Ethylene → Styrenesulfonic acid

HRID 2379302Notes

Reaction equation

HRID 2379302 reaction equation
N[C:2]1[C:3]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:12]=[CH2:13]>[Pd]>[CH2:12]=[CH:13][C:2]1[C:3]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6325EthyleneHCID 69262-Aminobenzenesulfonic acid

Product 1

HCID 168625Styrenesulfonic acid

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

EP-A 0 508 264 relates to a process for preparing arylolefins by reaction of aryldiazonium salts with olefins in the presence of a palladium catalyst. Although the use of heterogeneous palladium catalysts is mentioned (cf. EP-A 0 508 264 A1 page 4, lines 2 to 3), it is experimentally verified in only one case, namely the reaction of aniline-2-sulfonic acid with ethylene to give styrene-2-sulfonic acid (Example 6). However, as shown by comparison with Example 4 carried out using Pd(OAc)2, the yield decreases considerably when using a supported palladium catalyst (10% Pd on carbon) (Example 4: 87% yield; Example 7: 74% yield). In both examples the reaction is carried out with the addition of a base which is used in excess based on the aniline-2-sulfonic acid. As the experimental finding proves (see comparative experiment in the experimental section), the method practiced in the examples of EP-A 0 508 264, of preparing the aryldiazonium salts in situ and subsequently processing further, cannot be generally applied to the use of palladium-containing supported catalysts. The comparative experiment verifies that the desired aromatic olefin is not formed even in small amounts.

Workup

  1. customEP-A 0 508 264 relates to a process for preparing arylolefins

Sources & evidence

ORD record
ord-a5da4f8043f44c13a08f7eb2a540a2f9
Source dataset
uspto-grants-1994_11
Patent number
US05360924

Reaction notes

Loading…