查看“︁巴豆醛”︁的源代码

{{chembox
| Reference=<ref>''[[默克索引]]'', 11th Edition, '''2599'''</ref>
| Name = ''反式''-2-丁烯醛
| NameEn = Crotonaldehyde
| ImageFile = Crotonaldehyde.png
| ImageName = 巴豆醛
| ImageSize = 180px
| ImageFile1 = Crotonaldehyde-3D-balls.png
| ImageName1 = 球棍模型
| IUPACName = (2''E'')-but-2-enal
| OtherNames = 巴豆醛<br />''E''-丁-2-烯醛<br />3-甲基丙烯醛<br />反式丁烯醛
| Section1 = {{Chembox Identifiers
| CASNo = 123-73-9
| CASNo_Comment =  (''E'')
| CASNo_Ref = {{cascite|changed|CAS}}
| CASNo1 = 4170-30-3
| CASNo1_Comment =  (''E/Z'')
| CASNo1_Ref = {{cascite|changed|CAS}}
| CASNo2 = 15798-64-8
| CASNo2_Comment =  (''Z'')
| CASNo2_Ref = {{cascite|changed|CAS}}
|   EINECS  =  
|   PubChem  =  447466
|   SMILES  =  O=C/C=C/C
|   InChI  =  1S/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+
|   InChIKey  =  MLUCVPSAIODCQM-NSCUHMNNSA-N
|  IUPHAR_ligand  =  6288
|  ChemSpiderID_Ref  = {{chemspidercite|correct|chemspider}}|  ChemSpiderID  =  394562
|  StdInChI_Ref  = {{stdinchicite|correct|chemspider}}|  StdInChI  =  1S/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+
|  StdInChIKey_Ref  = {{stdinchicite|correct|chemspider}}|  StdInChIKey  =  MLUCVPSAIODCQM-NSCUHMNNSA-N
|  UNII_Ref  = {{fdacite|changed|FDA}}|  UNII  =   9G72074TUW 
|  UNII_Comment  =  ("E/Z")
|  UNII1_Ref  = {{fdacite|changed|FDA}}|  UNII1  =   6PUW625907 
|  UNII1_Comment  =  ("E")
|  UNII2_Ref  = {{fdacite|changed|FDA}}|  UNII2  =   RB9WCA91QT
|  UNII2_Comment  =  ("Z")
|  ChEMBL_Ref  = {{ebicite|correct|EBI}}|  ChEMBL  =  1086445
|  DrugBank_Ref  = {{drugbankcite|correct|drugbank}}|  DrugBank  =  DB04381
|  ChEBI_Ref  = {{ebicite|correct|EBI}}|  ChEBI  =  41607
|  KEGG_Ref  = {{keggcite|changed|kegg}}|  KEGG  =  C19377
}}
| Section2 = {{Chembox Properties
|  C = 4 | H = 6 | O = 1
|  Appearance = 无色液体
|  Density = 0.846 g/cm<sup>3</sup>
|  MeltingPtC = -76.5
|  BoilingPtC = 104.0
|  Solubility = 181 g/l，20 °C<ref name="GESTIS">{{GESTIS|ZVG=37140|CAS=4170-30-3|Datum=03.01.2008}}</ref>
|  SolubleOther = 12.17 M <ref>[http://oru.edu/cccda/sl/solubility/ugidata.php?solute=crotonaldehyde&solvent=methanol Solubility of crotonaldehyde in methanol]</ref>
|  Solvent = [[甲醇]] 
|  RefractIndex = 1.4362<ref name="zghg">中国化工产品大全 上卷，Da133 丁烯醛，页509</ref>
|  VaporPressure = 2.4 kPa，20 °C<ref name="GESTIS">{{GESTIS|ZVG=37140|CAS=4170-30-3|Datum=03.01.2008}}</ref>
  }}
| Section7 = {{Chembox Hazards
|  EUClass = {{Hazchem T+}} {{Hazchem F}} {{Hazchem N}}
|  RPhrases = {{R11}}-{{R26}}-{{R24/25}}-{{R37/38}}-{{R41}}-{{R48/22}}-{{R50}}-{{R68}}
|  SPhrases = {{S1/2}}-{{S26}}-{{S28}}-{{S36/37/39}}-{{S45}}-{{S61}}
|  NFPA-H = 4
|  NFPA-F = 3
|  NFPA-R = 2
|  NFPA-O =
|  FlashPt = 13 °C (开杯)<ref name="zghg" />
|  ExploLimits = 2.91～15.5％ (体积)<ref name="zghg" />
  }}
}}

'''巴豆醛'''，即'''2-丁烯醛'''，结构式CH<sub>3</sub>CH＝CHCHO。

==性质==
巴豆醛有[[顺反异构|顺式和反式]]两种双键异构体。市售商品为反式异构体，因顺式异构体不稳定。无色透明有窒息性刺激气味液体。露置于空气中或遇光时逐渐变为淡黄色液体，被氧化为[[巴豆酸]]。易溶于水，与[[乙醇]]、[[乙醚]]、[[苯]]、[[甲苯]]、[[汽油]]、[[煤油]]完全混溶。有毒，蒸气对呼吸道和眼部有刺激作用，皮肤接触时有灼烧痛感，且为很强的催泪剂。

==制备==
两分子[[乙醛]]在碱或阴离子交换树脂催化下液相[[羟醛缩合]]产生[[丁醇醛]]，后者在稀酸中加热脱水，得到巴豆醛。
:<math>\ 2CH_3CHO\rightarrow CH_3CH(OH)CH_2CHO\rightarrow </math><math>\ CH_3CH\!=\!CHCHO+H_2O</math>

<br />
[[File:Synthesis Crotonaldehyde.svg|thumb|450px|none|upright=2.0|从乙醛羟醛缩合制备巴豆醛。]]

==用途==
巴豆醛是重要的有机合成中间体，用于制造[[丁醛]]、食品防腐剂[[山梨酸]]、合成树脂、染料、杀虫剂、选矿用发泡剂、橡胶抗氧化剂等。巴豆醛也是有机合成中具[[前手性]]的[[双烯体]]和[[麦克尔受体]]等。

==参考资料==
{{reflist}}

{{Authority control}}
[[Category:烯烃]]
[[Category:醛]]
[[Category:催泪剂]]
[[Category:缺少物质图片的化学品条目]]