木材多元醇液化物的结构表征及缩聚反应路径
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摘要
为了弄清楚木材多元醇液化过程中分解与缩聚反应阶段液化物的结构特征,以及缩聚残余物的反应路径,本研究以多元醇(PEG400：丙三醇=4：1)为液化剂、72%硫酸为催化剂,对40～80目桦木(Betula dahurica Pall.)木粉在多元醇：木粉：硫酸=3：2：0.03(质量比)、温度150℃、时间0-180 min条件下进行液化。用FTIR、XRD、SEM、TGA、GPC、HPLC、GC-MS及NMR等方法,对液化残余物、液化产物的官能团、微细构造、热失重行为、分子量大小及其分布、糖类化合物含量、分子结构等方面进行测定与分析。
本研究得到主要结果如下：
1.在液化时间0-180 min,纤维素含量先减少后增大,木质素含量逐渐增大。与未液化木粉相比,纤维素和木质素含量分别从44.54%和19.04%降低到液化后的12.16～24.92%和3.93～15.23%。
2.液化残余物的羰基、木质素芳香环以及甲氧基随液化时间逐渐减少。液化残余物的结晶度增大5.10～7.38%,这主要基于液化过程中纤维素准结晶区发生降解以及缩聚残余物的分子取向引起的。在分解反应阶段,残余物中纤维尺度与平均表观面积随液化时间逐渐变小；在缩聚反应阶段,残余物中出现块状堆积物,平均表观面积增大。液化残余物的热稳定性随液化时间提高。
3.液化木质素的重均分子量主要分布在1160-1356,醛基数目随液化时间逐渐增加。在液化10 min时,愈疮木基、紫丁香基以及β-O-4位的C-O键几乎消失。纤维素的官能团变化不大。
4.随液化时间的延长,液化产物的羰基、酚羟基以及甲氧基数目逐渐增加,醇羟基数目减少。液化产物的热稳定性降低以及己糖、糠醛含量减少。液化产物的平均分子量显著降低,且重均分子量分布在1103～1337。产物中的糖类化合物降解生成糖苷与乙酰丙酸,木质素降解主要生成三类化合物。第一类化合物含有苯酚基本结构,由构成木质素的基本单元通过氧化和脱甲基作用得到；第二类化合物含有苯甲氧基单元,由第一类化合物通过氧化和乙酰化作用脱酚羟基得到；第三类化合物则是前两类化合物的缩聚产物。在150℃、酸性条件下,液化剂自身未氧化生成醛类化合物。
因此,在缩聚反应阶段,缩聚残余物的生成路径主要有三种：(1)纤维素降解产物与液化剂之间反应,生成EG-葡萄糖苷与2-羟乙基乙酰丙酸大分子化合物；(2)木质素及其降解产物与糖类化合物反应,生成大分子酚醛树脂和酯化产物；(3)木质素降解产物与液化剂在Cα、Cβ、Cγ位置以及苯环上的酯化或取代反应,生成含苯酚结构的大分子酯化产物或烷基醚。
To clarify the reaction pathways of condensed residues and the structural characterizations of liquefaction products at the stages of decomposition and condensation reaction during wood liquefaction, wood powder(Betula dahurica Pall.) of 40-80 mesh was liquefied at 150℃and 0-180 minites. The ratio of polyhydric alcohols to wood to acid was 3:2:0.03. Liquefying reagents was polyhydric alcohols (PEG400:glycerin=4:1). The catalyst was sulfuric acid (concentration of 72 percent). The methods such as FTIR, XRD, SEM, TGA, GPC, HPLC, GC-MS, NMR and etc, were used to analyze the functional groups, microstructure, theromal weight loss behavior, molecular weight and polydispersity, the content of carbohydrate and molecular structure of liquefied wood residues and products.
The main results of this study were as follows,
1. When liquefaction time was within 0-180 minites, the content of cellulose decreased firstly and then increased, and the content of lignin increased gradually. Compared with unliquefied wood powder, the contents of cellulose and lignin decreased from 44.54 percent and 19.04 percent before liquefaction to 12.16-24.92 percent and 3.93-15.23 percent after liquefaction, respectively.
2. The number of carbonyl, aromatic nucleus from lignin and methoxy group reduced as a function of liquefaction time, respectively. The crystallinity of liquefied wood residues increased by 5.10 percent to 7.38 percent, as was mainly because quasi crystalline region of cellulose was degraded and the molecular structure of condensed residues oriented crystallization. During decomposition reaction, the fiber dimension and the average apparent area of the residues became gradually smaller; during condensation reaction, blocky deposit was found in condensed residues, which resulted in bigger average apparent area. With the prolongation of the liquefaction time, the thermostability of liquefied wood residues was improved.
3. Weight average molecular weights of lignin from liquefaction wood residues were mainly distributed in the range from 1160 to 1356, the number of aldehydes group from the lignin increased as a function of liquefaction time. Guaiacyl, syringyl and C-O bond in (3-0-4 position almost desepeard when liquefaction time was 10 minutes. And functional groups of cellulose were changed less.
4. For the liquefied wood products, with the prolongation of liquefaction time, the number of carbonyl, phenolic hydroxyl group and methoxy group increased and hydroxyl group reduced. The thermal stability and the contents of hexose and furfural reduced. Average molecular weight decreased significantly, and weight-average molecular weight was distributed in the range from 1103 to 1337. Carbohydrates in the products were mainly degraded into glucoside and leculinic acid, and lignin was degraded and obtained three-group compounds. The compounds having phenol structure were in the first group, they were composed of the basic units of lignin by oxidation and demethylation; the second-group compounds having phenylmethoxy structure were obtained after the first-group compounds removed the hydroxyl in benzene-ring by oxidation and acetylation; the third-group compounds stemed from condensation reaction between the first-and second-group compounds. And liquefying reagents could not be oxidated to carbonyl compounds in the acidic condition at 150℃.
In conclusion, at the stage of condensation reaction, there are mainly three formation pathways for condensed residues:(1) Degraded cellulose reacts with polyhydric alcohols, and generats EG-Glucoside and 2-hydroxyethyl levulinate; (2) Lignin or the products from degraded lignin reacts with saccharide compounds, and gives macromolecular phenolic resin and esterification products; (3) Esterification or substitution reaction in Cα, Cβ, Cγand benzene ring positions between the products from degraded lignin and liquefying reagents, generates macromolecular esterification products and alkyl ether compounds.
本研究得到主要结果如下：
1.在液化时间0-180 min,纤维素含量先减少后增大,木质素含量逐渐增大。与未液化木粉相比,纤维素和木质素含量分别从44.54%和19.04%降低到液化后的12.16～24.92%和3.93～15.23%。
2.液化残余物的羰基、木质素芳香环以及甲氧基随液化时间逐渐减少。液化残余物的结晶度增大5.10～7.38%,这主要基于液化过程中纤维素准结晶区发生降解以及缩聚残余物的分子取向引起的。在分解反应阶段,残余物中纤维尺度与平均表观面积随液化时间逐渐变小；在缩聚反应阶段,残余物中出现块状堆积物,平均表观面积增大。液化残余物的热稳定性随液化时间提高。
3.液化木质素的重均分子量主要分布在1160-1356,醛基数目随液化时间逐渐增加。在液化10 min时,愈疮木基、紫丁香基以及β-O-4位的C-O键几乎消失。纤维素的官能团变化不大。
4.随液化时间的延长,液化产物的羰基、酚羟基以及甲氧基数目逐渐增加,醇羟基数目减少。液化产物的热稳定性降低以及己糖、糠醛含量减少。液化产物的平均分子量显著降低,且重均分子量分布在1103～1337。产物中的糖类化合物降解生成糖苷与乙酰丙酸,木质素降解主要生成三类化合物。第一类化合物含有苯酚基本结构,由构成木质素的基本单元通过氧化和脱甲基作用得到；第二类化合物含有苯甲氧基单元,由第一类化合物通过氧化和乙酰化作用脱酚羟基得到；第三类化合物则是前两类化合物的缩聚产物。在150℃、酸性条件下,液化剂自身未氧化生成醛类化合物。
因此,在缩聚反应阶段,缩聚残余物的生成路径主要有三种：(1)纤维素降解产物与液化剂之间反应,生成EG-葡萄糖苷与2-羟乙基乙酰丙酸大分子化合物；(2)木质素及其降解产物与糖类化合物反应,生成大分子酚醛树脂和酯化产物；(3)木质素降解产物与液化剂在Cα、Cβ、Cγ位置以及苯环上的酯化或取代反应,生成含苯酚结构的大分子酯化产物或烷基醚。
To clarify the reaction pathways of condensed residues and the structural characterizations of liquefaction products at the stages of decomposition and condensation reaction during wood liquefaction, wood powder(Betula dahurica Pall.) of 40-80 mesh was liquefied at 150℃and 0-180 minites. The ratio of polyhydric alcohols to wood to acid was 3:2:0.03. Liquefying reagents was polyhydric alcohols (PEG400:glycerin=4:1). The catalyst was sulfuric acid (concentration of 72 percent). The methods such as FTIR, XRD, SEM, TGA, GPC, HPLC, GC-MS, NMR and etc, were used to analyze the functional groups, microstructure, theromal weight loss behavior, molecular weight and polydispersity, the content of carbohydrate and molecular structure of liquefied wood residues and products.
The main results of this study were as follows,
1. When liquefaction time was within 0-180 minites, the content of cellulose decreased firstly and then increased, and the content of lignin increased gradually. Compared with unliquefied wood powder, the contents of cellulose and lignin decreased from 44.54 percent and 19.04 percent before liquefaction to 12.16-24.92 percent and 3.93-15.23 percent after liquefaction, respectively.
2. The number of carbonyl, aromatic nucleus from lignin and methoxy group reduced as a function of liquefaction time, respectively. The crystallinity of liquefied wood residues increased by 5.10 percent to 7.38 percent, as was mainly because quasi crystalline region of cellulose was degraded and the molecular structure of condensed residues oriented crystallization. During decomposition reaction, the fiber dimension and the average apparent area of the residues became gradually smaller; during condensation reaction, blocky deposit was found in condensed residues, which resulted in bigger average apparent area. With the prolongation of the liquefaction time, the thermostability of liquefied wood residues was improved.
3. Weight average molecular weights of lignin from liquefaction wood residues were mainly distributed in the range from 1160 to 1356, the number of aldehydes group from the lignin increased as a function of liquefaction time. Guaiacyl, syringyl and C-O bond in (3-0-4 position almost desepeard when liquefaction time was 10 minutes. And functional groups of cellulose were changed less.
4. For the liquefied wood products, with the prolongation of liquefaction time, the number of carbonyl, phenolic hydroxyl group and methoxy group increased and hydroxyl group reduced. The thermal stability and the contents of hexose and furfural reduced. Average molecular weight decreased significantly, and weight-average molecular weight was distributed in the range from 1103 to 1337. Carbohydrates in the products were mainly degraded into glucoside and leculinic acid, and lignin was degraded and obtained three-group compounds. The compounds having phenol structure were in the first group, they were composed of the basic units of lignin by oxidation and demethylation; the second-group compounds having phenylmethoxy structure were obtained after the first-group compounds removed the hydroxyl in benzene-ring by oxidation and acetylation; the third-group compounds stemed from condensation reaction between the first-and second-group compounds. And liquefying reagents could not be oxidated to carbonyl compounds in the acidic condition at 150℃.
In conclusion, at the stage of condensation reaction, there are mainly three formation pathways for condensed residues:(1) Degraded cellulose reacts with polyhydric alcohols, and generats EG-Glucoside and 2-hydroxyethyl levulinate; (2) Lignin or the products from degraded lignin reacts with saccharide compounds, and gives macromolecular phenolic resin and esterification products; (3) Esterification or substitution reaction in Cα, Cβ, Cγand benzene ring positions between the products from degraded lignin and liquefying reagents, generates macromolecular esterification products and alkyl ether compounds.
引文
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