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
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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.
Claims27
A method for producing at least one acyclic ketone, comprising contacting at least one ketone having a structure of formula (A) with catalyst in the presence of H2 or at least one secondary alcohol to produce at least one acyclic ketone having a structure of formula (L-I) or (L-II), wherein:
- the catalyst comprises:
- an apatite;
- a sepiolite;
- a chrysotile;
- a zeolite;
- a mesoporous silica;
- a hydrotalcite;
- or
- a synthetic talc,
- or any combinations thereof,
- the at least one ketone having the structure of formula (A) is:
- wherein:
- R1 is 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,
- R2 is 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,
- 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;
- x is an integer greater than or equal to 1;
- y is an integer greater than or equal to 0;
- and
- the at least one acyclic ketone having the structure of formula (L-I) or (L-II) is:
- wherein:
- R1, R2, x and y are as defined for formula (A), and
- n and m are each an integer greater than or equal to 1.
A method for producing at least one acyclic ketone, comprising contacting at least one ketone having a structure of formula (A) with catalyst in the presence of H2 or at least one secondary alcohol to produce at least one acyclic ketone having a structure of formula (L-I) or (L-II), wherein:
- the catalyst comprises:
- Mg—Al hydrotalcite, Li—Al hydrotalcite, Zn—Al hydrotalcite, Cu—Zn—Al hydrotalcite, Ni—Mg—Al hydrotalcite, or Ni—Mg—Al hydrotalcite;
- NaY zeolite, NaX zeolite, KY zeolite, RbY zeolite, CsY zeolite, KX zeolite, RbX zeolite, CsX zeolite, palladium/NaY zeolite, palladium/NH4-β zeolite, potassium oxide supported on zeolite Y, lanthanide imide on zeolite, or nitride on zeolite;
- Na/SiO2, Pd/Na/SiO2, Na/Ca/SiO2, Na/Ca/SiO2, or Cs/SiO2;
- hydroxyapatite, fluorapatite, or tert-butoxyapatite;
- Pd/HT, Cu/HT, Pd—Cu/HT, LaAlMgO, SiO2—NHMe, or SiO2—NMe2;
- Mg3(OH)4Si4O5, or cobalt(II)-substituted chrysotile,
- or any combinations thereof;
- the at least one ketone having the structure of formula (A) is:
- wherein:
- R1 is 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,
- R2 is 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,
- 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;
- x is an integer greater than or equal to 1;
- y is an integer greater than or equal to 0;
- and
- the at least one acyclic ketone having the structure of formula (L-I) or (L-II) is:
- wherein:
- R1, R2, x and v are as defined for formula (A), and
- n and m are each an integer greater than or equal to 1.
Dependencies are inferred from the claim text.