Acyclic monoterpenes as biofuels based on linalool and method for making the same

Patent metadata

Field	Value
Publication number	US-9816043-B1
Application number	US-201614991436-A
Country	US
Kind code	B1
Filing date	Jan 8, 2016
Priority date	Jul 29, 2009
Publication date	Nov 14, 2017
Grant date	Nov 14, 2017

Abstract

Acyclic monterpene alcohols, like linalool, to be converted through a series of highly efficient catalytic reactions a biogasoline blending component, and a drop-in biodiesel fuel.

First claim

What is claimed is:

1. A biolubricant additives produced by the methods, comprising:
hydrogenating at least one acyclic monoterpene alcohol with at least one transition metal hydrogenation catalyst to produce a fully saturated monoterpene alcohol tetrahydrolinalool (THL), wherein said at least one acyclic monoterpene alcohol is linalool or perillyl alcohol;
dehydrating said tetrahydrolinalool (THL) with at least one acid catalyst and azeotropic distillation to produce 3,7-dimethyloctene isomers;
acid catalyzing the oligomerization of said 3,7-dimethyloctene isomers to yield a mixture of C 10 and branched C 20 , C 30 , and C 40+ oligomers, wherein the C 40+ oligomers are defined as being comprised of oligomers having C n carbon atoms where n=10i and i is an integer greater than or equal to 4 and wherein the branches comprise C 2+ alkyl groups;
hydrogenating said C 10 and branched C 20 , C 30 , and C 40+ oligomers mixture with at least one transition metal catalyst to produce a mixture of 2,6-dimethyloctane (DMO), branched hydrogenated dimers (C 20 isomers), branched hydrogenated trimers (C 30 isomers) and branched heavier hydrogenated oligomers (C 40 +);
isolating said 2,6-dimethyloctane (DMO) and said branched hydrogenated dimers (C 20 isomers), and branched hydrogenated trimers (C 30 isomers) from said mixture to produce a substantially purified set of branched hydrogenated C 10 to C 30 isomers; and
leaving said branched hydrogenated C 40+ oligomers to produce biolubricant additives.

2. A biolubricant additives produced by the methods, comprising:
hydrogenating at least one acyclic monoterpene alcohol with at least one transition metal hydrogenation catalyst to produce a fully saturated monoterpene alcohol tetrahydrolinalool (THL), wherein said transition metal catalyst is palladium supported on carbon, wherein said at least acyclic monoterpene alcohol is linalool or perillyl alcohol;
dehydrating said tetrahydrolinalool (THL) with at least one acid catalyst and azeotropic distillation to produce 3,7-dimethyloctene isomers, wherein said at least one acid catalyst selected from the group consisting of montmorillonite K10, sulfonated polystyrene to include Amberlyst-15 and Amberlyst-35, sulfonated poly-p-phenylenes, sulfonated silica materials, and similar solid supports bearing a sulfonic acid moiety;
acid catalyzing oligomerization of said 3,7-dimethyloctene isomers to yield a mixture of C 10 and branched C 20 , C 30 , and C 40+ oligomers, wherein the C 40+ oligomers are defined as being comprised of oligomers having C n carbon atoms where n=10i and i is an integer greater than or equal to 4, and wherein the branches comprise C 2+ alkyl groups;
hydrogenating said C 10 and branched C 20 , C 30 , and C 40+ oligomers mixture with at least one hydrogenation catalyst to produce a mixture of 2,6-dimethyloctane (DMO), branched hydrogenated dimers (C 20 isomers), branched hydrogenated trimers (C 30 isomers) and heavier branched hydrogenated oligomers (C 40+ ), wherein said at least one hydrogenation catalyst is selected from the group consisting of palladium on carbon, palladium hydroxide on carbon, platinum oxide, platinum on carbon, nickel/aluminum alloy, and any combination thereof;
isolating said 2,6-dimethyloctane (DMO), branched hydrogenated dimers (C 20 isomers), and branched hydrogenated trimers (C 30 isomers) from said mixture to produce a substantially purified set of branched hydrogenated C 10 to C 30 isomers for producing fuel blends; and
leaving said branched hydrogenated C 40+ oligomers to produce biolubricant additives.

3. A biolubricant additive produced by the methods, comprising:
hydrogenating at least one acyclic monoterpene alcohol with at least one transition metal hydrogenation catalyst to produce a fully saturated monoterpene alcohol tetrahydrolinalool (THL);
dehydrating said tetrahydrolinalool (THL) with at least one acid catalyst and azeotropic distillation to produce 3,7-dimethyloctene isomers;
acid catalyzing the oligomerization of said 3,7-dimethyloctene isomers to yield a mixture of C 10 and branched C 20 , C 30 , and C 40+ oligomers, wherein the branches comprise C 2+ alkyl groups;
hydrogenating said 3,7-dimethyloctene isomers and branched C 20 , C 30 , and C 40+ oligomers with at least one transition metal catalyst to produce a mixture of 2,6-dimethyloctane (DMO), hydrogenated branched dimers (C 20 isomers), hydrogenated branched trimers (C 30 isomers), and heavier hydrogenated oligomers (C 40+ );
distilling said 2,6-dimethyloctane (DMO), hydrogenated branched dimers (C 20 isomers), and hydrogenated branched trimers (C 30 isomers) from said mixture to produce a substantially purified set of hydrogenated branched C 10 to C 30 oligomers; and
leaving said branched hydrogenated C 40+ oligomers to produce biolubricant additives, wherein the C 40+ oligomers are defined as being comprised of oligomers having C n carbon atoms where n=10i and i is an integer greater than or equal to 4.

4. A biolubricant additive produced by the methods, comprising:
hydrogenating at least one acyclic monoterpene alcohol with at least one transition metal hydrogenation catalyst to produce a fully saturated monoterpene alcohol tetrahydrolinalool (THL);
dehydrating said tetrahydrolinalool (THL) with at least one acid catalyst and azeotropic distillation to produce 3,7-dimethyloctene isomers;
acid catalyzing reaction of said 3,7-dimethyloctene isomers to yield a mixture of C 10 and branched C 20 , C 30 , and C 40+ oligomers, wherein the branches comprise C 2+ alkyl groups;
hydrogenating said 3,7-dimethyloctene isomers and branched C 20 , C 30 , and C 40+ oligomers with at least one transition metal catalyst to produce a mixture of 2,6-dimethyloctane (DMO), hydrogenated branched dimers (C 20 isomers), hydrogenated branched trimers (C 30 isomers) and heavier hydrogenated branched oligomers (C 40+ );
distilling said 2,6-dimethyloctane (DMO), hydrogenated branched dimers (C 20 isomers), and hydrogenated branched trimers (C 30 isomers) from said mixture to produce a substantially purified set of hydrogenated branched C 10 to C 30 for producing fuel blends; and
combining a mixture of hydrogenated branched C 20 dimer, hydrogenated branched C 30 trimer, and said hydrogenated branched C 40+ oligomers, wherein the C 40+ oligomers are defined as being comprised of oligomers having C n carbon atoms where n=10i and i is an integer greater than or equal to 4, to produce biolubricant additives.

Assignees

• Us Navy

Inventors

• Wright Michael E
• Quintana Roxanne L
• Harvey Benjamin G

Classifications

• C07C2531/10

  sulfonated · CPC title

• C10L2290/543

  Distillation, fractionation or rectification for separating fractions, components or impurities during preparation or upgrading of a fuel · CPC title

• C07C2521/18

  Carbon · CPC title

• C10L1/04

  essentially based on blends of hydrocarbons · CPC title

• C07C2523/42

  Platinum · CPC title