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Student Number 86321030
Author Chyuan-Jaqn Shieh(謝全展)
Author's Email Address No Public.
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Department Chemical and Materials Engineering
Year 1998
Semester 2
Degree Master
Type of Document Master's Thesis
Language zh-TW.Big5 Chinese
Title Reactioms of 2-chloride-5-nitrobenzensulfonic acid with aromatic alcohol, aromatic amine
Date of Defense
Page Count 47
Keyword
  • 2-chloride-5-nitrobenzensulfonic acid
  • aromatic alcohol
  • aromatic amine
  • intermediate of dyes
  • Abstract Benzidine and it's derivatives were identified that they would let the maker and user got cancer recently, so they were forbidden to use in the world. This proposal is going to study the reactions of 2-chloride-5-nitrobenzensulfonic acid (abbreviated to "CNBS") with aromatic alcohol and CNBS with aromatic amine. The products of the reactions may offer people another choice about producing and using intermediate of dyes. There are three products of CNBS with aromatic alcohol. They are 2-phenoxy-5-nitro-benzensulfonic acid { IR(cm-1) : 1520, 1350 (N-O) }, 2-(4'-amino-phenoxy)-5-nitro-benzensulfonate; potassium { IR(cm-1) : 3350, 3280 (N-H); 1540, 1360 (N-O) } and 2-(4'-acetylamino-phenoxy)-5-nitro-benzensulfonate; potassium { IR(cm-1) : 3340 (N-H); 1540, 1360 (N-O); 1660 (C=O) }. And there are four products of CNBS with aromatic amine. They are 2-anilino-benzensulfonic acid { IR(cm-1) : 3300 (N-H); 1540, 1340 (N-O) }, 2-(4'-hydroxy-anilino)-5-nitro-benzensulfonate; potassium { IR (cm-1) : 3300 (O-H); 3350 (N-H); 1540, 1340 (N-O) }, 2-(4'-hydroxy-2'-methyl-anilino)-5-nitro-benzensulfonate; sodium { IR (cm-1) : 3150 (O-H); 3270 (N-H); 1520,1350 (N-O) } and 2-(4'-amino-anilino)-5-nitro-benzensulfonate; sodium { IR (cm-1) : 3300, 3090, 2950 (N-H); 1520, 1340 (N-O) }. P-acetylamino-phenol has already been used to detect ozone in atmosphere. This proposal is going to synthesis the compounds which have the similar structure formula with p-acetylamino-phenol. There are two compounds which are 2-(4'-hydroxy-anilino)-5-nitro-benzensulfonate; potassium and 2-(4'-hydroxy-2'-methyl-anilino)-5-nitro-benzensulfonate; sodium. Studying and discussing the properties of the two compounds was going by another classmate of our laboratory.
    Table of Content 目錄
    圖目錄-----------------------------------------------------------------------------Ⅰ
    表目錄-----------------------------------------------------------------------------Ⅱ
    摘要--------------------------------------------------------------------------------Ⅲ
    英文摘要--------------------------------------------------------------------------Ⅴ
    第一章 緒論----------------------------------------------------------------------1
    第二章 文獻回顧----------------------------------------------------------------2
    第三章 實驗部份
    3-1 實驗儀器、葯品-------------------------------------------------------------4
    3-2 反應方程式
    3-2-1原料製備反應方程式--------------------------------------------------6
    3-2-2 CNBS與苯酚類之反應方程式--------------------------------------7
    3-2-3 CNBS與苯胺類之反應方程式--------------------------------------9
    3-3 操作流程
    3-3-1原料製備操作流程----------------------------------------------------11
    3-3-2 CNBS與苯酚之操作流程-------------------------------------------16
    3-3-3 CNBS與苯胺之操作流程-------------------------------------------17
    3-3-4 CNBS與苯酚類、苯胺類反應之操作流程-----------------------18
    3-4實驗步驟
    3-4-1原料製備----------------------------------------------------------------19
    3-4-2 CNBS與苯酚類之反應----------------------------------------------22
    3-4-3 CNBS與苯胺類之反應----------------------------------------------24
    第四章 結果與討論
    4-1化合物合成結果---------------------------------------------------------26
    4-2 化合物紅外光光譜特性吸收之討論--------------------------------28
    4-3 硝化、還原與乙醯化反應之討論-------------------------------------31
    4-4 CNBS與苯酚類、苯胺類反應之結果討論--------------------------33
    第五章 結論---------------------------------------------------------------------35
    第六章 參考文獻---------------------------------------------------------------36
    附圖--------------------------------------------------------------------------------37
    Reference 1. Vogel's, "Textbook of Partical Organic Chemistry", Fourth edition, 1978, P.745.
    2. Vogel's, "Textbook of Partical Organic Chemistry", Fourth edition, 1978, P.753.
    3. A.Proskouriakoff and R.J.Titherington, J.Am.Chem.Soc., 1930, 52, P.3979.
    4. Baroni and Kleinau, Monatsh.chem., 1936, 68, P.251.
    5. Poirier, Jean-Marie and Vottero, Catherine, Tetrahedron, 1989, 45, P.1415.
    6. Staedel and Kolb, Justus Liebigs Ann.Chem., 1890, 259, P.217.
    7. Nathan Kornblum and Arnold P. Lurie, J.Am.Chem.Soc., 1959, 81, P.2710.
    8. Chem.Abstr., 1955, P.2348. (Arh.Kem., 1953, 25, P.151.)
    9. Ficher P., Berichte der Deutschen Chemischen Gesellschaft, 1891, 24, P.3797.
    10. Ullmann and Dahmen, Berichte der Deutschen Chemischen Gesellschaft, 1908, 41, P.3746.
    11. Ullmann and Juengel, Berichte der Deutschen Chemischen Gesellschaft, 1909, 42, P.1077.
    12. The Merck Index; Eleventh edition; 1989.
    13. 吳建興, "國立中央大學化工碩士論文", 1995.
    Advisor
  • Kung-Tu Kuo(郭坤土)
  • Files No Any Full Text File.
    Date of Submission

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