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US 10,183,899 B2Granted
Normal alpha olefin synthesis using metathesis and dehydroformylation
AssigneeChevron Phillips Chemical Company LP
InventorSteven M. Bischof
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Abstract
The present invention discloses processes for producing normal alpha olefins, such as 1-hexene, 1-octene, and 1-decene, in a multistep synthesis scheme. Generally, a first normal alpha olefin is subjected to an olefin metathesis step to form a linear internal olefin, which is then subjected to an isomerization-hydroformylation step to form a linear aldehyde, which is then subjected to a dehydroformylation step to form a second normal alpha olefin.
Claims20
A process comprising:
- (i) contacting a first normal alpha olefin having the structure CH3(CH2)nHC═CH2 and a metathesis catalyst system to form a linear internal olefin having the structure CH3(CH2)nHC═CH(CH2)nCH3;
- (ii) contacting the linear internal olefin with a hydroformylation catalyst system, carbon monoxide, and hydrogen to form a linear aldehyde having the formula CH3(CH2)2n+3C(═O)H;
- and
- (iii) contacting the linear aldehyde with a dehydroformylation catalyst system comprising i) a transition metal compound, a diphosphine, and a carboxylic acid or carboxylic acid derivative, or ii) a diphosphine transition metal compound complex and a carboxylic acid or carboxylic acid derivative, to form a second normal alpha olefin having the structure CH3(CH2)2n+1HC═CH2;
- wherein n is an integer from 0 to 15.
2 more elements
A process comprising:
- (a) contacting a linear internal olefin having the structure CH3(CH2)pHC═CH(CH2)qCH3 with a hydroformylation catalyst system, carbon monoxide, and hydrogen to form a linear aldehyde having the formula CH3(CH2)p+q+3C(═O)H;
- and
- (b) contacting the linear aldehyde with a dehydroformylation catalyst system comprising i) a transition metal compound, a diphosphine, and a carboxylic acid or carboxylic acid derivative, or ii) a diphosphine transition metal compound complex and a carboxylic acid or carboxylic acid derivative, to form a normal alpha olefin having the structure CH3(CH2)p+q+1HC═CH2;
- wherein p and q independently are an integer from 0 to 15.
1 more element
Dependencies are inferred from the claim text.