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US 8,148,545 B2Granted
Processes for the synthesis of γ nitrocarbonyl and γ dicarbonyl compounds and their pyrrole derivatives
AssigneeChevron Phillips Chemical Company LP
InventorsHu Yang, Eduardo J. Baralt
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Abstract
The present invention discloses processes for producing γ-nitrocarbonyl and γ-dicarbonyl compounds, which can be precursors in the synthesis of pyrrole compounds. A process for producing pyrroles such as 2,5-dimethylpyrrole, and structurally similar pyrrole compounds, is also disclosed.
Claims25
A process for producing a γ-dicarbonyl compound comprising:
- a) contacting a primary nitro compound, an α,β-unsaturated carbonyl compound, a base, and water to produce a γ-nitrocarbonyl compound;
- and
- b) contacting a peroxide compound with the γ-nitrocarbonyl compound at a molar ratio of the peroxide compound to the γ-nitrocarbonyl compound in a range from about 1:1 to about 15:1 to produce the γ-dicarbonyl compound;
- wherein:
- the primary nitro compound has the formula:
- the α,β-unsaturated carbonyl compound has the formula:
- the γ-dicarbonyl compound has the formula:
- wherein:
- R, R1, R2, R3, and R4 independently are a hydrogen atom, a C1-C30 organyl group, a C1-C30 organyl group consisting of inert functional groups, or a C1-C30 hydrocarbyl group.
6 more elements
A process for producing a γ-dicarbonyl compound comprising:
- a) contacting a primary nitro compound, an α,β-unsaturated carbonyl compound, a base, and water to produce a γ-nitrocarbonyl compound;
- and
- b) contacting a peroxide compound with the γ-nitrocarbonyl compound at a molar ratio of the peroxide compound to the γ-nitrocarbonyl compound in a range from about 1:1 to about 15:1 to produce the γ-dicarbonyl compound;
- wherein:
- step b) is conducted at a temperature in a range from about 40° C. to about 100° C.;
- the base is an alkali metal carbonate;
- the primary nitro compound has the formula:
- the α,β-unsaturated carbonyl compound has the formula:
- the γ-dicarbonyl compound has the formula:
- wherein:
- R, R1, R2, R3, and R4 independently are a hydrogen atom, a C1-C30 organyl group, a C1-C30 organyl group consisting of inert functional groups, or a C1-C30 hydrocarbyl group.
8 more elements
Dependencies are inferred from the claim text.