Process for making isooctenes from aqueous isobutanol

Patent metadata

Field	Value
Publication number	US-9410098-B2
Application number	US-201313967696-A
Country	US
Kind code	B2
Filing date	Aug 15, 2013
Priority date	Jun 16, 2006
Publication date	Aug 9, 2016
Grant date	Aug 9, 2016

Abstract

The present invention relates to a catalytic process for making isooctenes using a reactant comprising isobutanol and water. The isooctenes so produced are useful for the production of fuel additives.

First claim

The invention claimed is:

1. A process for production of gasoline, diesel fuel, jet fuel, or transportation fuel additive comprising:
producing isobutanol from a feedstock derived from a renewable source by a genetically modified microorganism via a biosynthetic pathway comprising substrate to product conversions that include:
pyruvate to acetolactate;
acetolactate to 2,3-dihydroxyisovalerate;
2,3-dihydroxyisovalerate to α-ketoisovalerate;
α-ketoisovalerate to isobutyraldehyde; and
isobutyraldehyde to the isobutanol; and

reacting the isobutanol to produce an intermediate for the production of gasoline, diesel fuel, jet fuel, or transportation fuel additive.

2. The process of claim 1 , wherein the genetically modified microorganism is tolerant to isobutanol at levels greater than 1% weight per volume.

3. The process of claim 1 , further comprising refining the isobutanol prior to the reacting, wherein the isobutanol that results from the distillation is substantially free of one or more of ethanol or acetone.

4. The process of claim 3 , wherein the refining yields an aqueous stream that comprises at least about 5% water by weight of the water and isobutanol.

5. The process of claim 1 , wherein reacting comprises contacting the isobutanol with at least one acid catalyst.

6. The process of claim 5 , wherein the intermediate comprises isooctene, dibutyl ether, or butene.

7. The process of claim 6 , further comprising recovering the isooctene and converting the isooctene to isooctane, isooctanol, or isooctyl alkyl ether.

8. The process of claim 7 , wherein converting comprises contacting the isooctene with a hydrogenation catalyst in the presence of hydrogen.

9. The process of claim 7 , further comprising:
recovering the isooctane, isooctanol, or isooctyl alkyl ether; and
adding the isooctane, isooctanol, or isooctyl alkyl ether that is recovered to a transportation fuel.

10. The process of claim 6 , further comprising contacting the isooctene with an acid catalyst in the presence of at least one straight-chain or branched C1 to C5 alcohol.

11. A process for production of gasoline, diesel fuel, jet fuel, or transportation fuel additive comprising:
obtaining isobutanol that is essentially free of ethanol and is produced by a genetically modified microorganism via a biosynthetic pathway that implements a fermentation broth, the biosynthetic pathway comprising:
pyruvate to acetolactate;
acetolactate to 2,3-dihydroxyisovalerate;
2,3-dihydroxyisovalerate to α-ketoisovalerate;
α-ketoisovalerate to isobutyraldehyde; and
isobutyraldehyde to the isobutanol; and

contacting the isobutanol with an acid catalyst to produce an intermediate for the production of gasoline, diesel fuel, jet fuel, or transportation fuel additive.

12. The process of claim 11 , wherein contacting comprises contacting the isobutanol with the acid catalyst in an aqueous solution where water is at least about five percent (5%) by weight.

13. The process of claim 11 , wherein the intermediate comprises at least one of isooctene, dibutyl ether, or butene.

14. The process of claim 13 , further comprising converting the intermediate to isooctane by contacting the intermediate with a hydrogenation catalyst in the presence of hydrogen.

15. The process of claim 13 , further comprising contacting the intermediate with water in the presence of at least one acidic catalyst and least one straight-chain or branched C1 to C5 alcohol to produce isooctyl alkyl ether.

16. The process of claim 11 , wherein the genetically modified microorganism is tolerant to isobutanol at levels greater than 1% weight per volume.

17. The process of claim 11 , wherein the fermentation broth contains at least about fifty percent (50%) isobutanol by weight to water in the fermentation broth.

Assignees

• Butamax Advanced Biofuels Llc
• Bitamax Advanced Biofuels LLC

Inventors

• D'Amore Michael B
• Manzer Leo Ernest
• Miller Jr Edward S
• Knapp Jeffrey P

Classifications

• C10L2270/023

  for gasoline engines · CPC title

• C07C2529/18

  of the mordenite type · CPC title

• C12P5/026

  Unsaturated compounds, i.e. alkenes, alkynes or allenes · CPC title

• C07C1/20 Primary

  starting from organic compounds containing only oxygen atoms as heteroatoms · CPC title

• C07C2531/10

  sulfonated · CPC title