不同萃取剂对木醋液活性组分的富集研究

doi:10.3969/j.issn.0253-2417.2020.02.010

Abstract

Abstract:

The enrichment effect of different extraction agents on active components of wood vinegar from waste fir plate was studied. The results showed that different extraction agents exhibited different effects on the enrichment of active components in wood vinegar. Ethyl acetate, chloroform and ether exhibited good enrichment effect on phenolic substances, which ether present better extraction performance; ethyl acetate and chloroform had good enrichment effect on ketones; 3 extractants had no obviously enrichment effect on esters, aldehydes and alcohols, and they were not conducive to the enrichment of acid substances. Methanol addition was contributed to increase the enrichment effect of ether on phenolic substances. When the volume ratio of ether to methanol was 2:1, GC content of phenolic compounds reached to 66%, which was 1.96 times that of un-treated wood vinegar.

Key words: wood vinegar, active components, extraction method, enrichment, GC-MS analysis

CLC Number:

TQ35

Xincheng LU,Jianchun JIANG,Jing HE,Kang SUN,Yunjuan SUN. Effect of Different Extraction Agents on Enrichment of ActiveComponents from Wood Vinegar[J]. Chemistry and Industry of Forest Products, 2020, 40(2): 76-82.

Figures/Tables 5

Fig.1

Table 1

Composition of wood vinegar"

序号 No.	保留时间/min retention time	有机物名称 compounds	分子式 molecular formula	GC含量/% GC content
1	1.581	乙酸acetic acid	C₂H₄O₂	7.138
2	1.782	丙酸propanoic acid	C₃H₆O₂	2.383
3	22.867	戊酸pentanoic acid	C₆H₁₂O₂	20.284
4	25.900	3-甲氧基-4-羟基苯甲酸3-methoxy-4-hydroxybenzoic acid	C₉H₁₀O₄	3.819
		小计total		33.624
5	7.607	苯酚phenol	C₆H₆O	0.941
6	10.405	3-甲基苯酚3-methyl phenol	C₇H₈O	1.180
7	10.565	2-甲氧基苯酚2-methoxy phenol	C₇H₈O₂	6.733
8	13.672	4-甲基-2-甲氧基苯酚4-methyl-2-methoxy phenol	C₈H₁₀O₂	7.064
9	14.330	邻苯二酚1, 2-benzenediol	C₆H₆O₂	3.573
10	16.190	4-乙基-2-甲氧基苯酚4-ethyl-2-methoxy phenol	C₉H₁₂O₂	4.255
11	17.208	4-乙烯基-2-甲氧基苯酚4-vinyl-2-methoxy phenol	C₉H₁₀O₂	2.462
12	18.404	丁子香酚eugenol	C₁₀H₁₂O₂	0.604
13	19.079	4-丙烯基-2-甲氧基苯酚4-propenyl-2-methoxy phenol	C₁₀H₁₂O₂	3.781
14	21.185	4-丙基-2-甲氧基苯酚4-propyl-2-methoxy phenol	C₁₀H₁₄O₂	3.121
		小计total		33.714
15	2.732	1-羟基-2-丁酮1-hydroxy-2-butanone	C₄H₈O₂	1.231
16	2.903	丙酮acetone	C₃H₆O	2.163
17	5.581	2-呋喃酮2-furanone	C₄H₄O₂	2.179
18	5.850	1, 2-环戊二酮1, 2-cyclopentanedione	C₅H₆O₂	3.523
19	8.722	3-甲基-1, 2-环戊二酮3-methyl-1, 2-cyclopentanedione	C₆H₈O₂	3.783
20	21.894	4-羟基-3-甲氧基苯乙酮4-hydroxy-3-methoxy hypnone	C₉H₁₀O₃	1.333
		小计total		14.212
21	3.767	糠醛furfural	C₅H₄O₂	3.198
22	6.863	5-甲基-2-糠醛5-methyl-2-furfural	C₆H₆O₂	0.537
23	10.765	2-乙基己醛2-ethyl hexanal	C₄H₈O	3.755
24	19.600	香草醛vanilline	C₈H₈O₃	1.422
		小计total		8.912
25	3.721	甲酸四氢糠酯formic acid, tetrahydrofuryl eater	C₆H₁₀O₃	0.457
26	14.193	2-甲基-2-丙烯酸乙酯2-methyl-2-propenoic acid, ethyl eater	C₆H₁₀O₂	1.130
		小计total		1.587
27	4.242	2-呋喃甲醇2-furfuryl alcohol	C₅H₆O₂	1.552
28	23.022	4-羟基-3-甲氧基苯乙醇4-hydroxy-3-methoxy phenethyl alcohol	C₉H₁₂O₃	6.399
		小计total		7.951

Table 1

Table 2

Fig.2

Table 3

Composition of wood vinegar under different V(ether)/V(methanol)"

类别 class	有机物名称 compounds	GC含量GC content/%
类别 class	有机物名称 compounds	5:1	4:1	3:1	2:1
酸类 acids	乙酸acetic acid	6.022	4.614	4.386	3.360
	丙酸propanoic acid	2.104	1.843	1.616	1.219
	3-甲氧基-4-羟基苯甲酸3-methoxy-4-hydroxybenzoic acid	7.168	6.905	7.130	6.581
酚类 phenols	苯酚phenol	1.362	1.791	1.667	1.951
	2-甲基苯酚2-methyl phenol	2.254	1.063	0.961	1.245
	3-甲基苯酚3-methyl phenol	—	1.622	1.717	2.070
	2-甲氧基苯酚2-methoxy phenol	15.038	14.880	14.203	14.087
	2, 3-二甲基苯酚2, 3-dimethyl phenol	—	—	—	0.913
	3-甲基-2-甲氧基苯酚3-methyl-2-methoxy phenol	—	—	—	0.849
	4-甲基-2-甲氧基苯酚4-methyl-2-methoxy phenol	15.410	14.013	13.315	13.613
	邻苯二酚1, 2-benzenediol	10.579	10.153	9.722	8.950
	4-丙氧基苯酚4-propoxyphenol	—	—	—	0.372
	4-乙基-2-甲氧基苯酚4-ethyl-2-methoxy phenol	9.305	7.978	8.253	9.347
	4-甲基邻苯二酚4-methyl-1, 2-benzenediol	—	1.680	3.165	1.891
	2, 6-二甲氧基苯酚2, 6-dimethoxy phenol	—	0.861	0.749	0.755
	丁子香酚eugenol	2.446	2.039	2.119	3.934
	4-丙烯基-2-甲氧基苯酚4-propenyl-2-methoxy phenol	—	—	1.526	1.983
	4-丙基-2-甲氧基苯酚4-propyl-2-methoxy phenol	3.502	3.150	3.449	4.063
酮类 ketones	丙酮acetone	0.684	0.601	0.563	0.480
	1-羟基-2-丁酮1-hydroxy-2-butanone	—	0.591	0.689	0.548
	3-甲基-1, 2-环戊二酮3-methyl-1, 2-cyclopentanedione	4.787	4.353	3.903	3.179
	3-乙基-2-羟基环戊烯酮3-ethyl-2-hydroxyl cyclopentenone	1.676	1.169	1.165	1.035
	8-甲基-4-壬酮8-methyl-4-nonanone	—	0.901	0.862	0.741
	4-羟基-3-甲氧基苯乙酮4-hydroxy-3-methoxy hypnone	5.134	5.446	6.336	5.526
醛类 aldehydes	糠醛furfural	4.393	3.744	2.870	2.974
	5-甲基-2-糠醛5-methyl-2-furfural	—	1.320	1.334	1.093
	香草醛vanilline	2.344	2.594	2.577	2.660
醇类 alcohols	2-呋喃甲醇2-furfuryl alcohol	—	0.676	1.133	0.674
醇类 alcohols	4-羟基-3-甲氧基苯乙醇4-hydroxy-3-methoxy phenethyl alcohol	5.792	5.882	4.561	3.907

Table 3

References 16

1	GODFREY O , SARAH W , JEFFREY S , et al. Characterization of slow pyrolysis wood vinegar and tar from banana wastes biomass as potential organic pesticides[J]. Journal of Sustainable Development, 2017, 10 (3): 81- 92.
2	卢辛成, 蒋剑春, 孙康, 等. 木醋液的制备、精制与应用研究进展[J]. 林产化学与工业, 2017, 37 (3): 21- 30. doi: 10.3969/j.issn.0253-2417.2017.03.003
	LU X C , JIANG J C , SUN K , et al. Review on preparation and application of wood vinegar[J]. Chemistry and Industry of Forest Products, 2017, 37 (3): 21- 30. doi: 10.3969/j.issn.0253-2417.2017.03.003
3	GREWAL A , ABBEY L , GUNUPURU L R . Production, prospects and potential application of pyroligneous acid in agriculture[J]. Journal of Analytical and Appllied Pyrolysis, 2018, 135, 152- 159.
4	MA C H , SONG K G , YU J H , et al. Pyrolysis process and antioxidant activity of pyroligneous acid from Rosmarinus officinalis leaves[J]. Journal of Analytical and Applied Prolysis, 2013, 104, 38- 47.
5	胡瑞瑞, 苏印泉, 朱铭强. 不同精制工艺杜仲枝木醋液抑菌及抗氧化活性比较[J]. 西北林学院学报, 2014, 29 (2): 139- 143. doi: 10.3969/j.issn.1001-7461.2014.02.26
	HU R R , SU Y Q , ZHU M Q . Research on antimicrobial and antioxidant activities of pyroligneous acids of eucommia ulmoides branch dealing with different refined methods[J]. Journal of Northwest Forestry University, 2014, 29 (2): 139- 143. doi: 10.3969/j.issn.1001-7461.2014.02.26
6	邹勇, 蔚芹, 赵忠, 等. 木屑快速热解生物油中酚类提取物的抗氧化及抑真菌活性研究[J]. 西北林学院学报, 2014, 29 (1): 116- 121. doi: 10.3969/j.issn.1001-7461.2014.01.23
	ZOU Y , WEI Q , ZHAO Z , et al. Antioxidant and antimicrobial activities of phenols extract from bio-oil by fast pyrolysis of sawdust[J]. Journal of Northwest Forestry University, 2014, 29 (1): 116- 121. doi: 10.3969/j.issn.1001-7461.2014.01.23
7	许英梅, 张秋民, 安晓雯, 等. 木醋液中醋酸的有机络合萃取研究[J]. 大连民族学院学报, 2007, (5): 69- 72. doi: 10.3969/j.issn.1009-315X.2007.05.019
	XU Y M , ZHANG Q M , AN X W , et al. Research on extraction by chemical complexation of acetic acid from pyrolysis acid[J]. Journal of Dalian National University, 2007, (5): 69- 72. doi: 10.3969/j.issn.1009-315X.2007.05.019
8	杨頔, 刘学贵, 年中锋, 等. 木醋液中酚类物质的富集及其提取工艺的研究[J]. 宁夏农林科技, 2015, 56 (4): 55- 58. doi: 10.3969/j.issn.1002-204X.2015.04.024
	YANG D , LIU X G , NIAN Z F , et al. A study of extraction process of enriched phenols from wood vinegar[J]. Ningxia Journal of Agriculture and Forest Science & Technology, 2015, 56 (4): 55- 58. doi: 10.3969/j.issn.1002-204X.2015.04.024
9	卢辛成, 蒋剑春, 孙康, 等. 热解工艺对木醋液制备及性质的影响[J]. 林产化学与工业, 2018, 38 (5): 61- 69. doi: 10.3969/j.issn.0253-2417.2018.05.009
	LU X C , JIANG J C , SUN K , et al. Influence of pyrolysis parameters on properties of pyrolyzed wood vinegar[J]. Chemistry and Industry of Forest Products, 2018, 38 (5): 61- 69. doi: 10.3969/j.issn.0253-2417.2018.05.009
10	陈爱慧.生物质三组分热解试验研究[D].哈尔滨:东北农业大学, 2015.
	CHEN A H.Experimental study on the pyrolysis of three main components in biomass[D]. Harbin: Northeast Agricultural University, 2015.
11	王树荣, 刘倩, 郑赟, 等. 基于热重红外联用分析的生物质热裂解机理研究[J]. 工程热物理学报, 2007, 27 (2): 351- 353. doi: 10.3321/j.issn:0253-231X.2007.02.053
	WANG S R , LIU Q , ZHENG B , et al. Mechanism study of biomass pyrolysis by thermogravimetric analysis coupled with infrared spectroscopy[J]. Journal of Engineering Thermophysics, 2007, 27 (2): 351- 353. doi: 10.3321/j.issn:0253-231X.2007.02.053
12	卢辛成, 蒋剑春, 何静, 等. 杉木屑分段热解制备木醋液及其特性研究[J]. 林产化学与工业, 2019, 39 (2): 96- 102. doi: 10.3969/j.issn.0253-2417.2019.02.014
	LU X C , JIANG J C , HE J , et al. Preparation and properties of wood vinegar from pyrolysis of fir sawdust under different tempertures[J]. Chemistry and Industry of Forest Products, 2019, 39 (2): 96- 102. doi: 10.3969/j.issn.0253-2417.2019.02.014
13	辛善志, 杨海平, 王贤华, 等. 纤维素热解生物油特性研究[J]. 太阳能学报, 2014, 35 (11): 2191- 2197. doi: 10.3969/j.issn.0254-0096.2014.11.019
	XIN S Z , YANG H P , WANG X H , et al. Study on the bio-oil property from cellulose pyrolysis[J]. Acta Energiae Solaris Sinica, 2014, 35 (11): 2191- 2197. doi: 10.3969/j.issn.0254-0096.2014.11.019
14	COLLARD F X , BLIN J . A review on pyrolysis of biomass constituents:Mechanisms and composition of the products obtained from the conversion of cellulose, hemicellulose and lignin[J]. Renewable and Sustainable Energy Reviews, 2014, 38, 594- 608.
15	MAHMUD K N , YAHAYU M , SARIP S H M , et al. Evaluation on efficiency of pyroligneous acid from palm kernel shell as antifungal and solid pineapple biomass as antibacterial and plant growth promoter[J]. Sains Malaysiana, 2016, 45, 1423- 1434.
16	LATIF S , CHIAPUSION G , WESTON L A . Allelopathy and the role of allelochemicals in plant defence[J]. Advances in Botanical Research, 2017, 82, 19- 54. doi: 10.1016/bs.abr.2016.12.001

类别 class	有机物名称 compounds	GC含量GC content/%
类别 class	有机物名称 compounds	乙酸乙酯 ethyl acetate	氯仿 chloroform	乙醚 ether
酸类acids	乙酸acetic acid	0.276	—	6.228
	丙酸propanoic acid	3.064	0.705	0.466
	3-甲氧基-4-羟基苯甲酸3-methoxy-4-hydroxybenzoic acid	5.462	5.343	5.332
酚类phenols	苯酚phenol	—	—	1.489
	3-甲基苯酚3-methyl phenol	—	—	2.038
	2-甲氧基苯酚2-methoxy phenol	11.550	17.243	12.940
	4-甲基-2-甲氧基苯酚4-methyl-2-methoxy phenol	13.604	15.902	12.653
	邻苯二酚1, 2-benzenediol	3.657	—	9.554
	4-乙基-2-甲氧基苯酚4-ethyl-2-methoxy phenol	7.378	8.193	7.821
	4-乙烯基-2-甲氧基苯酚4-vinyl-2-methoxy phenol	3.337	—	1.311
	丁子香酚eugenol	7.259	2.010	2.242
	4-丙烯基-2-甲氧基苯酚4-propenyl-2-methoxy phenol	—	5.837	5.905
	4-丙基-2-甲氧基苯酚4-propyl-2-methoxy phenol	—	—	1.048
酮类ketones	1-羟基-2-丁酮1-hydroxy-2-butanone	1.692	1.851	0.800
	丙酮acetone	2.606	2.557	0.610
	2-呋喃酮2-furanone	2.837	3.548	1.021
	1, 2-环戊二酮1, 2-cyclopentanedione	6.036	5.906	3.556
	3-甲基-1, 2-环戊二酮3-methyl-1, 2-cyclopentanedione	6.471	7.624	5.239
	4-羟基-3-甲氧基苯乙酮4-hydroxy-3-methoxy hypnone	9.078	2.421	2.401
醛类aldehydes	糠醛furfural	5.965	6.931	5.041
	5-甲基-2-糠醛5-methyl-2-furfural	—	2.439	0.676
	香草醛vanilline	1.856	1.725	2.925
	4-羟基-2-甲氧基肉桂醛4-hydroxy-2-methoxy cinnamaldehyde	—	—	2.281
酯类eaters	甲酸四氢糠酯formic acid, tetrahydrofuryl eater	1.150	0.971	—
醇类alcohols	2-呋喃甲醇2-furfuryl alcohol	2.671	3.078	2.218
醇类alcohols	4-羟基-3-甲氧基苯乙醇4-hydroxy-3-methoxy phenethyl alcohol	4.053	5.716	4.204

[1]	Xincheng LU,Jianchun JIANG,Jing HE,Kang SUN,Yunjuan SUN. Preparation and Properties of Wood Vinegar from Pyrolysis of Fir Sawdust Under Different Temperatures [J]. Chemistry and Industry of Forest Products, 2019, 39(2): 96-102.
[2]	Xiyu QUAN,Pai PENG,Peiyao WEN,Jinjin WEI,Junhua ZHANG. Extraction and Properties Analysis of Polysaccharides, Extractum and Gutta-percha from Eucommia ulmoides Oliver Leaves [J]. Chemistry and Industry of Forest Products, 2019, 39(2): 122-128.
[3]	Jinjin WEI,Donglin XIN,Xiang CHEN,Xiyu QUAN,Junhua ZHANG. Effect of Steam Explosion on Extraction of Bioactive Components and Gutta-percha from Barks of Eucommia ulmoides Oliver [J]. Chemistry and Industry of Forest Products, 2019, 39(1): 88-94.
[4]	LU Xincheng, JIANG Jianchun, SUN Kang, SUN Yunjuan. Influence of Pyrolysis Parameters on Properties of Pyrolyzed Wood Vinegar [J]. Chemistry and Industry of Forest Products, 2018, 38(5): 61-69.
[5]	LU Xincheng, JIANG Jianchun, SUN Kang, SUN Yunjuan. Review on Preparation and Application of Wood Vinegar [J]. Chemistry and Industry of Forest Products, 2017, 37(3): 21-30.
[6]	SONG Xiao;ZENG Tao. Analysis on Chemical Components of Essential Oil of Chinese Sweetgum Resin [J]. , 2010, 30(5): 40-44.
[7]	MA Li-yi;YU Jian-xing;ZHANG Zhong-quan;WANG You-qiong;GAN Jin;ZHENG Hua;GUO Yuan-heng;ZHAO Hong;DUAN Qiong-fen. Aqueous Enzymatic Extraction of Moringa oleifera Lam.Seed Oil [J]. , 2010, 30(3): 53-56.
[8]	ZENG Tao;YANG Li-juan;WANG A-fa. Chemical Constitution of Pinus kesiya Oleoresin from Burma [J]. , 2009, 29(4): 23-26.
[9]	DU Ping;ZHANG Xian-jun;SUN Xiao-dong;. Chemical Constituents of Volatile Oil from Blumea balsamifera (Linn.) DC. in Yunnan [J]. , 2009, 29(2): 115-118.
[10]	LIU Wei-juan;. GC-MS Identification of Degradative Products from Catalytical Oxidation of Lutein [J]. , 2009, 29(2): 85-89.
[11]	LIU Wei-juan;. [J]. , 2008, 28(6): 20-24.
[12]	ZHAI Mei-zhi;JING Bing-nian;JIA Cai-xia;LIU Chao-bin . Study on Extraction Conditions of Active Antiviral Substance from Walnut Leaves [J]. , 2007, 27(2): 71-75.
[13]	FAN Gui-zhi;ZHAN Ya-guang;WANG Bo;QIU Lei;LIU Gui-feng;WANG Hui-ren. Research on Difference of Betulin Content in Different Parts and Provenances of Birch (Betula platyphylla Suk.) [J]. , 2007, 27(04): 103-106.
[14]	WANG Hai-ying;YANG Guo-ting;LIU Zhi-ming. CONSTITUENT ANALYSIS OF PHENOLS IN WOOD VINEGAR FROM MONGOLIAN OAK (QUERCUS MONGOLICA) [J]. , 2005, 25(S1): 143-145.
[15]	WANG Zong-de;XIAO Zhuan-quan;CHEN Jin-zhu. STRUCTURAL IDENTIFICATION OF THE PRODUCTS FROM NOPOL OZONIZATION BY GC-MS [J]. , 2003, 23(3): 6-10.

Effect of Different Extraction Agents on Enrichment of ActiveComponents from Wood Vinegar

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 5

References 16

Related Articles 15

Recommended Articles

Metrics

Comments