减压蒸馏法从生物质水解液中分离提纯乙酰丙酸

doi:10.3969/j.issn.1673-5854.2020.01.002

Abstract

Abstract:

The simulative hydrolysate containing levulinic acid(LA) and sulfuric acid was used to study the effect of sulfuric acid on LA distillation and purification. The effect of H⁺ concentration, the sulfate concentration and the distillation temperature were comprehensively studied for the separation of LA. Further investigation of the alkali neutralization revealed that the neutralization of H⁺ by sodium hydroxide could effectively increase the recovery of LA. The presence of sulfuric acid was not conducive to the separation and purification of LA, and the concentration of H⁺ was the main negative factor for LA recovery. The higher concentration of sulfate was beneficial to the LA recovery to a certain extent and the optimal distillation temperature was 170-180℃ at a constant H⁺ concentration. Using sodium hydroxide to neutralize hydrogen ions in the simulated hydrolysate, desirable LA recovery with high purity could be expected. When the simulative hydrolysate contained 100 mL water, 0.1 mol LA and 0.03 mol sulfuric acid, LA recovery of 84.5% with the purity of 93.3% could be obtained with the addition of 0.06 mol NaOH and distillation in vacuum at 170℃. Furthermore, the separation of LA from the hydrolysate derived from the acid-catalyzed hydrolysis of raw biomass was also studied. The separation of LA was carried out after the neutralization by adding sodium hydroxide, and the final recovery rate of LA(purity 93.5%) up to 91.8% was achieved when the molar ratio of NaOH to sulfate was 1.4.

Key words: levulinic acid, alkali neutralization, separation and purification, biomass

CLC Number:

TQ35

Chen GONG,Xuejuan CAO,Xing TANG,Xianhai ZENG,Yong SUN,Lu LIN. Separation and Purification of Levulinic Acid from Hydrolysate of Biomass by Using Compression Vacuum Distillation[J]. Biomass Chemical Engineering, 2020, 54(1): 9-15.

Figures/Tables 7

Table 1

Table 2

Table 3

Table 4

Table 5

Table 6

Table 7

References 17

1	SHELDON R A . Green chemistry and resource efficiency:Towards a green economy[J]. Green Chemistry, 2016, 18 (11): 3180- 3183. doi: 10.1039/C6GC90040B
2	HERBERT G J , KRISHNAN A U . Quantifying environmental performance of biomass energy[J]. Renewable and Sustainable Energy Reviews, 2016, 59, 292- 308. doi: 10.1016/j.rser.2015.12.254
3	TAN Z F , CHEN K T , LIU P K . Possibilities and challenges of China's forestry biomass resource utilization[J]. Renewable and Sustainable Energy Reviews, 2015, 41, 368- 378. doi: 10.1016/j.rser.2014.08.059
4	GIRISUTA B, HEERES H J. Levulinic Acid from Biomass: Synthesis and Applications[M]//FANG Z, SMITH R L, QI X H.Production of Platform Chemicals from Sustainable Resources.Singapore: Springer, 2017: 143 - 169.
5	朱仕林, 李静丹, 姜小祥, 等. 5-羟甲基糠醛与乙酰丙酸制备生物基化学品的研究进展[J]. 生物质化学工程, 2016, 50 (4): 53- 59. doi: 10.3969/j.issn.1673-5854.2016.04.010
6	王义刚, 聂小安, 刘振兴. 乙酰丙酸的制备及其应用前景分析[J]. 生物质化学工程, 2013, 47 (5): 45- 50. doi: 10.3969/j.issn.1673-5854.2013.05.009
7	PILEIDIS F D , TITIRICI M M . Levulinic acid biorefineries:New challenges for efficient utilization of biomass[J]. ChemSusChem, 2016, 9 (6): 562- 582. doi: 10.1002/cssc.201501405
8	彭红, 刘玉环, 张锦胜, 等. 生物质生产乙酰丙酸研究进展[J]. 化工进展, 2009, 28 (12): 2237- 2241. doi: 10.3321/j.issn:1000-6613.2009.12.030
9	王京拓, 张明慧. 乙酰丙酸生物质基平台分子的催化反应研究进展[J]. 石油化工, 2016, 45 (5): 513- 520. doi: 10.3969/j.issn.1000-8144.2016.05.001
10	刘凯, 方桂珍, 马艳丽, 等. 稻草酸水解制备乙酰丙酸的研究[J]. 生物质化学工程, 2007, 41 (4): 13- 16. doi: 10.3969/j.issn.1673-5854.2007.04.003
11	周存山, 林琳, 杨虎清, 等. 利用生物质转化制备乙酰丙酸的研究进展[J]. 安徽农业科学, 2010, 38 (28): 15832- 15834, 15837. doi: 10.3969/j.issn.0517-6611.2010.28.148
12	高学艺, 武彦伟, 王克冰. 沙柳酸催化水解制备乙酰丙酸及分离提纯[J]. 化工进展, 2014, 33 (1): 242- 246.
13	何柱生. 从造纸黑液中提取乙酰丙酸的研究[J]. 化学工业与工程, 2002, 19 (2): 163- 166. doi: 10.3969/j.issn.1004-9533.2002.02.006
14	李云, 蒋进元, 杨秀山, 等. 膜分离技术在木质纤维原料生物炼制领域的应用研究进展[J]. 生物质化学工程, 2018, 52 (1): 69- 74. doi: 10.3969/j.issn.1673-5854.2018.01.010
15	JIANG Y T , ZENG X H , LUQVE R , et al. Cooking with active oxygen and solid alkali:A promising alternative approach for lignocellulosic biorefineries[J]. ChemSusChem, 2017, 10 (20): 3982- 3993. doi: 10.1002/cssc.201700906
16	GONG C , WEI J N , TANG X , et al. Production of levulinic acid and ethyl levulinate from cellulosic pulp derived from the cooking of lignocellulosic biomass with active oxygen and solid slkali[J]. Korean Journal of Chemical Engineering, 2019, 36 (5): 740- 752. doi: 10.1007/s11814-019-0254-6
17	CHANG C , CEN P L , MA X J . Levulinic acid production from wheat straw[J]. Bioresource Technology, 2007, 98 (7): 1448- 1453. doi: 10.1016/j.biortech.2006.03.031

序号 No.	硫酸用量/mmol sulfuric acid dosage	蒸馏时间/min distillation time	残渣质量/g mass of residue	馏分质量/g mass of fraction	纯度/% purity	回收率% recovery
1	0	7	0	11.1	99.1	94.8
2	1	8	1.4	10.1	97.4	84.8
3	2	8	1.9	9.5	94.7	77.6
4	3	10	2.6	9.1	94.3	74.0
5	4	9	3.4	8.6	93.9	69.6
6	5	13	4.1	8.0	90.1	62.1
7	6	14	4.6	7.7	79.9	53.0
8	7	14	4.9	7.3	81.8	51.5
9	8	12	5.2	6.9	82.0	48.8
10	9	15	5.8	6.4	79.0	43.6
11	10	18	6.1	6.1	72.2	38.0

序号 No.	硫酸用量/mmol sulfuric acid dosage	硫酸钠用量/mmol Na₂SO₄ dosage	蒸馏时间/min distillation time	馏分质量/g mass of fraction	纯度/% purity	回收率/% recovery
1	0	10	7	11.1	99.2	94.9
2	1	9	7	11.0	97.3	92.3
3	2	8	8	10.6	95.4	87.2
4	3	7	9	10.2	94.7	83.3
5	4	6	10	9.3	92.1	73.8
6	5	5	9	8.9	90.6	69.5
7	6	4	10	8.7	85.3	64.0
8	7	3	13	8.1	81.1	56.6
9	8	2	13	7.2	77.3	48.0
10	9	1	16	6.7	78.6	45.4
11	10	0	18	6.1	72.4	38.1

序号 No.	硫酸钠用量/mmol Na₂SO₄ dosage	蒸馏时间/min distillation time	馏分质量/g mass of fraction	纯度/% purity	回收率/% recovery
1	1	14	7.4	81.7	52.1
2	3	13	8.1	81.5	56.9
3	5	14	8.8	82.0	62.2
4	7	15	9.2	84.9	67.3
5	9	14	9.4	89.8	72.8
6	11	13	9.6	89.1	73.7
7	13	13	9.6	91.6	75.8

序号 No.	蒸馏温度/℃ distillation temperature	蒸馏时间/min distillation time	蒸气温度/℃ vapor temperature	馏分质量/g mass of fraction	纯度/% purity	回收率/% recovery
1	140	22	109	3.5	76.1	23.0
2	150	17	115	5.6	80.7	39.0
3	160	14	118	6.5	83.5	46.8
4	170	13	123	7.3	82.3	51.8
5	180	9	126	7.5	85.7	55.4
6	190	9	130	7.6	84.1	55.1

序号 No.	氧化钙用量/mmol CaO dosage	蒸馏时间/min distillation time	馏分质量/g mass of fraction	纯度/% purity	回收率/% recovery
1	24	12	1.7	82.7	12.1
2	27	10	3.5	85.5	25.8
3	30	11	5.0	86.3	37.2
4	33	11	6.5	86.7	48.6
5	36	10	4.9	85.9	36.3

Separation and Purification of Levulinic Acid from Hydrolysate of Biomass by Using Compression Vacuum Distillation

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 7

References 17

Related Articles 15

Recommended Articles

Metrics

Comments

序号 No.	氢氧化钠用量/mmol NaOH dosage	蒸馏时间/min distillation time	馏分质量/g mass of fraction	纯度/% purity	回收率/% recovery
1	48	11	8.7	85.4	64.1
2	54	10	9.5	88.9	72.8
3	60	10	10.5	93.3	84.5
4	66	9	10.1	94.7	82.5
5	72	11	9.9	91.6	78.2

序号 No.	投加比¹⁾/% proportion	蒸馏时间/min distillation time	馏分质量/g mass of fraction	纯度/% purity	回收率/% recovery
1	0.7	20	4.0	83.7	39.3
2	0.8	18	6.0	85.6	60.0
3	0.9	20	6.1	86.2	61.1
4	1	19	6.1	85.9	61.7
5	1.1	18	6.7	87.7	68.4
6	1.2	17	7.5	89.3	78.4
7	1.3	17	8.3	92.1	89.0
8	1.4	16	8.5	93.5	91.8
9	1.5	16	8.4	91.7	90.2

[1]	Peng LYU,Guanghui WANG,Bing WANG,Deyu HU. Effect of Pyrolysis Temperature and Biomass Type on Adsorption of U(Ⅵ) by Biochar [J]. Biomass Chemical Engineering, 2020, 54(5): 15-24.
[2]	Xiaomeng QU,Ge YANG,Zehao ZHANG,Lan ZHANG. Preparation of High Purity Yacon Fructo-oligosaccharides by Nanofiltration and Its Characterization [J]. Biomass Chemical Engineering, 2020, 54(5): 37-44.
[3]	Guangbing LIANG,Yanhong LI,Changyu ZI,Yuanqin ZHANG,Zhaoxia PENG,Yulin ZHAO,Wenbo ZHAO. Fly Ash from Biomass Power Plant to Prepare Biochar [J]. Biomass Chemical Engineering, 2020, 54(2): 21-26.
[4]	Ping HUANG,Liangliang JIA,Jian LI,Dongbing LI. Characteristics of Fast Pyrolysis of Chestnut Shell Based on PY-GC/MS Technology [J]. Biomass Chemical Engineering, 2020, 54(2): 27-32.
[5]	Zhaoxia PENG,Yanhong LI,Yiqin CHEN,Guangbing LIANG,Yong HUANG,Changyu ZI. Progress in High Value-added Utilization of Silicon Resource from Biomass Ash [J]. Biomass Chemical Engineering, 2020, 54(2): 61-66.
[6]	Xinjun HE,Jiao MA,Kangjun WANG,Zhanwei XU,Songyan JIA. Catalytic Synthesis of 5-Hydroxymethylfurfural and Levulinic Acid from Agarose with ZrOCl₂ as Catalyst [J]. Biomass Chemical Engineering, 2019, 53(5): 15-20.
[7]	Weizhen LI,Yang JIANG,Wei WANG,Xiuli YIN,Mingfeng WANG. Effects of Temperature on Pelletization of Four Typical Types of Biomass [J]. Biomass Chemical Engineering, 2019, 53(5): 27-33.
[8]	Xu ZHANG,Jiao SUN,Ying FAN,Yongquan CAO,Wenyi CHEN. Pyrolysis Characteristics and Kinetic Analysis of Phragmites australis Stalk [J]. Biomass Chemical Engineering, 2019, 53(4): 9-18.
[9]	Wenxin JI,Ming ZENG,Hongbin CONG,Zonglu YAO,Haibo MENG,Lixin ZHAO. Research Status and Prospects of Biomass Pyrolysis Reactor [J]. Biomass Chemical Engineering, 2019, 53(3): 46-58.
[10]	Chenggong XU,Jinlong CUI,Zhiwei CHEN,Guibao GUO. Research Progress on Hemicellulose and Its Reducing Sugar Extraction by Hot-water Prehydrolysis [J]. Biomass Chemical Engineering, 2019, 53(3): 59-66.
[11]	Shun JI,Yongfeng QI,Meiting WANG,Ru MA,Panle GE. Effect of Additives on Combustion Characteristics of Straw Briquette Fuel [J]. Biomass Chemical Engineering, 2019, 53(1): 47-53.
[12]	FAN Fangyu, HUANG Yuanbo, YANG Xiaoqin, ZHENG Yunwu, LIU Can, WANG Zhen, ZHENG Zhifeng. Pyrolysis Characteristics and Kinetics of Shells Biomass [J]. bce, 2018, 52(6): 8-14.
[13]	YALKUNJAN Tursun, BIEERDEHAN Watihan, DILINUER Talifu, ABULIKEMU Abulizi, XU Shaoping. Co-pyrolysis Characteristics of Biomass and Coal and Influence of Catalyst on Pyrolysis [J]. bce, 2018, 52(5): 31-36.
[14]	ZHAI Qiaolong, XU Junming, SU Qiuli, LI Fanglin. Research Progress on Liquefaction of Lignocellulose Using Different Solvents [J]. bce, 2018, 52(5): 46-54.
[15]	NIU Miaomiao, YANG Jiayao, LI Shang, SUN Ke, CAO Jian, LI Xinyang. Review on Biomass Pyrolysis for Bio-oil and Upgrading Research [J]. bce, 2018, 52(5): 55-61.