Origin of Impurities Formed in a Polyurethane Production Chain. Part 2: A Route to the Formation of Colored Impurities

被引：5

作者：

Callison, June ^{[1
]}

Betzler, Franziska ^{[1
]}

de Cuba, Kimberly ^{[2
]}

van der Borden, Willem ^{[2
]}

van der Velde, Klaas ^{[2
]}

Carr, Robert H. ^{[2
]}

Senn, Hans M. ^{[1
]}

Farrugia, Louis J. ^{[1
]}

Winfield, John M. ^{[1
]}

Lennon, David ^{[1
]}

机构：

[1] Univ Glasgow, Sch Chem, Glasgow G12 8QQ, Lanark, Scotland

[2] Huntsman Europe BVBA, B-3078 Everberg, Belgium

来源：

INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH | 2012年 / 51卷 / 34期

关键词：

ISOCYANATES; PHOSGENE; HALOCARBONYL; CHEMISTRY; CATIONS;

D O I：

10.1021/ie300987v

中图分类号：

TQ [化学工业];

学科分类号：

0817 ;

摘要：

The quality of methylene diphenyl diisocyanate (MDI) products, which are valuable feedstocks in the industrial manufacture of polyurethanes, can be compromised by the presence of color, presumed to arise from trace impurities. One undesired branch in the synthesis chain originates with phosgenation of diaryl ureas, formed from reactions between aryl isocyanates and polyamine precursors. Subsequent key steps include, (i) breakdown of the primary compounds, substituted chloroformamidine-N-carbonyl chlorides (CCC), to give aryl isocyanide dichlorides, ArNCCl2, (ii) an apparent equilibrium connecting CCC with aryl carbodiimides, and (iii) the thennolysis of ArNCCl2 in the presence of MDI. Color formation is associated directly with the last process; it involves several events, including HCl elimination from reaction of ArNCCl2 and MDI, formation of carbon-centered radicals, and a contribution from oxidation at the methylene bridge.

引用

页码：11021 / 11030

页数：10

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