US2015267135A1PendingUtilityA1

Synthesis of c3-c7 alcohol fuel compositions

Assignee: PIONEER ENERGY INCPriority: Nov 10, 2011Filed: Apr 23, 2015Published: Sep 24, 2015
Est. expiryNov 10, 2031(~5.3 yrs left)· nominal 20-yr term from priority
C10L 1/18C10L 10/10C07C 29/149C10L 1/06C10L 1/1824C07D 305/12C07B 41/02C07C 1/22C07C 1/24C07C 5/03C07C 29/145C07C 29/177C07C 45/48C07C 51/00C07C 51/12C07D 309/36C10G 3/50C10L 1/023C10G 2400/02Y02P30/20C07C 1/2076C07C 29/175C07C 45/00C07C 67/46C10L 2200/0469C10L 2270/023C10L 2290/24
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Claims

Abstract

In one embodiment, the present application discloses methods to selectively synthesize higher alcohols and hydrocarbons useful as fuels and industrial chemicals from syngas and biomass. Ketene and ketonization chemistry along with hydrogenation reactions are used to synthesize fuels and chemicals. In another embodiment, ketene used to form fuels and chemicals may be manufactured from acetic acid which in turn can be synthesized from synthesis gas which is produced from coal, biomass, natural gas, etc.

Claims

exact text as granted — not AI-modified
What is claimed is:  
     
         1 .- 26 . (canceled) 
     
     
         27 . A method for the preparation of a C 3 -C 7  alcohol comprising:
 a) preparing a beta-lactone of the formula III:   
       
         
           
           
               
               
           
         
         wherein: 
         R 3  is H or a C 1 - 2  alkyl; 
         R 4  is H; 
         R 5  is H or C 1-2  alkyl; or 
         R 4  and R 5  are combined to form ethyledene or methyledene; and 
         b) hydrogenating the lactone to form the C 3 -C 7  alcohol. 
       
     
     
         28 . The method of  claim 27 , wherein the beta-lactone of the formula III is selected from the group consisting of beta-butyrolactone, 4-ethyl-3-methyloxetan-2-one and (E) and (Z)-4-ethylidene-3-methyloxetan-2-one or mixtures thereof. 
     
     
         29 . The method of  claim 27 , wherein:
 a) the beta-lactone of the formula III, wherein R 3  is H and R 4  is H and R 5  is —CH 3 , is prepared by the oxidation of propylene to form propylene oxide, carbonylation of propylene oxide to form beta-buyrolactone, and hydrogenation of beta-butyrolactone to form butanol; or   b) the beta-lactone of the formula III, wherein R 3  is H and R 4  is H and R 5  is —CH 3 , is prepared by a reaction of acetaldehyde and ketene to form beta-buyrolactone, and hydrogenation of beta-butyrolactone to form butanol; or   c) the beta-lactone of the formula III, wherein R 3  is H and R 4  is H and R 5  is —CH 3 , is prepared by the oxidation of propylene to form propylene oxide, carbonylation of propylene oxide to form beta-buyrolactone, hydrogenation of beta-butyrolactone to form butyric acid, and ketonization of butyric acid to form heptanone, and hydrogenation of heptanone to form 4-heptanol; or   d) the beta-lactone of the formula III, wherein R 3  is H and R 4  is H and R 5  is —CH 3 , is prepared by the reaction of acetaldehyde with ketene to from beta-butyrolactone, hydrogenation of beta-butyrolactone to form butyric acid, ketonization of butyric acid and hydrogenation of heptanone to form 4-heptanol; or   e) the beta-lactone of the formula III, wherein R 3  is —CH 3  and R 4  and R 5  are combined to form ═CH(CH 3 ), is prepared by preparing methyl ketene, converting the methyl ketene to (E) and (Z)-4-ethylidene-3-methyloxetan-2-one, and hydrogenating the (E) and (Z)-4-ethylidene-3-methyloxetan-2-one in the presence of a catalyst to form 2-methyl pentanol.   
     
     
         30 .- 31 . (canceled) 
     
     
         32 . A method for the preparation of propanol or butanol, or a mixture thereof, comprising:
 a) carbonylation of methanol or ethanol to form acetic acid or propanoic acid, respectively; and   b) reduction of acetic acid or propanoic acid to form ethanol or propanol, respectively;   c) carbonylation of ethanol or propanol to from propanoic acid or butanoic acid, respectively, or carbonylation of a mixture of ethanol and propanol to form a mixture of propionic acid and butyric acid; and   d) reduction of butanoic acid to form butanol; and optionally   e) hydrogenating a mixture of propionic acid and butyric acid to form a mixture of propanol and butanol.   
     
     
         33 . A fuel composition comprising the alkane compounds prepared by the method of  claim 32 . 
     
     
         34 . The fuel composition of  claim 33 , wherein the fuel composition is blended with gasoline. 
     
     
         35 . The fuel composition of  claim 34 , wherein the alkane compounds are selected from the group consisting of 1-butanol and 2-butanol, or comprising 1-butanol, 2-butanol, 2-pentanol, 3-pentanol, 2-hexanol, 3-hexanol, 2-heptanol, 4-heptanol, heptane, 3-methyl cyclohexanol, 2,6-dimethyl-4-heptanol and mixtures thereof, prepared by  claim 32 , further comprising gasoline to form gasoline fuel mixture. 
     
     
         36 . The gasoline fuel mixture of  claim 35 , wherein the gasoline comprises of at least 15%, 35%, 50%, 75% or 85% of the gasoline fuel. 
     
     
         37 . The gasoline fuel mixture of  claim 36 , wherein the mixture comprises at least 5%, 15%, 35%, 50%, 70%, 85% or 95% 3-pentanol or heptanol.

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