Water → Tridecanoic acid

HRID 2290996Notes

Reaction equation

HRID 2290996 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]CCC.[OH2:13].CN1[CH2:19][CH2:18][CH2:17][C:16]1=[O:20]>[Co]>[C:16]([OH:20])(=[O:13])[CH2:17][CH2:18][CH2:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 81831-DodeceneHCID 13387N-methyl-2-pyrrolidone

Product 1

HCID 12530Tridecanoic acidYield 83%

Reagents, catalysts & solvents 1

HCID 104730CobaltCatalyst

Procedure

Using the method described in Example 1, a solution of 165 g (=0.98 mole) of dodec-1-ene and 1.65 g (=0.28 mole equivalent) of cobalt in the form of dicobalt-octacarbonyl, and a mixture of 157 g of N-methylpyrrolidone and 23 g (=1.28 mole) of water, were hydrocarboxylated under a CO pressure of 300 bars at 190° C. Conventional working up gave a yield of 83% of tridecanoic acid, of which 60% consisted of the particularly valuable n-isomer. 13% of the olefin had not reacted and the remainder consisted of by-products, including 2% of dodecane.

Workup

  1. customat 190° C

Sources & evidence

ORD record
ord-e27036a731ac44d0b930c02e165076df
Source dataset
uspto-grants-1986_10
Patent number
US04619790

Reaction notes

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