 containing NaCI 0.1M then precipitated with addition of ammonium sulphate. Furthermore, the precipitated enzyme was solubilized in phosphate buffer pH 7.3, immobilized on Na-alginat (3%) and dried in freeze drier. Some variables for reaction were studied consisting of water concentration (20, 40, 60%), silica gel (0, 60, 120%) and reaction time (24,48,72 hours) with lipase concentration of 10%, and incubated at 45°C for those determined times and the acid value was monitored. In the second step, production of biosurfactant was also carried out using the semi-continuous methods, oleic acid and sorbitol were used as reactans and immobilzed-lipase of Carica papaya latex as a catalyst. Product fungsional properties were also determined including hydroxyl value, refraction index, melting point, fatty acid composition and HLB ( hydrophylic-lipophylic balance) value, surface tension and emulsifier characteristics. Result showed that : semi continuous production of sorbitol fatty acid ester with feed rate 0.1 ml per minute, temperature 45°C, 10% immobilized-lipse of Carica papaya latex, water: sorbitol ratio (40.16%), silica gel: water ratio (63.66%), sorbitol : oleic acid ratio (1:3 mol), incubation time 41.37 hours, resulted 54.96% product. The product characteristics were as follows : sorbitol oleiate acid ester content 70%, rendement 60%, hydroxil value 57 mg KOH/g, melting point 165°C, refractive index 1.4590, HLB value 7.5, surface tension 31.83 dyne/cm, capacity to keep emulsion (W/O) stability 140 minutes.
CYCLIZATION AND HYDROGENATION OF (+)-CITRONELLAL TO MENTHOLS OVER ZnBr2 AND Ni CATALYSTS SUPPORTED ON γ-Al2O3 Iftitah, Elvina Dhiaul; Muchalal, M.; Trisunaryanti, Wega; Armunanto, Ria
Indonesian Journal of Chemistry Vol 10, No 2 (2010)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (1114.243 KB) | DOI: 10.22146/ijc.21461

Abstract

Two steps transformation of (+)-citronellal, cyclization and hydrogenation, on ZnBr2/γ-Al2O3 and Ni/γ-Al2O3 catalyst have been realized with the selectivity to cyclization products (isopulegols) was very high (yield up to ~92.58%) over ZnBr2/γ-Al2O3 under mild condition (90 °C and 1 atm nitrogen atmosphere) with high Brønsted acid concentration, while at the same time very low cyclization rates were achieved over Ni/γ-Al2O3 with low or no Brønsted acidity, respectively. The highest cyclization rates were observed over Ni/ZnBr2/γ-Al2O3 under mild condition (90 °C and 1 atm hydrogen atmosphere). The second step transformation towards cyclization products, hydrogenation to menthols, was performed with Ni/γ-Al2O3 under hydrogen atmosphere. Surprisingly the one-step transformation of (+)-citronellal into menthols was investigated over Ni/γ-Al2O3 with yield ~84% under hydrogen atmosphere (90 °C, 1 atm) by exploiting the presence of acidic and hydrogenation sites on the catalyst surface. On the Ni/γ-Al2O3 catalyst it was found that the cyclization of (+)-citronellal to isopulegols occurs on the surface of the support. In the presence of the noble metal, the isopulegols are further hydrogenated to the menthols.   Keywords: cyclization, hydrogenation, citronellal, isopulegol, menthol
THE STEREOCHEMISTRY EFFECT OF EUGENOL, CIS-ISOEUGENOL AND TRANS-ISOEUGENOL ON THEIR CATALYTIC HIDROGENATION Muchalal, M.
Indonesian Journal of Chemistry Vol 4, No 2 (2004)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (230.435 KB) | DOI: 10.22146/ijc.21861

Abstract

The stereochemistry effect of eugenol, cis-isoeugenol and trans-isoeugenol on their catalytic hydrogenation by Ni/g-Al2O3 catalyst was investigated. In this investigation, the catalyst is prepared by impregnation of Nickel into solid of γ-Al2O3 in methanol as a solvent. The calcination process, which is followed by reduction, is performed on Muchalal reactor at 400 oC. After that, the catalytic hydrogenation is carried out under hydrogen gas atmosphere by mixing 10 mL sample and 0.5 g Ni/g-Al2O3 catalyst at 200 oC for 3 hours. The stereochemistry effect of reactants is evaluated by computer modelling using PM3 semiempirical methods. The mass spectrum of catalytic hydrogenation product from those compounds shows a molecular ion at m/z 164, which proves the existence of 2 -methoxy-4-propylphenol. The eugenol gives the highest conversion (99%), followed by cis-isoeugenol (81%) and trans-isoeugenol (67%). It was found that there is a correlation between the stereochemistry of those compounds and catalytic reactivity.   Keywords: stereochemistry effects, 2-methoxy-4-propylphenol
Isolation and Identification of Volatile Components in Tempe by Simultaneous Distillation-Extraction Method by Modified Extraction Method Syahrial, Syahrial; Muchalal, M.
Indonesian Journal of Chemistry Vol 1, No 2 (2001)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22146/ijc.21945

Abstract

An isolation and identification of volatile components in temps for 2, 5 and 8 days fermentation by simultaneous distillation-extraction method was carried out. Simultaneous distillation-extraction apparatus was modified by Muchalal from the basic Likens-Nickersons design. Steam distillation and benzena as an extraction solvent was used in this system. The isolation was continuously carried out for 3 hours which maximum water temperature In the Liebig condenser was 8 °C. The extract was concentrated by freeze concentration method, and the volatile components were analyzed and identified by combined gas chromatography-mass spectrophotometry (GC-MS). The Muchalals simultaneous distillation extraction apparatus have some disadvantage in cold finger condenser, and its extractor did not have condenser. At least 47, 13 and 5 volatile components were found in 2, 5 and 8 days fermentation, respectively. The volatile components in the 2 days fermentation were nonalal, ɑ-pinene, 2,4-decadienal, 5-phenyldecane, 5-phenylundecane, 4-phenylundecane, 5-phenyldodecane, 4-phenyldodecane, 3-phenyldodecane, 2-phenyldodecane, 5-phenyltridecane, and caryophyllene; in the 5 days fermentation were nonalal, caryophyllene, 4-phenylundecane, 5-phenyldodecane, 4-phenyldodecane, 3-phenyldodecane, 2-phenyldodecane; and in the 8 days fermentation were ethenyl butanoic, 2-methy1-3-(methylethenyl)ciclohexyl etanoic and 3,7-dimethyl-5-octenyl etanoic.
STUDY OF EPOXIDE DECYCLISATION OF CARYOPHYLENE OXIDE WITH SYNTHETIC ZEOLITE AS CATALYSTS Haryadi, Winarto; Muchalal, M.
Indonesian Journal of Chemistry Vol 4, No 2 (2004)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (263.633 KB) | DOI: 10.22146/ijc.21860

Abstract

The reaction of epoxide ring opening of caryophillene oxide has been done using zeolite H-Y, H-sodalit, and H-ZSM-5 as catalysts. The reactions were done in two types, there were in dioxane solvent at temperature of 110 oC and without solvent at temperature of 175 oC. The catalyst weight was 10 % from caryophillene oxide weight, and the time of reaction was four hours. The product of reaction was analyzed using GC, FTIR, and GC-MS. The reactions of caryophillene oxide in dioxane solvent with the three kinds of zeolites did not give any targeted product. Whereas, the reactions without solvent gave three main products, there was one compound with one group of secondary hidroxyl (secondary alcohol), and two compounds of ketone from caryophillene. The reaction product of caryophillene oxide obtained without using solvent with the three type of catalysts were then compared. Conversion of three main products produced by H-ZSM-5 catalyst, H-sodalit catalyst and H-Y catalyst were 82.11 %, 54.92 % and 38.53 % respectively. For that reason, the transformation of caryophillene oxide using H-ZSM-5 catalyst was considered to be the best selective product. The alcohol product was resulted from reaction between caryophillene oxide and Bronsted acid, and  the ketone products was resulted from the reaction with Lewis acid in zeolite.   Keywords: Epoxide ring opening, HY, H-sodalit and HZSM-5
STUDY OF CATALYTIC CYCLISATION OF (+)-CITRONELLAL WITH Zn/γ-ALUMINA AS CATALYST Iftitah, Elvina Dhiaul; Sastrohamidjojo, Hardjono; Muchalal, M.
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.   Keywords: catalytic cyclisation, impregnation, (+)-isopulegol