Azobisisobutyronitrile → HCID 86735441, compound

HRID 616004Notes

Reaction equation

HRID 616004 reaction equation
[CH2:1]=[CH:2][CH:3]=[CH:4][CH3:5].[C:6]1(=[O:12])[O:11][C:9](=[O:10])[CH:8]=[CH:7]1.N(C(C)(C)C#N)=NC(C)(C)C#N.C1(=O)CCCCC1>C1(C)C=CC=CC=1>[CH2:1]=[CH:2][CH:3]=[CH:4][CH3:5].[C:9]1(=[O:10])[O:11][C:6](=[O:12])[CH:7]=[CH:8]1

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 7923Maleic AnhydrideHCID 7967CyclohexanoneHCID 15301Penta-1,3-diene

Product 1

HCID 86735441HCID 86735441, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

of piperylene, 98g. of maleic anhydride, 1.6g. of azobisisobutyronitrile and 500 ml of cyclohexanone were fed in a 1 liter autoclave and a polymerization conducted for 2 hours at 80° C. under a nitrogen atmosphere. The resulting viscous polymerized solution was introduced in 5 liter of toluene to allow the copolymer to be deposited. The precipitates were collected by means of filtration, washed with toluene several times and dried under reduced pressure. As a result, there was obtained a purified piperylene-maleic anhydride copolymer in 35% (59g.) yield, which had an intrinsic viscosity of 0.42 determined in dimethylformamide at 30° C. 20g. of the copolymer, 13.5g. of potassium hydroxide and 400 ml. of water were fed in a separable 1 liter flask equipped with a cooler and a stirrer, and stirring was then applied for 1 hour at 100° C. under a nitrogen gas stream, to give a homogeneous aqueous solution with a pH of 12. A half amount of the aqueous solution was withdrawn into an Erlenmeyer flask and the pH thereof was brought down to 7.5 using an aqueous sulfuric acid solution. To the other aqueous solution without pH adjustment was added, little by little with continued stirring, a separately prepared aqueous solution consisting of 11g. of magnesium chloride hexahydrate and 200 ml. of water. To the pH adjusted one was added at a time 11g. of a solid magnesium choride hexahydrate and stirring was applied for 1 hour. After these operations, both aqueous solutions became whitely turbid and therefore they were left standing for 2 hours at room temperature. As a result, both were each separated into two liquid layers. Removal of the respective upper layers left viscous aqueous solutions of the respective lower layers, which on heating were converted into rubber-like solids and on cooling reverted to their original states of aqueous solutions.

Workup

  1. filtrationThe precipitates were collected by means of filtration
  2. washwashed with toluene several times
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-0347c6810d9742e583632e75a1d9631c
Source dataset
uspto-grants-1978_02
Patent number
US04072646

Reaction notes

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