生物基1,6-己二醇的研究进展
|
摘要
传统的以石油化工产品为原料的石化基1,6-己二醇(1,6-HDO)的生产存在能耗高、反应产物分离困难、污染环境等缺点,以5-羟甲基糠醛(5-HMF)为原料制备生物基1,6-HDO可以克服这些缺点。本文介绍了国内外制备生物基1,6-HDO的研究进展,总结并讨论了由5-HMF制备1,6-HDO的不同反应路径,并从反应物吸附、金属粒径、活性组分协同作用、载体等角度对比了不同催化剂体系及其催化机理,探讨了各种催化剂促进C=O加氢、呋喃环C=C加氢、呋喃环C—O氢解开环反应,抑制呋喃环、呋喃环侧链C—C氢解断裂反应的性能。与多步法相比,一步法制备1,6-HDO的反应步骤简单,但1,6-HDO的产率相对较低,因此开发高效的催化剂体系和反应工艺将是今后研究的重点。
Conventional production of 1,6-hexanediol(1,6-HDO) with petrochemicals, has disadvantages of high energy consumption, product separation difficulties and environmental contamination. These limitations can,to some extent,be overcome by biorefinery process,especially that of 5-HMF based. The status quo of production of biobased 1,6-HDO was summarized,and different reaction pathways for conversion of 5-HMF to 1,6-HDO was discussed. This review compared different catalysts and catalytic mechanisms in respect of adsorption of reagent,metal particle size,synergistic interaction,and support. The catalyst performance in promoting hydrogenation of C=O,hydrogenation of furan ring,and hydrogenolysis of C—O,yet restraining hydrogenolysis of C—C were also investigated. Compared with multistep reactions,one-step reaction was simpler but with lower 1,6-HDO production. Therefore,developing more efficient catalyst and process will be the focus of future research.
Conventional production of 1,6-hexanediol(1,6-HDO) with petrochemicals, has disadvantages of high energy consumption, product separation difficulties and environmental contamination. These limitations can,to some extent,be overcome by biorefinery process,especially that of 5-HMF based. The status quo of production of biobased 1,6-HDO was summarized,and different reaction pathways for conversion of 5-HMF to 1,6-HDO was discussed. This review compared different catalysts and catalytic mechanisms in respect of adsorption of reagent,metal particle size,synergistic interaction,and support. The catalyst performance in promoting hydrogenation of C=O,hydrogenation of furan ring,and hydrogenolysis of C—O,yet restraining hydrogenolysis of C—C were also investigated. Compared with multistep reactions,one-step reaction was simpler but with lower 1,6-HDO production. Therefore,developing more efficient catalyst and process will be the focus of future research.
引文
[1]Bozell J J,Petersen G R.Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy’s“Top 10”revisited[J].Green Chemistry,2010,12(4):539-554.
[2]Van Putten R J,Van Der Waal J C,De Jong E,et al.Hydroxymethylfurfural,a versatile platform chemical made from renewable resources[J].Chemical Reviews,2013,113(3):1499-1597.
[3]Hu L,Zhao G,Hao W,et al.Catalytic conversion of biomass-derived carbohydrates into fuels and chemicals via furanic aldehydes[J].RSC Advances,2012,2(30):11184-11206.
[4]程光剑.新型共聚单体1,6-己二醇的开发与应用[J].石油科技论坛,2011(7):58-72.
[5]鲁华,高伟.1,6-己二醇的产业现状及应用[J].精细与专用化学品,2013,21(7):9-11.
[6]Dias E L,Shoemaker J A W,Boussie T R,et al.Process for production of hexamethylenediamine from carbohydrate-containing materials and intermediates therefor:US,20130184495A1[P].2013-05-30.
[7]De Vries J G,Teddy,Phua P H,et al.Preparation of caprolactone,caprolactam,2,5-tetrahydrofurandimethanol,1,6-hexanediol or 1,2,6-hexanetriol from 5-hydroxymethyl-2-furfuraldehyde:WO,2011149339A1[P].2011-01-12.
[8]Nakagawa Y,Tomishige K.Total hydrogenation of furan derivatives over silica-supported Ni-Pd alloy catalyst[J].Catalysis Communications,2010,12(3):154-156.
[9]Nakagawa Y,Takada K,Tamura M,et al.Total hydrogenation of furfural and 5-hydroxymethylfurfural over supported Pd-Ir alloy catalyst[J].ACS Catalysis,2014,4(8):2718-2726.
[10]Utne Torleif W,Robert E,Jones Et Al.Process for producing1,6-hexanediol:US,3070633A[P].1962-12-25.
[11]Yao S,Wang X,Jiang Y,et al.One-step conversion of biomass-derived 5-hydroxymethylfurfural to 1,2,6-hexanetriol over Ni-Co-Al mixed oxide catalysts under mild conditions[J].ACS Sustainable Chemistry&Engineering,2014,2(2):173-180.
[12]Buntara T,Noel S,Phua P H,et al.From 5-hydroxymethylfurfural(HMF)to polymer precursors:Catalyst screening studies on the conversion of 1,2,6-hexanetriol to 1,6-hexanediol[J].Topics in Catalysis,2012,55(7-10):612-619.
[13]Chia M,Pagan-Torres Y J,Hibbitts D,et al.Selective hydrogenolysis of polyols and cyclic ethers over bifunctional surface sites on rhodium-rhenium catalysts[J].Journal of the American Chemical Society,2011,133(32):12675-12689.
[14]Buntara T,Melián-Cabrera I,Tan Q,et al.Catalyst studies on the ring opening of tetrahydrofuran–dimethanol to 1,2,6-hexanetriol[J].Catalysis Today,2013,210,106-116.
[15]Chen K,Koso S,Kubota T,et al.Chemoselective hydrogenolysis of tetrahydropyran-2-methanol to 1,6-hexanediol over rhenium-modified carbon-supported rhodium catalysts[J].Chem Cat Chem,2010,2(5):547-555.
[16]Utne T,Warrenville,Garber J D,et al.Hydrogenation of 5-hydroxymethyl furfural:US,3083236A[P].1963-03-26.
[17]Tuteja J,Choudhary H,Nishimura S,et al.Direct synthesis of1,6-hexanediol from HMF over a heterogeneous Pd/Zr P catalyst using formic acid as hydrogen source[J].Chem Sus Chem,2014,7(1):96-100.
[18]Waidmann C R,Pierpont A W,Batista E R,et al.Functional group dependence of the acid catalyzed ring opening of biomass derived furan rings:An experimental and theoretical study[J].Catalysis Science&Technology,2013,3(1):106-115.
[19]Weingarten R,Tompsett G A,Conner W C,et al.Design of solid acid catalysts for aqueous-phase dehydration of carbohydrates:The role of Lewis and Br?nsted acid sites[J].Journal of Catalysis,2011,279(1):174-182.
[2]Van Putten R J,Van Der Waal J C,De Jong E,et al.Hydroxymethylfurfural,a versatile platform chemical made from renewable resources[J].Chemical Reviews,2013,113(3):1499-1597.
[3]Hu L,Zhao G,Hao W,et al.Catalytic conversion of biomass-derived carbohydrates into fuels and chemicals via furanic aldehydes[J].RSC Advances,2012,2(30):11184-11206.
[4]程光剑.新型共聚单体1,6-己二醇的开发与应用[J].石油科技论坛,2011(7):58-72.
[5]鲁华,高伟.1,6-己二醇的产业现状及应用[J].精细与专用化学品,2013,21(7):9-11.
[6]Dias E L,Shoemaker J A W,Boussie T R,et al.Process for production of hexamethylenediamine from carbohydrate-containing materials and intermediates therefor:US,20130184495A1[P].2013-05-30.
[7]De Vries J G,Teddy,Phua P H,et al.Preparation of caprolactone,caprolactam,2,5-tetrahydrofurandimethanol,1,6-hexanediol or 1,2,6-hexanetriol from 5-hydroxymethyl-2-furfuraldehyde:WO,2011149339A1[P].2011-01-12.
[8]Nakagawa Y,Tomishige K.Total hydrogenation of furan derivatives over silica-supported Ni-Pd alloy catalyst[J].Catalysis Communications,2010,12(3):154-156.
[9]Nakagawa Y,Takada K,Tamura M,et al.Total hydrogenation of furfural and 5-hydroxymethylfurfural over supported Pd-Ir alloy catalyst[J].ACS Catalysis,2014,4(8):2718-2726.
[10]Utne Torleif W,Robert E,Jones Et Al.Process for producing1,6-hexanediol:US,3070633A[P].1962-12-25.
[11]Yao S,Wang X,Jiang Y,et al.One-step conversion of biomass-derived 5-hydroxymethylfurfural to 1,2,6-hexanetriol over Ni-Co-Al mixed oxide catalysts under mild conditions[J].ACS Sustainable Chemistry&Engineering,2014,2(2):173-180.
[12]Buntara T,Noel S,Phua P H,et al.From 5-hydroxymethylfurfural(HMF)to polymer precursors:Catalyst screening studies on the conversion of 1,2,6-hexanetriol to 1,6-hexanediol[J].Topics in Catalysis,2012,55(7-10):612-619.
[13]Chia M,Pagan-Torres Y J,Hibbitts D,et al.Selective hydrogenolysis of polyols and cyclic ethers over bifunctional surface sites on rhodium-rhenium catalysts[J].Journal of the American Chemical Society,2011,133(32):12675-12689.
[14]Buntara T,Melián-Cabrera I,Tan Q,et al.Catalyst studies on the ring opening of tetrahydrofuran–dimethanol to 1,2,6-hexanetriol[J].Catalysis Today,2013,210,106-116.
[15]Chen K,Koso S,Kubota T,et al.Chemoselective hydrogenolysis of tetrahydropyran-2-methanol to 1,6-hexanediol over rhenium-modified carbon-supported rhodium catalysts[J].Chem Cat Chem,2010,2(5):547-555.
[16]Utne T,Warrenville,Garber J D,et al.Hydrogenation of 5-hydroxymethyl furfural:US,3083236A[P].1963-03-26.
[17]Tuteja J,Choudhary H,Nishimura S,et al.Direct synthesis of1,6-hexanediol from HMF over a heterogeneous Pd/Zr P catalyst using formic acid as hydrogen source[J].Chem Sus Chem,2014,7(1):96-100.
[18]Waidmann C R,Pierpont A W,Batista E R,et al.Functional group dependence of the acid catalyzed ring opening of biomass derived furan rings:An experimental and theoretical study[J].Catalysis Science&Technology,2013,3(1):106-115.
[19]Weingarten R,Tompsett G A,Conner W C,et al.Design of solid acid catalysts for aqueous-phase dehydration of carbohydrates:The role of Lewis and Br?nsted acid sites[J].Journal of Catalysis,2011,279(1):174-182.