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TDI与甲基丙烯酸或者其他脂肪族羧基反应吗?
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原本一直以为TDI与脂肪族羧基反应要快过与仲醇，但是小木虫上也有帖子说不反应。不知道到底可以反应吗?活性比与仲醇反应高吗？ 反应条件是110度，0.02% Dibutyltin dilaurate，用甲基丙烯酸甲酯作溶剂。 |
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11楼2017-11-08 19:02:56
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请问有相关文献说为什么两者不反应吗`? 我觉得理论上应该是反应的。 我查到了一篇文献，TDI和甲基丙烯酸反应的，条件还挺温和的。Int. J. Mol. Sci. 2015, 16, 3656-3676; doi:10.3390/ijms16023656 但我没有查到其他相关文献，加上这个杂志也不咋地所以觉得可能可信性不高。 The molar concentration was chosen in this case, using a stoichiometry ratio of 0.5 M MAA: 1 M TDI: 0.5 M β-CD. An amount of 2.855 mL of TDI with 0.848 mL of MAA was mixed in 20 mL of DMAC solvent. Then, 0.1% (0.02 mL) of DBTDL catalyst was added. The solution was magnetically stirred at room temperature under nitrogen gas for an hour. It showed that the reaction between MAA and TDI was stoichiometric. It can be seen in step 1, that the intermediate I' containing an anhydride and carbamate group was formed at the consumption of carboxyl group in MAA. Intermediate I’ is unstable [48], and it converts to methacrylic amide containing an isocyanate group. Intermediate I contains methacrylic amide and –NCO, indicating that only one of the two –NCO groups in TDI took part in the reaction. |
22楼2017-11-16 21:57:56
23楼2017-11-19 13:11:12
24楼2017-11-20 16:41:14
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我自己花了点时间找到了一篇文献，结论是可以反应的。反应的生成物取决于酸。见下面英文。 RECENT ADVANCES IN ISOCYANATE CHEMISTRY, Chem. Rev., 1957, 57 (1), pp 47–76 DOI: 10.1021/cr50013a002 Page 52 Weak aromatic and aliphatic carboxylic acids readily form mixed anhydrides with isocyanates (reaction 1), whereas stronger acids such as cyanoacetic, trichloroacetic, and formic acid form mixed anhydrides which spontaneously decompose into amides and carbon dioxide (reaction 2). The more stable mixed anhydrides decompose at elevated temperatures into disubstituted ureas, carboxylic acid anhydrides, and carbon dioxide (reaction 3) (161, 162, 171, 184). ArNCO + RCOOH ----> ArNHCO-O-COR (1) |------------------> ARNHCOR + CO2 (2) | ------------------> (ArNCCO-O-CONHAr) + RCO-O-COR |--------------------> ARNHCONHAr + CO2 (3) |
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