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The Advances in Processes and Catalysts for the Production of Methyl Formate by Methanol Carbonylation – a Review

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The Advances in Processes and Catalysts for the Production of Methyl Formate by Methanol Carbonylation – a Review International Journal of Chemical & Petrochemical Technology (IJCPT) ISSN 2277-4807 Vol. 3, Issue 2, Jun 2013, 55-70 © TJPRC Pvt. Ltd. THE ADVANCES IN PROCESSES AND CATALYSTS FOR THE PRODUCTION OF METHYL FORMATE BY METHANOL CARBONYLATION – A REVIEW BIJAY N PATTANAIK R&D Centre, GNFC Ltd, Narmadanagar, Bharuch, Gujarat, India ABSTRACT Synthesis of methyl formate from six varieties of routes from different feed stocks is discussed. The commercial processes presently available for carbonylation of methanol to methyl formate using homogeneous catalyst (potassium methoxide /sodium methoxide) are summarized. This review also covers the advances in process technologies and research development to improve the efficiency of both homogeneous and heterogeneous catalysts for carbonylation of methanol to methyl formate. KEYWORDS: Methyl Formate, Methanol Carbonylation, Homogeneous Catalyst, Heterogeneous Catalyst, Anion Exchange Resins INTRODUCTION Methyl formate is one of the important chemical products of chemistry with varieties of applications. It is a versatile chemical precursor to a wide range of other chemicals such as formic acid, acetic acid, acetaldehyde, methyl acetate, ethylene glycol and formamide. The methyl formate is mainly used for production of formic acid by hydrolysis. The six routes for synthesis of methyl formate from different feed stocks are reported by Lee et.al[1].Presently industrial processes for production of methyl formate is dominated by methanol carbonylation using potassium methoxide /sodium methoxide catalyst[2]. Recent reported research studies to improve the current process technologies, alternative catalysts, both homogeneous and heterogeneous for carbonylation of methanol to methyl formate have been discussed. DIFFERENT ROUTES FOR METHYL FORMATE PRODUCTION Synthesis of methyl formate from six different routes is summarized in Figure 1. The details about different routes for the production of methyl formate are discussed below. Figure 1: Synthesis Routes for Methyl Formate 56 Bijay N Pattanaik Carbonylation of Methanol Dehydrogenation of Methanol Oxidative Dehydrogenation of Methanol Dimerization of Formaldehyde Direct Synthesis from Synthesis Gas Hydrocondensation of Carbon Dioxide with Methanol Carbonylation of Methanol The synthesis of methyl formate by carbonylation of methanol is well known chemistry. The methanol ─ carbonylation occurs through two step mechanism the methoxide ion reacts with CO to form CH3OCO which then reacts with methanol producing methyl formate and restoring the active catalyst. This is achieved by using an alkali metal methoxide catalyst dissolved in methanol at 60-120◦C and with 20-70 bar of CO. [3, 4] ─ ─ CH3O + CO (CH3OCO) (1) ─ ─ (CH3OCO) + CH3OH HCOOCH3 + CH3O (2) The overall reaction is given below CH3OH +CO HCOOCH3 (3) The nucleophilic attack of methoxide ion on carbon monoxide was proposed by Christansen [5] in 1942 and the kinetic studied by Tonner et.al.[6]. Some research work in methyl formate synthesis from methanol and CO aims at developing more robust catalyst systems that could avoid the problems experienced in alkali methoxide catalyst. This includes homogeneous ruthenium [7, 8], platinum [9] and tungsten [10] complexes and non metallic catalysts (guanidines) [11]. Unlike processes requiring the activation of carbon-oxygen bonds, these transition metal complex catalysts do not need halide promoters to form methyl formate by activation of the oxygen-hydrogen bond of methanol. These catalytic systems, however, are either in the stage of fundamental research or not as efficient as the current homogeneous sodium methoxide catalyst system. Details on the carbonylation of methanol using alkali metal methoxide are discussed later on. Dehydrogenation of Methanol Dehydrogenation of methanol over copper catalysts to yield methyl formate has been known since 1920s [12]. 2CH3OH HCOOCH3 + 2H2 (4) In addition to copper, silver, and tungsten carbide have been reported to be efficient catalyst for the dehydrogenation reaction. The catalytic dehydrogenation of methanol to methyl formate over copper supported catalysts has been studied [13].It is reported that the copper/silica and copper/zirconium oxide catalyst are very active and selective towards methyl formate formation. Oxidative Dehydrogenation of Methanol Methyl formate has also been synthesized by oxidative dehydrogenation of methanol to achieve a thermodynamically more favorable process. 2CH3OH + O2 HCOOCH3+ 2H2O (5) A liquid phase process at elevated pressure has been proposed due to the higher exothermic nature of the reaction soluble chromium compounds [14] or ruthenium complexes [15] are used as catalysts. The Advances in Processes and Catalysts for the Production of 57 Methyl Formate by Methanol Carbonylation – A Review The selective oxidation of methanol to formaldehyde, methyl formate and dimethoxymethane with the use of ruthenium oxide cluster supported on SnO2, ZrO2, TiO3 and SiO2 catalyst has been reported [16].The structure and properties of zirconia-supported ruthenium oxide catalyst for selective oxidation of methanol to methyl formate to design more effective catalysts has been studied in another paper[17]. A silver catalyst has been used for production of methyl formate for long catalyst life in an upgraded temperature [18]. The catalytic synthesis of methyl formate via a novel route from methyl nitrite in vapor phase has been reported ◦ by Zhuo et.al [19].The catalysts used for studies were H-Y zeolites, Na-Y zeolite, 4A molecular sieve, -Al2O3 and silica (KSG). The zeolites H-Y and Na-Y exhibit higher selectivity and yield of methyl formate. Two steps oxidation of methanol using heterogeneous catalyst have been suggested. The advantages of the process are the reaction conditions are fairly mild, the yield and selectivity of methyl formate was quite high and catalyst contained no precious metals i.e. Rh or Pd. Dimerization of Formaldehyde Methyl formate has been synthesized by dimerization of formaldehyde. This is a Tischenko type intermolecular oxidation-reduction reaction. 2HCHO HCOOCH3 (6) Methyl formate has also been synthesized by a Cannizaro reaction followed by esterification of formic acid with methanol. 2HCHO+ H2OCH3OH+HCOOH (7) CH3OH+HCOOHHCOOCH3+ H2O (8) Both homogeneous and heterogeneous catalytic systems have been reported for the above reactions. The reaction can be carried out more efficiently in the vapor phase over Cu-Zn. The reaction also can be carried out with SnO2-WO3 catalyst [20]. Direct Synthesis from Synthesis Gas The direct synthesis of methyl formate from synthesis gas can be achieved in a high-pressure liquid-phase reaction in the presence of homogeneous transition metal catalysts. 2CO + 2 H2 HCOOCH3 (9) Methyl formate and methanol are selectively produced with complexes of cobalt [21-23], ruthenium [23-26], or iridium [23] as a catalyst. Hydrocondensation of Carbon Dioxide with Methanol The hydrocondensation of carbon dioxide with alcohol has been described relatively recently. Methyl formate has been synthesized from methanol, CO2 and H2 in benzene in the presence of a catalyst composed of ruthenium, iridium, osmium or platinum complexes and BF3[27]. CO2+ H2+CH3OHHCOOCH3 + H2O (10) A low-valent complex of palladium, ruthenium, rhodium or iridium and a tertiary amine [28, 29], anionic ruthenium carbonyl clusters [30], and anionic group 6B metal carbonyl [31] are among recently reported catalysts. These catalysts show much greater activity for methyl formate formation from CO and CH3OH. 58 Bijay N Pattanaik A recent study for synthesis of methyl formate from methanol using a novel thermal coupled reactor (TCR) has been reported by Goosheneshin et.al. [32].The thermal coupled reactor containg methyl formate production in endothermic side and methanol synthesis in exothermic side has been investigated. The interesting feature of this TCR is the productive methanol in the exothermic side could be recycled and used as feed of the endothermic side for methyl formate synthesis. CARBONYLATION OF METHANOL TO METHYL FORMATE USING ALKALI METAL METHOXIDE CATALYST (POTASSIUM METHOXIDE / SODIUM METHOXIDE) Among these above routes to methyl formate, the carbonylation of methanol is more advantageous in terms of energy-efficiency and atom-efficiency, which currently, performed homogeneously using alkali metal methoxide catalysts dissolved in methanol with high CO conversions and methyl formate selectivities. However, the use of strong bases in this effective industrial process leads to inevitable problems such as corrosion and waste byproducts and in particular, deactivation by CO2 and H2O impurities. The carbonylation of methanol to methyl formate was described by BASF [33] in 1925. The sodium methoxide or potassium methoxide has also been proposed as a catalyst. It is more soluble in methyl formate and gives a higher reaction rate. High pressures were initially preferred for the carbonylation reaction but afterwards the carbonylation is carried out at lower pressure in the new plants. Under these conditions, reaction temperature and catalyst concentration must be increased to achieve acceptable conversion. The carbonylation reactions is carried out at 45 bar pressure, 80°C temperature and 2.5% sodium methoxide or potassium methoxide as catalyst. About 95 % carbon monoxide, but only about 30 % methanol, is converted under these circumstances. Nearly quantitative conversion of methanol to methyl formate can, nevertheless, be achieved by recycling the unreacted methanol.
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