二乙基氨基甲酸 | 24579-70-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 中文名称: 二乙基氨基甲酸
• 英文名称: diethylcarbamic acid
• CAS: 24579-70-2
• 化学式: C₅H₁₁NO₂
• 分子量: 117.148
• InChiKey: APRJFNLVTJWEPP-UHFFFAOYSA-N

物化性质

• 熔点：
  -15°C
• 沸点：
  218.95°C (rough estimate)
• 密度：
  0.9276

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  二乙基氨基甲酸 、 氯化苄 在 2-环己基-1,1,3,3-四甲基胍 作用下， 以 乙腈 为溶剂， 生成 苄基二乙基氨基甲酸酯
  参考文献：
  名称：

  Carbon Dioxide as a Phosgene Replacement: Synthesis and Mechanistic Studies of Urethanes from Amines, CO2, and Alkyl Chlorides

  摘要：

  Several carbamate esters were synthesized from amines, carbon dioxide, and alkyl chlorides. The effect of added base on the yield and selectivity of carbamate ester formation was found to be highly important with the use of sterically hindered guanidine bases giving the best results. Relative rate studies were carried out giving the following order of reactivity between carbamate anions in acetonitrile with benzyl chloride giving carbamate esters: Et(2)NCO(2)(-) = Bu(2)NCO(2)(-) > t-BuNHCO(2)(-) CyNHCO(2)(-) = s-BuNHCO(2)(-) > PhNHCO(2)(-) > CyCH(2)NHCO(2) = n-octylNHCO(2)(-) = n-BuNHCO(2)(-). Rate studies were carried out with the diethyl, s-butyl, phenyl, and n-butyl carbamates and activation parameters were determined to be Et(2)NCO(2)(-), Delta H-double dagger = 11.8 kcal/mol, Delta S-double dagger = -33 eu; s-BuNHCO(2)(-), Delta H-double dagger = 12.8 kcal/mol, Delta S-double dagger = -33 eu; PhNHCO(2)(-), Delta H-double dagger = 14.3 kcal/mol, Delta S-double dagger = -28 eu; n-BuNHCO(2)(-), Delta H-double dagger: = 23.4 kcal/mol, Delta S-double dagger = -3 eu. The unusual results obtained from the use of n-BuNHCO(2)(-) prompted further studies which showed that the rate of reaction was inversely dependent on carbon dioxide pressure (20 psig CO2, k = 4.84 x 10(-4) M(-1) s(-1); 120 psig CO2, k = 1.83 x 10(-4) M(-1) s(-1)). Nitrogen NMR spectroscopy indicated, via a labeling study with N-15 amines and C-13 enriched carbon dioxide, the formation of a doubly inserted product from the addition of two carbon dioxides to ethylamine in acetonitrile.

  DOI：

  10.1021/jo00114a035
• 作为产物：
  描述：

  二乙胺 生成 二乙基氨基甲酸
  参考文献：
  名称：

  TODA, TAKASHI;YOSHIDA, MASAAKI;YAGI, KAZUO, ASAXI GARASU GIDZYUTSU KOGE SEREHJKAJ KEHNKYU XOKOKU, 55,(1989) S. 317-32+

  摘要：

  DOI：

文献信息

• Electrochemical Reduction of Carbamates and Carbamic Acids: Implications for Combined Carbon Capture and Electrochemical CO₂ Recycling
  作者：Moumita Bhattacharya、Sepehr Sebghati、Yvensha Madeika Vercella、Caroline T. Saouma

  DOI：10.1149/1945-7111/ab8ed0

  日期：2020.1.5

  in solar-driven recycling of CO2 to fuels. While many reports focus on catalyst design or modification of additives such as Lewis or Bronsted acids, there is little focus on modification of the substrate, CO2 itself. Current carbon capture technology employs amines to capture CO2 as carbamates, suggesting that they may serve as a CO2 surrogate, streamlining carbon capture and recycling. Towards this

  将 CO2 电催化还原为 CO 可能代表太阳能驱动的 回收到燃料的第一步。虽然许多报告侧重于催化剂设计或添加剂（如路易斯酸或布朗斯台德酸）的改性，但很少关注底物 本身的改性。当前的碳捕获技术采用胺类以氨基甲酸酯的形式捕获 ，这表明它们可以作为 替代物，简化碳捕获和回收。为此，我们在此探索了在存在/不存在 的情况下七种胺的循环伏安法。我们表明，在乙腈 (MeCN) 中的玻碳电极上，与六氟磷酸四丁基铵 (TBAPF6) 电解质中的 Fc/Fc+ 相比，最高 -2.7 V，胺只能在 存在下还原。还原的潜力取决于胺的特性以及所得物质（氨基甲酸酯与氨基甲酸）的质子化状态。大量电解实验表明几乎没有或没有减少 CO 并且甲酸盐的法拉第效率低。这表明这些胺可用于后续的分子电催化剂研究，将 转化为 CO 而不是甲酸盐。
• Phenylureas. Part 1. Mechanism of the basic hydrolysis of phenylureas
  作者：Robert Laudien、Rolf Mitzner

  DOI：10.1039/b008532o

  日期：2001.11.1

  The mechanism of the hydrolytic decomposition of phenylureas in basic media in the pH range 12 to 14 is investigated. In this pH range a levelling of the rate–pH curve is observed as well as a change of the substituent influence on the hydrolysis rate. These experimental findings suggest the formation of an unreactive side product of the phenylurea in a parasitic side equilibrium at sufficiently high pH. The urea dissociates at the aryl–NH group to give its conjugate base. For the hydrolytic decomposition of phenylureas an addition–elimination mechanism is proposed as has been established for the alkaline hydrolysis of carboxylic acid esters and amides.

  在pH范围为12到14的碱性介质中，研究了苯基脲的水解分解机制。在这一pH范围内，观察到反应速率与pH曲线的平坦化以及取代基对水解速率影响的变化。这些实验结果表明，在足够高的pH下，苯基脲形成了一个不反应的副产物，处于一种寄生侧平衡中。尿素在芳基–氨基团处解离，形成其共轭碱。对于苯基脲的水解分解，提出了一种加成–消除机制，正如在酸酯和酰胺的碱性水解中所确立的那样。
• Promoting Selective Generation of Formic Acid from CO₂ Using Mn(bpy)(CO)₃Br as Electrocatalyst and Triethylamine/Isopropanol as Additives
  作者：Monica R. Madsen、Magnus H. Rønne、Marvin Heuschen、Dusanka Golo、Mårten S. G. Ahlquist、Troels Skrydstrup、Steen U. Pedersen、Kim Daasbjerg

  DOI：10.1021/jacs.1c10805

  日期：2021.12.8

  Urgent solutions are needed to efficiently convert the greenhouse gas CO2 into higher-value products. In this work, fac-Mn(bpy)(CO)3Br (bpy = 2,2′-bipyridine) is employed as electrocatalyst in reductive CO2 conversion. It is shown that product selectivity can be shifted from CO toward HCOOH using appropriate additives, i.e., Et3N along with iPrOH. A crucial aspect of the strategy is to outrun the dimer-generating

  需要紧急解决方案来有效地将温室气体 CO 2转化为更高价值的产品。在这项工作中，fac -Mn(bpy)(CO) 3 Br（bpy = 2,2'-联吡啶）用作还原 CO 2转化的电催化剂。结果表明，使用适当的添加剂，即 Et 3 N 和i PrOH ，可以将产物选择性从 CO 转变为 HCOOH 。该策略的一个关键方面是超越涉及fac -Mn(bpy)(CO) 3 Br 和 [Mn(bpy)(CO) 3 ] -的产生二聚体的亲子反应而是生产锰氢化物中间体。优选地，这是在第一次还原波中完成的，以便能够在低至 260 mV 的过电位和 59 ± 1% 的法拉第效率下形成 HCOOH。后者可以在 560 mV 的过电位下增加到 71 ± 3%，使用 2 M 浓度的 Et 3 N 和i PrOH。胺添加剂的性质对产品选择性至关重要，因为如果 Et 3 N 被 Et 2 NH取代，HCOOH 形成的法拉第效率会降低至
• Lund; Faurholt, Dansk Tidsskrift for Farmaci, 1948, vol. 22, p. 111
  作者：Lund、Faurholt

  DOI：——

  日期：——
• CTAMATOB, STEFAN DIMITROV;IVANOV, STEFAN ARXANGELOV
  作者：CTAMATOB, STEFAN DIMITROV、IVANOV, STEFAN ARXANGELOV

  DOI：——

  日期：——