糠醛的水解制备和应用研究进展

doi:10.16085/j.issn.1000-6613.2018-1844

摘要/Abstract

摘要：

糠醛是由可再生的生物质为原料转化得到的高价值化工产品，具有广阔的应用前景。本文综述了近年来生物质催化水解制备糠醛的研究进展，同时总结了糠醛衍生产品的制备和应用。在对半纤维素水解产糖反应和木糖脱水反应进行机理分析的基础上，从反应原料、溶剂体系、催化剂和分离方法等方面归纳总结了生物质催化水解制备糠醛的最新研究进展，并提出当前生物质制备糠醛方法中存在的问题和应对方案。在此基础上，分析了糠醛经氢化、胺化、氧化、缩醛化、聚合等反应获得高价值衍生产品的研究进展。提出要实现糠醛绿色高效的生产和应用，应着力设计低成本、低能耗、低污染且高效率的催化反应体系，同时推进重要糠醛衍生产品的综合高效利用。

关键词: 糠醛, 催化, 木糖, 半纤维素, 平台化合物

Abstract:

As a value-added chemical product derived from renewable biomass, the furfural has many promising applications. In this paper, recent advances in the furfural production from biomass via hydrolysis were summarized, and the important derivatives of furfural and their applications were discussed. Based on the mechanical analysis of hemicellulose hydrolysis reaction and xylose dehydration reaction, the production advances of furfural via hydrolysis were discussed from the aspects of feedstock, solvent system, catalyst, and separation process. Furthermore, the shortcomings and possible solutions of the current furfural production method were proposed. In addition, the synthesis of high value chemicals via the hydrogenation, amination, oxidation, acetal or polymerization of furfural was summarized. In order to realize the green and efficient production and application of furfural, the reaction system with low cost, low energy consumption, low pollution, and high efficiency should be designed. At the same time, it’s very important to develop an economic and environmentally-friendly method to achieve the complete utilization of furfural-derived products.

Key words: furfural, catalysis, xylose, hemicellulose, platform chemical

中图分类号:

TQ352

聂一凡, 候其东, 李维尊, 白川云龙, 鞠美庭. 糠醛的水解制备和应用研究进展[J]. 化工进展, 2019, 38(05): 2164-2178.

Yifan NIE, Qidong HOU, Weizun LI, Chuanyunlong BAI, Meiting JU. Advances in production furfural via hydrolysis and application of furfural[J]. Chemical Industry and Engineering Progress, 2019, 38(05): 2164-2178.

图/表 10

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催化剂	溶剂（/萃取剂）	温度/℃	时间/min	底物负载/%	转化率/%	产率/%	选择率/%	参考文献
酸性离子液体
[Bmim]Cl-AlCl₃	GVL-水	120	120	—	99.70	79.80	80.0	[31]
[Sbmim]HSO₄	水/MIBK	150	25	12.7	95.30	91.5	96.0	[36]
[SbPy]BF₄	水/THF	150	60	3.6	90.00	75.0	83.3	[37]
[SbPy]MeSO₃	水/THF	150	60	3.6	45.00	36.0	80.0	[37]
[Sbe₃N]BF₄	水/THF	150	60	3.6	50.00	40.0	80.0	[37]
[Sbe₃N]MeSO₃	水/THF	150	60	3.6	32.00	28.0	87.5	[37]
[Ch-SO₄H][CF₃SO₃]	1,4-二氧杂环乙烷	120	600	4.0	99.20	95.1	95.9	[54]
[Bmim][HSO₄]	[Bmim][HSO₄]	140	300	10.0	>95.00	36.7	38.6	[34]
	[Bmim][HSO₄]/甲苯	140	240	2.3	—	73.8	—	[34]
	[Bmim][HSO₄]/MIBK	140	360	2.3	—	80.3	—	[34]
	[Bmim][HSO₄]/二噁烷	140	240	2.3	—	82.2	—	[34]
金属氯盐
AlCl₃	[Bmim]Cl	160	1.5	1.9	97.27	82.2	84.5	[44]
SnCl₄	水	140	120	11.3	55.00	32.0	58.0	[33]
SnCl₄	水/正丁醇	140	300	4.3	90.00	77.0	85.0	[33]
SnCl₄+LiCl	水/正丁醇	140	300	4.3	95.00	84.0	88.0	[33]
SnCl₄	水-DMSO	140	240	20.0	93.70	48.9	52.2	[26]
SnCl₄+LiCl	水-DMSO	130	360	10.0	—	63.0	—	[26]
CrCl₂+LiBr	DMA	100	240	10.0	—	56.0	—	[22]
固体酸催化剂
PEG-OSO₃H	[Bmim]PF₆	120	18	3.8	82.00	65.0	79.3	[55]
PEG-OSO₃H+MnCl₂	[Bmim]PF₆	120	18	3.8	99.00	75.0	75.8	[55]
H₃PW₁₂O₄₀	[Bmim]Cl	160	7.5	19.0	—	84.2	—	[56]
铌酸+磷酸铌	水	160	30	2.0	74.70	32.9	44.0	[57]
Nb₂O₅	水	120	180	1.5	93.00	44.6	48.0	[35]
Nb₂O₅	水/ 甲苯	120	180	1.6	>99.00	71.3	72.0	[35]
介孔磷酸锡-MIL-101(Cr)	水/ 甲苯	150	180	3.0	94.00	86.7	92.3	[48]
SO₃H-MCM-41	水/甲苯	155	120	2.1	95.40	68.6	71.9	[58]
SO4^2-/Sn-MMT	NaCl水溶液/2-MTHF	160	120	1.1	—	79.6	—	[40]
Nafion NR50	NaCl水溶液/CPME	170	40	4.3	100.00	80.0	80.0	[38]
CHA-20沸石	水/甲苯	170	360	0.2	100.00	61.0	61.0	[59]
磺化纳米金刚石粉	NaCl水溶液/CPME	200	50	4.4	100.00	76.0	76.0	[60]
布朗斯特酸
H₂SO₄	GVL-水	170	15	2.0	2.30	87.0	—	[61]
甜菜碱+HCOOH	水/CPME	170	60	4.4	100	80.0	80.0	[39]
H₂SO₄	[Bmim]Cl/甲苯	100	240	—	83.00	44.0	53.0	[62]

催化剂	溶剂（/萃取剂）	温度/℃	时间/min	底物负载/%	转化率/%	产率/%	选择率/%	参考文献
酸性离子液体
[Bmim]Cl-AlCl₃	GVL-水	120	120	—	99.70	79.80	80.0	[31]
[Sbmim]HSO₄	水/MIBK	150	25	12.7	95.30	91.5	96.0	[36]
[SbPy]BF₄	水/THF	150	60	3.6	90.00	75.0	83.3	[37]
[SbPy]MeSO₃	水/THF	150	60	3.6	45.00	36.0	80.0	[37]
[Sbe₃N]BF₄	水/THF	150	60	3.6	50.00	40.0	80.0	[37]
[Sbe₃N]MeSO₃	水/THF	150	60	3.6	32.00	28.0	87.5	[37]
[Ch-SO₄H][CF₃SO₃]	1,4-二氧杂环乙烷	120	600	4.0	99.20	95.1	95.9	[54]
[Bmim][HSO₄]	[Bmim][HSO₄]	140	300	10.0	>95.00	36.7	38.6	[34]
	[Bmim][HSO₄]/甲苯	140	240	2.3	—	73.8	—	[34]
	[Bmim][HSO₄]/MIBK	140	360	2.3	—	80.3	—	[34]
	[Bmim][HSO₄]/二噁烷	140	240	2.3	—	82.2	—	[34]
金属氯盐
AlCl₃	[Bmim]Cl	160	1.5	1.9	97.27	82.2	84.5	[44]
SnCl₄	水	140	120	11.3	55.00	32.0	58.0	[33]
SnCl₄	水/正丁醇	140	300	4.3	90.00	77.0	85.0	[33]
SnCl₄+LiCl	水/正丁醇	140	300	4.3	95.00	84.0	88.0	[33]
SnCl₄	水-DMSO	140	240	20.0	93.70	48.9	52.2	[26]
SnCl₄+LiCl	水-DMSO	130	360	10.0	—	63.0	—	[26]
CrCl₂+LiBr	DMA	100	240	10.0	—	56.0	—	[22]
固体酸催化剂
PEG-OSO₃H	[Bmim]PF₆	120	18	3.8	82.00	65.0	79.3	[55]
PEG-OSO₃H+MnCl₂	[Bmim]PF₆	120	18	3.8	99.00	75.0	75.8	[55]
H₃PW₁₂O₄₀	[Bmim]Cl	160	7.5	19.0	—	84.2	—	[56]
铌酸+磷酸铌	水	160	30	2.0	74.70	32.9	44.0	[57]
Nb₂O₅	水	120	180	1.5	93.00	44.6	48.0	[35]
Nb₂O₅	水/ 甲苯	120	180	1.6	>99.00	71.3	72.0	[35]
介孔磷酸锡-MIL-101(Cr)	水/ 甲苯	150	180	3.0	94.00	86.7	92.3	[48]
SO₃H-MCM-41	水/甲苯	155	120	2.1	95.40	68.6	71.9	[58]
SO4^2-/Sn-MMT	NaCl水溶液/2-MTHF	160	120	1.1	—	79.6	—	[40]
Nafion NR50	NaCl水溶液/CPME	170	40	4.3	100.00	80.0	80.0	[38]
CHA-20沸石	水/甲苯	170	360	0.2	100.00	61.0	61.0	[59]
磺化纳米金刚石粉	NaCl水溶液/CPME	200	50	4.4	100.00	76.0	76.0	[60]
布朗斯特酸
H₂SO₄	GVL-水	170	15	2.0	2.30	87.0	—	[61]
甜菜碱+HCOOH	水/CPME	170	60	4.4	100	80.0	80.0	[39]
H₂SO₄	[Bmim]Cl/甲苯	100	240	—	83.00	44.0	53.0	[62]

底物	催化剂	溶剂/（萃取剂）	温度/℃	时间 /min	底物负载/% 产率/%		参考文献
木聚糖	H₂SO₄	水	180	20	1.0	29.0	[67]
木聚糖	HCl	水	180	20	1.0	34.3	[67]
木聚糖	H₃PW₁₂O₄₀	[Bmim]Cl	160	10	1.9	93.7	[56]
木聚糖	Amberlyst-15	[Bmim]Cl	140	10	1.9	87.8	[56]
木聚糖	[Emim]HSO₄	[Emim]HSO₄/甲苯	100	240	3.0	29.0	[62]
木聚糖	AlCl₃	[Bmim]Cl	170	0.1	1.9	84.8	[44]
木聚糖	SO₄ ^2-/Sn-MMT	水/2-MTHF	160	90	0.5	77.4	[40]
木聚糖	甜菜碱+HCOOH	水/CPME	170	60	4.4	76.0	[39]
木聚糖	Nafion NR50	NaCl水溶液/CPME	190	60	3.8	55.0	[38]
木聚糖	HCl+CrCl₂	[Emim]Cl	140	120	5.0	25.0	[22]
木聚糖	[Ch-SO₄H][CF₃SO₃]	1,4-二氧杂环乙烷	120	360	4.0	82.0	[54]
未处理玉米芯	AlCl₃	[Bmim]Cl	160	3	2.5	19.1	[44]
草	AlCl₃	[Bmim]Cl	160	3	2.5	31.4	[44]
松木	AlCl₃	[Bmim]Cl	160	3	2.5	33.6	[44]
玉米穗、柳枝稷、稻草、玉米秸秆、松木、白杨木	PEG-OSO₃H + MnCl₂	[Bmim]PF₆	120	18	15.0	22.0～36.0	[55]
玉米秸秆	HCl + CrCl₂	[Emim]Cl	140	120	—	22.0	[22]
竹叶粉	CHA-20沸石	水/甲苯	170	600	2.0	55.0	[59]
玉米秸秆	炭质固体酸ISC-CCA	水	190	240	2.2	43.1	[71]

底物	催化剂	溶剂/（萃取剂）	温度/℃	时间 /min	底物负载/% 产率/%		参考文献
木聚糖	H₂SO₄	水	180	20	1.0	29.0	[67]
木聚糖	HCl	水	180	20	1.0	34.3	[67]
木聚糖	H₃PW₁₂O₄₀	[Bmim]Cl	160	10	1.9	93.7	[56]
木聚糖	Amberlyst-15	[Bmim]Cl	140	10	1.9	87.8	[56]
木聚糖	[Emim]HSO₄	[Emim]HSO₄/甲苯	100	240	3.0	29.0	[62]
木聚糖	AlCl₃	[Bmim]Cl	170	0.1	1.9	84.8	[44]
木聚糖	SO₄ ^2-/Sn-MMT	水/2-MTHF	160	90	0.5	77.4	[40]
木聚糖	甜菜碱+HCOOH	水/CPME	170	60	4.4	76.0	[39]
木聚糖	Nafion NR50	NaCl水溶液/CPME	190	60	3.8	55.0	[38]
木聚糖	HCl+CrCl₂	[Emim]Cl	140	120	5.0	25.0	[22]
木聚糖	[Ch-SO₄H][CF₃SO₃]	1,4-二氧杂环乙烷	120	360	4.0	82.0	[54]
未处理玉米芯	AlCl₃	[Bmim]Cl	160	3	2.5	19.1	[44]
草	AlCl₃	[Bmim]Cl	160	3	2.5	31.4	[44]
松木	AlCl₃	[Bmim]Cl	160	3	2.5	33.6	[44]
玉米穗、柳枝稷、稻草、玉米秸秆、松木、白杨木	PEG-OSO₃H + MnCl₂	[Bmim]PF₆	120	18	15.0	22.0～36.0	[55]
玉米秸秆	HCl + CrCl₂	[Emim]Cl	140	120	—	22.0	[22]
竹叶粉	CHA-20沸石	水/甲苯	170	600	2.0	55.0	[59]
玉米秸秆	炭质固体酸ISC-CCA	水	190	240	2.2	43.1	[71]

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