木质素模型物紫丁香酚基丙三醇-β-愈创木基丙醚的合成与结构表征

doi:10.3969/j.issn.0253-2417.2015.05.011

林产化学与工业 ›› 2015, Vol. 35 ›› Issue (5): 65-70.doi: 10.3969/j.issn.0253-2417.2015.05.011

木质素模型物紫丁香酚基丙三醇-β-愈创木基丙醚的合成与结构表征

杨晓慧^1,2,3, 肖国民¹, 蒋剑春^2,3, 周永红^2,3

1. 东南大学化学化工学院, 江苏南京 211189;
2. 江苏强林生物能源材料有限公司, 江苏溧阳 213364;
3. 中国林业科学研究院林产化学工业研究所, 江苏南京 210042

收稿日期:2014-06-30 出版日期:2015-10-25 发布日期:2015-10-24
通讯作者: 肖国民,教授,博士生导师,从事生物质能源综合利用研究;E-mail:xiaogm@seu.edu.cn E-mail:xiaogm@seu.edu.cn
作者简介:杨晓慧(1980—),男,山东临沂人,副研究员,博士,从事生物质材料的研究与应用;E-mail:hmilydear@163.com
基金资助:
国家自然科学基金资助项目(31200449)

Synthesis and Characterization of A Novel Lignin Model Compound Named Guaiacylglycerol-β-guaiacyl Ether

YANG Xiao-hui^1,2,3, XIAO Guo-min¹, JIANG Jian-chun^2,3, ZHOU Yong-hong^2,3

1. School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, China;
2. Jiangsu Qianglin Biomass Energy and Materials Co., Ltd., Liyang 213364, China;
3. Institute of Chemical Industry of Forest Products, CAF, Nanjing 210042, China

Received:2014-06-30 Online:2015-10-25 Published:2015-10-24

摘要/Abstract

摘要： 以乙酰丁香酮为原料经溴代、取代、羟甲基化以及还原等反应,合成了一种新型的β-O-4型木质素模型物紫丁香酚基丙三醇-β-愈创木基丙醚(SG),并通过IR、 ¹H NMR、¹³C NMR 和HRMS以及X射线单晶衍射进行了结构鉴定和表征。X射线单晶衍射法测定表明,该化合物属三斜晶系,空间群为P-1,晶包参数a=0.724 20(14),b=1.077 0(2),c=1.205 4(2)nm,β=90.43(3)°,V=0.858 0(3)nm³,Z=2,M_r=350.36,F(000)=372,μ(MoKα)=0.104 mm^-1,D_C=1.356 g/cm³,λ=0.071 073 nm,R=0.0602,wR=0.162 1。另外,在晶体结构中分子间通过氢键作用形成二聚体结构。

关键词: 木质素, 模型物, 合成, 结构表征, 单晶衍射

Abstract: A novel lignin model compound named guaiacylglycerol-β-guaiacyl ether (SG) was synthesized from acetosyringone via bromination, substitution, hydroxyl methylation and reduction reaction. Its structure was characterized by FT-IR, ¹H NMR, ¹³C NMR, HRMS and single-crystal X-ray diffraction. Single-crystal X-ray diffraction analysis showed that the compound was of triclinic system, space group P-1 with a=0.724 20(14), b=1.077 0(2), c=1.2054(2) nm, β=90.43(3)°, V=0.858 0(3) nm³, Z=2, M_r=350.36, F(000)=372, μ(MoKα)=0.104 mm^-1, D_C=1.356 g/cm³, λ=0.071 073 nm, the final R=0.060 2 and wR=0.162 1. In addition, the dimer was formed through intermolecular hydrogen bonds in crystal packing of the title compound.

Key words: lignin, model compound, synthesis, structure characterization, single-crystal X-ray diffraction

中图分类号:

TQ35
O621.3

杨晓慧, 肖国民, 蒋剑春, 周永红. 木质素模型物紫丁香酚基丙三醇-β-愈创木基丙醚的合成与结构表征[J]. 林产化学与工业, 2015, 35(5): 65-70.

YANG Xiao-hui, XIAO Guo-min, JIANG Jian-chun, ZHOU Yong-hong. Synthesis and Characterization of A Novel Lignin Model Compound Named Guaiacylglycerol-β-guaiacyl Ether[J]. Chemistry and Industry of Forest Products, 2015, 35(5): 65-70.

参考文献

[1] 高国安,李忠正.甜竹木质素结构特征的研究[J].林产化学与工业,2010,30(2):37-42. CAO Quoc-an,LI Zhong-zheng.Research on structure characteristics of sweet-bamboo lignin[J].Chemistry and Industry of Forest Products,2010,30(2):37-42.
[2] GOSSELINK R J A,SNIJDER M H B,KRANENBARG A,et al.Characterisation and application of NovaFiber lignin[J].Industrial Crops and Products,2004,20(2):191-203.
[3] LUO Xiao-lin,ZHAN Huai-yu,CHAI Xin-sheng,et al.A novel method for determination of aromatic aldehyde monomers in lignin degradation liquor[J].Industrial & Engineering Chemistry Research,2009,48(5):2713-2716.
[4] SRIDHAR P,ARAUJO J D,RODRIGUES A E.Modeling of vanillin production in a structured bubble column reactor[J].Catalysis Today,2008,105(3/4):574-581.
[5] LAHTINEN M,KRUUS K,HEINONEN P,et al.On the reactions of two fungal laceases differing in their redox potential with lignin model compounds:Products and their rate of formation[J].Journal of Agricultural and Food Chemistry,2009,57(18):8357-8365.
[6] REALE S,ATTANASIO F,SPRETI N,et al.Lignin chemistry:Biosynthetic study and structural characterisation of coniferyl alcohol oligomers formed in vitro in a micellar environment[J].Chemistry-A European Journal,2010,16(20):6077-6087.
[7] HYATT J A.Synthesis of some tetrameric lignin model compounds containing β-O-4 and 5,5'-interunit linkages[J].Holzforsehung,1987,41(6):363-370.
[8] KATAHIRA R,KAMITAKAHAR H,TAKANO T,et al.Synthesis of β-O-4 type oligomeric lignin model compound by the nucleophilic addition of carbanion to the aldehyde group[J].Journal of Wood Science,2006,52(3):255-260.
[9] 吕银华,刘江燕,武书彬.两种β-O-4型木素高聚模型物的合成[J].化学研究与应用,2012,24(3):463-468. LV Ying-hua,LIU Jiang-yan,WU Shu-bin.Synthesis of two kinds of β-O-4 lignin model polymer[J].Chemical Research and Application,2012,24(3):463-468.
[10] 聂明才,霍淑平,孔振武.木质素模型化合物的研究进展[J].林产化学与工业,2010,30(5):115-121. NIE Ming-cai,HUO Shu-ping,KONG Zhen-wu.Research progress of lignin model compounds[J].Chemistry and Industry of Forest Products,2010,30(5):115-121.
[11] 胡周建,谢益民,欧国隆,等.愈创木基丙三醇-β-愈创木基醚的合成新方法及结构分析[J].造纸科学与技术,2002,21(4):4-7. HU Zhou-jian,XIE Yi-min,OU Guo-long,et al.A new method of synthesis of guaiacylglycerol-β-guaiacyl ether and its structural analysis[J].Paper Science & Technology,2002,21(4):4-7.
[12] 谢益民,胡周建,伍红,等.β-O-4型木质素模型化合物的合成及其在GIF型仿酶降解体系中的变化(Ⅱ)[J].林产化学与工业,2004,24(1):1-6. XIE Yi-min,HU Zhou-jian,WU Hong,et al.Synthesis of β-O-4 type lignin model compound and its biomimetic degradation with GIF system (II)[J].Chemistry and Industry of Forest Products,2004,24(1):1-6.
[13] 周燕,谢益民,杨志勇,等.愈创木基丙三醇-β-愈创木基醚-[α-¹³C] 的合成新方法及结构分析[J].化学研究与应用,2006,18(8):921-926. ZHOU Yan,XIE Yi-min,YANG Zhi-yong,et al.Synthesis of guaiacylglycerol-β-guaiacyl ether-[α-¹³C] [J].Chemical Research and Application,2006,18(8):921-926.
[14] TERASHIMA N,SEGUCHI Y.Selective ¹³C enrichment of side chain carbons of guaiacyl lignin in pine[J].Holzforschung,1991,45(Suppl.):35-39.
[15] YANG Xiao-hui,LIU Cheng-guo,ZHOU Yong-hong,et al.Facile synthesis and crystal structure of a novel cyanopyridine[J].Chinese Journal of Structural Chemistry,2011,30(7):1011-1015.

木质素模型物紫丁香酚基丙三醇-β-愈创木基丙醚的合成与结构表征

Synthesis and Characterization of A Novel Lignin Model Compound Named Guaiacylglycerol-β-guaiacyl Ether

PDF (PC)

可视化

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

关于本刊

投稿指南

在线期刊

相关单位

联系我们

[1]	张清桐, 运晓静, 颜德鹏, 李明富, 王双飞, 闵斗勇. 太阳光催化木质素制备银纳米颗粒[J]. 林产化学与工业, 2019, 39(4): 35-41.
[2]	孙永昌, 张冰清, 刘力鸣, 刘肖南, 史正军. 木质素基炭材料的制备及其对Cr(VI)的吸附机制研究[J]. 林产化学与工业, 2019, 39(4): 120-128.
[3]	卢言菊, 赵振东, 王婧, 徐士超, 毕良武, 陈玉湘. 异海松酸糠醛类酰腙化合物的合成及生物活性研究[J]. 林产化学与工业, 2019, 39(3): 43-48.
[4]	杨小华, 诸进华, 张燕, 李守海, 李梅. 蓖麻油基水性环氧固化剂的合成及性能[J]. 林产化学与工业, 2019, 39(3): 65-71.
[5]	陈超, 王傲, 孙康, 卢辛成, 许伟, 蒋剑春. 生物质原料的Ni催化石墨化研究[J]. 林产化学与工业, 2019, 39(3): 94-100.
[6]	徐士超, 曾小静, 董欢欢, 赵振东. 萜类植物源除草活性物开发及应用研究进展[J]. 林产化学与工业, 2019, 39(2): 1-8.
[7]	赵存异, 应文俊, 史正军, 杨海艳, 郑志锋, 杨静. 羟丙基化碱木质素的制备及其对纤维素酶水解的影响[J]. 林产化学与工业, 2019, 39(2): 109-114.
[8]	许利娜, 杨小华, 丁海阳, 李梅, 夏建陵. 氧化改性木质素磺酸钠-石墨烯复合量子点的制备及性能[J]. 林产化学与工业, 2019, 39(1): 29-34.
[9]	冯雪贞, 肖转泉, 卢平英, 范国荣, 王宗德. 氢化诺卜基二甲基烷基卤化铵的合成及抑菌活性[J]. 林产化学与工业, 2019, 39(1): 35-40.
[10]	檀贯妮, 高亚楠, 高宏, 商士斌, 宋湛谦. 含双萘的脱氢枞酸三芳胺化合物的合成及光谱性能[J]. 林产化学与工业, 2019, 39(1): 61-66.
[11]	李继辉, 孙康, 宋曜光, 王傲, 蒋剑春. 木质素基炭纳米片的制备及其电化学性能[J]. 林产化学与工业, 2019, 39(1): 67-74.
[12]	王广彬, 陈家宝, 谷利敏, 王春鹏, 许玉芝. 木质素基RAFT链转移剂的合成及其聚合特性研究[J]. 林产化学与工业, 2018, 38(6): 75-80.
[13]	周方浪, 郑志锋, 杨静, 杨海艳, 邓佳, 史正军. 木质素基酚醛树脂泡沫的制备及性能研究[J]. 林产化学与工业, 2018, 38(6): 103-109.
[14]	黄静, 鲍涵, 张夏, 莫悦, 罗金岳, 刘祖广. 3'-(3,3-二甲基双环[2.2.1]庚-2-亚基)-5'-苯基-异噁唑啉的合成与表征[J]. 林产化学与工业, 2018, 38(6): 110-116.
[15]	翟兆兰, 闫鑫焱, 许吉, 宋湛谦, 商士斌, 饶小平. 马来海松酸长链烷基酰(亚)胺钠的合成及其对小地老虎的拒食活性研究[J]. 林产化学与工业, 2018, 38(5): 23-29.