Methane → 4-Tetradecylbenzenediazonium nitrate

HRID 861182Notes

Reaction equation

HRID 861182 reaction equation
C.C1C(Br)=C(Br)[NH:4]C=1C(O)=O.N([O-])=O.[Na+].[CH2:16]([C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[N+:37]([O-:40])([OH:39])=[O:38]>O.CC(C)=O>[N+:37]([O-:40])([O-:39])=[O:38].[CH2:16]([C:30]1[CH:31]=[CH:32][C:33]([N+:34]#[N:4])=[CH:35][CH:36]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

8

Reactant 5

HCID 297Methane2×HCID 944Nitric AcidHCID 145224p-TetradecylanilineHCID 1618304,5-Dibromo-2-Pyrrolic AcidHCID 23668193Sodium Nitrite

Product 1

HCID 197024474-Tetradecylbenzenediazonium nitrate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent3×

Procedure

A carbon black with a surface area of 58 m2 /g and a DBPA of 46 ml/100 g was used. A suspension of 50 g of this carbon black was prepared by stirring it into 450 g of water. A solution of 0.85 g of NaNO2 in 4 g of cold water was slowly added to a dispersion of 2.98 g of 4-tetradecylaniline, 1.98 g of concentrated nitric acid and 4 ml of acetone in 15 g of water that was cooled in an ice bath. 4-Tetradecylbenzenediazonium nitrate was formed. After 15 minutes of stirring, the mixture was added to the stirring carbon black suspension. Bubbles were released. After 30 minutes, the product was collected by filtration, washed with water and tetrahydrofuran (THF) and dried in an oven at 125° C. The carbon black product had attached p-C6 H4C14H29 groups.

Workup

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

Sources & evidence

ORD record
ord-f7cbdd8d4b9c46aa8b4db7a1f2400d52
Source dataset
uspto-grants-1998_02
Patent number
US05713988

Reaction notes

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