Co-salen型仿酶体系的脱木素机理及其应用研究
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摘要
为了发展新型无(少)污染漂白技术及造纸废水处理新技术,越来越多的研究者开始用微生物、生物酶和仿酶等方法来解决纸浆漂白过程中的污染问题,并开发对环境友好的新型纸浆漂白技术。仿酶催化不仅具有酶催化与化学催化两者的优点,而且是实现绿色化学有效而直接的途径。由Co-salen、吡啶、H_2O_2、O_2构成的一种Co-salen型仿酶降解体系是模拟木素过氧化物酶的仿酶体系之一。为了揭示Co-salen型仿酶降解体系脱木素的反应机理,本文围绕β-O-4型木素模型化合物即愈创木基丙三醇-β-愈创木基醚在仿酶体系中的变化为研究核心,研究了β-O-4型木素模型化合物、三倍体毛白杨磨木木素(MWL)在仿酶体系中的降解机理以及Co-salen型仿酶体系在纸浆漂白和造纸综合废水处理中的应用,分析得到了β-O-4型木素模型化合物在仿酶体系中的反应机理,为实现该Co-salen型仿酶体系在纸浆漂白工艺中的应用提供了理论依据。
本文首先合成了一种酚型木素模型化合物即愈创木基丙三醇-β-愈创木基醚。对关键的中间产物中间产物4-(α-(2-甲氧基苯氧基)-乙酰基)-愈创木酚(Ⅳ)的合成方法进行了改良,缩短了减压蒸馏的时间。利用红外光谱、核磁共振谱(1H-NMR)等手段对其化学结构进行了分析。
本文利用合成出来的愈创木基丙三醇-β-愈创木基醚作为木素模型化合物。在采用由Co-salen、吡啶、H_2O_2、O_2构成的Co-salen型仿酶体系对其进行仿酶降解处理后,利用GC-MS分析手段对反应的产物进行了分析。研究发现:Co-salen型仿酶体系对β-O-4型木素模型化合物有较强的氧化降解能力,降解后的羧基和羟基明显增多。本研究阐明了这种β-O-4型木素模型化合物的结构在Co-salen型仿酶体系中的降解反应机理,推断出该仿酶体系能有效导致酚型的β-O-4型木素模型化合物氧化裂解反应类型有:β-O-4醚键断裂、Cα-Cβ键断裂、烷基-芳基键的断裂和苯环开环反应等。Co-salen型仿酶体系对三倍体毛白杨MWL的降解能力较强,降解后的羧基和羟基明显增多。木素被降解后一部分成为香草酸、紫丁香酸及其衍生物等低分子芳香族化合物,说明木素结构在侧链Cα的位置受到氧化作用而使结构单元之间的连接键断裂。
本文采用由Co-salen、吡啶、H_2O_2、O_2组成的Co-salen型仿酶体系进行了硫酸盐木浆的漂白研究,讨论了Co-salen仿酶预处理过程中预处理温度、预处理时间、NaOH用量,H_2O_2用量、吡啶用量、Co-salen用量、氧压等对终漂纸浆白度和粘度的影响,优化了Co-salen型仿酶体系预漂硫酸盐木浆的最佳条件。研究发现Co-salen仿酶预漂硫酸盐木浆比较适宜的条件为:Co-salen用量0.03%,吡啶与Co-salen摩尔比1:1,NaOH用量3%,H_2O_2用量1.5%,氧压0.2MPa,浆浓5%,温度90℃,反应时间5h。仿酶漂白使硫酸盐木浆卡伯值下降4.1,经过碱处理后卡伯值可以进一步降低5.2。经Co-salen仿酶处理白度提高10.3%ISO。经过碱抽提段纸浆白度进一步提高18.1%ISO。根据木素模型化合物实验所得结论,Co-salen仿酶漂白预处理过程中将木素氧化成香草酸、紫丁香酸等含羧基化合物,这些产物在仿酶处理段和碱抽提段被溶解出来,表现在仿酶处理段和碱抽提段有较大的白度升高值。
本文采用Co-salen—仿酶混凝法处理造纸综合废水,讨论温度、H_2O_2加入量、混凝剂种类和加入量、沉淀时间对废水处理效果的影响。优化了Co-salen—仿酶混凝法处理造纸综合废水的实验条件。研究发现,Co-salen—仿酶混凝法处理造纸综合废水的最佳条件为温度25℃,H_2O_2用量0.15g/L,硫酸铝加入量0.4g/L,沉降时间4h。Co-salen仿酶—混凝法处理造纸废水有效地提高了废水处理效果,在同样条件下,采用Co-salen仿酶—混凝法处理造纸综合废水,配合硫酸铝,CODCr去除率可以达到55.2%。由于仿酶—混凝除去了废水中的大部分木素,提高了废水的可生化性,使得废水的后续处理变得容易。
For the requirement of developing low impact bleaching technology and new technology of pulp and paper effluent treatment, many researchers try to use microorganisms, their enzymes and biomimetic system in pulp bleaching process to reduce the pollution and develop new environmental friendly bleaching technology. Biomimetic catalyst has characteristics of both enzymatic catalyst and chemical catalyst. Therefore, it is an efficient approach of green chemistry. The Co-salen biomimetic delignification system which is composed of Co(Ⅱ)-salen, pyridine, sodium hydroxide, hydrogen peroxide, oxygen is one of the most promising biomimetic system of lignin peroxidase. In order to understand the reaction mechanism of lignin with Co-salen biomimetic delignification system, a lignin model compound of phenolicβ-O-4 type, i.e. guaiacylglycerol-β-guaiacyl ether and milled wood lignin (MWL) from triploid clones of Populus tomentosa wood were treated with Co-salen biomimetic delignification system. In the present research, we have carried out many researches about the mechanism of the degradation ofβ-O-4 type lignin model compound and milled wood lignin (MWL). The application of bleaching softwood kraft pulp and paper effluent treatment by Co-salen biomimetic system. These results could help us to apply Co-salen biomimetic system in industrial non-pollution bleaching.
In this paper, a model compound of phenolicβ-O-4 type, i.e. guaiacylglycerol-β-guaiacyl ether was synthesized. The synthesis method of an impant intermediate, i.e. 4-[α-(2-methoxylphenoxy)-acetyl]-guaiacol was improved. The time of reduced pressure distillation shorten. The combination of infrared spectra, 1H-NMR analysis was used to identify the chemical structure of the product and related precursors.
The lignin model compound of guaiacylglycerol-β-guaiacyl ether was treated with Co-salen biomimetic system. The reaction products were analyzed by GC-MS. The mechanism of the biomimetic degradation of thisβ-O-4 structure was also explored. Results showed that Co-salen type biomimetic system had strong ability in degradation of phenolicβ-O-4 type model compound. It was found there were a lot of carbonyl and hydroxyl groups in the degraded products. It is suggested that the following reactions were caused by the Co-salen system: ether-bond cleavage, Cα-Cβcleavage, alkyl-aryl cleavage and aromatic ring opening. Co-salen type biomimetic system had strong ability in degradation of MWL. After MWL was treated, the content of hydroxyl and carboxyl groups increased. Some low molecule compounds as syringic acid and vanillic acid were produced. The results could prove that the oxidation of side chain lead to the cleavage of the linkage between the units of lignin substructure.
In this paper, unbleached softwood kraft pulp was treated with a biomimetic bleaching system, i.e. Co-salen system comprised of Co(Ⅱ) -salen, pyridine,hydrogen peroxide, oxygen. The effect of temperature, time, NaOH dosage, hydrogen peroxide dosage, pyridine dosage, Co-salen dosage and oxygen pressure on brightness and viscosity of the pulp after biomimetic treatment followed by EP bleaching were analyzed. The experimental condition was improved. The study found that optimum conditions are as follows: Co-salen 0.03%, molar ratio of Co-salen to pyridine 1:1, NaOH 3%, H_2O_2 1.5%, oxygen pressure 0.2 MPa, pulp consistency 5%, temperature 90℃, time 5h. Kappa number of softwood kraft pulp declined by 4.1 atter treated by Co-salen biomimetic system. Brightness was improved 10.3%ISO. After alkali treatment, Kappa number can further reduce 5.2, pulp brightness increased 18.1%ISO. According to the conclusion of lignin model compound experiment, lignin was oxidized and some low molecule compounds as syringic acid and vanillic acid were produced. These products were dissolved during biomimetic bleaching and alkali extraction. It was manifested mainly in improving brightness during biomimetic bleaching and alkali extraction.
In this paper, Co-salen biomimetic flocculation was used to treat the mixed wastewater treatment of a paper mill. The effect of temperature, hydrogen peroxide dosage, the kind and dosage of flocculant, sedimentation time were analyzed. The experimental conditions was optimized. The study found that optimum conditions are as follows: temperature 90℃, H_2O_2 dosage 0.15g/L, aluminium sulfate dosage 0.4g/L, sedimentation time 4h. The study found that CODCr can be improved 19.6% by using Co-salen biomimetic flocculation. Through lignin massive removing, the effect of subsequent biochemical was also enhanced. It made it easier for the following treatment.
本文首先合成了一种酚型木素模型化合物即愈创木基丙三醇-β-愈创木基醚。对关键的中间产物中间产物4-(α-(2-甲氧基苯氧基)-乙酰基)-愈创木酚(Ⅳ)的合成方法进行了改良,缩短了减压蒸馏的时间。利用红外光谱、核磁共振谱(1H-NMR)等手段对其化学结构进行了分析。
本文利用合成出来的愈创木基丙三醇-β-愈创木基醚作为木素模型化合物。在采用由Co-salen、吡啶、H_2O_2、O_2构成的Co-salen型仿酶体系对其进行仿酶降解处理后,利用GC-MS分析手段对反应的产物进行了分析。研究发现:Co-salen型仿酶体系对β-O-4型木素模型化合物有较强的氧化降解能力,降解后的羧基和羟基明显增多。本研究阐明了这种β-O-4型木素模型化合物的结构在Co-salen型仿酶体系中的降解反应机理,推断出该仿酶体系能有效导致酚型的β-O-4型木素模型化合物氧化裂解反应类型有:β-O-4醚键断裂、Cα-Cβ键断裂、烷基-芳基键的断裂和苯环开环反应等。Co-salen型仿酶体系对三倍体毛白杨MWL的降解能力较强,降解后的羧基和羟基明显增多。木素被降解后一部分成为香草酸、紫丁香酸及其衍生物等低分子芳香族化合物,说明木素结构在侧链Cα的位置受到氧化作用而使结构单元之间的连接键断裂。
本文采用由Co-salen、吡啶、H_2O_2、O_2组成的Co-salen型仿酶体系进行了硫酸盐木浆的漂白研究,讨论了Co-salen仿酶预处理过程中预处理温度、预处理时间、NaOH用量,H_2O_2用量、吡啶用量、Co-salen用量、氧压等对终漂纸浆白度和粘度的影响,优化了Co-salen型仿酶体系预漂硫酸盐木浆的最佳条件。研究发现Co-salen仿酶预漂硫酸盐木浆比较适宜的条件为:Co-salen用量0.03%,吡啶与Co-salen摩尔比1:1,NaOH用量3%,H_2O_2用量1.5%,氧压0.2MPa,浆浓5%,温度90℃,反应时间5h。仿酶漂白使硫酸盐木浆卡伯值下降4.1,经过碱处理后卡伯值可以进一步降低5.2。经Co-salen仿酶处理白度提高10.3%ISO。经过碱抽提段纸浆白度进一步提高18.1%ISO。根据木素模型化合物实验所得结论,Co-salen仿酶漂白预处理过程中将木素氧化成香草酸、紫丁香酸等含羧基化合物,这些产物在仿酶处理段和碱抽提段被溶解出来,表现在仿酶处理段和碱抽提段有较大的白度升高值。
本文采用Co-salen—仿酶混凝法处理造纸综合废水,讨论温度、H_2O_2加入量、混凝剂种类和加入量、沉淀时间对废水处理效果的影响。优化了Co-salen—仿酶混凝法处理造纸综合废水的实验条件。研究发现,Co-salen—仿酶混凝法处理造纸综合废水的最佳条件为温度25℃,H_2O_2用量0.15g/L,硫酸铝加入量0.4g/L,沉降时间4h。Co-salen仿酶—混凝法处理造纸废水有效地提高了废水处理效果,在同样条件下,采用Co-salen仿酶—混凝法处理造纸综合废水,配合硫酸铝,CODCr去除率可以达到55.2%。由于仿酶—混凝除去了废水中的大部分木素,提高了废水的可生化性,使得废水的后续处理变得容易。
For the requirement of developing low impact bleaching technology and new technology of pulp and paper effluent treatment, many researchers try to use microorganisms, their enzymes and biomimetic system in pulp bleaching process to reduce the pollution and develop new environmental friendly bleaching technology. Biomimetic catalyst has characteristics of both enzymatic catalyst and chemical catalyst. Therefore, it is an efficient approach of green chemistry. The Co-salen biomimetic delignification system which is composed of Co(Ⅱ)-salen, pyridine, sodium hydroxide, hydrogen peroxide, oxygen is one of the most promising biomimetic system of lignin peroxidase. In order to understand the reaction mechanism of lignin with Co-salen biomimetic delignification system, a lignin model compound of phenolicβ-O-4 type, i.e. guaiacylglycerol-β-guaiacyl ether and milled wood lignin (MWL) from triploid clones of Populus tomentosa wood were treated with Co-salen biomimetic delignification system. In the present research, we have carried out many researches about the mechanism of the degradation ofβ-O-4 type lignin model compound and milled wood lignin (MWL). The application of bleaching softwood kraft pulp and paper effluent treatment by Co-salen biomimetic system. These results could help us to apply Co-salen biomimetic system in industrial non-pollution bleaching.
In this paper, a model compound of phenolicβ-O-4 type, i.e. guaiacylglycerol-β-guaiacyl ether was synthesized. The synthesis method of an impant intermediate, i.e. 4-[α-(2-methoxylphenoxy)-acetyl]-guaiacol was improved. The time of reduced pressure distillation shorten. The combination of infrared spectra, 1H-NMR analysis was used to identify the chemical structure of the product and related precursors.
The lignin model compound of guaiacylglycerol-β-guaiacyl ether was treated with Co-salen biomimetic system. The reaction products were analyzed by GC-MS. The mechanism of the biomimetic degradation of thisβ-O-4 structure was also explored. Results showed that Co-salen type biomimetic system had strong ability in degradation of phenolicβ-O-4 type model compound. It was found there were a lot of carbonyl and hydroxyl groups in the degraded products. It is suggested that the following reactions were caused by the Co-salen system: ether-bond cleavage, Cα-Cβcleavage, alkyl-aryl cleavage and aromatic ring opening. Co-salen type biomimetic system had strong ability in degradation of MWL. After MWL was treated, the content of hydroxyl and carboxyl groups increased. Some low molecule compounds as syringic acid and vanillic acid were produced. The results could prove that the oxidation of side chain lead to the cleavage of the linkage between the units of lignin substructure.
In this paper, unbleached softwood kraft pulp was treated with a biomimetic bleaching system, i.e. Co-salen system comprised of Co(Ⅱ) -salen, pyridine,hydrogen peroxide, oxygen. The effect of temperature, time, NaOH dosage, hydrogen peroxide dosage, pyridine dosage, Co-salen dosage and oxygen pressure on brightness and viscosity of the pulp after biomimetic treatment followed by EP bleaching were analyzed. The experimental condition was improved. The study found that optimum conditions are as follows: Co-salen 0.03%, molar ratio of Co-salen to pyridine 1:1, NaOH 3%, H_2O_2 1.5%, oxygen pressure 0.2 MPa, pulp consistency 5%, temperature 90℃, time 5h. Kappa number of softwood kraft pulp declined by 4.1 atter treated by Co-salen biomimetic system. Brightness was improved 10.3%ISO. After alkali treatment, Kappa number can further reduce 5.2, pulp brightness increased 18.1%ISO. According to the conclusion of lignin model compound experiment, lignin was oxidized and some low molecule compounds as syringic acid and vanillic acid were produced. These products were dissolved during biomimetic bleaching and alkali extraction. It was manifested mainly in improving brightness during biomimetic bleaching and alkali extraction.
In this paper, Co-salen biomimetic flocculation was used to treat the mixed wastewater treatment of a paper mill. The effect of temperature, hydrogen peroxide dosage, the kind and dosage of flocculant, sedimentation time were analyzed. The experimental conditions was optimized. The study found that optimum conditions are as follows: temperature 90℃, H_2O_2 dosage 0.15g/L, aluminium sulfate dosage 0.4g/L, sedimentation time 4h. The study found that CODCr can be improved 19.6% by using Co-salen biomimetic flocculation. Through lignin massive removing, the effect of subsequent biochemical was also enhanced. It made it easier for the following treatment.
引文
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