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Immobilized Molybdenum Acetylacetonatecomplex On RSC Advances This is an Accepted Manuscript, which has been through the Royal Society of Chemistry peer review process and has been accepted for publication. Accepted Manuscripts are published online shortly after acceptance, before technical editing, formatting and proof reading. Using this free service, authors can make their results available to the community, in citable form, before we publish the edited article. This Accepted Manuscript will be replaced by the edited, formatted and paginated article as soon as this is available. You can find more information about Accepted Manuscripts in the Information for Authors. Please note that technical editing may introduce minor changes to the text and/or graphics, which may alter content. The journal’s standard Terms & Conditions and the Ethical guidelines still apply. In no event shall the Royal Society of Chemistry be held responsible for any errors or omissions in this Accepted Manuscript or any consequences arising from the use of any information it contains. www.rsc.org/advances Page 1 of 8 RSC Advances Journal Name RSC Publishing ARTICLE Immobilized molybdenum acetylacetonatecomplex on expanded starch for epoxidation of stillingia oil Cite this: DOI: 10.1039/x0xx00000x Mei Hong, Meng-Yue Yao and Hui Pan* Received 00th January 2012, An active heterogeneous, namely molybdenum acetylacetonate complex immobilized on Accepted 00th January 2012 expanded corn starch (ECS-MoO 2(acac) 2), was prepared and its catalytic activity for epoxidation of stillingia oil with tert -butyl hydroperoxide (TBHP) was investigated. The DOI: 10.1039/x0xx00000x heterogeneous catalysts were characterized using inductively coupled plasma optical emission www.rsc.org/ spectrometry, Fourier transform infrared spectra, thermogravimetry and differential thermal analyses, scanning electron microscopy, N 2 adsorption-desorption and X-ray photoelectron spectroscopy. By using this catalyst, an environmentally benign process for epoxide production in a heterogeneous manner was developed. The catalyst could be recovered easily and reused without significant degradation in activity for at least 5 times. Manuscript 1 Introduction homogeneous catalysts, such as facile separation and recovery of solid catalyst from the reaction mixture for recycling without Stillingia oil is the seed oil of Chinese tallow tree. It has tedious work. 8 Among the transition metal complexes chiefly great potential as an important raw material for the production used as catalysts, molybdenum complexes are currently of of oleochemicals because it has ca. 90% of unsaturated considerable interest to promote oxidation reactions. Several compounds and it is a non-edible oil. This oil could lead to a studies in the literature have reported the epoxidation of alkenes lower consumption of edible oils for chemical purposes. In using homogeneous 6 or heterogeneous Mo(VI) catalysts with addition, tallow tree can grow on most types of soil. The seed tert -butyl hydroperoxide (TBHP) as oxygen source. 9 Recently 1 Accepted output is more than 100,000 metric tons every year in China. Farias 10 reported the use of molybdenum compounds The epoxidation of vegetable oils is commercially important heterogenized on montmorillonite K-10 for catalytic since the epoxides produced from these renewable raw epoxidation of soybean and castor oils with TBHP. Epoxidation materials present numerous applications, including the reactions presenting high yields and selectivity have been fabrication of polyurethane foams (via oxirane ring opening to observed, as well as no leaching of metal, with an increase in 2 3 4 generate polyols), synthetic detergents, coatings and the catalytic activity of recycling experiments. 5 lubricants. The production of biodegradable lubricants from Starch is a non-toxic, naturally abundant, biodegradable and epoxidized vegetable oils is of particular interest considering high-functional biopolymer which can easily be modified by the undesirable impact on the environment associated with the relatively simple chemical/physical modifications. 11-13 use of mineral oil-based lubricants. However, the application of starch as a material in areas such as Advances On an industrial scale, the epoxidation of plant oils is composites, 14 adsorbents 15,16 and catalyst supports 17 is restricted currently carried out with a percarboxylic acid, such as by its naturally low surface areas (<1 m 2 g−1), pore volumes peracetic or performic acid. Soluble mineral acids, commonly (<0.1 cm 3 g−1) and low site accessibility. Therefore ， expanded sulfuric acid, are used as catalysts for this reaction. Therefore, starches, which have high surface area and pore volumes have environmental concerns related to the disposal of the salts emerged to be promising materials and their uses in catalysis RSC formed during the final neutralization of the mineral acid and are a key enabling area for the development of new and other technical problems associated with their use, such as improved processes for chemical reactions. 18 corrosion and separation operations, constitute a strong driving In the present study, we anchored molybdenum force for searching alternatives to this technology. acetylacetonate onto expanded corn starch (ECS) functionalized The use of transition metal complexes as homogeneous or with 3-aminopropyltriethoxysilane (APTES), through Schiff heterogeneous catalysts could eliminate many of these condensation between the carbonyl groups of the 6,7 problems and also provides a reaction that is very selective. acetylacetonate ligands and the APTES amine. The ability of Heterogeneous catalysts have some advantages over This journal is © The Royal Society of Chemistry 2013 J. Name ., 2013, 00 , 1-3 | 1 RSC Advances Page 2 of 8 Journal Name RSC Publishing ARTICLE Scheme 1 The epoxidation of stillingia oil using TBHP as oxidant. this heterogeneous catalytic system to catalyze the epoxidation 45 min and the gelatinous mixture was kept at 5 oC for 24 h. of stillingia oil, using toluene as solvent and TBHP as oxidizing Precipitation and washing this gel with ethanol retains a rigid agent has been investigated (Scheme 1). Reusability is one of porous gel network with surface areas of > 100 m 2 g-1. the most important properties of a supported heterogeneous The expanded corn starch is known to possess extensive catalyst because transition-metal complexes are often expensive hydroxyl groups on the framework surface of the porous material. and difficult to prepare. Therefore, recycling experiment of the These hydroxyl groups can react with APTES to yield amine Manuscript catalyst was also performed in this work. functionalized expanded corn starch (ECS-NH 2). MoO 2(acac) 2 was anchored onto the surface of amine functionalized expanded corn 2 Experimental starch (ECS-MoO 2(acac) 2) through Schiff-base condensation with free amine groups, covalently attached to the expanded corn starch 2.1 Materials surface with the carbonyl groups of the acetylacetonate ligand Degummed stillingia oil was purchased from Dawu County, coordinated to molybdenum (Ⅵ). Namely, expanded corn starch Hubei Province, PR China. The fatty acid composition (based (4.23 g) was added to a round bottom flask containing dry toluene on gas chromatography) is as follows: palmitic acid, 6.1%; (35 mL) and stirred under nitrogen. APTES (4.82 g, 22 mmol) was stearic acid, 2.2%; oleic acid, 14.9%; linoleic acid, 31.4%; then added and the slurry was refluxed for 24 hours. After this time the vessel was cooled to room temperature and ethanol (135 mL) linolenic acid, 44.3% and traces of other fatty acids. Accepted Toluene was acquired from Nanjing Chemical Factory were added. The resulting ECS-NH 2 was recovered by filtration and (Nanjing, China). Sodium bisulphite and anhydrous sodium washed with excess ethanol. The ECS-NH 2 (2 g) was then reacted sulphate were purchased in analytical grade from Sigma- with MoO 2(acac) 2 (0.30 g, 0.92 mmol) in toluene for 24 h under Aldrich. The solution of anhydrous TBHP in toluene was nitrogen and refluxing conditions. The colored material was then obtained by careful azeotropic distillation of 70% aqueous filtered and thoroughly washed with acetone to remove impurities solution (Merck) in toluene and the concentration of the and non-anchored material to yield the final catalyst product ECS- resulting solution was determined by 1H NMR spectroscopy. MoO 2(acac) 2. The preparation steps of the immobilization of Quantofix® Peroxide 100 test strips (Sigma) were used for the MoO 2(acac) 2 on expanded corn starch is presented in Scheme 2. semi-quantitative determination of peroxide. All chemicals 2.3 Catalyst characterization were used without further purification. High amylose corn Advances starch and molybdenum acetylacetonate (MoO 2(acac) 2) were The molybdenum content of the resulting solid ECS- purchased from Merck and used as received. It has been found MoO 2(acac) 2 was quantitatively determined by inductively that higher amylose starches generally give materials with coupled plasma optical emission spectrometry (ICP-OES) in a higher surface area after treatment than lower amylose starches Perkin Elmer Instruments Optima 2000 DV spectrometer and and retrograde more rapidly. 19 the loading was found to be 0.37 mmol g -1. The specific surface RSC area (SBET) of the samples was measured on a Autosorb-iQ 2.2 Catalyst preparation instrument by N 2 adsorption-desorption isotherms at 77 K using Expanded corn starch (ECS) was prepared according to the Brunauer-Emmett-Teller (BET) method.
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