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精细化工工艺学2015习题课
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ChangzhouUniversitySchoolofPetroChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering第1章绪论第一个公认的精细化工产品的化学名称是什么？发明的化学家是谁？第一个公认的精细化工产品的化学名称：
苯胺紫发明的化学家：W.H.Perkin
威廉.亨利.珀金
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ChangzhouUniversitySchoolofPetroChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering2.什么是“动脉工程”、“静脉工程”，“绿色化工”的主要含义是什么？
1995年美国提出绿色挑战计划，奖励和支持从源头清除化学污染并可工业化的发明，提出了“动脉工程”和“静脉工程”的概念。
把从石油及煤等原料合成塑料、纤维、橡胶等的工业化过程叫做“动脉工程”，把废塑料、废纤维、废橡胶的回收再生叫做“静脉工程”。
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ChangzhouUniversitySchoolofPetroChemicalEngineering绿色化学又称环境无害化学(EnvironmentallyBenignChemistry)环境友好化学(EnvironallyFriendlyChemistry)清洁化学(CleanChemistry)
绿色化学即是用化学的技术和方法去减少或消灭那些对人类健康、社区安全、生态环境有害的原料、催化剂、溶剂和试剂、产物、副产物等的使用和产生。绿色化学的理想在于不再使用有毒、有害的物质，不再产生废物。不再处理废物。它是一门从源头上阻止污染的化学。
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering精细有机合成的主要原料有哪些？来源是怎样的？在查阅文献的基础上写出“二十一世纪能源与化工合成原料”小论文。
三烯：乙烯、丙烯、丁烯；
三苯：苯、甲苯、二甲苯；
甲烷，共七种原料来源于石油、煤和天然气。
世界上约90%有机化工产品的原料来源于这七种原料！！
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering新世纪国内外精细化工工业的发展趋势与特点有哪些？
环境保护；合成关键技术（催化技术和生物技术）降低原材料消耗；节约能源；专用化技术与精细化工技术创新！！！
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering第2章精细有机合成反应理论1．确定下列化合物进行亲电取代反应时的难易顺序。
难易顺序：1-4-3-5-2
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ChangzhouUniversitySchoolofPetroChemicalEngineering2.以最合理合成工艺路线合成下列化合物。
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering1.
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering2.
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering3.
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering4.苯酚（1）早期：磺化碱熔法；（2）现在：异丙苯氧化酸解法；（3）其它：氯苯水解法；苯甲酸脱羧法等！
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering5.
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ChangzhouUniversitySchoolofPetroChemicalEngineering3.化学化工工程师必须具备的专业知识结构及内容有哪些？教材2.2-2.19相关知识，在将来工作中学习补充！！
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering
1.
合成下列化合物
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering第3章卤化反应1.
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering2.
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering3.
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering4.
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering5.
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering6.
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering7.
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering8.
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ChangzhouUniversitySchoolofPetroChemicalEngineering9.
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ChangzhouUniversitySchoolofPetroChemicalEngineering10.
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ChangzhouUniversitySchoolofPetroChemicalEngineering11.
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ChangzhouUniversitySchoolofPetroChemicalEngineering2.工业溴化反应进行时，为什么常常需要加入氧化剂？通常选择加入的氧化剂有哪些？
P1063.文献查阅下列常见卤化物的用途和工业合成方法？四氯化碳、氯乙酸、氯乙酰氯、对氯氯苄、2－氯甲基吡啶、间氯硝基苯、对氯苯酚、邻氯苯甲酸、2，6－二氯甲苯、环氧氯丙烷、氟乙酸乙酯。
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering第4章磺化1.以最合理的合成工艺路线合成下列化合物。（S表示为磺酸基团）
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering1.
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering2.
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering3.
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering4.
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering5.
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ChangzhouUniversitySchoolofPetroChemicalEngineering2．某工厂生产2-萘磺酸，每批投萘400Kg，98%硫酸343Kg，160℃反应2h，测得反应液总酸度为26%。此时2-萘磺酸的含量为68%，求：（1）萘和硫酸的投料比。（2）68%的2-萘磺酸折算成硫酸的酸度是多少？（3）2-萘磺酸的收率？
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering解：（1）萘和硫酸的投料比为：
400/128/(343×98%/98)=0.911:1(2)2-萘磺酸相当于硫酸的量为：（400+343）×68%/208×2×98=119Kg2-萘磺酸折算成硫酸的酸度为：
119/743×100%=16%（3）2-萘磺酸的收率：
Y=743×68%/208/(400/128)×100%=77%
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering3.某工厂生产1-萘磺酸，每批投萘400Kg，98%硫酸325Kg，100℃反应4h，测得反应液总酸度为27%。此时1-萘磺酸的含量为73%。求：（1）萘和硫酸的投料比。（2）73%的1-萘磺酸折算成硫酸的酸度？（3）1-萘磺酸的收率？
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering（1）萘和硫酸的投料比为：400/128/(325×98%/98)=0.961:1(2)1-萘磺酸相当于硫酸的量为：（400+325）×73%/208×2×98=124.7Kg2-萘磺酸折算成硫酸的酸度为：124.7/725×100%=17.2%（3）1-萘磺酸的收率：Y=725×73%/208/(400/128)×100%=81.4%
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ChangzhouUniversitySchoolofPetroChemicalEngineering4.文献查阅下列常见磺化物的用途和合成方法？间氨基苯磺酸、吐氏酸、对氯苯磺酰氯、2,4-氨基苯磺酸、氯磺酸乙酯、2－甲基－5－硝基苯磺酸、1－萘磺酸、5－磺酸基水杨酸。
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering第5章硝化及亚硝化甲苯一硝化时的D.V.S.值约为2.18，采用的Φ为1.02，现有一S、56，N、26的混酸，问：（1）该混酸能否用于甲苯的一硝化？（2）1000Kg甲苯硝化时，所需此混酸的量？（3）若用97%的硝酸、98%的硫酸来配此混酸，则分别用酸多少？（4）该混酸组成的F.N.A.值?
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering
解：（1）D.V.S.=S/(100-S-5/7N)=2.20
因为D.V.S.=2.20>2.18所以该混酸可以用于甲苯的一硝化反应（2）混酸量=1000/92×1.02×63/26%=2686.5Kg（3）设：分别用97%的硝酸、98%的硫酸分别为AKg、BKg则：97%×A=2686.5×26%A=720.1Kg98%×B=2686.5×56%B=1535.1Kg（4）F.N.A.=D.V.S./(1+D.V.S.)×100%=2.20/3.20×100%=68.75%
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering2.由硝基苯混酸硝化制备间二硝基苯时，需要配制的混酸组成为H2SO472%（质量，下同），HNO326%，H2O2%的混酸6000Kg，问需要20%的发烟硫酸，85%废酸和98%的硝酸各多少千克？
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ChangzhouUniversitySchoolofPetroChemicalEngineering解：设需要20%的发烟硫酸，85%废酸和98%的硝酸分别为x、y、z（kg）三种酸总质量：x+y+z=6000硝酸的平衡：0.98z=6000×0.26硫酸的平衡：（100%+0.225×20%）x+0.85y=6000×0.72解上述三个联立方程，得：x=2938.6kg；y=1469.6kg；z=1591.8kg
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ChangzhouUniversitySchoolofPetroChemicalEngineering
3.已知萘进行二硝化反应时所需的D.V.S.值为3.0，硝酸比φ值为2.2，相比为6.5。试计算：该二硝化反应正常发生时应选用的混酸组成为多少？（以1Kgmol的萘为计算基准）
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering解：以1kgmol的萘为计算基准：混酸量：m混=128×6.5=832kg=m(HNO3)+m（H2SO4）+m(H2O)
①硝酸：m(HNO3)=63×2.2=138.6kg硫酸：m（H2SO4）=D.V.S.(m(H2O)+2×18)=3m(H2O)+108
②解式①、②得m（H2SO4）=547kg；m(H2O)=146.4kg故混酸组成为：硫酸：m（H2SO4）×100/m混=65.75%硝酸：m(HNO3)×100/m混=16.65%水：m(H2O)×100/m混=17.60%
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering4.文献查阅下列常见的硝基物的用途和合成方法？
3－氯－4－氟苯胺、4－氯－3－硝基苯磺酸、2，4，6－三硝基甲苯、间二硝基苯、2，4－二硝基氯苯、硝基甲烷、间硝基三氟甲苯。
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering第6章还原1.某车间用22.5%Na2S水溶液还原对硝基甲苯，反应式为（1）若每批投98%的对硝基甲苯140Kg，Na2S的用量为理论量的1.2倍，求每批用22.5%Na2S水溶液多少Kg？（2）产品经干燥后得100Kg，从中取0.2253g用重氮法分析氨基物的含量,用0.1NNaNO2标准溶液20ml滴到终点,求产品纯度？产品收率？
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering解：（1）设：需22.5%硫化钠水溶液的量为AKgA=140×98%/137×1.20×6/4×78/22.5%=624Kg（2）产品纯度：C=0.1×20×107/0.2253/1000×100%=95%产品收率：
Y=100×95%/107×100%=88.8%
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering2.
某工厂以Na2S.9H2O为还原剂将98%间二硝基苯500Kg还原制备间硝基苯胺，还原剂用量为理论用量的1.20倍，求：（1）还原剂Na2S.9H2O的用量？（2）反应产物经水洗、重结晶、烘干得到335Kg，从中取0.2850g产品，用重氮法分析氨基物的含量，用0.1NNaNO2标准溶液20ml滴到终点，求产品纯度?产品收率?
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ChangzhouUniversitySchoolofPetroChemicalEngineering解：（1）Na2S.9H2O用量为：500×98%/168×6/4×1.20×240=1260Kg
（2）产品纯度：C=0.1×20×138/0.2850/1000×100%=96.84%产品收率：Y=335×96.84%/138/(500×98%/168)×100%=82.1%
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ChangzhouUniversitySchoolofPetroChemicalEngineering3.文献查阅下列常见氨基物的用途和合成方法？间硝基苯胺、1－萘胺、4，4，－二氨基二苯醚、对氨基乙酰苯胺、对氨基苯甲酸、间氯苯胺、对甲苯胺、4－氯苯胺－3－磺酸，2，5－二氯苯胺。
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering第7章氧化反应1．解释下列名词：自动氧化阻化剂诱导期
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering2．常用的工业氧化剂有哪些？各有何特点？3．文献查阅下列工业氧化产品的用途和合成方法？对氯苯甲酸、苯酚、环氧乙烷、富马酸、乙二醛、顺丁烯二酸酐、烟酸、过氧乙酸、邻苯二甲酸酐、环氧丙烷。
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering第8章重氮化及重氮盐的反应1.工业上重氮化反应终点是如何确定的？终点：芳胺消失，亚硝酸微过量。终点测定方法：淀粉、KI试纸立即变兰。特征反应！！！I2+淀粉→蓝色染料！
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering2.工业生产上偶合反应终点是如何确定的？（1）反应终点：重氮盐无，偶合物微过量。（2）反应终点测定：润圈试验，需反复多次检查确定终点。
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering3.举例说明由重氮化合物经转化后得到哪些工业化产品和中间体？4.文献查阅下列化合物用途和合成方法！刚果红、甲基橙、间氯苯酚、对氯苯磺酸。
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering第9章氨解和胺化1.以最合理的合成工艺路线合成下列化合物。（S表示为磺酸基团）
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering1.
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering2.
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering3.
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering4.
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering5.
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ChangzhouUniversitySchoolofPetroChemicalEngineering6.
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ChangzhouUniversitySchoolofPetroChemicalEngineering7.
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ChangzhouUniversitySchoolofPetroChemicalEngineering2．文献查阅下列氨基化合物的用途和合成方法？二甲基甲酰胺、2，4－二硝基苯胺、乙醇胺系列产品、2－萘胺、水杨酰苯胺（87－17－2）、对甲苯磺酰胺。
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering第10章烃化工业烃化反应试剂有哪些？烃化反应的主要特点有哪些？以最合理的合成工艺路线合成下列化合物。
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering1.
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering2.见黑板！！！
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering3.
A+B=产物
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering4.
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering3．文献查阅下列烃基化合物的用途和合成方法？
2，6－二乙基苯胺、N,N-二甲基苯胺、N,N-二甲基十八胺、邻甲氧基苯甲醛、
2－甲氧基萘、对羟基苯甲醚。
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering第11章酰化反应1.工业酰化反应试剂有哪些？酰化反应的主要特点有哪些？2．以最合理的合成工艺路线合成下列化合物。
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering1.
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering2.
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering3.
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering4.见黑板！！！
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering3．文献查阅下列酰基化合物的用途和合成方法？邻氯乙酰苯胺、2，4－二羟基苯乙酮、乙酸苯酯、氯甲酸苯酯、乙基苯基酮。
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering第12章水解苯酚的工业化合成路线有哪些？各有何特点？以最合理的合成工艺路线合成下列化合物。
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering
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ChangzhouUniversitySchoolofPetroChemicalEngineering1.2.
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JiangsuPolytechnicUniversityDeptofChemicalEngineering
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