精細有機合成化學(xué)與工藝學(xué)

精細化工工藝學(xué)2015習(xí)題課

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ChangzhouUniversitySchoolofPetroChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering第1章緒論第一個公認(rèn)的精細化工產(chǎn)品的化學(xué)名稱是什么？發(fā)明的化學(xué)家是誰？第一個公認(rèn)的精細化工產(chǎn)品的化學(xué)名稱：

苯胺紫發(fā)明的化學(xué)家：W.H.Perkin

威廉.亨利.珀金

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ChangzhouUniversitySchoolofPetroChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering2.什么是“動脈工程”、“靜脈工程”，“綠色化工”的主要含義是什么？

1995年美國提出綠色挑戰(zhàn)計劃，獎勵和支持從源頭清除化學(xué)污染并可工業(yè)化的發(fā)明，提出了“動脈工程”和“靜脈工程”的概念。

把從石油及煤等原料合成塑料、纖維、橡膠等的工業(yè)化過程叫做“動脈工程”，把廢塑料、廢纖維、廢橡膠的回收再生叫做“靜脈工程”。

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ChangzhouUniversitySchoolofPetroChemicalEngineering綠色化學(xué)又稱環(huán)境無害化學(xué)(EnvironmentallyBenignChemistry)環(huán)境友好化學(xué)(EnvironallyFriendlyChemistry)清潔化學(xué)(CleanChemistry)

綠色化學(xué)即是用化學(xué)的技術(shù)和方法去減少或消滅那些對人類健康、社區(qū)安全、生態(tài)環(huán)境有害的原料、催化劑、溶劑和試劑、產(chǎn)物、副產(chǎn)物等的使用和產(chǎn)生。綠色化學(xué)的理想在于不再使用有毒、有害的物質(zhì)，不再產(chǎn)生廢物。不再處理廢物。它是一門從源頭上阻止污染的化學(xué)。

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering精細有機合成的主要原料有哪些？來源是怎樣的？在查閱文獻的基礎(chǔ)上寫出“二十一世紀(jì)能源與化工合成原料”小論文。

三烯：乙烯、丙烯、丁烯；

三苯：苯、甲苯、二甲苯；

甲烷，共七種原料來源于石油、煤和天然氣。

世界上約90%有機化工產(chǎn)品的原料來源于這七種原料?。?/p>

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering新世紀(jì)國內(nèi)外精細化工工業(yè)的發(fā)展趨勢與特點有哪些？

環(huán)境保護；合成關(guān)鍵技術(shù)（催化技術(shù)和生物技術(shù)）降低原材料消耗；節(jié)約能源；專用化技術(shù)與精細化工技術(shù)創(chuàng)新?。。?/p>

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering第2章精細有機合成反應(yīng)理論1．確定下列化合物進行親電取代反應(yīng)時的難易順序。

難易順序：1-4-3-5-2

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ChangzhouUniversitySchoolofPetroChemicalEngineering2.以最合理合成工藝路線合成下列化合物。

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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：磺化堿熔法；（2）現(xiàn)在：異丙苯氧化酸解法；（3）其它：氯苯水解法；苯甲酸脫羧法等！

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering5.

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ChangzhouUniversitySchoolofPetroChemicalEngineering3.化學(xué)化工工程師必須具備的專業(yè)知識結(jié)構(gòu)及內(nèi)容有哪些？教材2.2-2.19相關(guān)知識，在將來工作中學(xué)習(xí)補充??！

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering

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合成下列化合物

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering第3章鹵化反應(yīng)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.工業(yè)溴化反應(yīng)進行時，為什么常常需要加入氧化劑？通常選擇加入的氧化劑有哪些？

P1063.文獻查閱下列常見鹵化物的用途和工業(yè)合成方法？四氯化碳、氯乙酸、氯乙酰氯、對氯氯芐、2－氯甲基吡啶、間氯硝基苯、對氯苯酚、鄰氯苯甲酸、2，6－二氯甲苯、環(huán)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.以最合理的合成工藝路線合成下列化合物。（S表示為磺酸基團）

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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．某工廠生產(chǎn)2-萘磺酸，每批投萘400Kg，98%硫酸343Kg，160℃反應(yīng)2h，測得反應(yīng)液總酸度為26%。此時2-萘磺酸的含量為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）萘和硫酸的投料比為：

400/128/(343×98%/98)=0.911:1(2)2-萘磺酸相當(dāng)于硫酸的量為：（400+343）×68%/208×2×98=119Kg2-萘磺酸折算成硫酸的酸度為：

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.某工廠生產(chǎn)1-萘磺酸，每批投萘400Kg，98%硫酸325Kg，100℃反應(yīng)4h，測得反應(yīng)液總酸度為27%。此時1-萘磺酸的含量為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）萘和硫酸的投料比為：400/128/(325×98%/98)=0.961:1(2)1-萘磺酸相當(dāng)于硫酸的量為：（400+325）×73%/208×2×98=124.7Kg2-萘磺酸折算成硫酸的酸度為：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.文獻查閱下列常見磺化物的用途和合成方法？間氨基苯磺酸、吐氏酸、對氯苯磺酰氯、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－磺酸基水楊酸。

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JiangsuPolytechnicUniversityDeptofChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering第5章硝化及亞硝化甲苯一硝化時的D.V.S.值約為2.18，采用的Φ為1.02，現(xiàn)有一S、56，N、26的混酸，問：（1）該混酸能否用于甲苯的一硝化？（2）1000Kg甲苯硝化時，所需此混酸的量？（3）若用97%的硝酸、98%的硫酸來配此混酸，則分別用酸多少？（4）該混酸組成的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

因為D.V.S.=2.20>2.18所以該混酸可以用于甲苯的一硝化反應(yīng)（2）混酸量=1000/92×1.02×63/26%=2686.5Kg（3）設(shè)：分別用97%的硝酸、98%的硫酸分別為AKg、BKg則：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備間二硝基苯時，需要配制的混酸組成為H2SO472%（質(zhì)量，下同），HNO326%，H2O2%的混酸6000Kg，問需要20%的發(fā)煙硫酸，85%廢酸和98%的硝酸各多少千克？

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ChangzhouUniversitySchoolofPetroChemicalEngineering解：設(shè)需要20%的發(fā)煙硫酸，85%廢酸和98%的硝酸分別為x、y、z（kg）三種酸總質(zhì)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解上述三個聯(lián)立方程，得：x=2938.6kg；y=1469.6kg；z=1591.8kg

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ChangzhouUniversitySchoolofPetroChemicalEngineering

3.已知萘進行二硝化反應(yīng)時所需的D.V.S.值為3.0，硝酸比φ值為2.2，相比為6.5。試計算：該二硝化反應(yīng)正常發(fā)生時應(yīng)選用的混酸組成為多少？（以1Kgmol的萘為計算基準(zhǔn)）

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JiangsuPolytechnicUniversityDeptofChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering解：以1kgmol的萘為計算基準(zhǔn)：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故混酸組成為：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.文獻查閱下列常見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、間二硝基苯、2，4－二硝基氯苯、硝基甲烷、間硝基三氟甲苯。

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JiangsuPolytechnicUniversityDeptofChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering第6章還原1.某車間用22.5%Na2S水溶液還原對硝基甲苯，反應(yīng)式為（1）若每批投98%的對硝基甲苯140Kg，Na2S的用量為理論量的1.2倍，求每批用22.5%Na2S水溶液多少Kg？（2）產(chǎn)品經(jīng)干燥后得100Kg，從中取0.2253g用重氮法分析氨基物的含量,用0.1NNaNO2標(biāo)準(zhǔn)溶液20ml滴到終點,求產(chǎn)品純度？產(chǎn)品收率？

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JiangsuPolytechnicUniversityDeptofChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering解：（1）設(shè)：需22.5%硫化鈉水溶液的量為AKgA=140×98%/137×1.20×6/4×78/22.5%=624Kg（2）產(chǎn)品純度：C=0.1×20×107/0.2253/1000×100%=95%產(chǎn)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.

某工廠以Na2S.9H2O為還原劑將98%間二硝基苯500Kg還原制備間硝基苯胺，還原劑用量為理論用量的1.20倍，求：（1）還原劑Na2S.9H2O的用量？（2）反應(yīng)產(chǎn)物經(jīng)水洗、重結(jié)晶、烘干得到335Kg，從中取0.2850g產(chǎn)品，用重氮法分析氨基物的含量，用0.1NNaNO2標(biāo)準(zhǔn)溶液20ml滴到終點，求產(chǎn)品純度?產(chǎn)品收率?

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ChangzhouUniversitySchoolofPetroChemicalEngineering解：（1）Na2S.9H2O用量為：500×98%/168×6/4×1.20×240=1260Kg

（2）產(chǎn)品純度：C=0.1×20×138/0.2850/1000×100%=96.84%產(chǎn)品收率：Y=335×96.84%/138/(500×98%/168)×100%=82.1%

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ChangzhouUniversitySchoolofPetroChemicalEngineering3.文獻查閱下列常見氨基物的用途和合成方法？間硝基苯胺、1－萘胺、4，4，－二氨基二苯醚、對氨基乙酰苯胺、對氨基苯甲酸、間氯苯胺、對甲苯胺、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章氧化反應(yīng)1．解釋下列名詞：自動氧化阻化劑誘導(dǎo)期

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JiangsuPolytechnicUniversityDeptofChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering2．常用的工業(yè)氧化劑有哪些？各有何特點？3．文獻查閱下列工業(yè)氧化產(chǎn)品的用途和合成方法？對氯苯甲酸、苯酚、環(huán)氧乙烷、富馬酸、乙二醛、順丁烯二酸酐、煙酸、過氧乙酸、鄰苯二甲酸酐、環(huán)氧丙烷。

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JiangsuPolytechnicUniversityDeptofChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering第8章重氮化及重氮鹽的反應(yīng)1.工業(yè)上重氮化反應(yīng)終點是如何確定的？終點：芳胺消失，亞硝酸微過量。終點測定方法：淀粉、KI試紙立即變蘭。特征反應(yīng)?。?！I2+淀粉→藍色染料！

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JiangsuPolytechnicUniversityDeptofChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering2.工業(yè)生產(chǎn)上偶合反應(yīng)終點是如何確定的？（1）反應(yīng)終點：重氮鹽無，偶合物微過量。（2）反應(yīng)終點測定：潤圈試驗，需反復(fù)多次檢查確定終點。

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JiangsuPolytechnicUniversityDeptofChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering3.舉例說明由重氮化合物經(jīng)轉(zhuǎn)化后得到哪些工業(yè)化產(chǎn)品和中間體？4.文獻查閱下列化合物用途和合成方法！剛果紅、甲基橙、間氯苯酚、對氯苯磺酸。

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JiangsuPolytechnicUniversityDeptofChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering第9章氨解和胺化1.以最合理的合成工藝路線合成下列化合物。（S表示為磺酸基團）

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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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ChangzhouUniversitySchoolofPetroChemicalEngineering3.

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ChangzhouUniversitySchoolofPetroChemicalEngineering4.

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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．文獻查閱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、乙醇胺系列產(chǎn)品、2－萘胺、水楊酰苯胺（87－17－2）、對甲苯磺酰胺。

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JiangsuPolytechnicUniversityDeptofChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering第10章烴化工業(yè)烴化反應(yīng)試劑有哪些？烴化反應(yīng)的主要特點有哪些？以最合理的合成工藝路線合成下列化合物。

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JiangsuPolytechnicUniversityDeptofChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering1.

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering2.見黑板?。?！

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JiangsuPolytechnicUniversityDeptofChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering3.

A+B=產(chǎn)物

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ChangzhouUniversitySchoolofPetroChemicalEngineering4.

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ChangzhouUniversitySchoolofPetroChemicalEngineering3．文獻查閱下列烴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、鄰甲氧基苯甲醛、

2－甲氧基萘、對羥基苯甲醚。

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JiangsuPolytechnicUniversityDeptofChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering第11章酰化反應(yīng)1.工業(yè)?；磻?yīng)試劑有哪些？酰化反應(yīng)的主要特點有哪些？2．以最合理的合成工藝路線合成下列化合物。

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JiangsuPolytechnicUniversityDeptofChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering1.

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ChangzhouUniversitySchoolofPetroChemicalEngineering2.

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ChangzhouUniversitySchoolofPetroChemicalEngineering4.見黑板?。?！

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JiangsuPolytechnicUniversityDeptofChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering3．文獻查閱下列酰基化合物的用途和合成方法？鄰氯乙酰苯胺、2，4－二羥基苯乙酮、乙酸苯酯、氯甲酸苯酯、乙基苯基酮。

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ChangzhouUniversitySchoolofPetroChemicalEngineering第12章水解苯酚的工業(yè)化合成路線有哪些？各有何特點？以最合理的合成工藝路線合成下列化合物。

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JiangsuPolytechnicUniversityDeptofChemicalEngineering

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JiangsuPolytechnicUniversitySchoolofPetroChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering

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JiangsuPolytechnicUniversityDeptofChemicalEngineering

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ChangzhouUniversitySchoolofPetroChemicalEngineering1.2.

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JiangsuPolytechnicUniversityDeptofChemicalEngineering