竹材主要化学成分及其点击化学和开环共聚研究
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摘要
能源危机和环境污染已经成为当今人们关注的热点，利用可再生木质纤维生物质转化为生物燃料、化学品和生物材料可有效补充或替代石油基产品。本论文以我国资源丰富的竹材为原料，对其主要化学成分（淀粉、纤维素、半纤维素和木质素）的分离纯化、结构鉴定、生物降解和化学改性进行了系统的研究，以期为竹材的高值化利用提供理论依据和技术支撑。本论文的主要研究内容有：
（1）利用梯度乙醇（0%、15%、30%、45%、60%和75%）对寿竹碱溶性半纤维素进行了分级纯化，并采用糖分析、凝胶色谱（GPC）、红外（FTIR）、气质联用、1D（~1H和~(13)C）和2D异核单量子相关核磁共振（2D HSQC NMR）以及热分析（TGA）对其化学组成、结构特征和热稳定性进行了研究。结果表明寿竹半纤维素是以(1→4)-β-D-木糖为主链、以O-3位α-L-阿拉伯糖（5-12mol%）以及O-2位4-O-甲基-葡萄糖醛酸单元和乙酰基（0.8-11mol%）为侧链的O-乙酰-4-O-甲基-葡萄糖醛酸阿拉伯糖木聚糖，分子量为13400-67500g/mol，并且较高浓度乙醇能够沉淀出侧链较多的半纤维素。通过对所得半纤维素进行酶水解制备出了聚合度为1-6的低聚木糖，得率为21.5-40.6%，同时探讨了半纤维素结构对酶解制备低聚木糖的影响。此外，对提取出的淀粉采用固体核磁~(13)CCP/MAS和X-射线衍射进行了结构研究。
（2）采用水、0.5%、1%、1%含60%乙醇、3%、5%和8%的NaOH对红壳雷竹进行了连续碱抽提分离出7种碱木质素，利用紫外、FTIR、GPC、2D HSQC NMR、硝基苯氧化以及TGA对该竹材碱木质素和磨木木质素的结构和热稳定性进行了对比研究。结果表明红壳雷竹磨木木素为SGH型木质素（S/G~1.3），且含有较多酯化的对香豆酸和醚化的阿魏酸，分子量为3320g/mol，而碱木质素分子量为970-3430g/mol。2D HSQCNMR结果表明，该竹材磨木木质素的主要连接键为-O-4'（65%），其次为-'（15%），此外，还含有少量的-5'(7%)，-1'(4%)，5-5'(4%)和末端肉桂酯（5%），并且45%的侧链γ位上发生了乙酰化。相比之下，碱木质素在碱分离过程中部分连接键发生了断裂。
（3）在NaH的存在下，将五月季竹纤维素和丙炔氯在DMA/LiCl均相体系中反应合成出了丙炔纤维素；另一方面，以DCC为催化剂，使壳聚糖与4-叠氮苯甲酸在离子液体[Amim]Cl均相体系中反应合成出4-叠氮苯甲酰壳聚糖，分别对其合成条件进行了优化，并探讨了丙炔基团在葡萄糖单元上反应的选择性。随后在铜(I)催化下利用点击化学首次合成出了新的纤维素-点击-壳聚糖聚合物。采用FTIR、固体核磁~(13)C CP/MAS、扫描电镜和TGA对其结构、形态和热性能进行了表征研究。结果表明该聚合物的热稳定性比纤维素、壳聚糖和纤维素-壳聚糖复合物都高，并且少量的纤维素-点击-壳聚糖聚合物具有厘米级长度的空心结构。
（4）在Al(Oi-Pr)3的存在下引发环氧丙烷开环，与五月季竹木聚糖发生接枝共聚反应，首次合成出了木聚糖接枝聚环氧丙烷，并探讨了不同反应条件对木聚糖接枝聚环氧丙烷的接枝度和分子量及其分布的影响。在此基础上，采用微波辅助合成了羧甲基木聚糖接枝聚环氧丙烷产物，利用FTIR及~1H和~(13)C NMR对木聚糖接枝聚环氧丙烷和羧甲基木聚糖接枝聚环氧丙烷结构进行了表征。
Currently, the main focus from people has been on the energy crisis and environmentalpollution. The conversion of lignocellulosic biomass into biofuels, chemicals, andbiomaterials is an alternative way for the supplement and/or replacement of petroleum-basedproducts. As one of the most important biomass, bamboo is rich-resource in China. In thisstudy, a series of research was carried out to focus on the isolation and purification of themain chemical compositions (starch, cellulose, hemicelluloses, and lignin) of bamboo andidentification of their structure as well as the biodegradation and chemical modification,which will provide the theory and technology for the high-valued utilization of bamboo. Theresearch and the results are described as follows:
(1) Alkalisoluble hemicelluloses were fractionated by graded precipitation at ethanolconcentrations of0,15,30,45,60, and75%(v/v). Chemical composition and structuralfeatures of the six hemicellulosic subfractions were investigated by a combination of sugaranalysis, GPC, FT-IR, GC-MS,1D (~1H and~(13)C) and2D (HSQC) NMR spectra, and thermalanalysis. The results showed that the bamboo (Phyllostachys bambusoides f. shouzhu Yi)hemicelluloses were O-acetylated4-O-methyl-glucuronoarabinoxylans consisting of a linear(1→4)-β-D-xylopyranosyl backbone decorated with branches at O-3of α-L-arabinofuranosyl(5-12mol%) or at O-2of4-O-methylglucuronic acid units and acetyl groups (0.8-11mol%).The molecular weights of these polysaccharides ranged between13400and67500g/mol. Itwas also found that more branched hemicelluloses were precipitated at higher ethanolconcentrations. Moreover, xylo-oligosaccharides (XOS) with DP1-6were produced byenzymatic hydrolysis of hemicelluloses and the total yields of XOS were range of21.5to40.6%. At the same time, the effect of structural features of hemicelluloses on the preparationof XOS by enzymatic hydrolysis was also discussed. In addition, Starch from bamboo wasevaluated by means of solid-state~(13)C CP/MAS NMR and X-ray diffraction.
(2) Seven lignin fractions from bamboo Phyllostachys incarnata Wen were isolated bythe sequential extractions with distilled water,0.5%and1%NaOH,60%ethanol containing1%NaOH, and3%,5%and8%NaOH. The chemical composition and structuralcharacterization of the milled wood lignin (MWL) and alkali-fractionated lignins werecomparatively investigated using FT-IR, GPC,2D HSQC, alkaline nitrobenzene oxidation,and thermal analysis. It was found that bamboo MWL (S/G~1.3) is of SGH type with aconsiderable amount of esterified p-coumaric acid and etherified ferulic acid. Molecularweights of3,320g/mol for MWL and varying weights between970and3,430g/mol for the alkali-fractionated lignins were obtained. Moreover,2D HSQC of MWL showed apredominance of β-O-4' linkages (65%), followed by β–β' linkages (15%) and lower amountsof β-5'(7%), β-1'(4%),5–5'(4%) linkages, and cinnamyl acetate end groups (5%). Inaddition, a percentage (~45%) of the lignin side chain was found to be acylated at theγ-carbon. However, the alkali-fractionated lignins lost parts of these linkages duringsuccessive alkaline fractionation processes.
(3) Propargyl cellulose was synthesized by etherification of bamboo Phyllostachysbambusoide cellulose with propargyl chloride in DMA/LiCl in the presence of NaH. On theother hand, the functional azide groups were introduced onto the chitosan chains byDCC-catalyzed reacting chitosan with4-azidobenzoic acid in [Amim]Cl/DMF. The synthesisconditions of reactions were respectively optimized. Meanwhile, the regioselectivity ofpropargylation on anhydrous glucose unit was determined. Subsequently, the novelcellulose-click-chitosan polymer was obtained via click reaction between the terminal alkynegroups of cellulose and the azide groups on the chitosan backbone. The successful binding ofcellulose and chitosan was confirmed and characterized by FTIR and CP/MAS~(13)C NMRspectroscopy. TGA analyses indicated that the cellulose-click-chitosan polymer had a higherthermal stability than that of cellulose and chitosan as well as cellulose-chitosan complex.More interestingly, some hollow tubes with near millimeter length were also observed bySEM.
(4) Xylan-g-PPO was firstly synthesized by grafting xylan from bamboo (Phyllostachysbambusoides) with poly(propylene oxide)(PPO) chains using the Al(Oi-Pr)3-initiatedring-opening polymerization. The effects of reaction conditions on the GD, molecular weightsand molecular weight distributions of xylan-g-PPO were also discussed. Furthermore, thecarboxymethyl groups were introduced onto xylan-g-PPO by microwave irradiation forsynthesis of carboxymethyl xylan-g-poly(propylene oxide). The resulted xylan-g-PPO andCMX-g-PPO were well characterized by FTIR and~(13)C NMR.
（1）利用梯度乙醇（0%、15%、30%、45%、60%和75%）对寿竹碱溶性半纤维素进行了分级纯化，并采用糖分析、凝胶色谱（GPC）、红外（FTIR）、气质联用、1D（~1H和~(13)C）和2D异核单量子相关核磁共振（2D HSQC NMR）以及热分析（TGA）对其化学组成、结构特征和热稳定性进行了研究。结果表明寿竹半纤维素是以(1→4)-β-D-木糖为主链、以O-3位α-L-阿拉伯糖（5-12mol%）以及O-2位4-O-甲基-葡萄糖醛酸单元和乙酰基（0.8-11mol%）为侧链的O-乙酰-4-O-甲基-葡萄糖醛酸阿拉伯糖木聚糖，分子量为13400-67500g/mol，并且较高浓度乙醇能够沉淀出侧链较多的半纤维素。通过对所得半纤维素进行酶水解制备出了聚合度为1-6的低聚木糖，得率为21.5-40.6%，同时探讨了半纤维素结构对酶解制备低聚木糖的影响。此外，对提取出的淀粉采用固体核磁~(13)CCP/MAS和X-射线衍射进行了结构研究。
（2）采用水、0.5%、1%、1%含60%乙醇、3%、5%和8%的NaOH对红壳雷竹进行了连续碱抽提分离出7种碱木质素，利用紫外、FTIR、GPC、2D HSQC NMR、硝基苯氧化以及TGA对该竹材碱木质素和磨木木质素的结构和热稳定性进行了对比研究。结果表明红壳雷竹磨木木素为SGH型木质素（S/G~1.3），且含有较多酯化的对香豆酸和醚化的阿魏酸，分子量为3320g/mol，而碱木质素分子量为970-3430g/mol。2D HSQCNMR结果表明，该竹材磨木木质素的主要连接键为-O-4'（65%），其次为-'（15%），此外，还含有少量的-5'(7%)，-1'(4%)，5-5'(4%)和末端肉桂酯（5%），并且45%的侧链γ位上发生了乙酰化。相比之下，碱木质素在碱分离过程中部分连接键发生了断裂。
（3）在NaH的存在下，将五月季竹纤维素和丙炔氯在DMA/LiCl均相体系中反应合成出了丙炔纤维素；另一方面，以DCC为催化剂，使壳聚糖与4-叠氮苯甲酸在离子液体[Amim]Cl均相体系中反应合成出4-叠氮苯甲酰壳聚糖，分别对其合成条件进行了优化，并探讨了丙炔基团在葡萄糖单元上反应的选择性。随后在铜(I)催化下利用点击化学首次合成出了新的纤维素-点击-壳聚糖聚合物。采用FTIR、固体核磁~(13)C CP/MAS、扫描电镜和TGA对其结构、形态和热性能进行了表征研究。结果表明该聚合物的热稳定性比纤维素、壳聚糖和纤维素-壳聚糖复合物都高，并且少量的纤维素-点击-壳聚糖聚合物具有厘米级长度的空心结构。
（4）在Al(Oi-Pr)3的存在下引发环氧丙烷开环，与五月季竹木聚糖发生接枝共聚反应，首次合成出了木聚糖接枝聚环氧丙烷，并探讨了不同反应条件对木聚糖接枝聚环氧丙烷的接枝度和分子量及其分布的影响。在此基础上，采用微波辅助合成了羧甲基木聚糖接枝聚环氧丙烷产物，利用FTIR及~1H和~(13)C NMR对木聚糖接枝聚环氧丙烷和羧甲基木聚糖接枝聚环氧丙烷结构进行了表征。
Currently, the main focus from people has been on the energy crisis and environmentalpollution. The conversion of lignocellulosic biomass into biofuels, chemicals, andbiomaterials is an alternative way for the supplement and/or replacement of petroleum-basedproducts. As one of the most important biomass, bamboo is rich-resource in China. In thisstudy, a series of research was carried out to focus on the isolation and purification of themain chemical compositions (starch, cellulose, hemicelluloses, and lignin) of bamboo andidentification of their structure as well as the biodegradation and chemical modification,which will provide the theory and technology for the high-valued utilization of bamboo. Theresearch and the results are described as follows:
(1) Alkalisoluble hemicelluloses were fractionated by graded precipitation at ethanolconcentrations of0,15,30,45,60, and75%(v/v). Chemical composition and structuralfeatures of the six hemicellulosic subfractions were investigated by a combination of sugaranalysis, GPC, FT-IR, GC-MS,1D (~1H and~(13)C) and2D (HSQC) NMR spectra, and thermalanalysis. The results showed that the bamboo (Phyllostachys bambusoides f. shouzhu Yi)hemicelluloses were O-acetylated4-O-methyl-glucuronoarabinoxylans consisting of a linear(1→4)-β-D-xylopyranosyl backbone decorated with branches at O-3of α-L-arabinofuranosyl(5-12mol%) or at O-2of4-O-methylglucuronic acid units and acetyl groups (0.8-11mol%).The molecular weights of these polysaccharides ranged between13400and67500g/mol. Itwas also found that more branched hemicelluloses were precipitated at higher ethanolconcentrations. Moreover, xylo-oligosaccharides (XOS) with DP1-6were produced byenzymatic hydrolysis of hemicelluloses and the total yields of XOS were range of21.5to40.6%. At the same time, the effect of structural features of hemicelluloses on the preparationof XOS by enzymatic hydrolysis was also discussed. In addition, Starch from bamboo wasevaluated by means of solid-state~(13)C CP/MAS NMR and X-ray diffraction.
(2) Seven lignin fractions from bamboo Phyllostachys incarnata Wen were isolated bythe sequential extractions with distilled water,0.5%and1%NaOH,60%ethanol containing1%NaOH, and3%,5%and8%NaOH. The chemical composition and structuralcharacterization of the milled wood lignin (MWL) and alkali-fractionated lignins werecomparatively investigated using FT-IR, GPC,2D HSQC, alkaline nitrobenzene oxidation,and thermal analysis. It was found that bamboo MWL (S/G~1.3) is of SGH type with aconsiderable amount of esterified p-coumaric acid and etherified ferulic acid. Molecularweights of3,320g/mol for MWL and varying weights between970and3,430g/mol for the alkali-fractionated lignins were obtained. Moreover,2D HSQC of MWL showed apredominance of β-O-4' linkages (65%), followed by β–β' linkages (15%) and lower amountsof β-5'(7%), β-1'(4%),5–5'(4%) linkages, and cinnamyl acetate end groups (5%). Inaddition, a percentage (~45%) of the lignin side chain was found to be acylated at theγ-carbon. However, the alkali-fractionated lignins lost parts of these linkages duringsuccessive alkaline fractionation processes.
(3) Propargyl cellulose was synthesized by etherification of bamboo Phyllostachysbambusoide cellulose with propargyl chloride in DMA/LiCl in the presence of NaH. On theother hand, the functional azide groups were introduced onto the chitosan chains byDCC-catalyzed reacting chitosan with4-azidobenzoic acid in [Amim]Cl/DMF. The synthesisconditions of reactions were respectively optimized. Meanwhile, the regioselectivity ofpropargylation on anhydrous glucose unit was determined. Subsequently, the novelcellulose-click-chitosan polymer was obtained via click reaction between the terminal alkynegroups of cellulose and the azide groups on the chitosan backbone. The successful binding ofcellulose and chitosan was confirmed and characterized by FTIR and CP/MAS~(13)C NMRspectroscopy. TGA analyses indicated that the cellulose-click-chitosan polymer had a higherthermal stability than that of cellulose and chitosan as well as cellulose-chitosan complex.More interestingly, some hollow tubes with near millimeter length were also observed bySEM.
(4) Xylan-g-PPO was firstly synthesized by grafting xylan from bamboo (Phyllostachysbambusoides) with poly(propylene oxide)(PPO) chains using the Al(Oi-Pr)3-initiatedring-opening polymerization. The effects of reaction conditions on the GD, molecular weightsand molecular weight distributions of xylan-g-PPO were also discussed. Furthermore, thecarboxymethyl groups were introduced onto xylan-g-PPO by microwave irradiation forsynthesis of carboxymethyl xylan-g-poly(propylene oxide). The resulted xylan-g-PPO andCMX-g-PPO were well characterized by FTIR and~(13)C NMR.
引文
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