Organophosphorus Complexes of Cobalt Carbonyl as Hydroformylation Catalysts

Tucci, Edmond R.

doi:10.1021/i360031a015

Cited by 6 publications

(8 citation statements)

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“…Carboxystearate [5] showed the very broad bonded OH stretching absorption at 2700-3300 cm-1 accompanied by a new strong carbonyl band at 1720 cm-t separated from the ester banff at 1750 cm -1. In the carbomethoxy derivative [7] the CO bands are not separated and absorb together between 1730 and 1750 cm -1 .…”

Section: Characterizationmentioning

confidence: 94%

“…No resolution of components resulted by TLC of either the dimethoxymethyl [31, which moved too fast (10% EE-90% PE), or the carboxy derivative [ 5 ], which moved too slowly and tailed (30% EE-70% PE). Resolution was best with the carbomethoxy derivative [7]. Multiple development with a weakly polar solvent (8% EE-92% PE) resulted in almost complete resolution of methyl carbomethoxystearate [7] into two components corresponding to the 9-and 10-carbomethoxystearates synthetic standards (Fig.…”

Section: Characterizationmentioning

confidence: 95%

“…Resolution was best with the carbomethoxy derivative [7]. Multiple development with a weakly polar solvent (8% EE-92% PE) resulted in almost complete resolution of methyl carbomethoxystearate [7] into two components corresponding to the 9-and 10-carbomethoxystearates synthetic standards (Fig. 1).…”

Section: Characterizationmentioning

confidence: 96%

“…GLC of methyl 9(10)-formylstearate [2] gave one sharp peak with retention time relative to methyl oleate [1] of 2.3 (for conditions, see Table II, footnote e). Sharp single peaks also occurred with the dimethoxymethyl [3], carbomethoxy [7] and acetoxymethyl [6] derivatives, with xespective retention times of 1.6, 2.0 and 2.5 relative to methyl oleate.…”

Section: Characterizationmentioning

confidence: 99%

“…Several novel hydroformylation catalysts reported include various substituted phosphine, phosphite, arsine and stibine ligands used together with organometallic complexes of cobalt (6)(7)(8), rhodium (9)(10)(11)(12)(13)(14) and iridium (15). These new catalysts are generally more active than cobalt carbonyl and promote hydroformylation of olefins under milder conditions.…”

Section: Introductionmentioning

confidence: 99%

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Methyl 9(10)‐formylstearate by selective hydroformylation of oleic oils

Frankel

1971

J Americ Oil Chem Soc

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A highly selective catalyst system has been discovered for the hydroformylation of methyl oleate into methyl 9(10)‐formylstearate in high yields. A rhodium catalyst in the presence of triphenylphosphine is used with oleic esters, acids or triglycerides. Hydroformylation proceeds smoothly at 95‐110C with a 1:1 mixture of H2 and CO at 500 to 2000 psi with or without a solvent, such as toluene. The formylstearate obtained in 90% to 99% conversion from oleate can be either hydrogenated (Raney Ni) or reduced (NaBH4) to hydroxymethylstearate or oxidized (KMnO4) to carboxystearate. According to TLC and mass spectrometry, the methylated carboxystearate consists of about equal proportions of the 9 and 10 isomers. Addition of triphenylphosphine inhibits isomerization of the double bond and leads to the formation of a rhodium carbonyl triphenylphosphine complex, which is apparently the active catalyst. Other known methods for hydroformylation (cobalt carbonyl) and carboxylation (Koch’s method) of oleate give a wide distribution of isomers.

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Section: Characterizationmentioning

confidence: 94%

Section: Characterizationmentioning

confidence: 95%