Renewable diamondoid fuels

Patent metadata

Field	Value
Publication number	US-9758737-B1
Application number	US-201615297285-A
Country	US
Kind code	B1
Filing date	Oct 19, 2016
Priority date	Jun 27, 2013
Publication date	Sep 12, 2017
Grant date	Sep 12, 2017

Abstract

A method to generate dense, multi-cyclic diamondoid fuels from bio-derived sesquiterpenes. This process can be conducted with both heterogeneous and homogenous catalysts and produces the targeted isomers in high yield. The resulting multi-cyclic structures impart significantly higher densities and volumetric net heats of combustion while maintaining low viscosities which allow for use at low temperature/high altitude. Moreover, bio-derived sesquiterpenes can be produced from renewable biomass sources. Use of these fuels will decrease Navy dependence on fossil fuels and will also reduce net carbon emissions.

First claim

What is claimed is:

1. A blended fuel producing by the method for synthesizing an alkyl-adamantane fuel, comprising:
providing a first isoprenoid and/or functionalized isoprenoid feedstock;
producing first mixture by hydrogenating said first feedstock with hydrogen gas using at least one first hydrogenation catalyst;
producing a second mixture by isomerizing said first mixture from about 0.3 hour to about 48 hours using a first acidic catalyst;
distilling said second mixture to produce said first alkyl-adamantane fuel; and
blending said first alkyl-adamantane fuel containing isoprenoid with fuels comprising Jet A, JP-10, JP-5, JP-8, F-76, butene oligomer fuel, hexene oligomer fuel, renewable fuels to produce fuel blends.

2. The blended fuels according to claim 1 , wherein said producing said first mixture said hydrogenation catalyst further comprises at least one transition-metal selected from the group consisting of nickel, palladium, platinum, ruthenium, and copper.

3. The blended fuels according to claim 1 , wherein said producing said first mixture said hydrogenating further comprises adding at least one polar solvent selected from the group consisting of ethyl acetate, other organic ester, acetic acid, other organic acid, methanol, ethanol, butanol, THF, dioxane, and other alcohols.

4. The blended fuels according to claim 1 , wherein producing said first mixture further comprises distilling said first mixture to produce at least one sesquiterpane.

5. The blended fuels according to claim 1 , wherein said homogeneous acidic catalyst is selected from the group consisting of AlCl 3 , FeCl 3 , TiCl 4 , ZnCl 2 , SbF 5 , BF 3 , Lewis acids based on Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Al, B, Sn, Sb in various oxidation states, and other homogeneous Lewis-acid compounds.

6. The blended fuels according to claim 5 , wherein said producing said second mixture by said isomerizing further comprises adding at least one ionic liquid selected from the group consisting of pyridinium ionic liquid, imidazolium ionic liquid, acidic ionic liquid, acidic chloroaluminate ionic liquid, clay-supported chloroaluminate ionic liquid, [1-butyl-3-methylimidazolium][bis(trifluoromethylsulfonyl imide)], [1-butyl-3-methylimidazolium][tricyanomethanide], [tri(butyltridecyl)phosphonium][bis(trifluoromethylsulfonyl imide)], triethylammonium chloroaluminate, [1-butyl-3-methylpyridinium] chloroaluminate, and [1-butyl-3-methylimidazolium] chloroaluminate.

7. The blended fuels according to claim 1 , wherein said acidic catalyst is a heterogeneous Lewis-acid selected from at least one of the group consisting of AlCl 3 , FeCl 3 , TiCl 4 , ZnCl 2 , SbF 5 , BF 3 , Lewis acids based on Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Al, B, Sn, Sb in various oxidation states, and other Lewis-acid compound, wherein said heterogeneous said acidic catalyst is supported on at least one solid material selected from the group consisting of zeolite, aluminosilicate, alumina, zirconia, titania, silica, and clay, other acidic metal oxide, cross-linked sulfonated polystyrene, other macroreticular resin, other acidic polymer, crosslinked ionic liquid, crosslinked poly(ionic liquid), and crosslinked ionic liquid gel.

8. The blended fuels according to claim 1 , wherein said producing said first mixture by hydrogenating said first feedstock is from about 1 hour to 48 hours with hydrogen gas at pressures ranging from about 1 atm to about 50 atm using said first hydrogenation catalyst at temperatures ranging from about 10° C. to 200° C. and wherein said producing said second mixture by isomerizing said first mixture is from about 0.3 hour to about 48 hours using said first acidic catalyst at pressures ranging from about 1 atm to about 10 atm at temperatures ranging from about 15° C. to about 350° C.

9. A blended fuel including Jet A, JP-10, JP-5, JP-8, F-76, butene oligomer fuel, hexene oligomer fuel, and other renewable fuels with said first alkyl-adamantane fuel produced by the methods of claim 1 .

10. A blended fuel including Jet A, JP-10, JP-5, JP-8, F-76, butene oligomer fuel, hexene oligomer fuel, and other renewable fuels with said second alkyl-adamantane fuel being 1-pentyl adamantane produced by the methods of claim 1 .

11. The blended fuels according to claim 1 , wherein said blended fuel having a density of at least 0.90 g/mL and a NHOC of at least 135,000 Btu/gal.

12. The blended fuels according to claim 9 , wherein said blended fuel having a density of at least 0.90 g/mL and a NHOC of at least 135,000 Btu/gal.

13. The blended fuels according to claim 1 , wherein said fuel having a cetane number ranging from about 30 to about 42.

14. The blended fuels fuel according to claim 1 , wherein said fuel having a cetane number ranging from about 30 to about 42.

15. The blended fuel having a cetane number ranging from about 42 to about 50 and having from about 1% to about 70% of the alkyl-adamantane fuel of claim 1 .

16. The blended fuel having a cetane number ranging from about 42 to about 50 and having from about 1% to about 70% of the alkyl-adamantane fuel of claim 9 .

Assignees

• Us Navy

Inventors

• Harvey Benjamin G

Classifications

• C10L10/12 Primary

  for improving the cetane number · CPC title

• C07C5/31

  changing the number of rings · CPC title

• C07C5/03

  of non-aromatic carbon-to-carbon double bonds · CPC title

• C07C45/68

  by increase in the number of carbon atoms · CPC title

• C10L2200/0469

  Renewables or materials of biological origin · CPC title