Methacrylic Acid → Methylenebisacrylamide

HRID 653232Notes

Reaction equation

HRID 653232 reaction equation
[C:1]([OH:5])(=O)[CH:2]=[CH2:3].[C:6]([OH:11])(=O)[C:7](C)=[CH2:8].CN(CC[CH2:17][NH2:18])C.C[N:20](NCC(C)(C)C)C.NC1C=CC=CC=1.C1C=CC2C=C(N)C=CC=2C=1.C(N)C1C=CC=CC=1>>[CH2:8]=[CH:7][C:6]([NH:20][CH2:17][NH:18][C:1]([CH:2]=[CH2:3])=[O:5])=[O:11]

Participants

8

Reactant 7

HCID 4093Methacrylic AcidHCID 6115AnilineHCID 6581Acrylic AcidHCID 70572-NaphthylamineHCID 7504BenzylamineHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 21831704Dimethylaminoneopentyl amine

Product 1

HCID 8041Methylenebisacrylamide

Procedure

The methods according to the present invention starting the methyl, ethyl, or butyl esters of acrylic acid or of methacrylic acid (R2 =methyl, ethyl, butyl) are particularly preferred, since they can be carried out on a technical scale and the alcohols which are cleaved in both reactions (R2OH of IV) can be easily removed from the reaction mixture. The embodiment employing primary amines should be particularly mentioned, i.e. wherein R3 represents hydrogen. Further, R4 preferably stands for a substituent which imparts to the amine a boiling point of 80° C. or more. Further, reaction with an aminoalkyl amine, particularly with dialkylaminoalkyl amines such as dimethylaminopropyl amine, or with dimethylaminoneopentyl amine inter alia is of interest, as is reaction with an aralkyl amine, and an aromatic amine such as aniline, naphthylamine, and benzylamine, as well as reaction with an alkylene diamine to form a bis-acrylamide or bis-methacrylamide.

Workup

  1. customcan be easily removed from the reaction mixture
  2. customFurther, reaction with an aminoalkyl amine

Sources & evidence

ORD record
ord-b344cff7f29145d9a8447841f7f2ceb1
Source dataset
uspto-grants-1987_06
Patent number
US04675442

Reaction notes

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