生物基1,6-己二醇的研究进展

doi:10.16085/j.issn.1000-6613.2015.12.013

化工进展 ›› 2015, Vol. 34 ›› Issue (12): 4209-4213.DOI: 10.16085/j.issn.1000-6613.2015.12.013

生物基1,6-己二醇的研究进展

丁璟, 赵俊琦, 程时标, 慕旭宏, 宗保宁

中国石化石油化工科学研究院, 北京 100083

收稿日期:2015-03-24 修回日期:2015-05-07 出版日期:2015-12-05 发布日期:2015-12-05
通讯作者: 程时标,教授级高级工程师,从事催化材料和有机合成研究。E-mailsbcheng.ripp@sinopec.com。
作者简介:丁璟(1991—),女,硕士研究生,研究方向为生物基化纤单体的研究。
基金资助:
国家重点基础研究发展计划(2012CB224804)及中石化总部项目(413024)。

Advances in production of biobased 1,6-HDO

DING Jing, ZHAO Junqi, CHENG Shibiao, MU Xuhong, ZONG Baoning

Research Institute of Petroleum Processing, SINOPEC, Beijing 100083, China

Received:2015-03-24 Revised:2015-05-07 Online:2015-12-05 Published:2015-12-05

摘要/Abstract

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。

关键词: 生物质, 5-羟甲基糠醛, 1,6-己二醇, 加氢, 氢解, 催化剂

Abstract: 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.

Key words: biomass, 5-HMF, 1,6-hexanediol, hydrogenation, hydrogenolysis, catalyst

中图分类号:

TQ223.1

丁璟, 赵俊琦, 程时标, 慕旭宏, 宗保宁. 生物基1,6-己二醇的研究进展[J]. 化工进展, 2015, 34(12): 4209-4213.

DING Jing, ZHAO Junqi, CHENG Shibiao, MU Xuhong, ZONG Baoning. Advances in production of biobased 1,6-HDO [J]. Chemical Industry and Engineering Progree, 2015, 34(12): 4209-4213.

参考文献

[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 producing 1,6-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]. ChemCatChem,2010,2(5):547-555.
[16] Utne T,Warrenville,Garber J D,et al. Hydrogenation of 5-hydroxy- methyl furfural:US,3083236A[P]. 1963-03-26.
[17] Tuteja J,Choudhary H,Nishimura S,et al. Direct synthesis of 1,6-hexanediol from HMF over a heterogeneous Pd/ZrP catalyst using formic acid as hydrogen source[J]. ChemSusChem,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 Brønsted acid sites[J]. Journal of Catalysis,2011,279(1):174-182.

生物基1,6-己二醇的研究进展

Advances in production of biobased 1,6-HDO

PDF (PC)

可视化

被引次数

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	张明焱, 刘燕, 张雪婷, 刘亚科, 李从举, 张秀玲. 非贵金属双功能催化剂在锌空气电池研究进展[J]. 化工进展, 2023, 42(S1): 276-286.
[2]	时永兴, 林刚, 孙晓航, 蒋韦庚, 乔大伟, 颜彬航. 二氧化碳加氢制甲醇过程中铜基催化剂活性位点研究进展[J]. 化工进展, 2023, 42(S1): 287-298.
[3]	谢璐垚, 陈崧哲, 王来军, 张平. 用于SO₂去极化电解制氢的铂基催化剂[J]. 化工进展, 2023, 42(S1): 299-309.
[4]	杨霞珍, 彭伊凡, 刘化章, 霍超. 熔铁催化剂活性相的调控及其费托反应性能[J]. 化工进展, 2023, 42(S1): 310-318.
[5]	王乐乐, 杨万荣, 姚燕, 刘涛, 何川, 刘逍, 苏胜, 孔凡海, 朱仓海, 向军. SCR脱硝催化剂掺废特性及性能影响[J]. 化工进展, 2023, 42(S1): 489-497.
[6]	邓丽萍, 时好雨, 刘霄龙, 陈瑶姬, 严晶颖. 非贵金属改性钒钛基催化剂NH₃-SCR脱硝协同控制VOCs[J]. 化工进展, 2023, 42(S1): 542-548.
[7]	程涛, 崔瑞利, 宋俊男, 张天琪, 张耘赫, 梁世杰, 朴实. 渣油加氢装置杂质沉积规律与压降升高机理分析[J]. 化工进展, 2023, 42(9): 4616-4627.
[8]	王鹏, 史会兵, 赵德明, 冯保林, 陈倩, 杨妲. 过渡金属催化氯代物的羰基化反应研究进展[J]. 化工进展, 2023, 42(9): 4649-4666.
[9]	张启, 赵红, 荣峻峰. 质子交换膜燃料电池中氧还原反应抗毒性电催化剂研究进展[J]. 化工进展, 2023, 42(9): 4677-4691.
[10]	王伟涛, 鲍婷玉, 姜旭禄, 何珍红, 王宽, 杨阳, 刘昭铁. 醛酮树脂基非金属催化剂催化氧气氧化苯制备苯酚[J]. 化工进展, 2023, 42(9): 4706-4715.
[11]	葛亚粉, 孙宇, 肖鹏, 刘琦, 刘波, 孙成蓥, 巩雁军. 分子筛去除VOCs的研究进展[J]. 化工进展, 2023, 42(9): 4716-4730.
[12]	吴海波, 王希仑, 方岩雄, 纪红兵. 3D打印催化材料开发与应用进展[J]. 化工进展, 2023, 42(8): 3956-3964.
[13]	毛善俊, 王哲, 王勇. 基团辨识加氢：从概念到应用[J]. 化工进展, 2023, 42(8): 3917-3922.
[14]	向阳, 黄寻, 魏子栋. 电催化有机合成反应的活性和选择性调控研究进展[J]. 化工进展, 2023, 42(8): 4005-4014.
[15]	王耀刚, 韩子姗, 高嘉辰, 王新宇, 李思琪, 杨全红, 翁哲. 铜基催化剂电还原二氧化碳选择性的调控策略[J]. 化工进展, 2023, 42(8): 4043-4057.