2-Methylglutaronitrile

It is the starting compound for the vitamin nicotinamide and for the diester dimethyl-2-methylglutarate and the ester amide methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate, which are promoted as green solvents.

Starting from 1,3-butadiene or a butadiene-rich C4-section (> 40% by volume) from a naphtha steamcracker in the first stage a mixture of pentenenitriles is obtained through hydrocyanation (using as catalyst Ni0-phosphine [PR3][2] or phosphite or phosphonite [P(OR)2R][3]).

[17] Starting from 2-methylglutaronitrile the hydrolysis to 2-methylglutaric acid can also be accomplished via the 2-methylglutarimide obtained by heating a 2-methylglutaronitrile/water mixture to 275 °C in the presence of a titanium dioxide catalyst in yields of 94%.

[21] The diester can be selectively converted into a mixture of 1- or 5-substituted methyl ester amides with dimethylamine in methanol/sodium methoxide,[22] which is used under the name Rhodiasolv Polarclean as formulation auxiliaries for crop protection preparations.

[6] The resulting ester amides are readily biodegradable and good solvents for a variety of different plant protection agents (such as insecticides or fungicides), also compared to the frequently used N-methylpyrrolidone, cyclohexanone or isophorone.

Other esteramides are derived, e. g. from 2-methylglutaronitrile which, after alkaline hydrolysis, is converted into 2-methylglutaric acid, cyclized with acetic anhydride to give 2-methylglutaric anhydride, reacted with dimethylamine to form the monoamide, reacted to an acid chloride with thionyl chloride and formed to an ester with more hydrophobic alcohols (like butanols or cyclohexanol).

1,3-Butsdien zu Pentennitrilen
1,3-Butsdien zu Pentennitrilen
Umsetzung von Pentennitrilen zu Dinitrilen
Umsetzung von Pentennitrilen zu Dinitrilen
3-Methylpyridin aus 2-MGN
3-Methylpyridin aus 2-MGN
Nicotinsäureamid aus 3-Methylpyridin
Nicotinsäureamid aus 3-Methylpyridin
2-Methylpentan-1,5-diamin aus 2-Methylglutaronitril
2-Methylpentan-1,5-diamin aus 2-Methylglutaronitril
4-Cyanopentansäure aus 2-Methylglutaronitril
4-Cyanopentansäure aus 2-Methylglutaronitril
Synthese von 1,5-Dimethyl-2-piperidon
Synthese von 1,5-Dimethyl-2-piperidon
2-Methylglutarsäure aus 2-Methylglutraronitril
2-Methylglutarsäure aus 2-Methylglutraronitril
2-MGN-Imid aus 2-Methylglutaronitril
2-MGN-Imid aus 2-Methylglutaronitril
Diester aus 2-MGN-Imid
Diester aus 2-MGN-Imid