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硝基苯

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硝基苯
英文名 Nitrobenzene
识别
CAS号 98-95-3  ✓
PubChem 7416
ChemSpider 7138
SMILES
InChI
InChIKey LQNUZADURLCDLV-UHFFFAOYAA
ChEBI 27798
RTECS QJ0525000
KEGG C06813
性质
化学式 C6H5NO2
摩尔质量 123.06 g·mol⁻¹
外观 黄色油状液体[1]
气味 像鞋油那样刺鼻[1]
密度 1.20 g/cm3(20 °C)[2]
熔点 6 °C[2]
沸点 211 °C[2]
溶解性 0.19 g/100 ml(20 °C)[2]
溶解性 乙醇乙醚混溶[3]
蒸气压 0.3 mmHg (25°C)[1]
磁化率 -61.80·10−6 cm3/mol
黏度 1.8112 mPa·s[4]
危险性
GHS危险性符号
《全球化学品统一分类和标签制度》(简称“GHS”)中有毒物质的标签图案
《全球化学品统一分类和标签制度》(简称“GHS”)中对人体有害物质的标签图案
GHS提示词 Danger
H-术语 H301, H311, H331, H351, H360, H372, H412
P-术语 P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+310, P302+352, P304+340, P308+313
NFPA 704
NFPA 704.svg
2
3
1
 
闪点 88 °C
爆炸极限 1.8%-?[1]
PEL TWA 1 ppm (5 mg/m3) [皮肤][1]
致死量或浓度:
LD50中位剂量
780 mg/kg(大鼠,口服)
600 mg/kg(大鼠,口服)
590 mg/kg(小鼠,口服)
[5]
LDLo最低
750 mg/kg(狗,口服)[5]
相关物质
相关化学品 苯胺
苯基重氮盐
亚硝基苯
若非注明,所有数据均出自一般条件(25 ℃,100 kPa)下。

硝基苯是最简单的芳香硝基化合物化学式C6H5NO2。它是由米修里希·伊尔哈得英语Eilhard Mitscherlich于1834年发现的。[6][7]

生产

硝基苯可以由硝酸和浓硫酸的混合物硝化而成。[8]反应首先会形成硝𬭩离子,然后硝𬭩离子和苯反应生成硝基苯:

由于反应高度放热(ΔH = −117 kJ/mol),硝基苯的生产是工业上最危险的生产流程之一。[9]

硝基苯在1985年的年产量约为 1,700,000 [9]

应用

生产出来的硝基苯有95%都会被氢化苯胺[9]而苯胺是聚氨酯橡胶化学品、除草剂、染料和药物的前体。[10][11]

C6H5NO2 + 3 H2 → C6H5NH2 + 2 H2O

硝基苯还用于掩盖鞋和地板抛光剂、皮革敷料、油漆溶剂和其它材料中的难闻气味。在之前,硝基苯还用于曾被用来使肥皂更香,但今天已经被毒性更低的化合物淘汰了。[12]硝基苯还可以生产镇痛剂扑热息痛[13]由于不寻常高的克尔常数,硝基苯也用于制造克尔盒。有证据表明硝基苯可以在农业中用作植物生长和开花的刺激剂。[14]

有机合成

除了氢化成苯胺外,硝基苯还可以被还原成氧化偶氮苯英语azoxybenzene[15]偶氮苯[16]亚硝基苯[17]二苯肼[18]苯基羟胺英语phenylhydroxylamine[19]斯克劳普合成反应中,硝基苯也用作温和的氧化剂。[20]

危害

长期暴露于硝基苯下会对中枢神经系统造成严重影响,还会损害视力、导致肝或肾损伤、贫血和刺激肺部。吸入蒸气可能会导致头痛、恶心、疲劳、头晕、紫绀、手臂和腿部虚弱,在极少数情况下可能是致命的。硝基苯很容易通过皮肤吸收,可能会增加心率,导致抽搐。摄入硝基苯同样会引起头痛、头晕、恶心、呕吐和胃肠道刺激、四肢失去知觉无法控制,还会导致内出血。[17]

硝基苯很可能是致癌物,[21]并被国际癌症研究机构归类为2B类致癌物(可能对人类致癌)。[22]它已被证明会导致大鼠的肝脏、肾脏和甲状腺得癌。[23]

硝基苯中毒可以用抗坏血酸(中毒较轻)或甲苯胺蓝英语Toluidine blue(中毒较重)解毒。使用甲苯胺蓝解毒时,患者的皮肤会暂时变蓝。对于可以危及生命的中毒则需要换血[24]

参考资料

  1. ^ 1.0 1.1 1.2 1.3 1.4 NIOSH Pocket Guide to Chemical Hazards 0450
  2. ^ 2.0 2.1 2.2 2.3 Record of Nitrobenzol in the GESTIS Substance Database from the IFA英语Institute for Occupational Safety and Health
  3. ^ Entry on Nitrobenzol. at: Römpp Online. Georg Thieme Verlag, retrieved 2014-09-29.
  4. ^ Ahluwalia, R.; Wanchoo, R. K.; Sharma, S. K.; Vashisht, J. L. Density, viscosity, and surface tension of binary liquid systems: Ethanoic acid, propanoic acid, and butanoic acid with nitrobenzene. Journal of Solution Chemistry. 1996, 25 (9): 905–917. ISSN 0095-9782. S2CID 95126469. doi:10.1007/BF00972581. 
  5. ^ 5.0 5.1 Nitrobenzene. Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). 
  6. ^ Mitscherlich, E. Ueber die Zusammensetzung des Nitrobenzids und Sulfobenzids;. Annalen der Pharmacie (Wiley). 1834, 12 (2-3): 305–311. ISSN 0365-5490. doi:10.1002/jlac.18340120281 (德语). 
  7. ^ Rolf Werner Soukup: Chemiegeschichtliche Daten organischer Substanzen, Version 2020, S. 120 pdf.
  8. ^ Buddrus, Joachim; Schmidt, Bernd. Grundlagen der organischen Chemie. Berlin: De Gruyter. 2011: 374-375. ISBN 978-3-11-024640-7. OCLC 754713666 (德语). 
  9. ^ 9.0 9.1 9.2 Booth G. Nitro Compounds, Aromatic. Ullmann's Encyclopedia of Industrial Chemistry 6th. Weinheim: Wiley-VCH. 2007. ISBN 978-3-527-30385-4. doi:10.1002/14356007.a17_411. 
  10. ^ Kahl, Thomas; Schröder, K. W.; Lawrence, F. R.; Elvers, Barbara; Höke, Hartmut; Pfefferkorn, R.; Marshall, W. J. Aniline. Ullmann, Fritz (编). Ullmann's encyclopedia of industrial chemistry. Wiley: New York. 2007. ISBN 978-3-527-20138-9. OCLC 11469727. doi:10.1002/14356007.a02_303. 
  11. ^ Aniline. The Chemical Market Reporter. [2007-12-21]. (原始内容存档于2002-02-19). 
  12. ^ Hogarth CW. a case of poisoning by oil of mirbane (nitro-benzol). British Medical Journal. January 1912, 1 (2665): 183. PMC 2344391可免费查阅. PMID 20765985. doi:10.1136/bmj.1.2665.183. 
  13. ^ Bhattacharya A, Purohit VC, Suarez V, Tichkule R, Parmer G, Rinaldi F. One-step reductive amidation of nitro arenes: application in the synthesis of Acetaminophen. Tetrahedron Letters. March 2006, 47 (11): 1861–1864. doi:10.1016/j.tetlet.2005.09.196. 
  14. ^ Flowering stimulant composition using nitrobenzene. 
  15. ^ "Azoxybenzene". Org. Synth.; Coll. Vol. 2: 57. 
  16. ^ (1955) "Azobenzene". Org. Synth.; Coll. Vol. 3: 103. 
  17. ^ 17.0 17.1 "Nitrosobenzene". Org. Synth.; Coll. Vol. 3: 668. 
  18. ^ Karwa, Shrikant L.; Rajadhyaksha, Rajeev A. Selective catalytic hydrogenation of nitrobenzene to hydrazobenzene. Industrial & Engineering Chemistry Research. January 1988, 27 (1): 21–24. ISSN 0888-5885. doi:10.1021/ie00073a005 (英语). 
  19. ^ "β-Phenylhydroxylamine". Org. Synth.; Coll. Vol. 1: 445. 
  20. ^ Clarke, HT; Davis, AW. Quinoline. Organic Syntheses: 478. 
  21. ^ Division, US EPA, ORD, Integrated Risk Information System. Nitrobenzene CASRN 98-95-3 - IRIS - US EPA, ORD. cfpub.epa.gov. [10 August 2017]. 
  22. ^ Agents Classified by the IARC Monographs, International Agency for Research on Cancer (PDF). [10 August 2017]. 
  23. ^ National Institutes of Health · U.S. Department of Health and Human Services, Nomination: Nitrobenzene Review committee, 02/02/2010
  24. ^ Lüllmann, Heinz; Mohr, Klaus; Wehling, Martin. Pharmakologie und Toxikologie Arzneimittelwirkungen verstehen - Medikamente gezielt einsetzen ; ein Lehrbuch für Studierende der Medizin, der Pharmazie und der Biowissenschaften, eine Informationsquelle für Ärzte, Apotheker und Gesundheitspolitiker ; 129 Tabellen. Stuttgart. 2006: 507-508. ISBN 978-3-13-368516-0. OCLC 180937412 (德语). 

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硝基苯
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