查看“︁苯甲醇”︁的源代码

{{Chembox
| Name = 苯甲醇
| ImageFile = Benzyl-alcohol-2D-skeletal.png
| ImageSize = 150px
| ImageName = 苯甲醇 键线式
| ImageFile1 = Benzyl-alcohol-3D-vdW.png
| ImageSize1 = 100px
| ImageName1 = 苯甲醇 空间填充模型
| NameEn = Benzyl alcohol
| IUPACName = Phenylmethanol
| OtherNames = 苄醇
| Abbreviations = [[苄基|Bn]]OH
| Section1 = {{Chembox Identifiers
| CASNo = 100-51-6
| CASNo_Ref = {{cascite|correct|CAS}}
|  SMILES  =  OCc1ccccc1
|  UNII_Ref  = {{fdacite|correct|FDA}}|  UNII  =  LKG8494WBH
|  KEGG_Ref  = {{keggcite|correct|kegg}}|  KEGG  =  D00077
|  InChI  =  1/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2
|  InChIKey  =  WVDDGKGOMKODPV-UHFFFAOYAH
|  SMILES1  =  c1ccc(cc1)CO
|  ChEMBL_Ref  = {{ebicite|correct|EBI}}|  ChEMBL  =  720
|  StdInChI_Ref  = {{stdinchicite|correct|chemspider}}|  StdInChI  =  1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2
|  StdInChIKey_Ref  = {{stdinchicite|correct|chemspider}}|  StdInChIKey  =  WVDDGKGOMKODPV-UHFFFAOYSA-N
|  EINECS  =  202-859-9
|  ChemSpiderID_Ref  = {{chemspidercite|correct|chemspider}}|  ChemSpiderID  =  13860335
|  ChEBI_Ref  = {{ebicite|correct|EBI}}|  ChEBI  =  17987
|  PubChem  =  244
|  RTECS  =  DN3150000
}}
| Section2 = {{Chembox Properties
| C=7|H=8|O=1
| Appearance = 无色芳香透明液体
| Density = 1.044 g/cm<sup>3</sup>
| MeltingPt = -15 ℃
| BoilingPt = 205 ℃
| VaporPressure = 3.7 mmHg（77℃）
| Solubility = 稍溶于水
| pKa = 15.4<ref>{{en}}{{cite web|url=http://sitem.herts.ac.uk/aeru/footprint/en/Reports/953.htm |title=存档副本 |accessdate=2009-04-29 |deadurl=yes |archiveurl=https://web.archive.org/web/20090726101848/http://sitem.herts.ac.uk/aeru/footprint/en/Reports/953.htm |archivedate=2009-07-26 }}</ref>
  }}
| Section7 = {{Chembox Hazards
| ExternalMSDS = [http://www.sciencelab.com/msds.php?msdsId=9927099 ScienceLab.com]
| RPhrases = {{R20}}, {{R21}}, {{R22}}, {{R36}}, {{R37}}, {{R38}}
| SPhrases = {{S26}}
| FlashPt = 94 ℃
| Autoignition = 436 ℃
  }}
}}
'''苯甲醇'''，也称'''[[苄]]醇'''，[[化学式]]为C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>OH，是最简单的含有苯基的脂肪[[醇]]，可以看作是[[羟甲基]]取代的[[苯]]，或[[苯基]]取代的[[甲醇]]。它是有微弱芳香气味的无色透明黏稠液体，有极性，低毒，[[蒸汽压]]低，因此用作醇类[[溶剂]]。可燃。稍溶于水（4 g/100 mL），可与[[乙醇]]、[[乙醚]]、[[苯]]、[[氯仿]]等[[有机溶剂]]混溶。

苄醇主要以游离态或[[酯]]的形式存在于[[香精油]]中，如[[茉莉花油]]、[[伊兰伊兰油]]、[[素馨花香油]][[风信子油]]、[[月下香油]]和[[妥鲁香脂]]中都含有此成分。<ref>''Merck Index'', 11th Edition, '''1138'''.</ref>

== 制取 ==

* 工业上由[[氯化苄]]在[[碱]]（如[[氢氧化钠]]、[[碳酸钠]]或[[碳酸钾]]）存在下加热[[水解]]制取：
: <math>\rm C_6H_5CH_2Cl+NaOH\rightarrow C_6H_5CH_2OH+NaCl\,</math>

此外苯甲醇的制取方法还有：

* [[苯甲醛]][[催化]][[还原]]得到苯甲醇。
* [[格氏试剂]][[苯基溴化镁]]（由[[溴苯]]与[[镁]]制取）与[[甲醛]]反应后酸化得到苯甲醇。
* [[苯甲醛]]在[[氢氧化钾]]存在下发生[[坎尼扎罗反应]]，[[歧化]]生成等量的苯甲醇和[[苯甲酸]]。

== 性质和应用 ==

苯甲醇用作[[药膏]]、[[抑菌劑注射用水]]以及特定[[注射劑]]的[[防腐剂]]，[[纤维]]、[[尼龙丝]]及[[塑料薄膜]]的[[干燥剂]]，[[聚氯乙烯]]的[[稳定剂]]，[[照相显影剂]]，[[醋酸纤维]]、[[墨水]]、[[涂料]]、[[油漆]]、[[环氧树脂]]涂料、[[染料]]、[[酪蛋白]]、[[虫胶]]及[[明胶]]等的[[溶剂]]，<ref>{{cite web|url=http://www.chemicalland21.com/industrialchem/solalc/BENZYL%20ALCOHOL.htm|title=Benzyl alcohol (Phenylcarbinol)|publisher=chemicalland21.com|accessdate=2009-04-25|deadurl=yes|archiveurl=https://web.archive.org/web/20090421060841/http://chemicalland21.com/industrialchem/solalc/BENZYL%20ALCOHOL.htm|archivedate=2009-04-21}}</ref><ref>{{cite journal | title = Nanowires get reconfigured | author = Alexander Wissner-Gross | date = 19 October 2006 | url = http://nanotechweb.org/articles/journal/5/10/2/1 | publisher = Nanotechweb.org | format = [http://scholar.google.co.uk/scholar?hl=en&lr=&q=intitle%3ANanowires+get+reconfigured&as_publication=&as_ylo=&as_yhi=&btnG=Search Scholar search] | journal =  | access-date = 2009-04-25 | archive-url = https://web.archive.org/web/20070522224736/http://nanotechweb.org/articles/journal/5/10/2/1 | archive-date = 2007-05-22 | dead-url = yes }}（链接已失效－[http://web.archive.org/web/20071104012053rn_2/nanotechweb.org/cws/article/lab/26192 互联网档案馆的存档]）</ref><ref>Alexander D. Wissner-Gross (2006). "Dielectrophoretic reconfiguration of nanowire interconnects". ''Nanotechnology'' '''17''': 4986-4990. {{doi|10.1088/0957-4484/17/19/035}}.</ref> 也用于制取[[香料]]和[[调味剂]]（多数为[[脂肪酸]]的苯甲醇[[酯]]），以作为[[肥皂]]、[[香水]]、[[化妆品]]和其他产品中的添加剂。由于与[[石英]]和[[羊毛纤维]]具有几乎相同的[[折射率]]，因此用作石英和羊毛纤维的鉴别剂。香料工业中用作[[定香剂]]和[[稀释剂]]。可用于制备苯甲酸<ref>Multifunctionality of Crystalline MoV(TeNb) M1 Oxide Catalysts in Selective Oxidation of Propane and Benzyl Alcohol, 2013, ACS Catalysis 3(6):1103-1113, DOI:10.1021/cs400010q <nowiki>https://www.researchgate.net/publication/278196177_Multifunctionality_of_Crystalline_MoVTeNb_M1_Oxide_Catalysts_in_Selective_Oxidation_of_Propane_and_Benzyl_Alcohol</nowiki></ref><ref>Nanodisperse gold catalysts in oxidation of benzyl alcohol: comparison of various supports under different conditions. ''Reac Kinet Mech Cat'' '''128''', 71–95 (2019). <nowiki>https://doi.org/10.1007/s11144-019-01615-8</nowiki> <nowiki>https://link.springer.com/article/10.1007/s11144-019-01615-8</nowiki></ref>。

苯甲醇的羟基很活泼，它可以与[[苯]]反应生成[[二苯甲烷]]，与[[丙烯腈]]反应生成''N''-苄基[[丙烯酰胺]]（[[Ritter反应]]），<ref>{{OrgSynth | author = Parris, C. L. | title = N-benzylacrylamide | collvol = 5 | collvolpages = 73 | year = 1973 | prep = cv5p0073}}</ref> 也可以与[[卤化磷]]和[[氢卤酸]]反应生成[[卤化苄]]。卤化苄和苯甲醇都是[[苄基]]（苯甲基）化试剂，用于给[[羧酸]]和[[醇]][[羟基]]上[[苄基]][[保护基]]。苄基保护基很容易通过[[氢化]]脱去。<ref>{{OrgSynth | author = Furuta, K.; Gao, Q.-Z.; Yamamoto, H. | title = Chiral (Acyloxy)borane Complex-Catalyzed Asymmetric Diels-Alder Reaction: (1R)-1,3,4-Trimethyl-3-Cyclohexene-1-Carboxaldehyde | collvol = 9 | collvolpages = 722 | year = 1998 | prep = cv9p0722}}</ref>

苯甲醇不宜久贮，它在空气中能缓慢[[氧化]]为[[苯甲醛]]和[[苯甲醚]]，因此市售的苯甲醇产品常带有苯甲醛特征的杏仁香味。此外，苯甲醇也容易被多种[[氧化剂]]（如[[浓硝酸]]）氧化成[[苯甲酸]]。

苯甲醇有麻醉作用，对眼部、皮肤和呼吸系统有强烈的刺激作用，吞食、吸入或皮肤接触均对身体有害。摄入后引起[[头痛]]、[[恶心]]、[[呕吐]]、胃肠道刺激、惊厥、昏迷，<ref>{{cite web|url=http://www.ep.net.cn/MSDS/wuzhi0/032.htm|title=化学品文档|publisher=中国环保网——突发性污染事故中危险品档案库|accessdate=2009-04-25|deadurl=yes|archiveurl=https://web.archive.org/web/20070914043004/http://www.ep.net.cn/msds/wuzhi0/032.htm|archivedate=2007-09-14}}</ref> 严重时可导致死亡。<ref>{{cite journal | url = http://www.cdc.gov/MMWR/preview/mmwrhtml/00001109.htm | title = Neonatal Deaths Associated With Use Of Benzyl Alcohol — United States | journal = Morbidity and Mortality Weekly Report | date = 11 June 1982 | volume = 31 | issue = 22 | pages = 290–1 | access-date = 2009-04-25 | archive-date = 2012-08-30 | archive-url = https://web.archive.org/web/20120830225243/http://www.cdc.gov/mmwr/preview/mmwrhtml/00001109.htm | dead-url = no }}</ref> 大鼠的[[半数致死量]]为1230mg/kg。苯甲醇进入人体后，首先被氧化为[[苯甲酸]]，然后与肝中的[[甘氨酸]]缩合，以[[马尿酸]]的形式排出体外。[[肌肉注射]]使用苯甲醇为溶剂可能导致[[臀肌挛缩]]。

新生兒若使用添加苯甲醇作為防腐劑的抑菌劑注射用水，將導致Gasping syndrome。

== 参见 ==

* [[苯甲醛]]、[[苯甲酸]]
* [[氯化苄]]、[[溴化苄]]

== 参考资料 ==
{{Reflist}}

==外部連結==
{{Portal|醫學}}
*{{ICSC|0833|08}}
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/benzyl%20alcohol | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Benzyl alcohol | access-date = 2020-08-02 | archive-date = 2021-02-28 | archive-url = https://web.archive.org/web/20210228090852/https://druginfo.nlm.nih.gov/drugportal/name/benzyl%20alcohol | dead-url = no }}

{{苯}}
{{苄基化合物}}
{{Authority control}}
[[Category:芳香溶剂]]
[[Category:伯醇]]
[[Category:醇类溶剂]]
[[Category:苄基化合物]]
[[Category:有E编码的食品添加剂]]