GB977322A - High energy fuels and methods - Google Patents

High energy fuels and methods

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Publication number
GB977322A
GB977322A GB44485/60A GB4448560A GB977322A GB 977322 A GB977322 A GB 977322A GB 44485/60 A GB44485/60 A GB 44485/60A GB 4448560 A GB4448560 A GB 4448560A GB 977322 A GB977322 A GB 977322A
Authority
GB
United Kingdom
Prior art keywords
formula
styrene
alkyl
compound
compounds
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
GB44485/60A
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 GB977322A publication Critical patent/GB977322A/en
Expired legal-status Critical Current

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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
    • 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
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G69/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process
    • C10G69/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only
    • C10G69/12—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only including at least one polymerisation or alkylation step
    • C10G69/126—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only including at least one polymerisation or alkylation step polymerisation, e.g. oligomerisation
    • 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
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/133—Compounds comprising a halogen and vanadium, niobium, tantalium, antimonium or bismuth
    • 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
    • C07C2527/135—Compounds comprising a halogen and titanum, zirconium, hafnium, germanium, tin or lead
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (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

Mixtures of position isomers of hydrocarbons of the general formula <FORM:0977322/C4-C5/1> which are useful as jet fuels, in which R1 and R11 are hydrogen, alkyl or Cyc-alkyl which together with the two adjacent carbon atoms have 2-12 carbon atoms, R11 is hydrogen or a C1-C12 alkyl or Cyc-alkyl, R111 is a C1-C12 alkyl, Cyc-cycloalkyl, hexahydroindanyl or alkhexahydroindanyl, Cyc is a C5 or C6 cycloalkane radical, m = 1-5, n = 1-3 and p = 1-5, are formed by exhaustive hydrogenation of compounds of the formula <FORM:0977322/C4-C5/2> which are obtained by alkylating a compound of the formula <FORM:0977322/C4-C5/3> with a compound of the formula <FORM:0977322/C4-C5/4> wherein R, and R1 are as above or in addition, Ar-alkyl, alkenyl or Ar-alkenyl, R11 is as above or Ar-alkyl or Ar-alkenyl, R111 is a C1-C12 alkyl, Ar-cycloalkyl, indanyl, or alkindanyl group and Ar is a C5 or C6 cycloalkane or benzene radical; the product may also contain dimers and self-alkylate derivatives of the compound of Formula I and, where the dimers are unsaturated, products obtained from the alkylation of Formula II compounds with such dimers, such products being within the scope of Formula III, and where the dimers are saturated these are Arcycloalkyl, indanyl or alkindanyl compounds within Formula II which may be alkylated to form more complicated compounds within Formula III; hydrogenated derivatives of these compounds also appear in the final product unless previously separated. The ratio of dimer and dimer alkylate to simple alkylate may be reduced by increasing the ratio of Formula II compound to Formula I compound or by variation of the catalyst which is a Lewis acid. The weight ratio of Formula II to Formula I compound is preferably 2-10: 1 and the alkylation temperature - 70 DEG to + 90 DEG C. Preferred products of Formula IV contain 14-30 carbon atoms. Hydrogenation may be effected in one or more stages, e.g. via the intermediates. <FORM:0977322/C4-C5/5> and <FORM:0977322/C4-C5/6> Examples refer to reactions between the following pairs of compounds followed by hydrogenation (1), (1A), (6) and (7) xylenes and styrene (2) toluene and styrene (3), (4) and (4A) ethylbenzene and styrene as obtained in mixture by the dehydrogenation of ethylbenzene; (5) ethylbenzene and styrene; (8) dodecylbenzene and styrene; (9) sec. amyl-benzene and styrene; (10 sec. butylbenzene and styrene; (11) cumene and styrene; (12) ethyltoluene and styrene; (13) toluene and alphamethyl-styrene; (14) xylenes and alphamethylstyrene (15) ethylbenzene and alphamethylstyrene; (16) cumene and alphamethylstyrene; (17) benzene and vinyltoluene; (18) toluene and vinyltoluene; (19 xylenes and vinyltoluene; (20) ethyltoluene and vinyltoluene; (21) toluene and divinylbenzene; (22) ethylbenzene and divinylbenzene. Specification 960,590 is referred to.
GB44485/60A 1959-12-28 1960-12-28 High energy fuels and methods Expired GB977322A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US862017A US3272879A (en) 1959-12-28 1959-12-28 High energy fuels and methods

Publications (1)

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GB977322A true GB977322A (en) 1964-12-09

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US (1) US3272879A (en)
FR (1) FR1281511A (en)
GB (1) GB977322A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2128457A1 (en) * 1971-03-02 1972-10-20 Nippon Petrochemicals Co Ltd
DE2932382A1 (en) * 1978-08-10 1980-02-28 Nippon Petrochemicals Co Ltd METHOD FOR ARALKYLATING BENZOL OR ALKYLBENZENE
DE3028132A1 (en) * 1979-07-24 1981-02-19 Nippon Petrochemicals Co Ltd METHOD FOR ARALKYLATING BENZOL OR ALKYLBENZENE
US4254292A (en) 1978-10-25 1981-03-03 Nippon Petrochemicals Co., Ltd. Method for preparing polycyclic aromatic hydrocarbons
US4816185A (en) * 1987-03-04 1989-03-28 Chevron Research Company Styrene alkylbenzene copolymers and sulfonates thereof and method of making

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3408416A (en) * 1966-10-20 1968-10-29 Goodrich Co B F Method for butenyl cyclohexenes
JPS5614705B2 (en) * 1972-03-07 1981-04-06
DE2937521A1 (en) * 1978-09-19 1980-03-27 Nippon Oil Co Ltd HYDRAULIC FLUID FOR TRANSMISSION
US5162048A (en) * 1989-09-27 1992-11-10 Kirsten, Inc. Additive for hydrocarbon fuels
CA2534083A1 (en) * 2003-08-01 2005-03-03 The Procter & Gamble Company Fuel for jet, gas turbine, rocket, and diesel engines
DE102022000497A1 (en) 2021-02-11 2022-08-11 Mathias Herrmann Reaction and design concept for engines for catalytic control / energetic triggering (e.g. with metal additives) of the internal speed (acceleration) and exit speed with influencing of temperature and pressure for improved efficiency and combustion chamber adaptation (driver concept)

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2246762A (en) * 1934-12-22 1941-06-24 Unichem Chemikalien Handels A Method for condensation
GB549930A (en) * 1941-06-09 1942-12-15 Denis Cheselden Quin Improvements relating to the manufacture and use of hydrocarbons derived from styrene and its homologues
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
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
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
US2761886A (en) * 1954-06-16 1956-09-04 Nat Distillers Prod Corp Method of coupling styrene with alkyl aromatics
US2898735A (en) * 1954-08-12 1959-08-11 Standard Oil Co Rocket propulsion method
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 (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2128457A1 (en) * 1971-03-02 1972-10-20 Nippon Petrochemicals Co Ltd
DE2932382A1 (en) * 1978-08-10 1980-02-28 Nippon Petrochemicals Co Ltd METHOD FOR ARALKYLATING BENZOL OR ALKYLBENZENE
FR2433007A1 (en) * 1978-08-10 1980-03-07 Nippon Petrochemicals Co Ltd PROCESS FOR ARALCOYLATION OF BENZENE AND ALCOYLBENZENES
US4287376A (en) 1978-08-10 1981-09-01 Nippon Petrochemicals Co., Ltd. Method for aralkylation
US4254292A (en) 1978-10-25 1981-03-03 Nippon Petrochemicals Co., Ltd. Method for preparing polycyclic aromatic hydrocarbons
DE3028132A1 (en) * 1979-07-24 1981-02-19 Nippon Petrochemicals Co Ltd METHOD FOR ARALKYLATING BENZOL OR ALKYLBENZENE
US4289918A (en) * 1979-07-24 1981-09-15 Nippon Petrochemical Company, Limited Aralkylation
US4816185A (en) * 1987-03-04 1989-03-28 Chevron Research Company Styrene alkylbenzene copolymers and sulfonates thereof and method of making

Also Published As

Publication number Publication date
FR1281511A (en) 1962-01-12
US3272879A (en) 1966-09-13

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