GB977323A - High energy fuels and methods - Google Patents

High energy fuels and methods

Info

Publication number
GB977323A
GB977323A GB44486/60A GB4448660A GB977323A GB 977323 A GB977323 A GB 977323A GB 44486/60 A GB44486/60 A GB 44486/60A GB 4448660 A GB4448660 A GB 4448660A GB 977323 A GB977323 A GB 977323A
Authority
GB
United Kingdom
Prior art keywords
formula
dimers
alkyl
compounds
catalyst
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB44486/60A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Texas Butadiene & Chem Int
Original Assignee
Texas Butadiene & Chem Int
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Texas Butadiene & Chem Int filed Critical Texas Butadiene & Chem Int
Publication of GB977323A publication Critical patent/GB977323A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/04—Liquid carbonaceous fuels essentially based on blends of hydrocarbons
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B43/00—Compositions characterised by explosive or thermic constituents not provided for in groups C06B25/00 - C06B41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
    • C07C2/66—Catalytic processes
    • C07C2/68—Catalytic processes with halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
    • C07C2/66—Catalytic processes
    • C07C2/70—Catalytic processes with acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
    • C07C5/10—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of aromatic six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2525/00—Catalysts of the Raney type
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2525/00—Catalysts of the Raney type
    • C07C2525/02—Raney nickel
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
    • C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
    • C07C2527/054—Sulfuric acid or other acids with the formula H2Sn03n+1
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/08—Halides
    • C07C2527/12—Fluorides
    • C07C2527/1206—Hydrogen fluoride
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/08—Halides
    • C07C2527/12—Fluorides
    • C07C2527/1213—Boron fluoride
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
    • C07C2527/126—Aluminium chloride
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/128—Compounds comprising a halogen and an iron group metal or a platinum group metal
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/14—Phosphorus; Compounds thereof
    • C07C2527/16—Phosphorus; Compounds thereof containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/14—Phosphorus; Compounds thereof
    • C07C2527/16—Phosphorus; Compounds thereof containing oxygen
    • C07C2527/167—Phosphates or other compounds comprising the anion (PnO3n+1)(n+2)-
    • C07C2527/173—Phosphoric acid or other acids with the formula Hn+2PnO3n+1
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/025—Sulfonic acids
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S149/00—Explosive and thermic compositions or charges
    • Y10S149/12—High energy fuel compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Fuel compositions comprising mixtures of position isomers of at least one of the formulae <FORM:0977323/C4-C5/1> <FORM:0977323/C4-C5/2> <FORM:0977323/C4-C5/3> <FORM:0977323/C4-C5/4> are obtained by reaction of compounds of the formula <FORM:0977323/C4-C5/5> with compounds of the formula <FORM:0977323/C4-C5/6> in the presence of a Lewis acid catalyst followed by partial or complete hydrogenation; the composition may and usually will also contain hydrogenated products of dimers of Formula II compounds and of alkylation products of Formula I compounds with such dimers; in Formulae I and II above R, R1 and R11 are hydrogen, alkyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl or aralkyl in which the cycloalkyl morities have 5 or 6 carbon atoms, R and R1 together with the two adjacent carbons having 2-12 carbons and R11 having up to 12 carbons, R111 is a hydrogen or C1-C12 alkyl, CYC is a radical derived from a C5-C10 cycloalkene or cycloalkadiene or a dimer, trimer or tetramer thereof or from a C7-C12 dicyclic or tricyclic alkene or alkadiene or a dimer thereof, m is 1-6, n is 1 or 2, p is 1-5, and q is 1-3 provided that in powders q is greater than 2, and m, n, p and q are such that a mixture of position isomers is formed and in formulae IV-VII the same definitions apply and HYD CYC is derived from Cyc by alkylation and/or hydrogenation. The Formula I compound may be a cyclopentene; cyclopentadiene; methylcyclopentadiene; polycyclic dimers, trimers or tetramers (which are dimers of the dimers) of butadiene, isoprene, piperylene, dimethylbutadiene, cyclopentadiene or methylcyclopentadiene; cyclohexene: bicyclohexene; bicycloheptadiene; indene; cyclopentene - ethyl; C1-C3 alkyl - cycopentenealkyl cyclohexene-propyl or C1-C3 alkyl-cyclohexene-propyl. Numerous alkyl benzenes of Formula II are specified. Suitable alkylation conditions are - 80 DEG to + 90 DEG C. with a weight ratio of Formula II to Formula I compound of 2-10: 1. The catalyst may be mixed with the Formula II compound and Formula I material added to prevent dimer formation or the mixed reactants are added to the catalyst or the catalyst to the reactants. Hydrogenation is effected over Raney nickel or cobalt at below 100 DEG C. and 1,000 p.s.i. to remove non-aromatic unsaturation or at 100-5,000 p.s.i. and 100-200 DEG C. to hydrogenate completely. Specifications 970,590 and 977,322 are referred to.
GB44486/60A 1959-12-28 1960-12-28 High energy fuels and methods Expired GB977323A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US862018A US3221071A (en) 1959-12-28 1959-12-28 High energy fuels and methods

Publications (1)

Publication Number Publication Date
GB977323A true GB977323A (en) 1964-12-09

Family

ID=25337413

Family Applications (1)

Application Number Title Priority Date Filing Date
GB44486/60A Expired GB977323A (en) 1959-12-28 1960-12-28 High energy fuels and methods

Country Status (3)

Country Link
US (1) US3221071A (en)
FR (1) FR1281512A (en)
GB (1) GB977323A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0166382A2 (en) * 1984-06-21 1986-01-02 Nippon Oil Co. Ltd. High-density liquid fuel
EP0226404A2 (en) * 1985-12-05 1987-06-24 Nippon Oil Co. Ltd. High-density fuel oil
DE102006038631A1 (en) * 2006-08-17 2008-02-21 Miltitz Aromatics Gmbh Preparation of ethyl cyclohexane comprises hydrogenation of ethyl cyclohexane contaminated with ethylbenzene, in a precious metal catalyst that is suspended in the liquid phase

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3371045A (en) * 1965-02-23 1968-02-27 Sun Oil Co Eutectic mixture of octahydroanthracene and octahydrophenanthrene
US8969641B1 (en) * 1976-09-03 2015-03-03 Richard E. Ware Isomerization of tetrahyd rotricyclopentadienes to missile fuel
US6039772A (en) * 1984-10-09 2000-03-21 Orr; William C. Non leaded fuel composition
DE102016004684A1 (en) * 2016-04-19 2017-10-19 Linde Aktiengesellschaft Fuel for aerospace vehicles

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2526896A (en) * 1947-11-28 1950-10-24 Universal Oil Prod Co Production of diaryl alkanes
US2514546A (en) * 1948-01-30 1950-07-11 Universal Oil Prod Co Production of cycloalkylperhydroindan hydrocarbons
US2721226A (en) * 1949-08-17 1955-10-18 Atlantic Refining Co Conversion of aromatic hydrocarbons into alkyl cycloparaffins
US2623912A (en) * 1949-12-19 1952-12-30 Phillips Petroleum Co Manufacture of polycyclic aromatic compounds
US2645669A (en) * 1950-02-23 1953-07-14 Universal Oil Prod Co Hydrogen transfer process
US2622110A (en) * 1950-02-28 1952-12-16 Universal Oil Prod Co Production of di(cycloalkyl) alkanes
US2671815A (en) * 1950-06-21 1954-03-09 Universal Oil Prod Co Manufacture of diarylalkanes
US2691686A (en) * 1951-05-05 1954-10-12 Universal Oil Prod Co Condensation of aromatic compounds with cyclic polyolefins
US2842936A (en) * 1952-05-09 1958-07-15 Phillips Petroleum Co Rocket propellants and their utilization
US2765617A (en) * 1952-10-22 1956-10-09 Monsanto Chemicals Method of operating a turbojet engine
US2755317A (en) * 1952-11-10 1956-07-17 Universal Oil Prod Co Hydrogenation of benzene to cyclohexane
US2898735A (en) * 1954-08-12 1959-08-11 Standard Oil Co Rocket propulsion method
US3014081A (en) * 1959-04-16 1961-12-19 Exxon Research Engineering Co Synthesis of long chain alkylated aromatic compounds
US3105351A (en) * 1959-08-17 1963-10-01 Sinclair Research Inc High energy fuel consisting of a mixture of bridged polycyclichydrocarbons and methods

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0166382A2 (en) * 1984-06-21 1986-01-02 Nippon Oil Co. Ltd. High-density liquid fuel
EP0166382A3 (en) * 1984-06-21 1988-02-03 Nippon Oil Co. Ltd. High-density liquid fuel
EP0226404A2 (en) * 1985-12-05 1987-06-24 Nippon Oil Co. Ltd. High-density fuel oil
EP0226404A3 (en) * 1985-12-05 1988-02-17 Nippon Oil Co. Ltd. High-density fuel oil
DE102006038631A1 (en) * 2006-08-17 2008-02-21 Miltitz Aromatics Gmbh Preparation of ethyl cyclohexane comprises hydrogenation of ethyl cyclohexane contaminated with ethylbenzene, in a precious metal catalyst that is suspended in the liquid phase

Also Published As

Publication number Publication date
FR1281512A (en) 1962-01-12
US3221071A (en) 1965-11-30

Similar Documents

Publication Publication Date Title
GB977323A (en) High energy fuels and methods
US3219716A (en) Production of oligomers of butadiene-(1,3)
US2563074A (en) Production of spirohydrocarbons
DE1261699B (en) Jet fuels
GB977322A (en) High energy fuels and methods
US2991317A (en) Cycloolefin production
US3794692A (en) Process for the production of squalene-type-hydrocarbons
Harpp et al. Photodimerization of thianaphthene 1, 1-dioxide. Structure
GB907180A (en) A process for the preparation of alkenyl cycloalkanes
US3271438A (en) Production of polycyclic compounds
GB631839A (en) Inhibitors for motor fuels
US2363687A (en) Antioxidants
US2739993A (en) Conversion of toluene into naphthenes, benzene, and xylene
US3258502A (en) Polycyclic hydrocarbon production
US3159659A (en) Cyclopentadienyl metal diene complexes
US2998451A (en) Unsaturated mercapto amines
GB903062A (en) Dimeric p-isopropenylphenol, a process for its production and its use in the preparation of 1:3:3:trimethyl-1-p-hydroxyphenyl-indan-6-ol
Bowie et al. Studies in mass spectrometry. Part XIII. Mass spectra of disulphides; skeletal rearrangements upon electron impact
US3009001A (en) Isomerization of cyclo triene compounds
US3326992A (en) Polycyclic hydrocarbon composition
US2641600A (en) Alkenylation of furans
GB960590A (en) Improvements in or relating to chemical compositions
US3671599A (en) Oxidative dehydrogenation of multicyclic hydrocarbons
US3078309A (en) Preparation of organoboron compounds
US3886225A (en) Process for the catalytic oligomerization of 1,3-diolefins to form open-chain compounds