Methane → Benzenediazonium, nitrate (1:1)

HRID 861183

Reaction equation

HRID 861183 reaction equation
C.C1C(Br)=C(Br)[NH:4]C=1C(O)=O.N([O-])=O.[Na+].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[N+:23]([O-:26])([OH:25])=[O:24]>C(O)(C)C.O>[N+:23]([O-:26])([O-:25])=[O:24].[C:17]1([N+:16]#[N:4])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 5

HCID 297Methane2×HCID 944Nitric AcidHCID 6115AnilineHCID 1618304,5-Dibromo-2-Pyrrolic AcidHCID 23668193Sodium Nitrite

Product 1

HCID 61161Benzenediazonium, nitrate (1:1)

Reagents, catalysts & solvents 2

HCID 3776IsopropanolCatalystHCID 962WaterSolvent3×

Procedure

A carbon black with a CTAB surface area of 350 m2 /g and a DBPA of 120 ml/100 g was used. A suspension of 50 g of this carbon black was prepared by stirring it into 450 g of water that contained a few drops of isopropanol. A solution of 5.12 g of NaNO2 in 10 g of cold water was slowly added to a solution of 5.62 g of aniline and 11.88 g of concentrated nitric acid in 10 g of water that was cooled in an ice bath. Benzenediazonium nitrate was formed. After 15 minutes of stirring, the mixture was added to the stirring carbon black suspension. Bubbles were released. When the bubbling had stopped, the product was collected by filtration, washed twice with water and dried in an oven at 125° C. The carbon black product had attached phenyl groups.

Workup

  1. customwas prepared
  2. temperaturewas cooled in an ice bath

Sources & evidence

ORD record
ord-e5450e9857384a10bea6844106c7285e
Source dataset
uspto-grants-1998_02
Patent number
US05713988

Linked notes

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