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Methylene diphenyl diisocyanate (MDI) is an aromatic diisocyanate. Three isomers are common, varying by the positions of the isocyanate groups around the rings: 2,2′-MDI, 2,4′-MDI, and 4,4′-MDI. The 4,4′ isomer is most widely used, and is also known as 4,4′-diphenylmethane diisocyanate. [3] This isomer is also known as Pure MDI.
The global market for diisocyanates in the year 2000 was 4.4 million tonnes, of which 61.3% was methylene diphenyl diisocyanate (MDI), 34.1% was toluene diisocyanate (TDI), 3.4% was the total for hexamethylene diisocyanate (HDI) and isophorone diisocyanate (IPDI), and 1.2% was the total for various others. [18]
MDA is also used extensively as a precursor to methylene diphenyl diisocyanate (MDI). Here, MDA is treated with phosgene to produce MDI. MDI, in turn, is a precursor to many polyurethane foams. [6] [7] Lower quantities are used as hardeners in epoxy resins and adhesives, as well as in the production of high-performance polymers. [3]
Polymethylene polyphenylene isocyanate (PPI), is a polyurea-based polymer derived from isocyanate monomers that is used in some glues, aerosol foams, plastics, paint and household products. [1] PPI is listed as a "hazardous agent" by the National Institutes of Health because it irritates skin and breathing passages at high concentrations.
More specifically, it is an aliphatic diisocyanate. It is a water white liquid at room temperature and is manufactured in relatively small quantities. It is also known as 4,4'-methylenedi(cyclohexyl isocyanate) or methylene bis(4-cyclohexylisocyanate) [2] and has the formula CH 2 [(C 6 H 10)NCO] 2.
Formaldehyde is also a precursor to polyfunctional alcohols such as pentaerythritol, which is used to make paints and explosives. Other formaldehyde derivatives include methylene diphenyl diisocyanate, an important component in polyurethane paints and foams, and hexamine, which is used in phenol-formaldehyde resins as well as the explosive RDX.
The acidity of the methylene group in diphenylmethane is due to the weakness of the (C 6 H 5) 2 CH–H bond, which has a bond dissociation energy of 82 kcal mol −1 (340 kJ mol −1). [5] This is well below the published bond dissociation energies for comparable C–H bonds in propane , where BDE((CH 3 ) 2 CH–H)=98.6 kcal mol −1 , and ...
Phosgenation of diamines gives di-isocyanates, like toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), hexamethylene diisocyanate (HDI), and isophorone diisocyanate (IPDI). In these conversions, phosgene is used in excess to increase yield and minimize side reactions.