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The Liquid-Phase Hydrogenation of Citral to Citronellal at Hydrogen Pressure

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The Liquid-Phase Hydrogenation of Citral to Citronellal at Hydrogen Pressure International Journal of Chemical Engineering and Applications, Vol. 7, No. 2, April 2016 The Liquid-Phase Hydrogenation of Citral to Citronellal at Hydrogen Pressure U. Syunbayev, D. Kh. Churina, G. Y. Yergaziyeva, N. A. Assanov, and K. K. Kalihanov plant to a continuous process for producing desired products Abstract—The aim of the work is to obtain citronellal that is will allow to successfully solve the task. the odoriferous substance and refers to the fragrant compounds It should be noted that in the literature as well as in the used in perfumery and in the food industry as a flavoring. It is a production of practically no data for the selective raw material for producing aromatic substances - izopulegol, hydrogenation of organic compounds with conjugated double menthol, citronellol et al. The hydrogenation of citral to citronellal was investigated bond on stationary catalysts in the liquid phase [4], [5]. over the catalysts on the base of VIII group metals using special Thus, a systematic study of the influence of different high-pressure kinetic (KEHP) equipment allowing to keep the parameters on the selectivity of the hydrogenation of aromatic liquid phase hydrogenation process for any constant hydrogen substances in batch mode and in the channel of interest in two pressure in a wide variation of the experimental conditions. respects. On the activity of the catalysts studied are located in the On the one hand, these data provide new information that following sequence: NiR > Pt > Pd > Rh > Ni-black > Ir > Os > Ru. enhance understanding of the general laws of this process, The effect of different key parameters of the process (nature supplementing and clarifying the existing theoretical views on of the solvent, reduction temperature of catalyst, hydrogen this issue. On the other hand - allows optimum suspended and pressure, etc.) on the kinetics and selectivity of the fixed catalysts and conditions for the batch and continuous hydrogenation of citral to citronellal over the supported nickel process for selective hydrogenation of organic substances catalysts were studied. taken. In this regard, the development of scientific bases and Index Terms—Nickel-containing catalyst, citral, citronellal, hydrogen. cooking techniques of new, cheaper, selective catalysts and cost-effective technologies for the synthesis of continuous commercial products offer great prospects for the production I. INTRODUCTION of perfume and food industries [6]-[9]. This article presents the results of a study of the Experts estimate that over a prolonged time for obtaining of liquid-phase hydrogenation of citral as a model substance in complex organic compounds to relatively mild temperature the presence of VIII Group metals (Pd, Ni, Pt, Os, Rh, Ru, Ir conditions is using the method of liquid-phase hydrogenation -black, NiR) in a wide variation of the experimental in the presence of a catalyst batch wise. Increase in production conditions. A feature of this work is to study the kinetics of of perfumery and cosmetic industry can't be achieved by the development of active catalysts for the selective simply increasing the number of machines, plants and hydrogenation of citral in batch mode. factories. It is necessary to intensify the process and increase the removal of output per unit volume of the device. Progress in this area will significantly reduce the capital cost to II. EXPERIMENTAL implement the plan of perfume and cosmetics industry, will allow to emerge victorious in the competition, as well, is very In carrying out this work were used all the main types of important for the existence and prosperity of the industry or a equipment used for the study of hydrogenation processes at single plant in the world economy [1]-[3]. pressurizing hydrogen pressures (Fig. 1). To solve the Only for comprehensive works on the development and problems we used a special high-pressure kinetic (KEHP) implementation of new and effective technological schemes, equipment allowing to keep the liquid phase hydrogenation intensification of the main stages of production of odoriferous process for any constant hydrogen pressure of 0.1 to 9.8 MPa substances, in particular, the hydrogenation processes and and the reaction rate measured by the absorption of hydrogen per unit time. Major components of the apparatus (reactor surge vessel, piping) are made of stainless steel H18N1OT, Manuscript received April 7, 2015; revised June 20, 2015. This work was fine adjustment of the valves and other parts of steel X 45. supported in part by Ministry of Education and Science of the Republic of Reaction was carried out in a glass ampoule, which bears a Kazakhstan. U. Syunbayev and Yergaziyeva G. are with Institute of Combustion weighed catalyst and hydrogenated substance solvent. Problems MES RK Almaty, Kazakhstan (e-mail: [email protected], Supported catalysts Ni/Cr2O3, Ni/Al2O3, Ni/SiO2 were [email protected]). laboratory prepared to work as follows. The catalyst must be Churina D. and Assanov N. A. are with Center of Physical-chemical Methods of Investigations and Analysis of al-Farabi Kazakh National crushed in a conventional porcelain mortar, and then add as a University, Almaty, Kazakhstan (email: [email protected], powder to a special recovery furnace. Reduction is carried out [email protected]). in a stream of hydrogen at a predetermined temperature for a K. Kalihanov is with Institute of Combustion Problems MES RK, Almaty, Kazakhstan (email: [email protected]). certain time. After furnace cooling the reduced catalyst in DOI: 10.7763/IJCEA.2016.V7.557 133 International Journal of Chemical Engineering and Applications, Vol. 7, No. 2, April 2016 hydrogen must be transferred to a special solvent ampoule. The citronellal is the odoriferous substance and refers to The thus prepared catalyst can also be applied in an autoclave the fragrant compounds used in perfumery and in the food to carry out a hydrogenation process. industry as a flavoring. It is a raw material for producing Hydrogen from cylinders containing 0.3 mg / liter of aromatic substances - izopulegol, menthol, citronellol et al. moisture, oxygen, not more than 0.003%, obtained by In the hydrogenation of citral to citronellal were studied electrolysis, used without further purification. VIII group metals (Pd, Ni, Pt, Os, Rh, Ru, Ir -black, NiR) Chromatographic analysis of citral and citronellal and under the condition of 2.0 MPa and 303 K, as a solvent was hydrogenation products was carried out on a chromatograph used 96% ethanol. The results are shown in Table I. "Chromium 1000" with a flame ionization detector, carrier gas - helium. TABLE I: CATALYSATE COMPOSITION (AT THE TIME DESORBTION OF 1 MOL H2) IN THE HYDROGENATION OF CITRAL ON METALS OF GROUP VIII Yield of the products, % S, % citral citronellal citronellol Pd 13.5 74.5 11.0 75.3 Pt 39.0 22.0 38.4 36.1 Rh 24.0 52.0 24.0 68.4 Ru 4.0 90.0 6.0 93.7 Ni 11.5 77.0 11.5 87.0 Ir 21.0 60.0 12.0 60.3 29.6 Os 46.0 16.0 16.0 Table I shows that on the selectivity for the hydrogenation 1 - a cylinder with H2 of 150 atm; 3 - burette; 5 - surge vessel; 7 - flame arrester; 9 - catalytic "duck"; 10 - Fleet rocking chair; 2,4,6,8,11 - fine of citral to citronellal investigated catalysts arranged in the adjustment valves; 12 - buffer with H2; 13 - ultra-thermostat; B - manometer, following: Ru (93.7%) > Ni (87.0%) > Pd (75.3%) > Rh A - substance vial. (68.4%) > Ir (60.3%) > Pt (36.1%) > Os (29.2%). Fig. 1. Technological scheme of installation KEHP. On the activity of the catalysts studied are located in the following order: NiR > Pt > Pd > Rh > Ni- black > Ir > Os > Ru. The experiments were carried out in the following order. A At the hydrogenation on Pt and Os in catalysate remains hitch of the catalyst included in the vial with a specific volume unreacted citral (≈ 40%). of solution per hour is saturated with hydrogen at a So, more selective catalysts for hydrogenation of citral to predetermined pressure and temperature of the experiment, is citronellal than the more complete is the hydrogenation then introduced citral weighed for hydrogenation. process. In catalysate remains about 4 % of citral. Before saturation and hydrogenation the system was These results indicate that for the hydrogenation of citral as purged with hydrogen volume of 1.5-2.0 l, which selective catalysts may be used metals based on nickel, corresponded to 7-10 times the volume of gas in the system. ruthenium and palladium. Impermeability of the system before the experiment was Given the number of indicators of economy and availability tested for 20-30 minutes at zero mark. The ampoule was of our further studies for the selective hydrogenation of citral placed in a catalytic "duck", mounted on a high-speed shaker to citronellal were used deposited nickel catalysts. The with a stirring rate of 700 per minute sided swing at the application of nickel on the carrier increases the catalyst amplitude of the oscillations of 10 cm, which allows to realize lifetime, enhance its activity and in most cases, a change of its the reaction in the out kinetic area. selective action. Reliability is characterized by kinetic results Nickel catalyst supported on carrier: γ -Al2O3, SiO2, Cr2O3, reproducibility of experimental data and the accuracy of a Al2O3- Cr2O3 are widely used in industry. Therefore, we single measurement, according to our experimental data and investigated the influence of the nature of the solvent, the calculation of the maximum possible error kinetic temperature reduction and other key parameters of the measurements in our experiments does not exceed 5-7%. process on the catalytic properties of industrial supported When carrying out the experiments, the emphasis was clean nickel catalysts.
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