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Pyrocatechol borates: Synthesis, reaction with formaldehyde, and solvent effect on polycondensation process
Polymer ( IF 4.6 ) Pub Date : 2020-01-07 , DOI: 10.1016/j.polymer.2020.122162
Maxim A. Lenskiy , Elvira E. Shul'ts , Dmitriy V. Korabel'nikov , Andrey V. Ozhogin , Alexey N. Novitskiy

Pyrocatechol (I) and dipyrocatechol (II) borates were synthesized by esterification between pyrocatechol (1,2-dihydroxybenzene) and boric acid in о-xylene with azeotropic distillation of water. The co-esterification between pyrocatechol and boric acid with added equimolar quantities of phenol or 2,6-di-tert-butylphenol was studied, and pyrocatechol phenyl (III) and pyrocatechol-(2,6-di-tert-butyl)phenyl (IV) borates were prepared. The reaction of the resultant esters with formaldehyde in the presence of boron trifluoride etherate as a catalyst was examined. The coupling of the methylene moiety in several position of molecule III was found to be dependent on the solvent used. The electrophilic substitution on the phenol substituent took place in о-xylene, while the reaction in either benzene or molten monomer proceeded to substitute the methylene moiety for the proton on the catechol moiety. The molecular weights of the compounds were measured. Some properties of the synthesized oligomers were determined and thermal and thermooxidative destruction was examined.



中文翻译:

邻苯二酚硼酸酯:合成,与甲醛反应以及溶剂对缩聚反应的影响

邻苯二酚()和dipyrocatechol(II)硼酸盐是由邻苯二酚(1,2-二羟基苯)和硼酸之间的酯化中合成о二甲苯与水的共沸蒸馏。研究了邻苯二酚与硼酸在等摩尔量的苯酚或2,6-二叔丁基苯酚之间的共酯化反应,以及邻苯二酚(III)和邻苯二酚-(2,6-二叔丁基)苯基(IV)制备硼酸盐。在三氟化硼醚化物作为催化剂的存在下,检查了所得酯与甲醛的反应。亚甲基部分在分子III几个位置的偶联被发现取决于所使用的溶剂。在酚取代基的亲电取代发生在о二甲苯,而在任一苯或熔融单体反应进行替代的亚甲基部分供于邻苯二酚部分的质子。测量化合物的分子量。测定了合成低聚物的一些性质,并研究了热和热氧化破坏。

更新日期:2020-01-07
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