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Mass Transfer Equipment Design

by: Adriel Nader

Mass Transfer Equipment Design CHE T312

Marketplace > West Virginia University > Chemical Engineering > CHE T312 > Mass Transfer Equipment Design
Adriel Nader
GPA 3.7


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This 6 page Class Notes was uploaded by Adriel Nader on Saturday September 12, 2015. The Class Notes belongs to CHE T312 at West Virginia University taught by Staff in Fall. Since its upload, it has received 18 views. For similar materials see /class/202702/che-t312-west-virginia-university in Chemical Engineering at West Virginia University.

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Date Created: 09/12/15
Molecules 2002 7 264270 molecules ISSN 1420 3049 httpwwwmdpiorg Mn BrsTPPS Supported on Amberlite IRA400 as a Robust and Ef cient Catalyst for Alkene Epoxidation and Alkane Hydroxylation S Tangestaninejadquot M H Habibi V Mirkhani and M Moghadam Department of Chemistry Isfahan University Isfahan 81744 Iran Fax 98 3116689732 Author to whom correspondence should be addressed E mail majidmsciuiacir Received 29 June 2001 in revised form 1 7F ebruary 2002 Accepted 18 February 2002 Published 28 February 2002 Abstract Manganese III meso tetrakispsulfonatopheny1Boctabromoporphyrin supported on Amberlite IRA400 MnBr8TPPSAd400 is a robust and efficient catalyst for epoxidation of alkenes and hydroxylation of alkanes with sodium periodate at room temperature Keywords Octabromoporphyrin epoxidation hydroxylation sodium periodate Introduction Epoxidation of alkenes and hydroxylation of alkanes catalyzed by metalloporphyrin catalysts is a subject of much investigation A variety of oxygen donors like iodosylarenes hypochlorites alkylhydroperoxides hydrogen peroxide and periodates have been used these transformations 1 In fact the majority of the studies are directed toward understanding the mechanism of the catalytic activity of hemecontaining enzymes such as cytochrome P450 Homogeneous metalloporphyrin catalysts with steric hindrance and those containing sophisticated chiral auxiliaries or strongly electronwithdrawing groups can exhibit high regio 25 shape 46 and enantioselectivity 7 and high catalyst turnovers 89 However difficulty in recovery and the high cost of the catalysts outweigh these appealing features and so far have made their applications to synthesis impractical A Molecules 2002 7 265 potential approach to prepare commercial metalloporphyrin catalysts is to immobilize them onto solid supports Such immobilization makes the catalysts separable from reaction mixtures and reusable enhance the catalyst stability towards oxidation and allow preparation of environmentally friendly catalysts Many heterogenized metalloporphyrin catalysts have been reported for alkene epoxidation and alkane hydroxylation 1023 Results and Discussion This report describes the use of MnBr8TPPS supported on Amberlite IRA400 for epoxidation of alkenes and hydroxylation of alkanes with sodium periodate in a CH3CNHZO mixture at room temperature MnBr8TPPS is a sulfonated hindered metalloporphyrin with electron withdrawing substituents at the Bpositions of the pyrroles The electronegative groups on the pyrrole moieties enhance the reactivity of the metal oxo species and immobilization of the metalloporphyrin on ion exchange resin Amberlite IRA400 and avoid uoxo formation The catalyst exhibits a high activity and stability in alkene epoxidation and alkane hydroxylation by NaIO4 Scheme 1 shows the reaction conditions Scheme 1 Mn111Br8TPPSAd 400imidazole 0 NaIO4CH3CNH20 39 or or Q RlCHZRZ OH RlCHR2 and R1 R2 It is found that addition of a heterocyclic nitrogen base such as imidazole or lmethylimidazole to this catalytic system improves the activity of the catalyst In the presence of imidazole the MnBr8TPPS iAd400 system converts different olefins efficiently to their corresponding epoxides Tablel Epoxidation of transstilbene proceeds in a stereospecific manner with complete retention of configuration In contrast epoxidation of cisstilbene is associated with some lose of stereochemistry and affords 80 cis and 10 transstilbene oxides respectively This catalytic system exhibits a good regioselectivity for epoxidation of R limonene The ratio among l2 and 89epoxides was found to be 23 l Selective partial alkane hydroxylation is a particularly challenging problem in organic chemistry MnBr8TPPSAd400 catalytic system oxidizes different alkanes to corresponding alcohols and ketones with sodium periodate in CH3CNHZO mixture at room temperature Table 2 Overoxidation of the alkane hydroxylation product is highly dependent on the nature of the hydrocarbon itself In the case of benzylic hydroxylation the main products detected were ketones due to the subsequent transformation of alcohols to ketones in the reaction mixtures The hydroxylation of cisdecaline gives the cis9decanol and cisldecalone in yield 20 and 36 respectively In the case of Molecules 2002 7 tetrahydronaphtalene and propylbenzene only OLtetralone and ethylphenylketone have been identi ed in the reaction mixtures respectively Table 1 Epoxidation of alkenes with NaIO4 catalyzed by MnBr8TPPSAd400 in the presence of imidazole at room temperature Entry Alkene l 10 I m gawao C0nve1 si0na Epoxide yielda Reaction timell 92 92 6 93 78 6 90 67 6 90 65 4 70 70 6 5 5 5 5 10 88 88 6 86 6012epoxide 6 2689epox1de 60 60trans epoxideb 6 90 80cis epoxideb 6 10trans epoxideb a GLC yield based on starting alkene bBoth 1HNMR and GLC data confirmed the reported yields Molecules 2002 7 Table 2 Hydroxylation of alkanes with NaIO4 catalyzed by MnBr8TPPS Ad400 in presence of imidazole at room temperature Entry Alkane Ketonea Alcohola Reaction timell l O 28 17 10 2 O 50 4 10 3 36 20 10 4 2 57 10 5 GA 39 10 6 m 27 10 7 one 90 0 a GLC yield based on starting alkane Conclusions 267 This robust and stable catalytic system is a convenient and efficient system that expands the scope of utilization of metalloporphyrins in useful organic transformations Acknowledgements The partial support of this work by the University of Isfahan Research Council is greatfully acknowledged Experimental General Alkenes alkanes and alkylaromatic compounds were obtained from Merck and Fluka and purified prior to use by passing through a column containing active alumina to remove peroxidic impurities Molecules 2002 7 268 The porphyrin ligand HZTPPS was prepared 39 39 J and quot J J39 to literature procedures 2426 Immobilization of MnBr8TPPS on Amberlite IRA 400 MnBr8TPPS 05 g was dissolved in a 11 mixture of acetonewater and Amberlite IRA400 5 g was added to the solution The mixture was stirred at 80 0C for 8 h The mixture was cooled to room temperature ltered washed with water and acetone and dried The polymer supported porphyrin is insoluble in common organic solvents The re ectance spectrum clearly indicates a Soret band at 488 nm and a Q band at 566 nm IR spectrum of the solid supported manganese porphyrin shows VSO at 1400 and 1180 cm39l The degree of manganese porphyrin incorporation into the polymer was determined by neutron activation analysis NAA which gave a value of about 029 ww Typical procedure for oxidation reactions catalyzed by M nBr8TPPS Aal 400 All of the reactions were carried out at room temperature under air in a 25 mL ask equipped with a magnetic stirring bar A solution of NaIO4 2 mmol in H20 10 mL was added to a mixture of alkene or alkane 1 mmol MnBr8TPPSAd 400 11 umol and imidazole 02 mmol in CH3CN 10 mL The progress of reaction was monitored by GLC The reaction mixture was diluted with CHzClz 20 mL and ltered The resin was thoroughly washed with CHzClz and combined washings and ltrates were puri ed on silicagel plates or a silicagel column IR and 1HNMR spectral data con rmed the identities of the products Catalyst reuse anal stability The stability of MnBr8TPPSAd 400 was studied in repeated epoxidation reactions The epoxidation of OLmethylstyrene was chosen as a model substrate for studying of catalyst reuse and stability The reaction was carried out as described above At the end of the reaction the catalyst was removed by ltration and washed with water and acetonitrile and reused The dried catalyst was consecutively reused four times After the use of catalyst for four consecutive times the conversion yield was 88 The amount of leached Mn 10 was determined by atomic absorption References and Notes 1 a Meunier B Chem Rev 1992 92 1411 b Mansuy D Cooral Chem Rev 1993 125 129 2 Groves J T Nemo T E J Am Chem Soc 1983 105 5786 3 Tabushi 1 Morimitsu K J Am Chem Soc 1984 106 6871 Molecules 2002 7 00080st N D i LA 4 VI 269 Collman J P Brauman J 1 Meunier B Hayashi T Kodadek T Raybuck S A J Am Chem Soc 1985 107 2000 Groves J T Neumann R J Am Chem Soc 1987 109 5045 Collman J F Zhang X Hembre R T Brauman J I J Am Chem Soc 1990 112 5356 Collman J F Zhang X M Lee V J Uffelman E S Brauman J 1 Science 1993 261 1404 Traylor P S Dolphin D Traylor T G J Chem Soc Chem Commun 1984 279 Collman J P Wang Z Straumanis A and Quelquejeu M J Am Chem Soc 1999 121 460 a Wohler D Gitzel J Makromol Chem Rapid Commun 1988 9 229 b Wohler D Gitzel J Krawczyk G Tsuchida E Ohno H Okura 1 Nishisaka T J Macromol Sci Chem 1988 A25 1227 a Leonard D R Lindsay Smith J R J Chem Soc Perkin Trans 2 1990 1917 b Leonard D R Lindsay Smith J R J Chem Soc Perkin Trans 2 1991 25 a Turk H Ford W T J Org Chem 1991 56 1253 b Traylor T G Byun Y S Traylor P S Battioni P Mansuy D J Am Chem Soc 1991 113 7821 a Barloy L Lallier J P Battioni P Mansuy D Pilfard Y ToumouX M Valim J B Jones W New J Chem 1992 16 71 b Campestrini S Meunier B Inorg Chem 1992 31 1999 a Cooke P R Lindsay Smith J R Tetrahedron Lett 1992 33 2737 b Battioni P Bartoli J F Mansuy D Byun Y S Traylor T G J Chem Soc Chem Commun 1992 1051 a Cooke P R Lindsay Smith J R J Chem Soc Perkin Trans 1 1994 1913 b Gilmartin C Lindsay Smith J R J Chem Soc Perkin Trans 2 1995 243 a das Dores Assis M Lindsay Smith J R J Chem Soc Perkin Trans 2 1998 222 b Geier G R Sasaki T Tetrahedron 1999 55 1859 a Liu C J Li S G Pang W Q Che C M J Chem Soc Chem Commun 1997 65 b Liu C J Yu W Y Li S G Che C M J Org Chem 1998 63 7364 Tangestaninejad S Mirkhani V J Chem Res S 1998 788 Yu X Q Huang J S Yu W Y Che C M J Am Chem Soc 2000 122 5337 Tangestaninejad S Moghadam M J Chem Res S 1998 242 Tangestaninejad S Moghadam M Synth Commun 1998 28 427 Mirkhani V Tangestaninejad S Moghadam M J Chem Res S 1999 722 Mirkhani V Tangestaninejad S Moghadam M Yadollahi B J Chem Res S 2000 515 Busby C A DiNello R K Dolphin D Can J Chem 1975 53 1554 D Souza F Hsieh Y 7Y DeViprasad G R J Electroanal Chem 1997 426 17 Harriman A Proter G J Chem Soc Faraday 2 1979 75 1532 Sample availability Samples of the catalyst MnBr8TPPS are available from MDPI 2002 by MDPI httpwwwmdpiorg Reproduction is permitted for non commercial purposes


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