Ethylene → Ethylene/methyl acrylate monoethyl maleate

HRID 28069

Reaction equation

HRID 28069 reaction equation
[C:1](OC)(=O)[CH:2]=C.[C:7]([O:14][CH2:15][CH3:16])(=[O:13])/[CH:8]=[CH:9]\[C:10]([O-:12])=[O:11].C=C.C(OOC(C)(C)C)(=O)C(C)(C)C>C1C=CC=CC=1>[CH2:1]=[CH2:2].[C:7]([O:14][CH3:15])(=[O:13])[CH:8]=[CH2:9].[C:7]([O:14][CH2:15][CH3:16])(=[O:13])/[CH:8]=[CH:9]\[C:10]([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 6325Ethylene2×HCID 7294Methyl AcrylateHCID 61238tert-BUTYL PEROXYPIVALATEHCID 86733784(Z)-4-ethoxy-4-oxobut-2-enoate

Product 1

HCID 86733783Ethylene/methyl acrylate monoethyl maleate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of methyl acrylate, monoethyl maleate, and benzene (weight ratio: 68.28/2.46/29.26) was pressured to about 422 kg./sq. cm.; ethylene was separately pressured to about 422 kg./sq. cm. Separate streams of this mixture (0.91 kg./hr.) and ethylene (6.35 kg./hr.) were joined and pressured to 1900 kg./sq. cm. The resulting feed stream then entered the autoclave. Simultaneously, a catalyst solution, made by adding 50 ml. of tert-butyl peroxypivalate to 4.5 kg. of benzene was introduced at the rate of 0.00204 kg./hr. to keep the temperature at 170° C. The effluent from the autoclave passed through a let-down valve to a chamber at atmospheric pressure where most of the residual monomers and solvent flashed off. The ethylene/methyl acrylate/monoethyl maleate terpolymer thus isolated was freed from the small amount of residual volatiles by heating for 16 hours at 80° C. in a nitrogen stream. Acid-base titration indicated that 0.25 meq. of acid groups was present per gram of terpolymer. This corresponds to 3.6 weight percent of monoethyl ester of maleic acid.

Workup

  1. additionby adding 50 ml
  2. customat 170° C
  3. customThe effluent from the autoclave passed through a let-down valve to a chamber at atmospheric pressure where most of the residual monomers and solvent

Sources & evidence

ORD record
ord-3c30bea125f6436ead167a3c70ae52bc
Source dataset
uspto-grants-1980_09
Patent number
US04225476

Linked notes

Loading…