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异丙胺

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异丙胺
Skeletal formula of isopropylamine
Ball-and-stick model of the isopropylamine molecule
IUPAC名
Propan-2-amine
2-丙胺
别名
  • 2-氨基丙烷
  • 异丙基胺
  • 一异丙胺
  • IPA
  • MIPA
识别
CAS号 75-31-0  checkY
PubChem 6363
ChemSpider 6123
SMILES
 
  • CC(C)N
Beilstein 605259
3DMet B01040
UN编号 1221
EINECS 200-860-9
ChEBI 15739
RTECS NT8400000
KEGG C06748
MeSH 2-propylamine
性质
化学式 C3H9N
摩尔质量 59.11 g·mol−1
外观 无色液体
气味 氨味
密度 0.694 g·cm−3(15 °C)
熔点 -101 °C(172 K)
沸点 32 °C(305 K)
溶解性 混溶
log P 0.391
蒸气压 63.41 kPa(20 °C)
折光度n
D
1.3742
热力学
ΔfHm298K −113.0–−111.6 kJ mol−1
ΔcHm −2.3540–−2.3550 MJ mol−1
S298K 218.32 J K−1 mol−1
热容 163.85 J K−1 mol−1
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”)中易燃物的标签图案 《全球化学品统一分类和标签制度》(简称“GHS”)中有害物质的标签图案
GHS提示词 危险
H-术语 H224, H315, H319, H335
P-术语 P210, P261, P305+351+338
爆炸极限 2–10.4%
PEL TWA 5 ppm (12 mg/m3)[1]
致死量或浓度:
LD50中位剂量
  • 380 mg kg−1 (兔,皮)
  • 550 mg kg−1 (大鼠,口)
LC50中位浓度
4,000 ppm (大鼠, 4 h)[2]
LCLo最低
7000 ppm (小鼠, 40 min)[2]
相关物质
相关化学品 正丙胺
异丙醇
2-硝基丙烷
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

异丙胺(简写IPA、MIPA)是一种有机化合物,化学式为C3H9N,它是具有氨味的无色吸湿性液体,可燃。它是重要的化工中间体。[3]

合成

异丙胺可由异丙醇氨气在氢气的存在下,以氧化铝负载的氧化铜氧化镍催化剂催化,在180~220 °C、30~60 bar下反应得到:[4]

2-硝基丙烷的还原反应也可制得异丙胺。[5]

性质

异丙胺可以和发生缩合反应,如和苯甲醛反应,生成N-亚苄基异丙胺;[6]它也能和酰氯反应,如和联苯-4,4'-二甲酰氯在三乙胺的存在下反应,生成N,N '-二异丙基联苯-4,4'-二甲酰胺。[7]

它是一种碱,可以和酸反应:[8][9]

C3H9N + HNO3 → [C3H9NH]NO3
C3H9N + HCOOH → [C3H9NH]HCOO

参考文献

  1. ^ NIOSH Pocket Guide to Chemical Hazards. #0360. NIOSH. . 2019-10-30. [2021-09-09]
  2. ^ 2.0 2.1 Isopropylamine. Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health. 4 December 2014 [14 April 2015]. (原始内容存档于2021-09-09) (英语). 
  3. ^ Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut, Amines, Aliphatic, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2000-06-15, doi:10.1002/14356007.a02_001 (英语) 
  4. ^ Asprion, Norbert; Bey, Oliver; Huyghe, Kevin; Julius, Manfred; Kummer, Matthias; Melder, Johann-Peter; Moors, Maarten; Mägerlein, Wolfgang; Stein, Frank; Werland, Stefanie. Method for Producing Ethylamines and Monoisopropylamine (MIPA). EP2782898B1. [2021-09-09]. (原始内容存档于2021-09-09) (德语). 
  5. ^ Zhou, Junjie; Li, Yunong; Sun, Hong-bin; Tang, Zhike; Qi, Li; Liu, Lei; Ai, Yongjian; Li, Shuang; Shao, Zixing; Liang, Qionglin. Porous silica-encapsulated and magnetically recoverable Rh NPs: a highly efficient, stable and green catalyst for catalytic transfer hydrogenation with “slow-release” of stoichiometric hydrazine in water. Green Chemistry (Royal Society of Chemistry (RSC)). 2017, 19 (14): 3400–3407. ISSN 1463-9262. doi:10.1039/c7gc00986k (英语). 
  6. ^ Talotta, Carmen; Concilio, Gerardo; De Rosa, Margherita; Soriente, Annunziata; Gaeta, Carmine; Rescifina, Antonio; Ballester, Pablo; Neri, Placido. Expanding Coefficient: A Parameter To Assess the Stability of Induced-Fit Complexes. Organic Letters (American Chemical Society (ACS)). 2021-02-16, 23 (5): 1804–1808. ISSN 1523-7060. doi:10.1021/acs.orglett.1c00165 (英语). 
  7. ^ Maiti, Avijit; Chandra, Shubhadeep; Sarkar, Biprajit; Jana, Anukul. Acyclic diaminocarbene-based Thiele, Chichibabin, and Müller hydrocarbons. Chemical Science (Royal Society of Chemistry (RSC)). 2020, 11 (43): 11827–11833. ISSN 2041-6520. doi:10.1039/d0sc03622f (英语). 
  8. ^ Reynolds, John L.; Erdner, Kimberly R.; Jones, Paul B. Photoreduction of Benzophenones by Amines in Room-Temperature Ionic Liquids. Organic Letters (American Chemical Society (ACS)). 2002, 4 (6): 917–919. ISSN 1523-7060. doi:10.1021/ol017290o (英语). 
  9. ^ Collins, Matthew P.; Zhou, Ling; Camp, Suzanne E.; Danielson, Neil D. Isopropylammonium Formate as a Mobile Phase Modifier for Liquid Chromatography. Journal of Chromatographic Science (Oxford University Press (OUP)). 2012-06-19, 50 (10): 869–876. ISSN 1945-239X. doi:10.1093/chromsci/bms084 (英语). 

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