Aniline reaction with maleic anhydride

Amidation. Reaction of maleic anhydride or its isomeric acids with ammonia [7664-41-7] (qv), primary amines (qv), and secondary amines produces mono- or diamides. The monoamide derivative from the reaction of ammonia and maleic anhydride is called maleamic acid [557-24-4] (8). Another monoamide derivative formed from the reaction of aniline [62-53-3] and maleic anhydride is maleanilic acid [555-59-9] (9). 

Allylmagnesium bromide, 41, 49 reaction with acrolein, 41, 49 5-Allyl-l,2,3,4,5-pentachlorocyclopen-tadiene, 43, 92 Allyltriphenyltin, 41, 31 reaction with phenyllithium, 41, 30 Aluminum chloride, as catalyst, for isomerization, 42, 9 for nuclear bromination and chlorination of aromatic aldehydes and ketones, 40, 9 as Friedel-Crafts catalyst, 41, 1 Amidation, of aniline with maleic anhydride, 41, 93... 

Aniline, 4,4 -azodi-, 40,18 Aniline, reaction with hexachlotoace-tone to form a, ,a-trichloro-acetanilide, 40, 103 reaction with maleic anhydride, 41,94 Anisoin, reduction to deoxyanisoin by tin and hydrochloric add, 40, 16... 

There are a few alternative approaches to imide copolymers that allow the resin producer to make imide-modified high heat ABS without incurring the cost of the synthesized imide monomer. One is by reacting styrene-maleic anhydrides with a primary amine, either during the polymerization reaction with styrene or in a separate step. Mitsubishi Monsanto has practiced imidiza-tion on a commercial scale and described a process which follows the formation of S-MA with addition of amine and AN [60]. They described the manufacture of maleimide copolymers by heating the SMA copolymers with aniline in an extruder [61]. The maleimidation of the anhydride function is not complete, as there is unreacted amine or maleic anhydride in the product. The polymer stability and physical properties depend on the mole percent of maleimidation. 

ANILINE, A -PHENYL (122-39-4) Comhustible solid. Dust forms explosive mixture with air. Violent reaction when added to hexachloromelamine, trichloromelamine. Often shipped in liquid form (flash point, liquid 307°F/153°C oc). An organic base. Incompatible with strong acids (forms salts), aldehydes, organic anhydrides, isocyanates, oxidizers. Reacts with nitrogen oxides to form Al-nitrosodiphenylamine and mono- and poly-nitro products. Incompatible with organic anhydrides, acrylates, alcohols, aldehydes, alkylene oxides, substituted allyls, cellulose nitrate, cresols, caprolactam solution, epichlorohydrin, ethylene dichloride, isocyanates, ketones, glycols, nitrates, phenols, vinyl acetate. Exothermic decomposition with maleic anhydride. Increases the explosive sensitivity of nitromethane. Attacks light metals in the presence of moisture. 

Using a Fhsteur pipet, add the aniline-acetonitrUe solution in one portion to the stirred maleic anhydride-acetonitrile solution. Rinse the -dram vial with 100 p,L of anhydrous acetonitrile and also transfer this rinse to the reaction solution. 

An ethereal soln. of aniline added to a stirred ethereal soln. of maleic anhydride, stirring continued 1 hr. maleanilic acid (Y 97-98%) added to a mixture of acetic anhydride and anhydrous Na-acetate, heated with swirling on a steam bath until almost dissolved after 30 min. N-phenylmaleimide (Y 75-80%).— The product is an active dienophile in the Diels-Alder reaction and usually gives crystalline adducts. M. P. Gava et al., Org. Synth. Al, 93 (1961). 

Recently, the bulk polymerization of N-phenylmaleimide, which was prepared from maleic anhydride and aniline prior to the reaction, under microwave irradiation was presented.The final yield of the polymer was 57%, while the bulk homopolymerization under conventional conditions (an oil bath preheated to 95 °C) afforded the polymer with a relatively low yield of about 19%. 

Monomer IXb was prepared starting from racemic 4-aminophenyl-p-tolylsulfoxide which was resolved in its enantiomers using J-camphorsulfonic acid, and reacted with maleic anhydride it polymerizes with aniline and is resolved into its enantiomers using J-camphor-sulfonic acid. The monomer obtained by reaction with maleic anhydride polymerized in good yield but with a weak degree of polymerization with radical initiators (Mn between 1800 and 3200). 

---