Fuel compositions comprising isoprene derivatives

• US 8,933,282 B2
• Filed: 06/17/2011
• Issued: 01/13/2015
• Est. Priority Date: 06/17/2010
• Status: Expired due to Fees

• Current Assignee: Danisco USA Incorporated (International Flavors & Fragrances Incorporated)
• Original Assignee: Danisco USA Incorporated (International Flavors & Fragrances Incorporated)
• Inventors: McAuliffe, Joseph C.
• Primary Examiner(s): BHAT, NINA NMN
• Application Number:
  US13/163,601
• Publication Number:
  US 20120157725A1
• Time in Patent Office: 1,306 Days
• Field of Search: 585/240, 585/242, 585/615, 446/05
• US Class Current: 585/240
• CPC Class Codes: B01J 2231/543 alkene metathesis
• CPC Class Codes: B01J 23/38 of noble metals
• CPC Class Codes: B01J 23/70 of the iron group metals or copper
• CPC Class Codes: B01J 2531/821 Ruthenium
• CPC Class Codes: B01J 31/003 containing enzymes
• CPC Class Codes: B01J 31/10 sulfonated
• CPC Class Codes: B01J 31/2273 with only nitrogen as heteroatomic ring members, e.g. 1,3-diarylimidazoline-2-ylidenes
• CPC Class Codes: B01J 31/2278 Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts
• CPC Class Codes: C10G 2300/1011 Biomass
• CPC Class Codes: C10G 2300/1081 Alkanes
• CPC Class Codes: C10G 2300/807 Steam
• CPC Class Codes: C10G 2400/20 C2-C4 olefins
• CPC Class Codes: C10G 2400/22 Higher olefins
• CPC Class Codes: C10G 29/205 by reaction with hydrocarbons added to the hydrocarbon oil
• CPC Class Codes: C10G 45/00 Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
• CPC Class Codes: C10G 45/32 Selective hydrogenation of the diolefin or acetylene compounds
• CPC Class Codes: C10G 45/34 characterised by the catalyst used
• CPC Class Codes: C10G 45/58 to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point; Selective hydrocracking of normal paraffins C10G32/00 takes precedence; improving or increasing the octane number or aromatic content of naphtha C10G35/00
• CPC Class Codes: C10G 45/60 characterised by the catalyst used
• CPC Class Codes: C10G 65/043 at least one step being a change in the structural skeleton
• CPC Class Codes: C10G 65/06 : at least one step being a selective hydrogenation of the diolefins
• CPC Class Codes: C10G 69/123 : alkylation
• CPC Class Codes: C10L 1/04 : essentially based on blends of hydrocarbons
• CPC Class Codes: C12P 5/02 : acyclic C12P5/007 takes precedence
• CPC Class Codes: C12P 5/026 : Unsaturated compounds, i.e. alkenes, alkynes or allenes
• CPC Class Codes: Y02E 50/30 : Fuel from waste, e.g. synthetic alcohol or diesel

Abstract

Methods, compositions and systems using isoprene from a bioisoprene composition derived from renewable carbon for production of a variety of hydrocarbon fuels, fuel additives, and additives for fine chemistry and other uses is described.

Claims

1. A method for producing a fuel constituent from a bioisoprene composition comprising chemically transforming a substantial portion of the isoprene in the bioisoprene composition to one or more non-isoprene compounds by:

(a) contacting the bioisoprene composition with a catalyst for olefin metathesis to produce one or more olefin products and then catalytically hydrogenating the one or more olefin products to form one or more alkane fuel constituents;

(b) partially hydrogenating the bioisoprene composition to produce an isoamylene and then alkylating the isoamylene with an isoparaffin to form a high octane alkylate fuel constituent;

or

(c) partially hydrogenating the bioisoprene composition to produce one or more isoamylenes, then contacting the one or more isoamylenes with a catalyst for olefin metathesis to form one or more olefin products, and then catalytically hydrogenating the one or more olefin products to form one or more alkane fuel constituents.

2. The method of claim 1 wherein at least about 95% of isoprene in the bioisoprene composition is converted to non-isoprene compounds.

3. The method of claim 1 wherein the bioisoprene composition comprises or contains greater than about 2 mg of isoprene and comprises or contains greater than or about 99.94% isoprene by weight compared to the total weight of all C5 hydrocarbons in the composition.

4. The method of claim 1 wherein the olefin metathesis catalyst comprises or involves, at least, a metal complex.

5. The method of claim 4 wherein the metal complex is a rhenium complex, a ruthenium complex, a rhodium complex, an osmium complex, a tungsten complex, a molybdenum complex or a titanium complex.

6. The method of claim 1 wherein the olefin product comprises a higher (>

C5) olefin or a lower (<

C5) olefin or both.

7. The method of claim 6 wherein the one or more olefin products from isoprene metathesis comprise one or more olefins selected from the group consisting of ethylene, isobutylene and olefins containing 6, 8 and 12 carbon atoms (e.g., dimethylhexatrienes).

8. The method of claim 1 wherein the step of partially hydrogenating the bioisoprene composition comprises contacting the bioisoprene composition with hydrogen gas and a catalyst for catalyzing partial hydrogenation of isoprene.

9. The method of claim 8 wherein the catalyst for catalyzing partial hydrogenation of isoprene comprises a palladium catalyst.

10. The method of claim 1 wherein the step of alkylating the isoamylene with an isoparaffin comprises contacting the isoamylene with the isoparaffin in the presence of an acid catalyst.

11. The method of claim 10 wherein the acid catalyst is hydrofluoric acid, sulfuric acid, fluorosulfonic acid or perhaloalkylsulfonic acid.

12. The method of claim 10 wherein the isoparaffin is propane, isobutane or isopentane.

13. The method of claim 1 wherein the olefin metathesis catalyst for isoamylene metathesis is different from the olefin metathesis catalyst for bioisoprene metathesis.

14. The method of claim 1 wherein the olefin metathesis catalyst for isoamylene metathesis is the same as the olefin metathesis catalyst for bioisoprene metathesis.

15. The method of claim 1 wherein the olefin product from isoamylene metathesis comprises one or more olefins selected from the group consisting of ethylene and olefins containing 6, 8 and 12 carbon atoms (e.g., dimethylhexenes).

16. A method for producing a fuel constituent from a bioisoprene composition comprising:

(a) contacting a bioisoprene composition with an acid catalyst to produce one or more mixed olefin products of C5-C50 olefins wherein the mixed olefin products comprise higher molecular weight olefin products of C16-C50 olefins and lower molecular weight olefin products of C5-C15 olefins;

(b) converting the higher molecular weight olefin products of C16-C50 olefins to lower molecular weight olefin products of C5-C15 olefins; and

(c) hydrogenating the lower molecular weight olefin products of C5-C15 olefins to produce saturated hydrocarbon of C5-C15 alkanes fuel constituents;

wherein a substantial portion of the isoprene in the bioisoprene composition is chemically converted to one or more non-isoprene compounds.

17. The method of claim 16 wherein the step of converting the higher molecular weight olefin products of C16-C50 olefins to lower molecular weight olefin products of C5-C15 olefins comprises thermal cracking, steam cracking or metathesis.