Methane → 4-Sulfobenzenediazonium hydroxide

HRID 1898751Notes

Reaction equation

HRID 1898751 reaction equation
[S:1]([OH:11])(=[O:10])([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)=[O:2].C.C1C(Br)=C(Br)[NH:15]C=1C(O)=O.N([O-])=O.[Na+]>O>[OH-:2].[S:1]([C:3]1[CH:4]=[CH:5][C:6]([N+:9]#[N:15])=[CH:7][CH:8]=1)([OH:11])(=[O:10])=[O:2]

Participants

6

Reactant 4

HCID 297MethaneHCID 8479Sulfanilic acidHCID 1618304,5-Dibromo-2-Pyrrolic AcidHCID 23668193Sodium Nitrite

Product 1

HCID 227152964-Sulfobenzenediazonium hydroxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A pin pelletizer was charged with 42.4 g of sulfanilic acid and with 200 g of a carbon black having a CTAB surface area of 350 m2 /g and a DBPA of 120 ml/100 g. After mixing for 30 seconds, a solution of 17.4 g NaNO2 in 150 g of boiling water was added and the mixture was pelletized for 45 seconds. 4-Sulfobenzenediazonium hydroxide inner salt is formed, which reacts with the carbon black. The product, which was then at 35° C. was dried in an oven at 120° C. The product had a 325 mesh residue of 0.2%, compared to 97% for the unreacted carbon black. The product has attached p--C6H4SO3- groups.

Workup

  1. additionAfter mixing for 30 seconds

Sources & evidence

ORD record
ord-6b8a95fb5bc040eda9834ce1555fa3f8
Source dataset
uspto-grants-1996_11
Patent number
US05571311

Reaction notes

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