Aniline → Disperse orange 3

HRID 846446

Reaction equation

HRID 846446 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(C1C=CC=CC=1S(O)(=O)=O)CCCCCCCCCCC.[N:33]([O-])=O.[Na+].[NH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[CH:43]1[C:38]([NH2:37])=[CH:39][CH:40]=[C:41]([N:33]=[N:8][C:7]2[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH:42]=1

Participants

5

Reactant 4

HCID 6115AnilineHCID 74754-NitroanilineHCID 25457Dodecylbenzenesulphonic acidHCID 23668193Sodium Nitrite

Product 1

HCID 12896Disperse orange 3

Procedure

13.8 grams of p-nitroaniline from Aldrich were added to 70 grams of alpha-methylnaphthylene from Crowley Chemical Company, New York, N.Y. and 49 grams of dodecylbenzene sulfonic acid from Pilot and the mixture was stirred at 45° C. until all ingredients had dissolved. Seven grams of NaNO2 from Pfaltz and Bauer were then added and the mix allowed to stir for twenty minutes and heated to 55° C. at which time 9.3 grams of aniline from Kessler Chemical of Pipersville, Pa. was added. The mixture immediately turned bright orange but was allowed to stir for six hours at about 65° C. The resulting material produced a bright orange dyeing on polyester similar in shade to Disperse Orange 3 purchased from Aldrich Chemical.

Workup

  1. dissolutionhad dissolved
  2. additionwas added
  3. stirringto stir for six hours at about 65° C

Sources & evidence

ORD record
ord-5b26401937b946d1a2fbf5de4328aa93
Source dataset
uspto-grants-1992_08
Patent number
US05136098

Linked notes

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