Azobisisobutyronitrile → HCID 57254888, compound

HRID 1975226Notes

Reaction equation

HRID 1975226 reaction equation
[CH2:1]([SH:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].N([C:25]([CH3:29])([CH3:28])C#N)=NC(C)(C)C#N.[CH2:30]([O:33][CH2:34][C:35]([CH2:46][O:47][CH2:48][CH:49]=[CH2:50])([CH2:41][O:42][CH2:43][CH:44]=[CH2:45])[CH2:36][O:37][CH2:38][CH:39]=[CH2:40])[CH:31]=[CH2:32]>>[CH2:1]([S:17][CH2:50][CH2:49][CH2:48][O:47][CH2:46][C:35]([CH2:36][O:37][CH2:38][CH2:39][CH2:40][S:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:29][CH2:25][CH3:28])([CH2:41][O:42][CH2:43][CH2:44][CH2:45][S:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:34][O:33][CH2:30][CH2:31][CH2:32][S:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 3

HCID 6547Azobisisobutyronitrile3×HCID 18015Hexadecanethiol2×HCID 738553,3'-((2,2-Bis((allyloxy)methyl)-1,3-propanediyl)bis(oxy))dipropene

Product 1

HCID 57254888HCID 57254888, compound

Conditions

Temperature
80 °C

Procedure

A 250 ml three-necked flask equipped with a magnetic stirrer, a condenser and a nitrogen inlet tube was first purged with nitrogen 107 grams of n-hexadecyl mercaptan (0.417 mole) was then charged and heated to 80° C. To the heated and stirred n-hexadecyl mercaptan, a solution of 0.2 gram of 2,2'-azobis(isobutyronitrile) in 29.64 grams (0.1 mole) of pure pentaerythritol tetraallyl ether was added dropwise over a 15-minute period. One-half hour after this addition was completed, 0.1 gram of 2,2'-azobis(isobutyronitrile) was added. Two more 0.1 gram additions of 2,2'-azobis-(isobutyronitrile) were made at half-hour intervals. After the last addition, the reaction was held at 80° C. for an additional hour. The crude product was recrystallized three times in 300 ml. of hexane yielding 57 grams of a white solid having a melting point of 55°-57° C. The elemental analysis found: C - 73.4%, H - 11.9%, S(total) - 10.0%, and S(mercapto) - 3 ppm. Calculated for C98H164S2 ; C - 73.12%, H-12.43%, S(total) - 9.64% and S(mercapto) - 4 ppm.

Workup

  1. customA 250 ml three-necked flask equipped with a magnetic stirrer, a condenser and a nitrogen inlet tube
  2. additionwas then charged
  3. temperatureTo the heated
  4. additionOne-half hour after this addition
  5. additionAfter the last addition
  6. waitthe reaction was held at 80° C. for an additional hour
  7. customThe crude product was recrystallized three times in 300 ml

Sources & evidence

ORD record
ord-e02f9d242db54acb9ec70d4a4ec2bc17
Source dataset
uspto-grants-1994_02
Patent number
US05284886

Reaction notes

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