USA As Represented by Secretary of the Navy

Princeton University

Benjamin G Harvey

Michael E Wright

Heather A Meylemans

Matthew C Davis

Roxanne L Quintana

William Lai

Andrew P Chafin

Michael D Garrison

Alfred J Baca

Kyle E Rosenkoetter

Calvin Luke Keller

Gregory Stephen Ostrom

Kale Warren Harrison

Paul J Chirik

David C Morris

M Joseph Roberts

Lee Cambrea

Joseph W Tsang

Raymond J Meilunas

C Rose Kennedy

Karan R Doppalapudi

Joseanne Dee Woodroffe

Kenneth R McClain

The invention relation to an efficient, high-throughput method for converting isoprene and α-olefins to sustainable fuels and fuel blendstocks. The method includes coupling biologically-derived isoprene and α-olefins via hydrovinylation to generate heavier acyclic hydrocarbons, and hydrogenating the acyclic hydrocarbons to produce sustainable fuel and fuel blendstocks. The sustainable fuels and fuel blendstocks produced by this method have applications that include use as both aviation and diesel fuels and fuel blendstocks.

Sustainable turbine and diesel fuels from isoprene and α olefins

A molecular complex including a cationic lanthanide metal, two anionic ligands bonded to the cationic lanthanide metal, and a non-coordinating anion. The two anionic ligands bonded to the cationic lanthanide metal selected from the group consisting of an anionic carbon ring ligand, an anionic monodentate ligand, an anionic polydentate ligand, and combinations thereof.

Molecular complexes

The present invention provides a novel method for chemoselectively hydrogenating cyclic monoterpene precursors with reduced PtOat low temperatures, to yield products in which the alkene groups are saturated while the cyclopropane rings from the parent hydrocarbons are conserved.

Chemoselective hydrogenation of terpenes with cyclopropane groups

A novel family of cycloalkanes compounds having one or more allylidene functionalities which can be used to create cross-linked thermosets and thermoplastics having thermal stability. An example heptacyclo [6.6.0.00000] tetradecane (HCTD) complex with terminal allylidene groups at the 7- and 12-positions (HCTD-7,12-diallylidene) was generated from norbornadiene via an efficient six-step synthesis. Thermal polymerization at temperatures ranging from 160 to 240° C. yielded a robust cross-linked material with thermal stability up to 485° C. in air, a glass transition temperature of 377° C., and a char yield (600° C.) of 56% in air. Applications include heat resistant composites utilized in the aerospace, electronic, automotive and textile industries.

High density polymers based on norbornadiene

The invention relates to cyanate ester resin blends containing resveratrol-based cyanate esters. At room temperature, the cyanate ester resin blend offers improved processability by remaining a liquid or forming a solid that melts at less than 70° C. The cyanate ester resin blend includes a resveratrol-based cyanate ester and a flexible cyanate ester having a configuration different than that of the resveratrol-based cyanate ester, where the resveratrol-based cyanate ester is no more than 80% of the total mass of the cyanate esters in the cyanate ester resin blend. A composite product can include the cyanate ester resin blend and a support material. When making the composite product, the support material is combined with the cyanate resin blend and cured at temperatures ranging from about 100° C. to about 300° C.

High performance resveratrol cyanate ester formulations

The invention relates to an efficient, high-throughput method of converting monoterpenes to high performance aviation fuel blendstocks. The method is a one pot, two-step process that includes a dehydration step followed by a hydrogenation step. Both steps can proceed without the use of solvents. Use of biosynthetically generated monoterpenes by this method produces sustainable aviation fuel blendstocks having applications that include use as a full-performance or an ultra-performance jet fuel blendstock.

Method for producing high-performance aviation fuel blendstocks from monoterpenes

This invention describes resins with phosphate cores and a simple, three-step process for their synthesis. Preferred resins are cyanate ester resins with bridging phosphate groups. These resins can be cured to produce thermoset polymers having Ts of between 131 and >360° C. depending on the number of cyanate ester groups per phosphate and the substitution pattern of the aromatic rings. The high char yields of these resins, up to about 67%, coupled with the phosphate core means that these materials will have applications as fire-resistant polymers. Additionally, these materials can potentially be blended with conventional cyanate esters or other compatible thermosetting resins to improve the fire resistance of composite materials. Other applications may include use in fire-resistant circuit boards, or as surface coatings to reduce flammability of conventional composite materials or thermoplastics.

Fire resistant phosphate cyanate esters

A method for making thermosetting polyimides from resveratrol including converting resveratrol to trisaniline, reacting trisaniline with one or more dianhydride and thermosetting endcap to form amic acid, thermally imidizing amic acid to form polyimide oligomer, and cross-linking polyimide oligomer with heat and pressure to generate polyimide thermoset.

Thermosetting polyimides derived from resveratrol

A method for making crown ether functionalized substrates, which includes modifying crown ether-based molecules by reacting with carboxylic acid functionalize chains. The crown ether-based molecules are then attached to substrates, thereby forming crown ether functionalized substrates.

Crown ether functionalized substrates

A biodiesel fuel consisting of a dioxolane with one to three alkyl groups, a (CH)CHalkyl group where n ranges from 6 to 14, and the dioxolane has a total number of carbons that is equal to or less than 24 carbons.

Renewable high cetane dioxolane fuels

A diamondoid fuel comprising a cage structure including 10, 14, 18, or 22 carbons. The diamondoid fuel also includes one of one to four cyclopropyl groups bonded to the cage structure or two to four functional groups bonded to the cage structure where the functional groups are an alkyl group, an allyl group, a cyclopropyl group, or combinations thereof. Additionally, at least one functional group is an allyl group and at least one functional group is a cyclopropyl group.

Diamondoid fuels

In the present method a reaction mixture is comprised of a source of adamantane, mixed with an alkane or cycloalkane. A Lewis acid catalyst is added to the reaction mixture which is heated and then purified. The resulting alkyl diamondoid mixtures have significantly higher densities and volumetric net heats of combustion while maintaining low viscosities which allow for use at low temperature.

High density turbine and diesel fuels derived from adamantane

A method for making cyclopentadiene fuels comprising producing cyclopent-2-en-1-one or a mixture of cyclopent-2-en-1-one from a bio-based source. The cyclopent-2-en-1-one or the mixture of cyclopent-2-en-1-one is hydrogenated, thereby forming cyclopent-2-en-1-ol or a mixture of cyclopent-2-en-1-ol. The cyclopent-2-en-1-ol or the mixture of cyclopent-2-en-1-ol is dehydrated with a dehydrating agent, thereby forming cyclopentadiene or a mixture of cyclopentadiene. The cyclopentadiene or mixture of cyclopentadiene is converted to dicyclopentadiene or dihydrodicyclopentadiene. The dicyclopentadiene or dihydrodicyclopentadiene is hydrogenated, thereby forming tetrahydrodicyclopentadiene. The tetrahydrodicyclopentadiene is isomerized, thereby forming exo-tetrahydrodicyclopentadiene.

Growing community of inventors

Ridgecrest, CA, United States of America

Benjamin G Harvey