糠醛生产工艺研究及糠醛废渣的综合利用
摘要
在当今社会，人们极大的开发和利用化石燃料资源，整个世界经济的发展都是建立在石油和煤炭等化石资源的过度消耗上。由于煤炭和石油等是不可再生资源，因此可再生资源就进入了人们的视野。生物质是目前认为最可能取代石油等化石燃料来生产化工产品的材料，生物质资源的开发和利用也越来越受到人们的重视。
生物质（狭义）主要是由半纤维素、木质素和纤维素这三种有机组分构成。其中半纤维素水解后可生产木糖，木糖再进一步脱水就可制得糠醛。糠醛的分子结构比较特殊，有不饱和双键、氧醚键、二烯等官能团，因此性质比较活泼，可以发生氢化、氧化、氯化、硝化和缩聚等反应，可以生产大量的下游衍生品，在医药、食品、合成树脂、石油精炼、农药、合成纤维等领域有着广泛的应用。糠醛经过一系列的加氢和还原反应还可以制得烃类，可见在燃料领域有着潜在的价值。糠醛的工业生产是生物质资源利用的一个非常成功的范例。早在20世纪20年代，糠醛的生产就已经实现了工业化。我国是目前世界上糠醛生产和出口量最大的国家，在我国分布着几百家大大小小的糠醛厂。但是目前糠醛行业存在着很多的问题急需解决。原料利用率低，糠醛的产率低，能耗大，环境污染严重等都极大制约了糠醛企业的发展，甚至已经使我国的糠醛行业处于半瘫痪状态。本论文正是以改善甚至解决这些行业现状与问题为目的进行了大量的实验研究。
本论文首先用木糖为原料，研究糠醛生产两步法的第二步，木糖脱水环化制备糠醛。在常压条件下对木糖脱水制备糠醛进行了研究，最佳实验条件是：硫酸浓度10%，木糖浓度10%，甲苯用量150mL，水10mL，氯化钠用量2.4g，糠醛产率达到82%。证明了两步法提高糠醛的产率是可行的。DMSO（二甲基亚砜）、NaCl和FeCl_3对糠醛的产率提高也有着明显的促进作用，根据Cl-对木糖脱水生成糠醛的作用提出了催化过程的机理。本论文还研究了用市售固体酸催化剂生产糠醛，实验的最佳条件是催化剂2.5g，木糖2g，DMSO30mL，反应温度160℃。此方法的优点是固体酸可重复利用，分离容易，对环境污染小。对解决糠醛行业产品产率低及环境污染严重等问题有重要的指导意义。
然后用玉米芯为原料，在用水量很少的情况下，以有机溶剂甲苯做萃取剂，同步萃取糠醛。在低压条件（反应釜）下制得了糠醛，此方法用水量极少。最佳反应条件是温度140℃，甲苯用量25mL，玉米芯1g，硫酸浓度6%，反应时间3.5h。在此最佳条件下糠醛的产率为44%.其中反应温度和酸浓度是反应的主要影响因素。之后在常压下用近无水法以玉米芯为原料生产糠醛，最佳实验条件玉米芯2g，DMSO5mL，15%的硫酸5mL，反应时间5h，甲苯萃取剂用量为50mL，最佳糠醛产率为45%。在常压下引入DMSO做溶剂，提高了糠醛的产率，使常压的产率接近低压产率。此外在常压下反应温度低，硫酸浓度也比较大。实验证明此方法虽然加入了有机溶剂同步萃取，但糠醛的产率相对于目前工业的收率提高不大。
糠醛工业生产中，玉米芯提取糠醛之后的残渣就是糠醛渣，其中含有大量的木质素和纤维素，是极好的碳源。生产上多把糠醛渣直接回填锅炉燃烧，为反应提供热源，造成了极大的资源浪费和环境污染。本论文以糠醛渣为原料，磷酸做活化剂化学活化法制备了多孔活性炭。最佳制备条件是糠醛渣2g，浓磷酸（85%）6mL，在200℃炭化60min或300℃炭化30min，500℃活化105min。通过对活性炭的孔容和比表面积分析，确定活性炭孔以微孔为主，并含有一部分大孔。并分析了磷酸活化糠醛渣制备活性炭的机理。因为糠醛渣内含有纤维素，所以初步以糠醛渣为原料浓酸水解制备水热炭进行了分析，通过FTIR及TEM表征水热炭的形貌和表面官能团。综合以上两步处理，实现了对糠醛废渣的综合利用。
糠醛废水含有大量有机物如果直接排放不仅浪费掉了大量重要的化工原料，而且对水体造成酸性污染，破坏了环境结构。因此本论文以各种生物质原料为吸附剂，对糠醛废水进行了初步的处理，考察了废水中醋酸和糠醛的含量变化。降低了废水的COD值，对糠醛废水的处理具有一定的指导意义。
总之，本论文针对目前糠醛工业糠醛收率低和污染严重的问题展开研究，通过以木糖为原料制备糠醛，提高了糠醛的产率；以玉米芯为原料生产糠醛，减少水的用量避免向环境排放废水；用糠醛渣制备活性炭和水热碳实现了糠醛渣的综合利用；以生物质原料为吸附剂处理糠醛废水，为糠醛的生产及废水废渣处理提供可贵的参考意见。
In today's society, the entire world economy is built on the basis of fossilresources such as oil and coal. The great development and utilization of fossil fuelresources has accelerated the consumption of fossil resources. Because coal and oilare non-renewable resources，renewable resources come into the people's vision.Biomass is currently considered the most likely materials to replace oil and otherfossil fuels to produce chemical products. The development and utilization of biomassresources, more and more attention has been paid.
Biomass is mainly composed of hemicellulose, lignin and cellulose.Hemicellulose is hydrolyzed to produce xylose, and xylose in further dehydration canbe prepared furfural. Furfural molecular structure, which has unsaturated double bond,oxygen ether bond, diene functional group, is rather special. Therefore, the Furfuralnature is much lively which can perform hydrogenation, oxidation, chlorination,nitration, and condensation and other reactions. Furfural can produce a large numberof derivatives and it has been widely applied in the field of medicine, food, syntheticresin, petroleum refining, pesticides and synthetic fibers. After a series ofhydrogenation and reduction reactions, furfural can also be prepared hydrocarbons,which has a potential value in the fuel sector. The furfural industrial production is theraw material resources to take advantage of a very successful example. As early as the1920s, the production of furfural has been achieved industrialization. China is thelargest country in the world on the furfural production and exports, and there arehundreds of large and small furfural plants in China. In furfural industry there aremany problems, such as low utilization of raw material, the low yield of furfural, energy consumption and serious environmental pollution, needed to be resolved. Thedevelopment of enterprises of furfural is so greatly restricted, and furfural industry inChina has been even in a semi-paralyzed.
In this paper, xylose was used as the raw material to study the second step of thetwo-step method for the production of furfural. Xylose was dehydrated to producefurfural in the atmospheric conditions. The optimal reaction conditions: concentrationof sulfuric acid10%,10%of the xylose concentration, toluene amount of150mL,water10mLl, the amount of sodium chloride2.4g. The best yield of furfural was82%.DMSO (dimethyl sulfoxide), NaCl, and FeCl_3increased the yield of furfural. SingleFeCl_3without acid had poor advancement in xylose dehydration to furfural. We alsostudied the production of furfural using a commercially available solid acid catalyst.The best conditions of the experiment is the catalyst2.5g, the xylose2g, DMSO30mL,reaction temperature160℃.This method has the advantage of solid acid recycle, easyseparation, and a small pollution on the environment.
Then the corn cob was used as the raw material. In the amount of water rarely,the organic solvent toluene was used as the extractant.Furfural was prepared underlow pressure conditions (reactor), and this method of water consumption is minimal.The optimal reaction conditions: the reaction temperature of140℃, toluene25ml,corncob1g,6%of the sulfuric acid concentration, reaction time of3.5h. Underoptimal conditions furfural yield was44%. The reaction temperature and acidconcentration is the main influencing factors of the reaction. The near anhydrousmethod was performed for production of furfural at atmospheric pressure usingcorncob as raw material. The optimal experimental conditions: corncob2g, DMSO5ml,15%sulfuric acid5mL, reaction time5h, extracted with toluene dosage of50mL, best furfural yield was45%. The introduction of DMSO as solvent atatmospheric pressure, improved the yield of furfural close to yield of low pressure.The amount of DMSO should not be too large, because extraction of organic solventswould result in the loss.
The furfural residue was corncob residue after extraction of furfural. Furfuralresidue, which contains large amounts of lignin and cellulose, is an excellent carbon source. More production of furfural residue was burned to provide heat for thereaction, resulting in a tremendous waste of resources and environmental pollution. Inthis thesis, furfural residue was activated by phosphoric acid for preparation ofactivated carbon. Optimal preparation conditions: furfural residue2g, phosphoric acid(85%)6ml, carbonized at200℃for60min or300℃for30min, and activated at500℃for105min。 Pore volume and surface area of activated carbon weredetermined. Furfural residue contains cellulose, so furfural residue was used as rawmaterial to produce hydrothermal carbon.
Furfural wastewater contains large amounts of organic, so it can not be directlydischarged.We take a variety of biomass materials as an adsorbent for furfuralwastewater preliminary treatment. The effects of the content of acetic acid andfurfural in wastewater were investigated.
In summary, furfural was prepared from xylose. The yield of furfural reached83%. Corncob as raw material reduced the amount of water to avoid wastewaterdischarges to the environment. Preparation of activated carbon and hydrothermalcarbon from furfural residue was investigated. Furfural production and waste watertreatment to provide valuable suggestions for the development of furfural industry.
生物质（狭义）主要是由半纤维素、木质素和纤维素这三种有机组分构成。其中半纤维素水解后可生产木糖，木糖再进一步脱水就可制得糠醛。糠醛的分子结构比较特殊，有不饱和双键、氧醚键、二烯等官能团，因此性质比较活泼，可以发生氢化、氧化、氯化、硝化和缩聚等反应，可以生产大量的下游衍生品，在医药、食品、合成树脂、石油精炼、农药、合成纤维等领域有着广泛的应用。糠醛经过一系列的加氢和还原反应还可以制得烃类，可见在燃料领域有着潜在的价值。糠醛的工业生产是生物质资源利用的一个非常成功的范例。早在20世纪20年代，糠醛的生产就已经实现了工业化。我国是目前世界上糠醛生产和出口量最大的国家，在我国分布着几百家大大小小的糠醛厂。但是目前糠醛行业存在着很多的问题急需解决。原料利用率低，糠醛的产率低，能耗大，环境污染严重等都极大制约了糠醛企业的发展，甚至已经使我国的糠醛行业处于半瘫痪状态。本论文正是以改善甚至解决这些行业现状与问题为目的进行了大量的实验研究。
本论文首先用木糖为原料，研究糠醛生产两步法的第二步，木糖脱水环化制备糠醛。在常压条件下对木糖脱水制备糠醛进行了研究，最佳实验条件是：硫酸浓度10%，木糖浓度10%，甲苯用量150mL，水10mL，氯化钠用量2.4g，糠醛产率达到82%。证明了两步法提高糠醛的产率是可行的。DMSO（二甲基亚砜）、NaCl和FeCl_3对糠醛的产率提高也有着明显的促进作用，根据Cl-对木糖脱水生成糠醛的作用提出了催化过程的机理。本论文还研究了用市售固体酸催化剂生产糠醛，实验的最佳条件是催化剂2.5g，木糖2g，DMSO30mL，反应温度160℃。此方法的优点是固体酸可重复利用，分离容易，对环境污染小。对解决糠醛行业产品产率低及环境污染严重等问题有重要的指导意义。
然后用玉米芯为原料，在用水量很少的情况下，以有机溶剂甲苯做萃取剂，同步萃取糠醛。在低压条件（反应釜）下制得了糠醛，此方法用水量极少。最佳反应条件是温度140℃，甲苯用量25mL，玉米芯1g，硫酸浓度6%，反应时间3.5h。在此最佳条件下糠醛的产率为44%.其中反应温度和酸浓度是反应的主要影响因素。之后在常压下用近无水法以玉米芯为原料生产糠醛，最佳实验条件玉米芯2g，DMSO5mL，15%的硫酸5mL，反应时间5h，甲苯萃取剂用量为50mL，最佳糠醛产率为45%。在常压下引入DMSO做溶剂，提高了糠醛的产率，使常压的产率接近低压产率。此外在常压下反应温度低，硫酸浓度也比较大。实验证明此方法虽然加入了有机溶剂同步萃取，但糠醛的产率相对于目前工业的收率提高不大。
糠醛工业生产中，玉米芯提取糠醛之后的残渣就是糠醛渣，其中含有大量的木质素和纤维素，是极好的碳源。生产上多把糠醛渣直接回填锅炉燃烧，为反应提供热源，造成了极大的资源浪费和环境污染。本论文以糠醛渣为原料，磷酸做活化剂化学活化法制备了多孔活性炭。最佳制备条件是糠醛渣2g，浓磷酸（85%）6mL，在200℃炭化60min或300℃炭化30min，500℃活化105min。通过对活性炭的孔容和比表面积分析，确定活性炭孔以微孔为主，并含有一部分大孔。并分析了磷酸活化糠醛渣制备活性炭的机理。因为糠醛渣内含有纤维素，所以初步以糠醛渣为原料浓酸水解制备水热炭进行了分析，通过FTIR及TEM表征水热炭的形貌和表面官能团。综合以上两步处理，实现了对糠醛废渣的综合利用。
糠醛废水含有大量有机物如果直接排放不仅浪费掉了大量重要的化工原料，而且对水体造成酸性污染，破坏了环境结构。因此本论文以各种生物质原料为吸附剂，对糠醛废水进行了初步的处理，考察了废水中醋酸和糠醛的含量变化。降低了废水的COD值，对糠醛废水的处理具有一定的指导意义。
总之，本论文针对目前糠醛工业糠醛收率低和污染严重的问题展开研究，通过以木糖为原料制备糠醛，提高了糠醛的产率；以玉米芯为原料生产糠醛，减少水的用量避免向环境排放废水；用糠醛渣制备活性炭和水热碳实现了糠醛渣的综合利用；以生物质原料为吸附剂处理糠醛废水，为糠醛的生产及废水废渣处理提供可贵的参考意见。
In today's society, the entire world economy is built on the basis of fossilresources such as oil and coal. The great development and utilization of fossil fuelresources has accelerated the consumption of fossil resources. Because coal and oilare non-renewable resources，renewable resources come into the people's vision.Biomass is currently considered the most likely materials to replace oil and otherfossil fuels to produce chemical products. The development and utilization of biomassresources, more and more attention has been paid.
Biomass is mainly composed of hemicellulose, lignin and cellulose.Hemicellulose is hydrolyzed to produce xylose, and xylose in further dehydration canbe prepared furfural. Furfural molecular structure, which has unsaturated double bond,oxygen ether bond, diene functional group, is rather special. Therefore, the Furfuralnature is much lively which can perform hydrogenation, oxidation, chlorination,nitration, and condensation and other reactions. Furfural can produce a large numberof derivatives and it has been widely applied in the field of medicine, food, syntheticresin, petroleum refining, pesticides and synthetic fibers. After a series ofhydrogenation and reduction reactions, furfural can also be prepared hydrocarbons,which has a potential value in the fuel sector. The furfural industrial production is theraw material resources to take advantage of a very successful example. As early as the1920s, the production of furfural has been achieved industrialization. China is thelargest country in the world on the furfural production and exports, and there arehundreds of large and small furfural plants in China. In furfural industry there aremany problems, such as low utilization of raw material, the low yield of furfural, energy consumption and serious environmental pollution, needed to be resolved. Thedevelopment of enterprises of furfural is so greatly restricted, and furfural industry inChina has been even in a semi-paralyzed.
In this paper, xylose was used as the raw material to study the second step of thetwo-step method for the production of furfural. Xylose was dehydrated to producefurfural in the atmospheric conditions. The optimal reaction conditions: concentrationof sulfuric acid10%,10%of the xylose concentration, toluene amount of150mL,water10mLl, the amount of sodium chloride2.4g. The best yield of furfural was82%.DMSO (dimethyl sulfoxide), NaCl, and FeCl_3increased the yield of furfural. SingleFeCl_3without acid had poor advancement in xylose dehydration to furfural. We alsostudied the production of furfural using a commercially available solid acid catalyst.The best conditions of the experiment is the catalyst2.5g, the xylose2g, DMSO30mL,reaction temperature160℃.This method has the advantage of solid acid recycle, easyseparation, and a small pollution on the environment.
Then the corn cob was used as the raw material. In the amount of water rarely,the organic solvent toluene was used as the extractant.Furfural was prepared underlow pressure conditions (reactor), and this method of water consumption is minimal.The optimal reaction conditions: the reaction temperature of140℃, toluene25ml,corncob1g,6%of the sulfuric acid concentration, reaction time of3.5h. Underoptimal conditions furfural yield was44%. The reaction temperature and acidconcentration is the main influencing factors of the reaction. The near anhydrousmethod was performed for production of furfural at atmospheric pressure usingcorncob as raw material. The optimal experimental conditions: corncob2g, DMSO5ml,15%sulfuric acid5mL, reaction time5h, extracted with toluene dosage of50mL, best furfural yield was45%. The introduction of DMSO as solvent atatmospheric pressure, improved the yield of furfural close to yield of low pressure.The amount of DMSO should not be too large, because extraction of organic solventswould result in the loss.
The furfural residue was corncob residue after extraction of furfural. Furfuralresidue, which contains large amounts of lignin and cellulose, is an excellent carbon source. More production of furfural residue was burned to provide heat for thereaction, resulting in a tremendous waste of resources and environmental pollution. Inthis thesis, furfural residue was activated by phosphoric acid for preparation ofactivated carbon. Optimal preparation conditions: furfural residue2g, phosphoric acid(85%)6ml, carbonized at200℃for60min or300℃for30min, and activated at500℃for105min。 Pore volume and surface area of activated carbon weredetermined. Furfural residue contains cellulose, so furfural residue was used as rawmaterial to produce hydrothermal carbon.
Furfural wastewater contains large amounts of organic, so it can not be directlydischarged.We take a variety of biomass materials as an adsorbent for furfuralwastewater preliminary treatment. The effects of the content of acetic acid andfurfural in wastewater were investigated.
In summary, furfural was prepared from xylose. The yield of furfural reached83%. Corncob as raw material reduced the amount of water to avoid wastewaterdischarges to the environment. Preparation of activated carbon and hydrothermalcarbon from furfural residue was investigated. Furfural production and waste watertreatment to provide valuable suggestions for the development of furfural industry.
引文
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