Methods for the conversion of a substituted furan to a substituted pyrrole
AssigneeChevron Phillips Chemical Company LP
InventorsBruce E. Kreischer, Orson L. Sydora, Steven Hutchinson, Eduardo J. Baralt, Ron D. Knudsen
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Abstract
The present invention discloses processes for producing substituted pyrrole compounds, such as 2,5-disubstituted pyrroles. Synthetic processes which directly convert substituted furan compounds to substituted pyrrole compounds, via a reaction of the substituted furan compound with ammonia and/or an ammonium salt in the presence of a catalyst, also are described.
Claims26
(canceled)
The process of claim 24, wherein the substituted pyrrole compound has the formula:
- wherein:
- R2p, R3p, R4p, and R5p independently are a hydrogen atom, a C1-C30 organyl group, or a C3-C60 silyl group, and
- at least one of R2p, R3p, R4p, and R5p is not a hydrogen atom.
The process of claim 24, wherein the substituted pyrrole compound comprises a compound having formula P2, P3, P4 or P5:
- wherein R12p, R13p, R14p, R22p, R24p, R33p, R34, R42, and R45 independently are a C1-C18 hydrocarbyl group.
The process of claim 24, wherein the substituted pyrrole compound comprises 2,5-dimethylpyrrole, 2-methyl-5-ethylpyrrole, 2,5-diethylpyrrole, 2-ethyl-5-methylpyrrole, 2-ethyl-5-n-propylpyrrole, 2,5-di-n-propylpyrrole, 2,5-diisopropylpyrrole, 2,5-di-n-butylpyrrole, 2,5-di-n-pentylpyrrole, 2,5-di-n-hexylpyrrole, 2,5-di-n-heptylpyrrole, 2,5-di-n-octylpyrrole, 2,3,5-triethylpyrrole, 2,3,5-tri-n-butylpyrrole, 2,3,5-tri-n-pentylpyrrole, 2,3,5-tri-n-hexylpyrrole, 2,3,5-tri-n-heptylpyrrole, 2,3,5-tri-n-octylpyrrole, 2,3,4,5-tetraethylpyrrole, 2,3,4,5-tetra-n-butylpyrrole, 2,3,4,5-tetra-n-hexylpyrrole, 2,5-dibenzylpyrrole, 2,4-dimethylpyrrole, 2-methyl-4-isopropylpyrrole, 2,4-dimethyl-3-ethylpyrrole, 2,4-diethylpyrrole, 2-ethyl-4-isopropylpyrrole, 2-methyl-4-sec-butylpyrrole, 2-ethyl-4-sec-butylpyrrole, 2-methyl-4-isobutylpyrrole, 2-ethyl-4-isobutylpyrrole, 2-methyl-4-t-butylpyrrole, 2-ethyl-4-t-butylpyrrole, 2-methyl-4-neopentylpyrrole, 2-ethyl-4-neopentylpyrrole, 3,4-dimethylpyrrole, 3,4-diethylpyrrole, 3,4-diisopropylpyrrole, 3,4-di-sec-butylpyrrole, 3,4-diisobutylpyrrole, 3,4-di-t-butylpyrrole, 3,4-di-neopentylpyrrole, or any combination thereof.
The process of claim 24, wherein the substituted pyrrole compound comprises 2,5-dimethylpyrrole.
The process of claim 24, wherein ammonia is contacted with the substituted furan compound and the catalyst.
The process of claim 24, wherein the ammonium salt is contacted with the substituted furan compound and the catalyst, and wherein the ammonium salt comprises ammonium acetate, ammonium carbonate, ammonium bicarbonate, ammonium chloride, ammonium hydroxide, ammonium nitrate, ammonium phosphate, ammonium sulfate, or any combination thereof.
12-14. (canceled)
The process of claim 23, wherein the treated solid oxide comprises fluorided alumina, chlorided alumina, bromided alumina, sulfated alumina, fluorided silica-alumina, chlorided silica-alumina, bromided silica-alumina, sulfated silica-alumina, fluorided silica-zirconia, chlorided silica-zirconia, bromided silica-zirconia, sulfated silica-zirconia, fluorided silica-titania, fluorided silica-coated alumina, sulfated silica-coated alumina, phosphated silica-coated alumina, or any combination thereof.
The process of claim 24, wherein the acidic resin comprises an AMBERLYST® catalyst resin, a NAFION® catalyst resin, or a combination thereof.
17-18. (canceled)
The process of claim 24, wherein an equivalent ratio of the ammonia, the ammonium salt, or a combination thereof, to the substituted furan compound is in a range from 0.975:1 to 50:1.
The process of claim 24, wherein the substituted pyrrole compound is formed:
- at a pressure in a range from 25 psig to 3500 psig;
- at a temperature in a range from 50° C. to 400° C.;
- at a weight hourly space velocity in a range from 0.05 to 50;
- in the presence of added water;
- in the presence of an organic solvent;
- in a continuous reactor;
- or
- any combination thereof.
The process of claim 24, wherein the substituted pyrrole compound is formed:
- in the substantial absence of added water;
- in the presence of a water scavenger;
- or
- both.
The process of claim 24, wherein step 1 and step 2 are conducted in a single reactor.
A process for producing a substituted pyrrole compound, the process comprising:
- 1) contacting
- a) a substituted furan compound;
- b) ammonia, an ammonium salt, or a combination thereof;
- and
- c) a catalyst comprising a treated solid oxide;
- and
- 2) forming the substituted pyrrole compound;
- wherein the treated solid oxide comprises a solid oxide treated with an electron-withdrawing anion, wherein:
- the solid oxide comprises silica, alumina, titania, zirconia, magnesia, boria, zinc oxide, silica-alumina, silica-coated alumina, silica-titania, silica-zirconia, alumina-titania, alumina-zirconia, zinc-aluminate, alumina-boria, silica-boria, aluminum phosphate, aluminophosphate, aluminophosphate-silica, titania-zirconia, or any combination thereof;
- and
- the electron-withdrawing anion comprises sulfate, bisulfate, fluoride, chloride, bromide, iodide, fluorosulfate, fluoroborate, phosphate, fluorophosphate, trifluoroacetate, triflate, fluorozirconate, fluorotitanate, phospho-tungstate, or any combination thereof.
A process for producing a substituted pyrrole compound, the process comprising:
- 1) contacting
- a) a substituted furan compound;
- b) ammonia, an ammonium salt, or a combination thereof;
- and
- c) a catalyst comprising an acidic resin;
- and
- 2) forming the substituted pyrrole compound.
(canceled)
Dependencies are inferred from the claim text.