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1. WO2013162566 - HIGH DENSITY RENEWABLE FUELS BASED ON THE SELECTIVE DIMERIZATION OF PINENES

Publication Number WO/2013/162566
Publication Date 31.10.2013
International Application No. PCT/US2012/035155
International Filing Date 26.04.2012
IPC
C07C 403/00 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
403Derivatives of cyclohexane or of a cyclohexene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene rings, e.g. vitamin A, beta-carotene, beta-ionone
CPC
B01J 21/16
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
21Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
16Clays or other mineral silicates
B01J 23/42
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
23Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
38of noble metals
40of the platinum group metals
42Platinum
B01J 27/14
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
27Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
14Phosphorus; Compounds thereof
C10G 29/205
CCHEMISTRY; METALLURGY
10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION
29Refining of hydrocarbon oils in the absence of hydrogen, with other chemicals
20Organic compounds not containing metal atoms
205by reaction with hydrocarbons added to the hydrocarbon oil
C10G 3/47
CCHEMISTRY; METALLURGY
10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION
3Production of liquid hydrocarbon mixtures from oxygen-containing or organic materials, e.g. fatty oils, fatty acids
42Catalytic treatment
44characterised by the catalyst used
47containing platinum group metals or compounds thereof
C10G 3/50
CCHEMISTRY; METALLURGY
10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION
3Production of liquid hydrocarbon mixtures from oxygen-containing or organic materials, e.g. fatty oils, fatty acids
50in the presence of hydrogen, hydrogen donors or hydrogen generating compounds
Applicants
  • THE GOVERNMENT OF THE UNITED STATES OF AMERICA as represented by THE SECRETARY OF THE NAVY [US]/[US] (AllExceptUS)
  • HARVEY, Benjamin, G. [US]/[US] (UsOnly)
  • WRIGHT, Michael, E. [US]/[US] (UsOnly)
  • QUINTANA, Roxanne, L. [US]/[US] (UsOnly)
Inventors
  • HARVEY, Benjamin, G.
  • WRIGHT, Michael, E.
  • QUINTANA, Roxanne, L.
Agents
  • HALEY, Charlene, A.
Priority Data
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) HIGH DENSITY RENEWABLE FUELS BASED ON THE SELECTIVE DIMERIZATION OF PINENES
(FR) CARBURANTS RENOUVELABLES DE DENSITÉ ÉLEVÉE, BASÉS SUR LA DIMÉRISATION SÉLECTIVE DE PINÈNES
Abstract
(EN)
A process for making a high density fuel includes providing a catalytic amount of a selected first catalyst, such as a heterogeneous acidic catalyst, slurried in a nonpolar organic solvent under an inert atmosphere, and adding β- pinene incrementally to the slurry with stirring to form a first reaction mixture. The first reaction mixture is heated to a suitable temperature and stirred until reaction of reactants is substantially complete to form a second reaction mixture. The first catalyst is removed from the second reaction mixture. A hydrogenation catalyst, such as platinum dioxide, is added to the second reaction mixture under a hydrogen atmosphere. The second reaction mixture is stirred to allow contact of reactants until reaction of reactants is substantially complete to form a third reaction mixture containing hydrogenated α-pinene dimer and hydrogenated β-pinene dimer. The hydrogenation catalyst is removed from the third reaction mixture. The nonpolar organic solvent can be removed from the third reaction mixture to form a residue. The hydrogenated α-pinene dimer and hydrogenated β-pinene dimer are isolated from the residue to form a high density fuel.
(FR)
L'invention concerne un procédé de fabrication d'un carburant de densité élevée qui consiste à se procurer une quantité catalytique d'un premier catalyseur choisi, tel qu'un catalyseur acide hétérogène, mis en bouillie dans un solvant organique non polaire sous une atmosphère inerte, et ajouter de β-pinène par incréments à la bouillie avec une agitation pour former un premier mélange réactionnel. Le premier mélange réactionnel est chauffé à une température appropriée et agité jusqu'à ce que la réaction des réactifs soit sensiblement complète pour former un deuxième mélange réactionnel. Le premier catalyseur est retiré du deuxième mélange réactionnel. Un catalyseur d'hydrogénation, tel que le dioxyde de platine, est ajouté au deuxième mélange réactionnel sous une atmosphère d'hydrogène. Le deuxième mélange réactionnel est agité pour permettre un contact des réactifs jusqu'à ce que la réaction des réactifs soit sensiblement complète pour former un troisième mélange réactionnel contenant un dimère d'α-pinène hydrogéné et un dimère de β-pinène hydrogéné. Le catalyseur d'hydrogénation est retiré du troisième mélange réactionnel. Le solvant organique non polaire peut être éliminé du troisième mélange réactionnel pour former un résidu. Le dimère d'α-pinène hydrogéné et le dimère de β-pinène hydrogéné sont isolés du résidu pour former un carburant de densité élevée.
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