Process for making isooctenes from aqueous isobutanol

• US 20090099401A1
• Filed: 06/13/2007
• Published: 04/16/2009
• Est. Priority Date: 06/16/2006
• Status: Abandoned Application

• Current Assignee: Butamax Advanced Biofuels LLC (International Flavors & Fragrances Incorporated)
• Original Assignee: Butamax Advanced Biofuels LLC (International Flavors & Fragrances Incorporated)
• Inventors: Knapp, Jeffrey P., D'Amore, Michael B., Manzer, Leo Ernest, Miller, Edward S. JR.
• Application Number:
  US11/818,354
• Publication Number:
  US 20090099401A1
• Time in Patent Office: Days
• US Class Current: 585/639
• CPC Class Codes: C07C 1/20 starting from organic compounds containing only oxygen atoms as heteroatoms
• CPC Class Codes: C07C 1/22 by reduction
• CPC Class Codes: C07C 11/02 Alkenes
• CPC Class Codes: C07C 2521/08 Silica
• CPC Class Codes: C07C 2527/054 Sulfuric acid or other acids with the formula H2Sn03n+1
• CPC Class Codes: C07C 2529/18 of the mordenite type
• CPC Class Codes: C07C 2529/40 of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
• CPC Class Codes: C07C 2531/10 sulfonated
• CPC Class Codes: C07C 29/04 by hydration of carbon-to-carbon double bonds
• CPC Class Codes: C07C 31/12 containing four carbon atoms
• CPC Class Codes: C07C 31/125 containing five to twenty-two carbon atoms
• CPC Class Codes: C07C 41/06 by addition of organic compounds only
• CPC Class Codes: C07C 43/04 Saturated ethers
• CPC Class Codes: C07C 5/03 of non-aromatic carbon-to-carbon double bonds
• CPC Class Codes: C07C 9/21 2, 2, 4-Trimethylpentane
• CPC Class Codes: C10G 2300/4006 Temperature
• CPC Class Codes: C10G 2300/4012 Pressure
• CPC Class Codes: C10G 2300/805 Water
• CPC Class Codes: C10G 2400/22 Higher olefins
• CPC Class Codes: C10L 1/16 Hydrocarbons
• CPC Class Codes: C10L 1/1608 : Well defined compounds, e.g. hexane, benzene
• CPC Class Codes: C10L 1/18 : containing oxygen
• CPC Class Codes: C10L 1/1824 : mono-hydroxy
• CPC Class Codes: C10L 1/1852 : Ethers; Acetals; Ketals; Orthoesters
• CPC Class Codes: C10L 2200/0469 : Renewables or materials of biological origin
• CPC Class Codes: C10L 2270/023 : for gasoline engines
• CPC Class Codes: C10L 2270/026 : for diesel engines, e.g. automobiles, stationary, marine
• CPC Class Codes: C10L 2270/04 : for turbines, planes, power generation
• CPC Class Codes: C10L 2290/26 : Composting, fermenting or anaerobic digestion fuel components or materials from which fuels are prepared
• CPC Class Codes: C12P 5/026 : Unsaturated compounds, i.e. alkenes, alkynes or allenes

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.

Claims

1. A process for making at least one isooctene comprising contacting a reactant comprising isobutanol and at least about 5% water (by weight relative to the weight of the water plus isobutanol) with at least one acid catalyst at a temperature of about 50 degrees C. to about 450 degrees C. and a pressure from about 0.1 MPa to about 20.7 MPa to produce a reaction product comprising said at least one isooctene, and recovering said at least one isooctene from said reaction product to obtain at least one recovered isooctene.

2. The process of claim 1, wherein the reactant is obtained from a fermentation broth.

3. The process of claim 2, wherein the reactant is obtained by subjecting the fermentation broth to a refining process that comprises at least one step selected from the group consisting of pervaporation, gas-stripping, adsorption, liquid-liquid extraction, and distillation.

4. The process of claim 3, wherein said distillation produces a vapor phase having a water concentration of at least about 33% (by weight relative to the weight of water plus isobutanol), and wherein the vapor phase is used as the reactant.

5. The process of claim 1 or claim 4, wherein the at least one acid catalyst is a heterogeneous catalyst, and the temperature and the pressure are chosen so as to maintain the reactant and the reaction product in the vapor phase.

6. The process of claim 3, wherein said distillation produces a vapor phase, wherein the vapor phase is condensed to produce an isobutanol-rich liquid phase having a water concentration of at least about 16% (by weight relative to the weight of the water plus isobutanol) and a water-rich liquid phase, wherein the isobutanol-rich liquid phase is separated from the water-rich phase, and wherein the isobutanol-rich liquid phase is used as the reactant.

7. A process for making a reaction product comprising at least one isooctane, contacting a reactant comprising isobutanol and at least about 5% water (by weight relative to the weight of the water plus isobutanol) with at least one acid catalyst at a temperature of about 50 degrees C. to about 450 degrees C. and a pressure from about 0.1 MPa to about 20.7 MPa to produce a first reaction product comprising at least one isooctene, recovering said at least one isooctene from said first reaction product to obtain at least one recovered isooctene, and

(a) contacting the at least one recovered isooctene with hydrogen in the presence of at least one hydrogenation catalyst to produce said reaction product comprising at least one isooctane;

and

(b) optionally recovering at least one isooctane from the reaction product to obtain at least one recovered isooctane.

8. The process of claim 7, wherein the reactant is obtained from a fermentation broth.

9. A process for making a reaction product comprising at least one isooctanol, comprising contacting a reactant comprising isobutanol and at least about 5% water (by weight relative to the weight of the water plus isobutanol) with at least one acid catalyst at a temperature of about 50 degrees C. to about 450 degrees C. and a pressure from about 0.1 MPa to about 20.7 MPa to produce a first reaction product comprising at least one isooctene, recovering said at least one isooctene from said first reaction product to obtain at least one recovered isooctene, and

(a) contacting the at least one recovered isooctene with water and at least one acid catalyst to produce said reaction product comprising at least one isooctanol;

and

(b) optionally recovering at least one isooctanol from the reaction product to obtain at least one recovered isooctanol.

10. The process of claim 9, wherein the reactant is obtained from a fermentation broth.

11. A process for making a reaction product comprising at least one isooctyl alkyl ether, comprising contacting a reactant comprising isobutanol and at least about 5% water (by weight relative to the weight of the water plus isobutanol) with at least one acid catalyst at a temperature of about 50 degrees C. to about 450 degrees C. and a pressure from about 0.1 MPa to about 20.7 MPa to produce a first reaction product comprising at least one isooctene, recovering said at least one isooctene from said first reaction product to obtain at least one recovered isooctene, and

(a) contacting the at least one recovered isooctene with at least one straight-chain or branched C₁ to C₅ alcohol and at least one acid catalyst to produce said reaction product comprising at least one isooctyl alkyl ether;

and

(b) optionally recovering at least one isooctyl alkyl ether from the reaction product to obtain at least one recovered isooctyl alkyl ether.

12. The process of claim 11, wherein the reactant is obtained from a fermentation broth.

13. A process for making at least one isooctane comprising:

(a) contacting a reactant comprising isobutanol and at least about 5% water (by weight relative to the weight of the water plus isobutanol) with at least one acid catalyst at a temperature of about 50 degrees C. to about 450 degrees C. and a pressure from about 0.1 MPa to about 20.7 MPa to produce a first reaction product comprising at least one isooctene;

(b) contacting said first reaction product with hydrogen in the presence of at least one hydrogenation catalyst to produce a second reaction product comprising at least one isooctane; and

(c) recovering the at least one isooctane from the second reaction product to produce a recovered isooctane.

14. The process of claim 13, wherein the reactant is obtained from a fermentation broth.

15. A process for making at least one isooctanol comprising:

(a) contacting a reactant comprising isobutanol and at least about 5% water (by weight relative to the weight of the water plus isobutanol) with at least one acid catalyst at a temperature of about 50 degrees C. to about 450 degrees C. and a pressure from about 0.1 MPa to about 20.7 MPa to produce a first reaction product comprising at least one isooctene;

(c) contacting said first reaction product with water and at least one acid catalyst to produce a second reaction product comprising at least one isooctanol; and

(d) optionally recovering the at least one isooctanol from the second reaction product to obtain at least one recovered isooctanol.

16. The process of claim 15, wherein the reactant is obtained from a fermentation broth.