EP0049995A1 - Composition d'essence et méthode pour sa préparation - Google Patents

Composition d'essence et méthode pour sa préparation Download PDF

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Publication number
EP0049995A1
EP0049995A1 EP81304627A EP81304627A EP0049995A1 EP 0049995 A1 EP0049995 A1 EP 0049995A1 EP 81304627 A EP81304627 A EP 81304627A EP 81304627 A EP81304627 A EP 81304627A EP 0049995 A1 EP0049995 A1 EP 0049995A1
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Prior art keywords
iso
butane
methanol
methyl
butyl ether
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EP81304627A
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German (de)
English (en)
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EP0049995B1 (fr
Inventor
Ghazi Rashid Al-Muddarris
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Davy McKee AG
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Davy McKee AG
ZiAG Plant Engineering GmbH
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    • 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
    • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • C10L1/023—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for spark ignition

Definitions

  • This invention relates to a process for the production from natural gas of a novel gasoline additive and to the additive itself.
  • Gasoline is essentially a mixture of hydro- carbons containing usually 4 and more carbon atoms.
  • a gasoline must have a sufficiently high "octane rating".
  • an "anti-knock" compound such as lead tetra-ethyl.
  • anti-pollution legislation in many countries now limits the permissible levels of carbon monoxide, nitrogen oxides and hydrocarbons in exhaust gas emissions and has led to the adoption of catalytic converters as a part of motor car exhaust gas systems.
  • -Such converters utilise noble metal catalysts whose effectiveness is destroyed by the use of lead-containing gasoline.
  • aromatic compounds can be added to the gasoline in order to improve its octane rating.
  • Benzene is, however, a known carcinogen and if too much aromatic material is added the hydrocarbon emission in the exhaust gas tends to increase.
  • available quantities of aromatic compounds are limited by the nature of the crude oil used as gasoline feedstock.
  • it is expensive to cyclise and dehydrogenate linear aliphatic hydrocarbons in order to produce aromatic compounds for use as gasoline additives and production of aromatic compounds in this way represents a loss of aliphatic hydrocarbons which could otherwise be used as such in gasoline.
  • German Offenlegungsschrift No. 2626883 proposes a motor fuel consisting of a mixture of petrol and methanol, with additions of iso-propanol and motor oil.
  • oxygenated compounds that have been proposed as gasoline additives there can be mentioned acetals, and mixtures thereof with alcohols, (see United States Patent Specification No. 3869262) and a mixture of a methyl-substituted phenol, e.g. p-cresol, and an ether, e.g. methyl methoxymethyl propane, optionally together with a C l to C 4 acyclic alcohol (see United States Patent Specification No. 3976437).
  • methyl t-butyl ether is made by etherification of methanol by reaction with iso-butene, which is usually a product of oil refinery operations, e.g. in the by-product stream from steam crackers, and fluidised bed crackers (see, for example British Patent Specification No. 2049693A and French Patent -Specifications Nos. 2371408 and 2283116)
  • iso-butene is also required for production of alkylate petroleum and chemical products.
  • the supply of iso-butene from conventional oil refinery sources is limited and is inadequate to satisfy the potential market for methyl t-butyl ether as well as to meet the demands for its use in alkylate petroleum production.
  • British Patent Specification No. 1493754 and German Offenlegun g sschrift No. 2620011 describe a process for producing methyl t-butyl ether for use as a gasoline additive by processing a stream of n-butane, the n-butane first being partially isomerised to iso-butane, and the resulting n-butane/iso-butane mixture being dehydrogenated to form a mixture of n-butenes and iso-butene. This dehydrogenated mixture is then etherified with excess methanol so as to convert iso- butene to methyl t-butyl ether.
  • Unreacted methanol is extracted with water from the reaction mixture, whilst the remaining C 4 hydrocarbons are separated by distillation from the ether and returned to the dehydrogenation stage. Because of the necessary presence of n-butane which is a feature of this process it is necessary to increase the size of the plant for a given throughput in order to allow the n-butane to be circulated through the plant. Moreover, since n-butenes are recycled to the dehydrogenation stage, it is possible for butadiene to be formed as by-product which can lead to disruption in operation of the plant and which would have to be prevented from appearing in the methyl t-butyl ether product so as to obviate the risk of gum formation in the final gasoline composition. In addition the use of water extraction to separate the product ether from unreacted methanol is disadvantageous since methanol has to be recovered from the aqueous phase and the ether has to be dried.
  • British Patent Specification No. 1443745 and German Offenlegungsschrift No. 2248841 propose the production of a water-free mixture of iso-propanol, di-iso-propyl ether and by-products, suitable for use as a gasoline additive, by catalytic hydration of propylene in the gas phase.
  • Propylene is usually available as a by-product of catalytic cracking or similar oil refinery operations.
  • the present invention seeks to provide a novel gasoline additive and a process for the production thereof from natural gas which utilises the components of natural gas to optimum advantage.
  • a novel gasoline additive comprising a mixture of methanol, iso-propanol, methyl t-butyl ether and, optionally a C 5+ isomerate.
  • a preferred additive comprises, per 100 parts by weight of additive, from about - 5 to about 90 parts by weight methanol, from about 3 to about 35 parts by weight of iso-propanol, from about 3 to about 35 parts by weight of methyl t-butyl ether, and from 0 to about 35 parts by weight of a C 5+ isomerate.
  • Such an additive can be admixed with a gasoline precursor in amounts of, for example, from about 1 to about 10 parts by weight or more of additive, e.g. up to about 50 parts by weight of additive, per 100 parts by weight of gasoline precursor to form a gasoline composition.
  • Suitable gasoline precursors include gasoline itself or a component which is substantially miscible with the additive mixture and with gasoline, is substantially immiscible with water, and does not have a deleterious effect on a gasoline.
  • the gasoline precursor may include a proportion of aromatic compounds e.g. up to about 30% by weight of benzene, toluene, xylene(s), ethyl benzene, or a mixture of two or more thereof.
  • the use as gasoline precursor of alkylates, of natural gas condensates, and of paphtha is also contemplated in the preparation of the gasoline compositions of the invention.
  • a process for the production of a gasoline additive comprising a mixture of methanol, methyl t-butyl ether and isb-propanol which comprises isomerising n-butane component of a natural gas stream to iso-butane, dehydrogenating propane component of the natural gas stream to propylene and iso-butane formed by isomerisation of n-butane to iso-butene respectively, converting resulting propylene to iso-propanol, etherifying resulting iso-butene with methanol to form methyl t-butyl ether, and blending resulting iso-propanol and methyl t-butyl ether with methanol to form the gasoline additive.
  • a particularly preferred process in accordance with the invention comprises splitting a natural gas stream containing C l to C 4 hydrocarbons to provide a C l - 2 hydrocarbon-containing stream, a C 3 hydrocarbon-containing stream and a C 4 hydrocarbon-containing stream, catalytically dehydrogenating propane in the C 3 hydrocarbon-containing stream to propylene, converting resulting propylene to iso-propanol, isomerising n-butane in the C 4 hydrocarbon-containing stream to form iso-butane, catalytically dehydrogenating resulting iso-butane to form an iso-butane/iso-butene mixture, converting natural gas hydrocarbons to methanol, etherifying a portion of the resulting methanol with iso-butene in the iso-butene/iso-butane mixture to form methyl t-butyl ether, separating iso-butane from the etherification mixture, recycling separated iso-butane to the iso-
  • the C l - 2 hydrocarbon-containing stream is steam reformed to form a synthesis gas and resulting synthesis gas is catalytically converted to methanol.
  • methanol can be used without extensive purification, the sole purification step necessary being separation from any excessive amount of water in order to avoid miscibility problems.
  • the C 3 and C 4 hydrocarbons need not be separated prior to the isomerisation step, in which n-butane is isomerised to iso-butane, so that dehydrogenation of propane and of iso-butane to propylene and to iso-butene respectively can be carried out simultaneously in the same reactor or reactors.
  • separation of the C 3 and C 4 hydrocarbons is effected prior to the n-butane isomerisation step and iso-butane and n-butane are separated prior to the iso-butane dehydrogenation step.
  • Natural gas usually contains varying amounts of C 5 and heavier hydrocarbons. If the natural gas contains little or no C 7+ hydrocarbons any C 5 and C 6 hydro- carbons are preferably separated from the C 4 hydrocarbons of a C 4+ hydrocarbon-containing stream, which is formed as bottom product during separation of the C 3 hydrocarbon- containing stream, and the resulting C 5 and C 6 hydrocarbons are then subjected to isomerisation, using a conventional catalyst such as platinum. Alternatively the C 4 and C 5 + hydro- carbons separated from the natural gas can be passed together through the same isomerisation reactor or reactors and then separated into C 4 and C 5+ hydrocarbon streams, the latter of which is then subjected to isomerisation.
  • the natural gas contains significant quantities of C 7+ hydrocarbons
  • the resulting C 5 + isomerate produced by isomerisation of the C 5 and C 6 hydrocarbon components of the natural gas can then be blended in any order with the other essential components --of the gasoline additive, i.e. methanol, iso-propanol and methyl t-butyl ether, and also, if desired, with the gasoline precursor.
  • Any C 7+ hydrocarbons from the natural gas can also be blended at this stage into the gasoline additive or into the gasoline composition as part of the gasoline precursor.
  • the olefins propylene and iso-butene are produced by dehydrogenation of propane and iso-butane respectively.
  • C 4 olefins can be produced by dehydrogenating n-butane.
  • Such C 3 and/or C 4 olefins can be alkylated by reaction with iso-butane to form C 7+ hydrocarbon alkylates in the presence of a conventional catalyst, such as hydrofluoric acid or sulphuric acid.
  • the resulting alkylate can be used as, or as part of, the gasoline precursor.
  • a mixed gaseous hydrocarbon feedstock for example a natural gas which has been pretreated for removal of H 2 0, H 2 S and C0 2 therefrom, is supplied by way of line 1 to a rectifier or stripping column 2 in which the mixture is separated by distillation into a C l - 2 stream and a C 3+ stream.
  • the C l - 2 stream passes overhead and is
  • the reformer tubes which may be made for example of an alloy steel are packed with a suitable catalyst, e.g. a supported nickel oxide catalyst.
  • Suitable preheaters (not shown) are provided to raise the C l - 2 stream to a suitable inlet temperature e. g. about 350°C prior to entry to the reformer tubes.
  • the bottom fraction from column 2 consisting of C 3 and heavier hydrocarbons, passes through line 6 to a column 7 in which the C 3 fraction is distilled overhead whilst C 4 and higher hydrocarbons are removed through line 8 as bottom product and are passed to a further column 9 in which the C 4 fraction is distilled overhead and C 5 and higher hydrocarbons are removed through line 10 as bottom product.
  • the C 4 fraction which consists mainly of n-butane, passes through line 11 to a de-iso-butanisation column 12 in which the C 4 hydrocarbons are split into an iso-butane fraction and an n-butane fraction.
  • n-butane is drawn off as bottom product through line 13 and is supplied to a catalytic isomerisation reactor 14, in which n-butane is partially isomerised to iso-butane by passage, for example, over a platinum-containing catalyst at 150 to 200°C.
  • the iso-butane/n-butane fixture is removed from the reactor 14 through line 15 and is freed from C l - 3 hydrocarbons in a depropanisation column 16, the C l - 3 hydrocarbons and hydrogen being discharged overhead by way of line 17.
  • the bottom product of the column 16 consists essentially of a mixture of n-butane and iso-butane and is returned to the de-iso-butanisation column 12 through line 18.
  • reactors 22a and 22b are supplied in turn with the iso-butane stream and the other reactors that are switched off at'any time are simultaneously regenerated with hot air which burns off coke deposited on the catalyst.
  • Dehydrogenation may be effected, for example, by passage of the iso-butane stream over a chromium oxide/aluminium oxide catalyst at a temperature in the range of from about 540°C to about 640 o C.
  • the product gas from the reactors 22a, 22b consists essentially of an iso-butane/iso-butene/hydrogen mixture and is passed via line 23 to a cooling system 24 in which it is cooled.
  • the cooled iso-butene/iso-butane/hydrogen mixture then flows through line 27 to a multi-stage compressor 28 with intermediate cooling by means of which the pressure of the mixture is raised to a pressure of, for example, 12 bar.
  • the compressed mixture then travels by way of line 29 into an absorption column 30, in which iso-butene and iso-butane are washed out of the gas mixture with an absorption oil. Hydrogen and light hydrocarbons which are formed as dehydrogenation by-products remain in the gas phase and are recovered overhead in line 31.
  • the cold absorption oil now loaded with iso-butene and iso-butane, passes via line 32 into a stripper 33, in which the iso-C 4 hydrocarbons are driven off by heating the absorption solution.
  • the regenerated absorption oil is fed through line 34 and is cooled, e.g.
  • the gas mixture consisting essentially of iso-butene and iso-butane, leaves the stripper 33 through line 35.
  • the C l - 2 hydrocarbons supplied in line 3 are steam reformed to form a synthesis gas which is then compressed in compressor 36 and passed via line 37 to a methanol synthesis reactor 38, in which methanol formation takes place in the presence of a catalyst.
  • the methanol'formed is separated from the unreacted synthesis gas by condensation in a condenser (not shown), whilst the unreacted synthesis gas is recirculated via lines 39 and 37 to the methanol synthesis reactor.
  • Line 40 serves for discharge of the purge gas from the synthesis gas loop.
  • the crude methanol is passed, after water removal, along lines 41 and 42 and is combined with the iso-C 4 hydrocarbons mixture in line 35 and with a methanol/methyl t-butyl ether mixture in line 43.
  • the resulting mixture is fed via line 44 and a preheater (not shown) to a catalytic etherification reactor 45.
  • Reactor 45 contains a solid bed catalyst, e.g. an acidic ion exchange resin having -S0 3 H or - COOH groups, and cooling means for dissipating the heat of reaction.
  • the iso-butene introduced in the mixed iso- butene/iso-butane stream in line 35 reacts with methanol to form methyl t-butyl ether.
  • the bottom product of column 47 is a mixture of methyl t-butyl ether and methanol and is fed by way of line 48 to a second pressurised column 49.
  • An azeotrope, consisting of methanol and methyl t-butyl ether, is recovered overhead from column 49 and is recycled to the etherification reactor 45 by way of lines 43 and 44. Methyl t-butyl ether is recovered as bottom product from column 49 through line 50.
  • the overhead product from column 7 consists essentially of C 3 hydrocarbons, mainly n-propane, and is recovered in line 51.
  • This C 3 hydrocarbon stream is combined with propane recycled through line 52 and the combined stream flows on through heater 53 to a plurality of C 3 dehydrogenation reactors, of which two only are shown, i.e. reactors 54a, 54b which are charged with a suitable dehydrogenation catalyst, e.g. a chromium oxide/aluminium oxide catalyst.
  • a suitable dehydrogenation catalyst e.g. a chromium oxide/aluminium oxide catalyst.
  • the reactors 54a, 54b are fed in turn with the C 3 hydrocarbon feed stream whilst the other reactors are regenerated with hot air to burn off coke deposited on the catalyst.
  • Typical dehydrogenation temperatures in reactors 54a, 54b range from about 540°C to about 640°C.
  • the resulting propylene/propane gas mixture flows on by way of line 55 to an iso-propanol plant 56 in which propylene is catalytically hydrated in the gas phase to iso-propanol. Further details of the construction and operation of plant 56 can be obtained, for example, from German Offenlegungsschrift Ko. 2248841. Unreacted propylene and propane from plant 56 pass along line 57, to a propane/propylene splitter 58 in which propane and propylene are essentially separated from each other, the propane being returned by way of line 52 to the dehydrogenation reactors 54a, 54b, while the propylene is recycled to the iso-propanol plant 56 by way of line 59.
  • the product from plant 56 is a water-free mixture of iso-propanol, di-iso-propyl ether and by-products and is suitable for use, without further purification, as a gasoline additive. This is passed along line 60.
  • the C 5+ hydrocarbon stream in line 10 is heated in heater 61 and passed to a reactor 62 charged with an isomerisation catalyst, such as a platinum-containing catalyst, and maintained at a temperature of, for example 150°C to 200°C.
  • the resulting C 5+ isomerate passes on via line 63 to a condenser 64.
  • the resulting condensate is recovered in line 65.
  • methanol plant 38 exceeds the requirements of the methyl t-butyl ether synthesis section of the illustrated plant. This excess methanol passes on through line 66 and then is either exported beyond plant limits in line 67 or is passed forward for blending with the other products of the illustrated plant by way of line 68.
  • Methyl t-butyl ether in line 50 can either be exported beyond plant limits by way of line 69 or can be passed forward for blending with the other products of the illustrated plant by way of line 70.
  • water-free crude iso-propanol in line 60 can be passed forward for blending via line 71 or exported beyond plant limits in line 72.
  • C 5+ isomerate in line 65 can likewise be passed forward for blending in line 73 whilst any excess is exported beyond plant limits in line 74.
  • the resulting blend in line 79 contains methyl t-butyl ether, iso-propanol, methanol and C 5+ isomerate, can be 'us;ed as a gasoline additive and has valuable octane rating improving qualities.
  • the streams of hydrogen and C 1-3 hydrocarbons in lines 17 and 31 are combined in line 75 and pass on for use as fuel in reformer furnace 4, the stream in line 75 being mixed with the purge gas stream in line 40 from the methanol plant 38 and with a purge gas stream in line 76 from iso-propanol plant 56. Further fuel, e.g. natural gas, is supplied through line 77 to the burners of reformer furnace 4. Reference numeral 78 indicates the line for supplying combustion air to reformer furnace 4.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)
EP81304627A 1980-10-10 1981-10-06 Composition d'essence et méthode pour sa préparation Expired EP0049995B1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB8032839 1980-10-10
GB8032839 1980-10-10
GB8107435 1981-03-10
GB8107435 1981-03-10

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EP0049995A1 true EP0049995A1 (fr) 1982-04-21
EP0049995B1 EP0049995B1 (fr) 1984-09-12

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EP81304627A Expired EP0049995B1 (fr) 1980-10-10 1981-10-06 Composition d'essence et méthode pour sa préparation

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EP (1) EP0049995B1 (fr)
CA (1) CA1169652A (fr)
DE (1) DE3166058D1 (fr)
NO (1) NO813424L (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0505843A1 (fr) * 1991-03-15 1992-09-30 Phillips Petroleum Company Procédé intégré au traitement d'oléfines
US5232464A (en) * 1991-02-26 1993-08-03 Omv Aktiengesellschaft Fuel for internal combustion engines and use of methyl formate as fuel additive
EP1203803A1 (fr) * 2000-10-24 2002-05-08 Oil Invest Ltd. Essence sans plomb du type Premium/Eurosuper

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2419439A1 (de) * 1974-04-23 1975-11-13 Huels Chemische Werke Ag Bleiarmer umweltfreundlicher vergaserkraftstoff hoher klopffestigkeit
GB1493754A (en) * 1975-06-06 1977-11-30 Texaco Development Corp Method for preparation of ethers

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2104021A (en) * 1935-04-24 1938-01-04 Callis Conral Cleo Fuel

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2419439A1 (de) * 1974-04-23 1975-11-13 Huels Chemische Werke Ag Bleiarmer umweltfreundlicher vergaserkraftstoff hoher klopffestigkeit
GB1493754A (en) * 1975-06-06 1977-11-30 Texaco Development Corp Method for preparation of ethers

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5232464A (en) * 1991-02-26 1993-08-03 Omv Aktiengesellschaft Fuel for internal combustion engines and use of methyl formate as fuel additive
AT404596B (de) * 1991-02-26 1998-12-28 Oemv Ag Treibstoff für verbrennungsmotoren und verwendung von methylformiat
EP0505843A1 (fr) * 1991-03-15 1992-09-30 Phillips Petroleum Company Procédé intégré au traitement d'oléfines
EP1203803A1 (fr) * 2000-10-24 2002-05-08 Oil Invest Ltd. Essence sans plomb du type Premium/Eurosuper

Also Published As

Publication number Publication date
CA1169652A (fr) 1984-06-26
DE3166058D1 (en) 1984-10-18
NO813424L (no) 1982-04-13
EP0049995B1 (fr) 1984-09-12

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