乙基丁二腈 | 17611-82-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 乙基丁二腈
• 英文名称: ethylsuccinonitrile
• 英文别名: alpha-ethylsuccinonitrile；2-Ethylsuccinonitrile；2-ethylbutanedinitrile
• CAS: 17611-82-4
• 化学式: C₆H₈N₂
• 分子量: 108.143
• InChiKey: GDCJAPJJFZWILF-UHFFFAOYSA-N

物化性质

• 熔点：
  -40.9°C
• 沸点：
  192.78°C (rough estimate)
• 密度：
  0.9581 (rough estimate)
• 溶解度：
  0.20 M
• 蒸汽压力：
  0.02 mmHg

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  乙基丁二腈 在 镍 ammonium hydroxide 、 氢气 作用下， 以 水 为溶剂， 27.0~160.0 ℃ 、3.45 MPa 条件下， 反应 185.0h， 生成 4-乙基-2-吡咯烷酮
  参考文献：
  名称：

  Chemoenzymic Production of Lactams from Aliphatic α,ω-Dinitriles

  摘要：

  Five- and six-membered ring lactams have been prepared by first converting an aliphatic alpha,omega-dinitrile to an omega-cyanocarboxylic acid ammonium salt, using a microbial cell catalyst having an aliphatic nitrilase activity (Acidovorax: facilis 72W, ATCC 55746) or a combination of nitrile hydratase and amidase activities (Comamonas testosteroni 5-MGAM-4D, ATCC 55744). The omega-cyanocarboxylic acid ammonium salt was then directly converted to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate omega-cyanocarboxylic acid or omega-aminocarboxylic acid. Only one of two possible lactam products was produced from alpha-alkyl-substituted alpha,omega-dinitriles, where the nitrilase of A. facilis 72W regioselectively hydrolyzed only the omega-cyano group to produce a single cyanocarboxylic acid ammonium salt in greater than 98% yield.

  DOI：

  10.1021/jo9804386
• 作为产物：
  描述：

  氢氰酸 、 顺-2-戊烯腈 在 alumina 作用下， 100.0 ℃ 、101.32 kPa 条件下， 反应 4.0h， 以89%的产率得到乙基丁二腈
  参考文献：
  名称：

  [EN] HETEROGENEOUS HYDROCYANATION
  [FR] HYDROCYANATION HÉTÉROGÈNE

  摘要：

  公开号：

  WO2015095594A8

文献信息

• Process for preparing diacid compounds
  申请人：RHODIA OPERATIONS

  公开号：US20150175515A1

  公开（公告）日：2015-06-25

  The present invention relates to a process for preparing at least one diacid compound, comprising a step of hydrolysis reaction of at least one imide compound, performed in the absence of catalyst.

  本发明涉及一种制备至少一种二酸化合物的方法，包括在无催化剂的情况下进行至少一种亚胺化合物的水解反应的步骤。
• Method of producing nitrile compounds from ethylenically-unsaturated compounds
  申请人：Bourgeois Damien

  公开号：US20060142609A1

  公开（公告）日：2006-06-29

  The present invention relates to a process for hydrocyanating a hydrocarbon-based compound containing at least one ethylenic unsaturation by reaction in liquid medium with hydrogen cyanide in the presence of a catalyst comprising a metal element chosen from transition metals and an organophosphorus ligand, characterized in that the organophosphorus ligand is a monodentate organophosphorus compound. The present invention is in particular useful for the synthesis of adiponitrile from butadiene.

  本发明涉及一种通过在液体介质中与氢氰酸在过渡金属和有机膦配体选择的金属元素的存在下反应，对含有至少一种乙烯不饱和度的碳氢化合物进行氢氰化的过程，其特征在于有机膦配体是一种单齿有机膦化合物。本发明特别适用于从丁二烯合成己二腈。
• PRODUCTION OF COMPOUNDS COMPRISING NITRILE FUNCTIONAL GROUPS
  申请人：Mastroianni Sergio

  公开号：US20110021804A1

  公开（公告）日：2011-01-27

  The present invention relates to a process for producing compounds comprising at least one nitrile function by hydrocyanation of a compound comprising at least one non-conjugated unsaturation. The invention proposes a process for producing compounds comprising at least one nitrile function by hydrocyanation of an organic compound comprising at least one non-conjugated unsaturation, comprising from 2 to 20 carbon atoms, by reaction with hydrogen cyanide in the presence of a catalytic system comprising a complex of nickel having the oxidation state of zero with at least one organophosphorus ligand chosen from the group comprising organophosphites, organophosphonites, organophosphinites and organosphosphines and a cocatalyst of the Lewis acid type of formula in which M1 and M2 represent elements chosen from the group comprising zinc, boron, aluminium, cadmium, gallium, indium and tin.

  该发明涉及通过对至少含有一个非共轭不饱和度的化合物进行氢氰化来生产包含至少一个腈基的化合物的方法。 该发明提出了一种通过对至少含有一个非共轭不饱和度的有机化合物与氢氰酸在存在一种催化体系的条件下反应来生产包含至少一个腈基的化合物的方法，所述有机化合物含有2至20个碳原子，所述催化体系包括氧化态为零的镍配合物和至少一种有机膦配体，所述有机膦配体选自包括有机膦酯、有机膦酸酯、有机膦酮和有机膦烷的群组，并且包括一种Lewis酸类型的辅助催化剂，其化学式为 其中M1和M2代表从锌、硼、铝、镉、镓、铟和锡的群组中选择的元素。
• PREPARATION OF NITRILES FROM ETHYLENICALLY UNSATURATED COMPOUNDS
  申请人：Mastroianni Sergio

  公开号：US20110118499A1

  公开（公告）日：2011-05-19

  A process for the hydrocyanation of a hydrocarbon-based compound having at least one site of ethylenic unsaturation into a nitrile compound includes reaction thereof, in a liquid medium, with hydrogen cyanide in the presence of a catalyst containing a metal element selected from among the transition metals and an organophosphorus ligand, wherein the organophosphorus ligand is a compound of formula (I): The subject process is particularly useful for the synthesis of adiponitrile from butadiene.

  将至少具有一个乙烯不饱和位点的碳氢化合物进行氢氰化的过程包括在液体介质中，在过渡金属和有机磷配体中选择的金属元素存在的催化剂存在下，将其与氢氰酸反应，其中有机磷配体是符合以下化学式(I)的化合物： 该过程特别适用于从丁二烯合成己二腈。
• Cage Phosphinites: Ligands for Efficient Nickel-Catalyzed Hydrocyanation of 3-Pentenenitrile
  作者：Igor S. Mikhel、Michael Garland、Jonathan Hopewell、Sergio Mastroianni、Claire L. McMullin、A. Guy Orpen、Paul G. Pringle

  DOI：10.1021/om101023e

  日期：2011.3.14

  alcohol or phenol. The cage phosphinites are remarkably stable to water. All the ligands La−h have been tested for nickel(0)-catalyzed hydrocyanation of 3-pentenenitrile in the presence of Lewis acids (ZnCl2, Ph2BOBPh2, or iBu2AlOAliBu2), and tentative structure−activity relationships are suggested. The hydrocyanation activities obtained with catalysts derived from monophosphinite Lf (with iBu2AlOAliBu2)

  笼状单亚膦酸酯CgPOR（其中CgP = 6-磷酸-2,4,8-三氧杂-金刚烷，R = C 6 H 5（L a）；2-C 6 H 4 CH 3（L b）；2,4,6-C 6 H 2（CH 3）3（L c）；2,4-C 6 H 3 t Bu 2（L d）; CH 3（L e）；通道2 CF 3（L f}}和二亚膦酸酯CgPZPCg 其中ZH 2 = 2,2'-双酚（L g）或1,2-苯二甲醇（L h）}由CgPBr和相应的醇或苯酚制得。笼型次膦酸盐对水非常稳定。所有配体大号A-H已经过测试，镍（0）在路易斯酸存在下3-戊烯腈的催化的氢氰化（的ZnCl 2中，Ph 2 BOBPh 2，或我卜2 AlOAl我卜2），并建议尝试性的构效关系。用衍生自单亚膦酸酯L f（具有i Bu 2 AlOAl i Bu 2）和二亚膦酸酯L h（具有ZnCl 2）的催化剂获得的氢氰化活性与基于P（OTol）3的市售催化剂相当。反式-