Methods for producing cyclic and acyclic ketones
AssigneesThe Regents of the University of California, BP Corporation North America Inc.
InventorsSanil Sreekumar, F. Dean Toste, Amit A. Gokhale, Gorkem Gunbas, Balakrishnan Madhesan, Alexis T. Bell, Eric Sacia, George E. Arab
Life of this patent
Estimating the term…
Abstract
Provided herein are methods for producing cyclic and acyclic ketones from trimerization and dimerization of alkyl ketones, including for example methyl ketones. Such cyclic and acyclic ketones may be suitable for use as fuel and lubricant precursors, and may be hydrodeoxygenated to form their corresponding cycloalkanes and alkanes. Such cycloalkanes and alkanes may be suitable for use as fuels, including jet fuels, and lubricants.
Claims35
A method for producing at least one cyclic ketone, comprising:
- contacting at least one ketone independently having a structure of formula (A) with catalyst to form a reaction mixture, wherein the contacting of the at least one ketone with the catalyst produces at least one cyclic ketone having a structure of formula (I), (II), (III) or (IV), or any isomers thereof, from at least a portion of the at least one ketone, wherein:
- the at least one ketone independently having the structure of formula (A) is:
- wherein:
- each R1 and R2 is independently H, unsubstituted alkyl, substituted alkyl, —C(Rt)3, —CH(Rt)2, unsubstituted aryl, substituted aryl, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted alicyclyl, substituted alicyclyl, unsubstituted heterocyclyl, or substituted heterocyclyl,
- wherein each Rt is independently unsubstituted aliphatic, substituted aliphatic, unsubstituted aryl, substituted aryl, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted alicyclyl, substituted alicyclyl, unsubstituted heterocyclyl, or substituted heterocyclyl;
- each x and y is independently an integer greater than or equal to 1, provided that when x and y are both 1, either R1 or R2 is other than H;
- the cyclic ketone having the structure of formula (I) is:
- or any isomers thereof, wherein:
- Ra1 is —(CH2)x-1R1;
- Rb1 is —(CH2)xR1;
- Rc1 is —(CH2)y-1R2;
- Rd1 is —(CH2)xR1;
- Re1 is —(CH2)yR2;
- and
- Rf1 is —(CH2)y-1R2;
- the cyclic ketone having the structure of formula (II) is:
- or any isomers thereof, wherein:
- Ra2 is —(CH2)y-1R2;
- Rb2 is —(CH2)xR1;
- Rc2 is —(CH2)y-1R2;
- Rd2 is —(CH2)xR1;
- Re2 is —(CH2)yR2;
- and
- Rf2 is —(CH2)x-1R1;
- the cyclic ketone having the structure of formula (III) is:
- or any isomers thereof, wherein:
- Ra3 is —(CH2)x-1R1;
- Rb3 is —(CH2)yR2;
- Rc3 is —(CH2)x-1R1;
- Rd3 is —(CH2)xR1;
- Re3 is —(CH2)yR2;
- and
- Rf1 is —(CH2)y-1R2;
- the cyclic ketone having the structure of formula (IV) is:
- or any isomers thereof, wherein:
- Ra4 is —(CH2)y-1R2;
- Rb4 is —(CH2)yR2;
- Rc4 is —(CH2)x-1R1;
- Rd4 is —(CH2)xR1;
- Re4 is —(CH2)yR2;
- and
- Rf4 is —(CH2)x-1R1, and
- the catalyst comprises:
- an apatite;
- a sepiolite;
- a chrysotile;
- a zeolite;
- a mesoporous silica;
- a hydrotalcite;
- or a synthetic talc, or any combinations thereof.
Dependencies are inferred from the claim text.