查看“︁1-氯丁烷”︁的源代码

{{chembox
| Name = 1-氯丁烷
| ImageFile = 1-chlorobutane.svg
| ImageSize =
| IUPACName = 1-chlorobutane
| OtherNames = 正丁基氯<br />氯丁烷<br />丁基氯<br />氯代正丁烷
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = ZP7R667SGD
| InChI = 1/C4H9Cl/c1-2-3-4-5/h2-4H2,1H3
| InChIKey = VFWCMGCRMGJXDK-UHFFFAOYAR
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 47259
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H9Cl/c1-2-3-4-5/h2-4H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VFWCMGCRMGJXDK-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=109-69-3
| PubChem=8005
| SMILES = ClCCCC
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=7714
 }}
|Section2={{Chembox Properties
| C = 4 | H = 9 | Cl = 1 
| Appearance = 无色有类似[[氯仿]]气味的挥发性液体
| Density = 0.88 g/mL
| MeltingPt = -123 °C
| BoilingPt = 79 °C
| Solubility = 0.5 g/L (20 °C)<ref name="BGIA GESTIS">{{GESTIS|ZVG=26510|CAS=109-69-3|Datum=11. Februar 2009}}</ref>
| VaporPressure = 10.8 kPa (20 °C)
| RefractIndex = 1.4018 (20 °C)<ref name="Gerrard">Gerrard, W.; Hudson, H. R.; Murphy, W. S. "s-Butyl Chloride from n-Butyl Dichloroborinate and from n-Butanol-Hydrogen Chloride." ''J. Org. Chem.'' '''1962''', 1099–1101</ref>
 }}
|Section3={{Chembox Hazards
| ExternalMSDS = [http://msds.chem.ox.ac.uk/CH/1-chlorobutane.html Oxford MSDS]
| EUClass = 可燃 ('''F''')
| NFPA-H = 1
| NFPA-F = 3
| NFPA-R = 1
| RPhrases = {{R11}}
| SPhrases = {{S2}}, {{S9}}, {{S16}}, {{S29}}
| LD50 = 2670 mg·kg<sup>-1</sup> (大鼠经口)<ref>[http://www.applichem.de/fileadmin/datenblaetter/a3501_de.pdf SICHERHEITSDATENBLATT]{{dead link|date=十一月 2017 |bot=InternetArchiveBot }}</ref>
 }}
}}

'''1-氯丁烷'''，分子式C<sub>4</sub>H<sub>9</sub>Cl。

==性质==
无色挥发性易燃液体，有类似[[三氯甲烷|氯仿]]的气味。几乎不溶于水，与[[乙醇]]和[[乙醚]]混溶。

*[[粘度]]：0.45 mPa·s（20°C）
*[[闪点]]（开杯）：-9.4 °C
*[[自燃点]]：460 °C
*与水的共沸物：水 6.6 wt%，共沸点 68.1 °C<ref name="Ullmann">Ullmann's Encyclopedia of Industrial Chemistry, Wiley Interscience, Release 2009, 7th Edition</ref>
*与醇的共沸物：<ref name="Ullmann" />
**甲醇 28.5 wt%，共沸点 57.2 °C
**乙醇 21.5 wt%，共沸点 66.2 °C
**正丙醇 16.0 wt%，共沸点 75.6 °C
*蒸气压方程（[[安托万方程]]）：
:<math>\ \log_{10} (P) = A-\frac{B}{T+C}</math>
**P 的单位：bar，T 的单位：K
**A = 3.99588, B = 1182.903, C = −54.885 (T = 256.4–351.6&nbsp;K)<ref>Kemme, H.R.; Kreps, S.I., ''Vapor Pressure of Primary n-Alkyl Chlorides and Alcohols'' in  J. Chem. Eng. Data, 1969, 14, 1, 98-102.</ref>
*[[标准摩尔生成焓]]：
**−188.2&nbsp;kJ·mol<sup>−1</sup>（Δ<sub>f</sub>H<sup>0</sup><sub>liquid</sub>）
**−154.6&nbsp;kJ·mol<sup>−1</sup>（Δ<sub>f</sub>H<sup>0</sup><sub>gas</sub>）<ref name="Stridth Sunner">Stridth, G.; Sunner, S.: ''Enthalpies of formation of some 1-chloroalkanes and the CH<sub>2</sub>-increment in the 1-chloroalkanes series'' in J. Chem. Thermodyn., 1975, 7, 161-168.</ref>
*[[标准摩尔燃烧焓]]：−2695.8&nbsp;kJ·mol<sup>−1</sup>（Δ<sub>c</sub>H<sup>0</sup><sub>liquid</sub>）<ref name="Stridth Sunner" />
*[[热容]]（c<sub>p</sub>）：159.53&nbsp;J·mol<sup>−1</sup>·K<sup>−1</sup> (25&nbsp;°C，液)<ref> Grolier, J.-P.E.; Roux-Desgranges, G.; Berkane, M.; Jimenez, E.; Wilhelm, E.: ''Heat capacities and densities of mixtures of very polar substances 2. Mixtures containing N,N-dimethylformamide'' in J. Chem. Thermodynam., 1993, 25(1), 41-50. </ref>
*[[汽化焓]]：30.39&nbsp;kJ·mol<sup>−1</sup>（Δ<sub>V</sub>H<sup>0</sup>，常压沸点）<ref name="Majer Svoboda">Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300</ref>

==制备==
[[正丁醇]]与[[盐酸|浓盐酸]]在[[氯化锌]][[催化]]下进行作用，产生1-氯丁烷。反应后将产物洗涤、干燥、分馏，收集75～78.5°C馏分，得到成品。
:<math>\ CH_3CH_2CH_2CH_2OH+HCl \ \xrightarrow {ZnCl_2} \ CH_3CH_2CH_2CH_2Cl+H_2O</math>

==反應==
===親核取代反應===
1-氯丁烷的1號碳（連著氯原子的碳）因爲連著[[电负性|電負性]]比碳高的氯，所以帶部分正電荷，變得[[亲电体|親電]]，可以被[[亲核体|親核體]]進攻。而由於它是個一級[[氯代烷]]，[[位阻效应|位阻效應]]比較小，同時相應的[[碳正离子|碳陽離子]]不穩定，因此它主要發生[[双分子亲核取代反应|雙分子親核取代反應]]，而不是[[单分子亲核取代反应|單分子親核取代反應]]。例如1-氯丁烷與[[氢氧化钠|氫氧化鈉]]反應，[[氢氧根|氫氧根離子]]進攻1號碳，氯以[[氯化物|氯離子]]的方式離去，生成[[1-丁醇]]。

==用途==
用作有机合成原料、医药中间体，也用作溶剂和脱蜡剂等。有机合成中，用于引入正丁基，也用于与金属[[锂]]作用制取[[正丁基锂]]：
:<math>\ 2 Li + C_4H_9Cl \rightarrow C_4H_9Li + LiCl</math>

1-氯丁烷对油、脂和蜡有较好的溶解性，也用于[[高效液相色谱|HPLC]]中。

==参考资料==
{{reflist}}

[[Category:氯代烷烃]]
[[Category:卤代烃类溶剂]]
[[Category:正丁基化合物]]
[[Category:一卤丁烷]]