过渡金属化合物催化合成环氧增塑剂研究进展
|
摘要
从过渡金属元素化合物的元素种类、催化剂类型、反应条件以及反应机理等方面综述了过渡金属化合物催化剂催化制备环氧增塑剂的研究进展。文中提出了催化过程中存在的问题,并对未来的研究方向进行展望。
This review summarizes the progress in the preparation of epoxide plasticizers catalyzed by transition metal compounds from the element types,types of catalysts,reaction conditions and reaction mechanism of the transition metal compounds.The problems existing in the catalysis process are pointed out,and the future research directions are prospected.
This review summarizes the progress in the preparation of epoxide plasticizers catalyzed by transition metal compounds from the element types,types of catalysts,reaction conditions and reaction mechanism of the transition metal compounds.The problems existing in the catalysis process are pointed out,and the future research directions are prospected.
引文
[1] 陈浩乾,张颖,许馨予,等.绿色增塑剂环氧大豆油的开发与应用[J].广州化工,2008,36(4):6-8.
[2] Cortese B,de Croon M H J M,Hessel V.High-temperature epoxidation of soybean oil in flow speeding up elemental reactions wanted and unwanted[J].Industrial & Engineering Chemistry Research,2011,51(4):1680-1689.
[3] Goud V V,Patwardhan A V,Pradhan N C.Studies on the epoxidation of Mahua oil (Madhumica indica) by hydrogen peroxide[J].Bioresource Technology,2006,97(12):1365-1371.
[4] Sepulveda J,Teixeira S,Schuchardt U.Alumina-catalyzed epoxidation of unsaturated fatty esters with hydrogen peroxide[J].Applied Catalysis A:General,2007,318:213-217.
[5] 李玉芳,伍小明.环氧大豆油合成技术研究进展[J].精细与专用化学品,2015(1):44-47.
[6] 蔡双飞,王利生.环氧植物油基增塑剂的合成工艺进展[J].塑料助剂,2010(5):1-6.
[7] 金飞,丁杭军,栾奕,等.钼,钨系过氧化物在催化 Sharpless 烯烃环氧化反应中的应用[J].化学进展,2008,20(12):1886-1895.
[8] Farias M,Martinelli M,Bottega D P.Epoxidation of soybean oil using a homogeneous catalytic system based on a molybdenum (VI) complex[J].Applied Catalysis A:General,2010,384(1/2):213-219.
[9] Yang X L,Zhang Y.Lyophilization-based synthesis of HKUST-1 encapsulated molybdenyl acetylacetonate nanocrystals:An effective soybean oil epoxidation catalyst[J].Catalysis Communications,2017,94:9-12.
[10] Sobczak J M,Zió?kowski J J.Molybdenum complex-catalysed epoxidation of unsaturated fatty acids by organic hydroperoxides[J].Applied Catalysis A:General,2003,248(1/2):261-268.
[11] Miao Y X,Liu J P.Epoxidation of soybean oil under acid-free condition[J].Advanced Materials Research,2014,881:140-143.
[12] 欧阳小月,江焕峰.以双氧水为氧源的烯烃环氧化反应[J].有机化学,2007,27(3):358-367.
[13] Zhou M D,Liu M J,Huang L L,et al.Olefin epoxidation with hydrogen peroxide using octamolybdate-based self-separating catalysts[J].Green Chemistry,2015,17(2):1186-1193.
[14] Beattie I R,Jones P J.Methyltrioxorhenium.An air-stable compound containing a carbon-rhenium bond[J].Inorganic Chemistry,1979,18(8):2318-2319.
[15] Herrmann W A,Fischer R W,Scherer W,et al.Methyltrioxorhenium (VII) as catalyst for epoxidations:structure of the active species and mechanism of catalysis[J].Angewandte Chemie International Edition,1993,32(8):1157-1160.
[16] Herrmann W A,Fischer R W,Marz D W.Methyltrioxorhenium as catalyst for olefin oxidation[J].Angewandte Chemie International Edition in English,1991,30(12):1638-1641.
[17] Kühn F E,Scherbaum A,Herrmann W A.Methyltrioxorhenium and its applications in olefin oxidation,metathesis and aldehyde olefination[J].Journal of Organometallic Chemistry,2004,689(24):4149-4164.
[18] Jiang P,Chen M,Dong Y,et al.Novel two-phase catalysis with organometallic compounds for epoxidation of vegetable oils by hydrogen peroxide[J].Journal of the American Oil Chemists’ Society,2010,87(1):83-91.
[19] Gerbase A E,Gregório J R,Martinelli M,et al.Epoxidation of soybean oil by the methyltrioxorhenium-CH2Cl2/H2O2 catalytic biphasic system[J].Journal of the American Oil Chemists’ Society,2002,79(2):179-181.
[20] Bouh A O,Espenson J H.Epoxidation reactions with urea-hydrogen peroxide catalyzed by methyltrioxorhenium (VII) on niobia[J].Journal of Molecular Catalysis A:Chemical,2003,200(1/2):43-47.
[21] 常慧.烯烃环氧化技术及其催化剂发展概述[J].石油化工技术与经济,2015(6):45-49.
[22] Poli E,Clacens J M,Barrault J,et al.Solvent-free selective epoxidation of fatty esters over a tungsten-based catalyst[J].Catalysis Today,2009,140(1/2):19-22.
[23] Kozhevnikov I V,Mulder G P,Steverink-de Zoete M C,et al.Epoxidation of oleic acid catalyzed by peroxo phosphotungstate in a two-phase system[J].Journal of Molecular Catalysis A:Chemical,1998,134(1/2/3):223-228.
[24] Poli E,Bion N,Barrault J,et al.Selective epoxidation of unsaturated fatty esters over peroxophosphotungstic catalysts (POW) under solvent free conditions:Study of the POW catalyst’s mechanism[J].Catalysis Today,2010,157(1/2/3/4):371-377.
[25] Zhang H,Yang H,Guo H,et al.Solvent-free selective epoxidation of soybean oil catalyzed by peroxophosphotungstate supported on palygorskite[J].Applied Clay Science,2014,90:175-180.
[26] Jiang J,Zhang Y,Yan L,et al.Epoxidation of soybean oil catalyzed by peroxo phosphotungstic acid supported on modified halloysite nanotubes[J].Applied Surface Science,2012,258(17):6637-6642.
[27] 聂丽娟,王可,田世炯,等.杂多酸及其季铵盐催化剂催化H2O2环氧化1-辛烯[J].化学世界,2014,55(1):29-33.
[28] 朱超,雷梦,冯波,等.磷钨杂多酸季铵盐催化合成环氧大豆油的研究[J].粘接,2016,37(8):39-42.
[29] Cheng W,Liu G,Wang X,et al.Kinetics of the epoxidation of soybean oil with H2O2 catalyzed by phosphotungstic heteropoly acid in the presence of polyethylene glycol[J].European Journal of Lipid Science and Technology,2015,117(8):1185-1191.
[30] Jing L,Liu G Q,Liu X Q,et al.Synthesis of epoxidized soybean oil via phase transfer catalysis[J].Advanced Materials Research,2013,690:1061-1064.
[31] 李坤兰,高爽,奚祖威.无酸法合成环氧大豆油的研究[J].化学世界,2008,49(5):293-295.
[32] 吴亚,魏俊发,张敏,等.过氧钨配合物催化过氧化氢制备环氧大豆油的研究[J].应用化工,2005,34(2):119-120.
[33] Lu X Z,Liu G Q,Liu X Q,et al.Study on the regeneration of quaternary ammonium heteropolyphosphatotungstate catalyst[J].Advanced Materials Research,2014,1004:1000-1004.
[34] 左轶,刘民,郭新闻.钛硅分子筛的合成及其催化氧化反应研究进展[J].石油学报:石油加工,2015,31(2):343-359.
[35] Bellussi G,Rigutto M S.Cheminform abstract:metal ions associated to the molecular sieve framework:Possible catalytic oxidation sites[J].Cheminform,1994,85(3):177-213.
[36] Clerici M G,Ingallina P.Epoxidation of lower olefins with hydrogen peroxide and titanium silicalite[J].Journal of Catalysis,1993,140(1):71-83.
[37] Wilde N,Worch C,Suprun W,et al.Epoxidation of biodiesel with hydrogen peroxide over Ti-containing silicate catalysts[J].Microporous and Mesoporous Materials,2012,164:182-189.
[38] Wilde N,Pelz M,Gebhardt S G,et al.Highly efficient nano-sized TS-1 with micro-/mesoporosity from desilication and recrystallization for the epoxidation of biodiesel with H2O2[J].Green Chemistry,2015,17(6):3378-3389.
[39] Ye X,Jiang P,Zhang P,et al.Novel Ti and Mn mesoporous molecular sieves:synthesis,characterization and catalytic activity in the epoxidation of vegetable oil[J].Catalysis Letters,2010,137(1/2):88-93.
[40] Guidotti M,Gavrilova E,Galarneau A,et al.Epoxidation of methyl oleate with hydrogen peroxide.The use of Ti-containing silica solids as efficient heterogeneous catalysts[J].Green Chemistry,2011,13(7):1806-1811.
[41] Guidotti M,Ravasio N,Psaro R,et al.Epoxidation of unsaturated FAMEs obtained from vegetable source over Ti(IV)-grafted silica catalysts:A comparison between ordered and non-ordered mesoporousmaterials[J].Journal of Molecular Catalysis A:Chemical,2006,250(1/2):218-225.
[42] Rios L A,Weckes P,Schuster H,et al.Mesoporous and amorphous Ti-silicas on the epoxidation of vegetable oils[J].Journal of Catalysis,2005,232(1):19-26.
[43] Guidotti M,Ravasio N,Psaro R,et al.Heterogeneous catalytic epoxidation of fatty acid methyl esters on titanium-grafted silicas[J].Green Chemistry,2003,5(4):421-424.
[44] Turco R,Vitiello R,Tesser R,et al.Niobium based catalysts for methyl oleate epoxidation reaction[J].Topics in Catalysis,2017,60(15/16):1054-1061.
[45] Shima H,Tanaka M,Imai H,et al.IR Observation of selective oxidation of cyclohexene with H2O2 over mesoporous Nb2O5[J].Journal of Physical Chemistry C,2009,113(52):21693-21699.
[46] Dworakowska S,Tiozzo C,Niemczyk-Wrzeszcz M,et al.Mesoporous molecular sieves containing niobium(V) as catalysts for the epoxidation of fatty acid methyl esters and rapeseed oil[J].Journal of Cleaner Production,2017,166:901-909.
[47] Di Serio M,Turco R,Pernice P,et al.Valuation of Nb2O5-SiO2 catalysts in soybean oil epoxidation[J].Catalysis Today,2012,192(1):112-116.
[48] Feliczak A,Walczak K,Wawrzyńczak A,et al.The use of mesoporous molecular sieves containing niobium for the synthesis of vegetable oil-based products[J].Catalysis Today,2009,140(1/2):23-29.
[49] Leng Y,Zhao J,Jiang P,et al.Amphiphilic polyoxometalate-paired polymer coated Fe3O4:Magnetically recyclable catalyst for epoxidation of bio-derived olefins with H2O2[J].ACS Applied Materials & Interfaces,2014,6(8):5947-5954.
[50] Jiang P P,Zhang W J,Zhang P B.Epoxidation of soybean oil with tert-butyl hydroperoxide over manganese (Ⅲ) tetraphenylporphyrin chloride catalyst[J].Advanced Materials Research,2012,486:328-333.
[2] Cortese B,de Croon M H J M,Hessel V.High-temperature epoxidation of soybean oil in flow speeding up elemental reactions wanted and unwanted[J].Industrial & Engineering Chemistry Research,2011,51(4):1680-1689.
[3] Goud V V,Patwardhan A V,Pradhan N C.Studies on the epoxidation of Mahua oil (Madhumica indica) by hydrogen peroxide[J].Bioresource Technology,2006,97(12):1365-1371.
[4] Sepulveda J,Teixeira S,Schuchardt U.Alumina-catalyzed epoxidation of unsaturated fatty esters with hydrogen peroxide[J].Applied Catalysis A:General,2007,318:213-217.
[5] 李玉芳,伍小明.环氧大豆油合成技术研究进展[J].精细与专用化学品,2015(1):44-47.
[6] 蔡双飞,王利生.环氧植物油基增塑剂的合成工艺进展[J].塑料助剂,2010(5):1-6.
[7] 金飞,丁杭军,栾奕,等.钼,钨系过氧化物在催化 Sharpless 烯烃环氧化反应中的应用[J].化学进展,2008,20(12):1886-1895.
[8] Farias M,Martinelli M,Bottega D P.Epoxidation of soybean oil using a homogeneous catalytic system based on a molybdenum (VI) complex[J].Applied Catalysis A:General,2010,384(1/2):213-219.
[9] Yang X L,Zhang Y.Lyophilization-based synthesis of HKUST-1 encapsulated molybdenyl acetylacetonate nanocrystals:An effective soybean oil epoxidation catalyst[J].Catalysis Communications,2017,94:9-12.
[10] Sobczak J M,Zió?kowski J J.Molybdenum complex-catalysed epoxidation of unsaturated fatty acids by organic hydroperoxides[J].Applied Catalysis A:General,2003,248(1/2):261-268.
[11] Miao Y X,Liu J P.Epoxidation of soybean oil under acid-free condition[J].Advanced Materials Research,2014,881:140-143.
[12] 欧阳小月,江焕峰.以双氧水为氧源的烯烃环氧化反应[J].有机化学,2007,27(3):358-367.
[13] Zhou M D,Liu M J,Huang L L,et al.Olefin epoxidation with hydrogen peroxide using octamolybdate-based self-separating catalysts[J].Green Chemistry,2015,17(2):1186-1193.
[14] Beattie I R,Jones P J.Methyltrioxorhenium.An air-stable compound containing a carbon-rhenium bond[J].Inorganic Chemistry,1979,18(8):2318-2319.
[15] Herrmann W A,Fischer R W,Scherer W,et al.Methyltrioxorhenium (VII) as catalyst for epoxidations:structure of the active species and mechanism of catalysis[J].Angewandte Chemie International Edition,1993,32(8):1157-1160.
[16] Herrmann W A,Fischer R W,Marz D W.Methyltrioxorhenium as catalyst for olefin oxidation[J].Angewandte Chemie International Edition in English,1991,30(12):1638-1641.
[17] Kühn F E,Scherbaum A,Herrmann W A.Methyltrioxorhenium and its applications in olefin oxidation,metathesis and aldehyde olefination[J].Journal of Organometallic Chemistry,2004,689(24):4149-4164.
[18] Jiang P,Chen M,Dong Y,et al.Novel two-phase catalysis with organometallic compounds for epoxidation of vegetable oils by hydrogen peroxide[J].Journal of the American Oil Chemists’ Society,2010,87(1):83-91.
[19] Gerbase A E,Gregório J R,Martinelli M,et al.Epoxidation of soybean oil by the methyltrioxorhenium-CH2Cl2/H2O2 catalytic biphasic system[J].Journal of the American Oil Chemists’ Society,2002,79(2):179-181.
[20] Bouh A O,Espenson J H.Epoxidation reactions with urea-hydrogen peroxide catalyzed by methyltrioxorhenium (VII) on niobia[J].Journal of Molecular Catalysis A:Chemical,2003,200(1/2):43-47.
[21] 常慧.烯烃环氧化技术及其催化剂发展概述[J].石油化工技术与经济,2015(6):45-49.
[22] Poli E,Clacens J M,Barrault J,et al.Solvent-free selective epoxidation of fatty esters over a tungsten-based catalyst[J].Catalysis Today,2009,140(1/2):19-22.
[23] Kozhevnikov I V,Mulder G P,Steverink-de Zoete M C,et al.Epoxidation of oleic acid catalyzed by peroxo phosphotungstate in a two-phase system[J].Journal of Molecular Catalysis A:Chemical,1998,134(1/2/3):223-228.
[24] Poli E,Bion N,Barrault J,et al.Selective epoxidation of unsaturated fatty esters over peroxophosphotungstic catalysts (POW) under solvent free conditions:Study of the POW catalyst’s mechanism[J].Catalysis Today,2010,157(1/2/3/4):371-377.
[25] Zhang H,Yang H,Guo H,et al.Solvent-free selective epoxidation of soybean oil catalyzed by peroxophosphotungstate supported on palygorskite[J].Applied Clay Science,2014,90:175-180.
[26] Jiang J,Zhang Y,Yan L,et al.Epoxidation of soybean oil catalyzed by peroxo phosphotungstic acid supported on modified halloysite nanotubes[J].Applied Surface Science,2012,258(17):6637-6642.
[27] 聂丽娟,王可,田世炯,等.杂多酸及其季铵盐催化剂催化H2O2环氧化1-辛烯[J].化学世界,2014,55(1):29-33.
[28] 朱超,雷梦,冯波,等.磷钨杂多酸季铵盐催化合成环氧大豆油的研究[J].粘接,2016,37(8):39-42.
[29] Cheng W,Liu G,Wang X,et al.Kinetics of the epoxidation of soybean oil with H2O2 catalyzed by phosphotungstic heteropoly acid in the presence of polyethylene glycol[J].European Journal of Lipid Science and Technology,2015,117(8):1185-1191.
[30] Jing L,Liu G Q,Liu X Q,et al.Synthesis of epoxidized soybean oil via phase transfer catalysis[J].Advanced Materials Research,2013,690:1061-1064.
[31] 李坤兰,高爽,奚祖威.无酸法合成环氧大豆油的研究[J].化学世界,2008,49(5):293-295.
[32] 吴亚,魏俊发,张敏,等.过氧钨配合物催化过氧化氢制备环氧大豆油的研究[J].应用化工,2005,34(2):119-120.
[33] Lu X Z,Liu G Q,Liu X Q,et al.Study on the regeneration of quaternary ammonium heteropolyphosphatotungstate catalyst[J].Advanced Materials Research,2014,1004:1000-1004.
[34] 左轶,刘民,郭新闻.钛硅分子筛的合成及其催化氧化反应研究进展[J].石油学报:石油加工,2015,31(2):343-359.
[35] Bellussi G,Rigutto M S.Cheminform abstract:metal ions associated to the molecular sieve framework:Possible catalytic oxidation sites[J].Cheminform,1994,85(3):177-213.
[36] Clerici M G,Ingallina P.Epoxidation of lower olefins with hydrogen peroxide and titanium silicalite[J].Journal of Catalysis,1993,140(1):71-83.
[37] Wilde N,Worch C,Suprun W,et al.Epoxidation of biodiesel with hydrogen peroxide over Ti-containing silicate catalysts[J].Microporous and Mesoporous Materials,2012,164:182-189.
[38] Wilde N,Pelz M,Gebhardt S G,et al.Highly efficient nano-sized TS-1 with micro-/mesoporosity from desilication and recrystallization for the epoxidation of biodiesel with H2O2[J].Green Chemistry,2015,17(6):3378-3389.
[39] Ye X,Jiang P,Zhang P,et al.Novel Ti and Mn mesoporous molecular sieves:synthesis,characterization and catalytic activity in the epoxidation of vegetable oil[J].Catalysis Letters,2010,137(1/2):88-93.
[40] Guidotti M,Gavrilova E,Galarneau A,et al.Epoxidation of methyl oleate with hydrogen peroxide.The use of Ti-containing silica solids as efficient heterogeneous catalysts[J].Green Chemistry,2011,13(7):1806-1811.
[41] Guidotti M,Ravasio N,Psaro R,et al.Epoxidation of unsaturated FAMEs obtained from vegetable source over Ti(IV)-grafted silica catalysts:A comparison between ordered and non-ordered mesoporousmaterials[J].Journal of Molecular Catalysis A:Chemical,2006,250(1/2):218-225.
[42] Rios L A,Weckes P,Schuster H,et al.Mesoporous and amorphous Ti-silicas on the epoxidation of vegetable oils[J].Journal of Catalysis,2005,232(1):19-26.
[43] Guidotti M,Ravasio N,Psaro R,et al.Heterogeneous catalytic epoxidation of fatty acid methyl esters on titanium-grafted silicas[J].Green Chemistry,2003,5(4):421-424.
[44] Turco R,Vitiello R,Tesser R,et al.Niobium based catalysts for methyl oleate epoxidation reaction[J].Topics in Catalysis,2017,60(15/16):1054-1061.
[45] Shima H,Tanaka M,Imai H,et al.IR Observation of selective oxidation of cyclohexene with H2O2 over mesoporous Nb2O5[J].Journal of Physical Chemistry C,2009,113(52):21693-21699.
[46] Dworakowska S,Tiozzo C,Niemczyk-Wrzeszcz M,et al.Mesoporous molecular sieves containing niobium(V) as catalysts for the epoxidation of fatty acid methyl esters and rapeseed oil[J].Journal of Cleaner Production,2017,166:901-909.
[47] Di Serio M,Turco R,Pernice P,et al.Valuation of Nb2O5-SiO2 catalysts in soybean oil epoxidation[J].Catalysis Today,2012,192(1):112-116.
[48] Feliczak A,Walczak K,Wawrzyńczak A,et al.The use of mesoporous molecular sieves containing niobium for the synthesis of vegetable oil-based products[J].Catalysis Today,2009,140(1/2):23-29.
[49] Leng Y,Zhao J,Jiang P,et al.Amphiphilic polyoxometalate-paired polymer coated Fe3O4:Magnetically recyclable catalyst for epoxidation of bio-derived olefins with H2O2[J].ACS Applied Materials & Interfaces,2014,6(8):5947-5954.
[50] Jiang P P,Zhang W J,Zhang P B.Epoxidation of soybean oil with tert-butyl hydroperoxide over manganese (Ⅲ) tetraphenylporphyrin chloride catalyst[J].Advanced Materials Research,2012,486:328-333.