WO2003031539A1 - Composant d'essence oxygenee et procede de production - Google Patents

Composant d'essence oxygenee et procede de production Download PDF

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Publication number
WO2003031539A1
WO2003031539A1 PCT/FI2002/000795 FI0200795W WO03031539A1 WO 2003031539 A1 WO2003031539 A1 WO 2003031539A1 FI 0200795 W FI0200795 W FI 0200795W WO 03031539 A1 WO03031539 A1 WO 03031539A1
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WO
WIPO (PCT)
Prior art keywords
unit
etherification
gasoline
ethanol
trimethyl
Prior art date
Application number
PCT/FI2002/000795
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English (en)
Inventor
Jouni Kivi
Reetta Karinen
Outi Krause
Original Assignee
Fortum Oyj
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 Fortum Oyj filed Critical Fortum Oyj
Publication of WO2003031539A1 publication Critical patent/WO2003031539A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
    • C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/046—Alkyl tert-alkyl ether, e.g. CH3OC(CH3)3
    • 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
    • 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
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • 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
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
    • 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
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • 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
    • Y02P20/10—Process efficiency

Definitions

  • the present invention relates to a gasoline composition known as reformulated gasoline.
  • the invention concerns oxygenated gasoline components and gasoline oxygenates.
  • the invention concerns a high-octane oxygenated gasoline component and a method of producing thereof.
  • Oxygenates are oxygen-containing organic compounds added to gasoline to enhance the combustion reactions of gasoline in an engine and, due to this, to reduce carbon monoxide and hydrogen carbon emissions.
  • Commonly used oxygenates are alcohols (Cx-O-H) and ethers (Cy-O-Cz) containing 1 to 6 carbons.
  • Methyl tertiary butyl ether (MTBE) is the most widely used oxygenate in motor petrol.
  • MTBE Methyl tertiary butyl ether
  • MTBE MTBE free, high-octane oxygenated gasoline compositions are needed to comply with the regulations on gasoline in connection with air quality and to meet the requirements set by current automotive engines.
  • suitable substituting chemicals of MTBE are alcohols and ethers, such as ethanol, methanol, tert-butanol and other tertiary alkyl ethers.
  • ethanol which has good octane numbers. It can be predicted that the use of ethanol as a component of automobile gasolines will increase in near future. However, ethanol increases the vapour pressure of the gasoline and it is water-soluble.
  • Finnish Patent Application No. 20001679 concerns gasoline containing an oxygenate and a method of producing a suitable oxygenate of gasoline, namely 2,4,4-trimethyl-2- pentanol.
  • the total oxygenate concentration of the gasoline is 2 - 20 vol-% and the oxygenate consists of one or more of following compounds: 2,4,4-trimethyl-2-pentanol, 2,4,4-trimethyl-2-metoxypentane and ditertbutyl ether.
  • the research octane number (RON) and the motor octane number (MON) of the gasoline thereof is more than 90 and 80, respectively.
  • the present invention concerns a method of producing an oxygenated, MTBE free, gasoline component and the gasoline component product.
  • the invention is based on the idea that ethanol and/or heavier ethanol ethers are used as oxygenates in gasoline. Further, the invention is based on the idea of converting at least a part of the ethanol, which may remain as an oxygenate in the final gasoline, to water-insoluble ethers. Water-insoluble heavier ethers can be obtained via reacting isooctenes, in particular a mixture that consists essentially of 2,4,4-trimethyl-l-pentene and 2,4,4-trimethyl-2- pentene, with ethanol.
  • the basic raw materials suitable for the new gasoline component produced according to the present invention are field butanes and ethanol.
  • the overall process has three steps:
  • the recovered mixture is suitable for a gasoline component as such or as blended with the product recovered from the dimerization unit.
  • a remarkable advantageous feature of the process is that it is unnecessary to remove the remaining ethanol from the etherification product. Excess of ethanol can be used in the etherification step to increase the ether conversion.
  • n-butane is isomerised to isobutane with known isomerisation catalysts, such as platinum supported on alumina or zeolites.
  • known isomerisation catalysts such as platinum supported on alumina or zeolites.
  • Catofin, Oleflex, Phillips and Snamprogetti-Yarsynthesis The catalysts used are based either on supported chromia or on supported noble metal. The other difference between the processes is the way how the heat required for highly endothermic dehydrogenation reaction is supplied.
  • isobutene is converted to isooctenes on an ion-exchange resin catalyst.
  • the reaction is carried out typically under pressure in a liquid phase.
  • a small amount of an oxygenate such as methanol, tert-butyl alcohol (TB A) or MTBE, is added to improve the reaction selectivity to dimers.
  • the isooctene product consists of mainly two isomers, viz. 2,4,4-trimethyl-l-pentene and 2,4,4-trimethyl-2-pentene, which both have a carbon atom attached to a methyl group and a double bond. This type of carbon has been shown to be reactive in the etherification reaction.
  • the isooctenes react with ethanol forming the ether, 2-ethoxy-2,4,4- trimethyl pentane.
  • This reaction is also carried out in a liquid phase using a strong cation-exchange resin as a catalyst. Also other acid catalysts can be used.
  • the etherification temperature is typically less than 100 °C, since the thermodynamic equilibrium for the exothermic reaction decreases with an increase in temperature. The equilibrium conversion can be improved by applying excess of ethanol in the reaction mixture.
  • the reaction product contains unreacted isooctenes, unreacted ethanol and the formed ether, and it can be used directly as a gasoline blending component without any further separation steps.
  • the formed 2-etoxy-2,4,4-trimethylpentane has excellent properties as a gasoline component. It is almost insoluble in water, its vapour pressure is low and it has high octane numbers.
  • the liquid mixture produced according to the process of the present invention is an excellent gasoline component having high octane numbers and lower vapour pressure compared to a mixture, where only pure ethanol is used as an oxygenate.
  • the olefin content of the gasoline component decreases and the octane number increases as the result of etherification.
  • the boiling point of the used ethers is higher than that of MTBE.
  • the solubility in water of the used ethers is crucially lower than the solubility of MTBE.
  • the process for producing the gasoline component is advantageous.
  • the moderately low conversion of the ether can be improved by using excess of ethanol and the ethanol can remain in the final gasoline component.
  • the expensive process step for separating the ethanol from the product is avoided.
  • the overall process contains the step for removing alcohol from the product.
  • Ethanol is a favourable raw material of the process, since it can be produced from biomass via fermentation and therefore it is a renewable compound.
  • an oxygenated gasoline component means a liquid mixture of hydrocarbons and one or more oxygen-containing organic compounds that enhance combustion reactions of gasoline and/or reduce carbon monoxide and/or hydrocarbon emissions of automobiles.
  • FIG. 1 shows the process flow chart of the process according to the present invention.
  • Flow 1 consists essentially of isobutene.
  • Flow 2 is the dimerised product flow of flow 1, i.e. mainly di-isobutene.
  • Flow 3 contains ethanol and flow 4 is the reaction product mixture of the etherification unit 6.
  • the product contains ether, ethanol and di- isobutene.
  • unit 7 the product from the etherification is mixed with a basic gasoline, such as non-oxygenated gasoline 95.
  • a part of the dimerised product of unit 5 is separated to an other flow and mixed with the etherified product of unit 6 in unit 7.
  • the method of producing an oxygenated gasoline component comprises the following steps in the indicated order: - feeding n-butane into an isomerising unit,
  • N-butane is introduced into the isomerisation as a feed, which essentially consists of n- butane.
  • the method according to a preferred embodiment may comprise a step of blending the recovered reaction product of the etherification step with the product recovered from the dimerization unit.
  • the process may, when needed, comprise a step of separating the ethanol from the etherified product before bleinding it to the final gasoline product.
  • the molar ratio of ethanol to isooctenes that are fed to the etherification unit ranges preferably between 1 and 8.
  • the etherifcation is preferred to be carried out at a temperature below 200 °C, especially the temperature between 70 and 90 °C is preferred.
  • the preferred ether to be produced in the etherification is 2-ethoxy-2,4,4-trimethyl pentane.
  • the preferred feed to the etherification unit contains hydrocarbon feed consisting essentially of 2,4,4-trimethyl-l-pentene and 2,4,4-trimethyl-2-pentene.
  • the molar ratio of 2,4,4-trimethyl-l-pentene to 2,4,4-trimethyl-2-pentene in the hydrocarbon mixture that is fed to the etherification unit corresponds to the thermodynamic equilibrium of the mixture.
  • the oxygenated gasoline component produced according to the present invention typically consists of 2-ethoxy-2,4,4-trimethyl pentane in a quantity ranging from 2 to 20 % by weight, methyl tertbutyl ether less than 1 % by weight, ethanol in a quantity ranging from 1 to 65 % by weight, and isooctenes in a quantity ranging from 15 to 85 % by weight.
  • the oxygenated gasoline component can be blended with any type of gasoline, typically with lead-free gasoline, such as 95 and 98 type gasolines.
  • 2-ethoxy-2,4,4-trimethyl pentane is a suitable oxygenate in a reformulated gasoline.
  • the ether is used as oxygenate of a gasoline the amount of the ether is below 20 vol-%, preferably from 1 to 5 vol-%.
  • the ether can be blended with a lead-free gasoline, such as 95 and 98 type gasolines.
  • 2-ethoxy-2,4,4- trimethylpentane is formed in the etherification process according to the present invention.
  • the properties of the ether and MTBE were compared by measuring octane numbers and water solubility. Oxygenates were blended with a typical gasoline and RON and MON values were determined. In following (table 1) characteristics of 2-etoxy-2,4,4-trimethylpentane and MTBE are compared.
  • Di-isobutene was etherified with ethanol in an etherificaiton unit.
  • the feed of the etherification unit had the ethanol to di-isobutene (DIB) molar ratio of 4, i.e. the DIB content of the feed was 37.8 wt-% and the ethanol (EtOH) content was 62.2 wt-%.
  • DIB di-isobutene
  • EtOH ethanol
  • the product composition (calculated with a conversion of 10%) was roughly DIB 34.1 wt-%, EtOH 60.6 wt-% and ether 5.3 wt-% , when the etherification temperature was 50 °C.
  • the mixture had an oxygen content of 21.6 wt-%.
  • the product composition would be: DIB 26.5 wt-%, EtOH 57.5 wt-% and ether 16.0 wt-%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Abstract

L'invention concerne de l'essence composée et, en particulier, des composants d'essence oxygénée et des composés oxygénés d'essence. L'invention concerne, plus particulièrement, un procédé de production d'un composant d'essence oxygénée à indice d'octane élevé et un composant d'essence obtenu, ainsi que l'utilisation de 2-éthoxy-2,4,4-triméthyl pentane comme composant d'essence. Tout le processus de production du composant d'essence comprend trois étapes : l'isomérisation de n-butane en isobutane et la déshydrogénation d'isobutane en isobutène, la dimérisation d'isobutène en un mélange d'isooctanes, et l'étherification des isooctanes avec de l'éthanol.
PCT/FI2002/000795 2001-10-12 2002-10-10 Composant d'essence oxygenee et procede de production WO2003031539A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FI20011996 2001-10-12
FI20011996A FI111463B (fi) 2001-10-12 2001-10-12 Menetelmä oksygenoidun bensiinikomponentin valmistamiseksi ja bensiinikomponentti

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WO2003031539A1 true WO2003031539A1 (fr) 2003-04-17

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007149373A2 (fr) * 2006-06-16 2007-12-27 E. I. Du Pont De Nemours And Company Procédé d'obtention d'isooctènes à partir d'isobutanol aqueux
WO2007149371A2 (fr) * 2006-06-16 2007-12-27 E. I. Du Pont De Nemours And Company Procédé de production d'isooctènes à partir d'isobutanol sec
WO2007149372A2 (fr) * 2006-06-16 2007-12-27 E. I. Du Pont De Nemours And Company Procédé de production d'isooctènes à partir de 1-butanol aqueux
WO2008016428A2 (fr) * 2006-06-16 2008-02-07 E. I. Du Pont De Nemours And Company Procédé permettant de fabriquer des butènes à partir d'isobutanol sec
WO2008066577A1 (fr) * 2006-12-01 2008-06-05 E. I. Du Pont De Nemours And Company Procédé de fabrication d'isooctènes à partir de 2-butanol aqueux
WO2008066578A1 (fr) * 2006-12-01 2008-06-05 E. I. Du Pont De Nemours And Company Procédé de fabrication d'isooctènes à partir de 2-butanol sec
WO2008069841A2 (fr) * 2006-12-01 2008-06-12 E. I. Du Pont De Nemours And Company Procédé de préparation de butènes à partir de 2-butanol anhydre
WO2009038547A2 (fr) * 2006-06-16 2009-03-26 E. I. Du Pont De Nemours And Company Procédé de fabrication de butènes à partir de 1-butanol déshydraté

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4080180A (en) * 1976-02-17 1978-03-21 Suntech, Inc. Methyl 1,1,3,3-tetramethylbutyl ether and admixture thereof with diisobutylene
EP0408318A1 (fr) * 1989-07-10 1991-01-16 SUN COMPANY, INC. (R&M) Isomérisation d'alcanes en phase liquide
WO1991009826A1 (fr) * 1990-01-05 1991-07-11 Exxon Chemical Patents Inc. Procede de preparation d'octenes
WO2001079146A1 (fr) * 2000-04-14 2001-10-25 Fortum Oyj Procede de production d'ether

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4080180A (en) * 1976-02-17 1978-03-21 Suntech, Inc. Methyl 1,1,3,3-tetramethylbutyl ether and admixture thereof with diisobutylene
EP0408318A1 (fr) * 1989-07-10 1991-01-16 SUN COMPANY, INC. (R&M) Isomérisation d'alcanes en phase liquide
WO1991009826A1 (fr) * 1990-01-05 1991-07-11 Exxon Chemical Patents Inc. Procede de preparation d'octenes
WO2001079146A1 (fr) * 2000-04-14 2001-10-25 Fortum Oyj Procede de production d'ether

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
KARINEN R.S. ET AL.: "Etherification of C5- and C8-alkenes with C1- to C4-alcohols", CATALYSIS LETTERS, vol. 76, no. 1-2, September 2001 (2001-09-01), pages 81 - 87, XP002960567 *

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009038547A2 (fr) * 2006-06-16 2009-03-26 E. I. Du Pont De Nemours And Company Procédé de fabrication de butènes à partir de 1-butanol déshydraté
WO2007149373A2 (fr) * 2006-06-16 2007-12-27 E. I. Du Pont De Nemours And Company Procédé d'obtention d'isooctènes à partir d'isobutanol aqueux
WO2007149372A2 (fr) * 2006-06-16 2007-12-27 E. I. Du Pont De Nemours And Company Procédé de production d'isooctènes à partir de 1-butanol aqueux
WO2008016428A2 (fr) * 2006-06-16 2008-02-07 E. I. Du Pont De Nemours And Company Procédé permettant de fabriquer des butènes à partir d'isobutanol sec
US9410098B2 (en) 2006-06-16 2016-08-09 Bitamax Advanced Biofuels LLC Process for making isooctenes from aqueous isobutanol
WO2007149371A3 (fr) * 2006-06-16 2008-02-28 Du Pont Procédé de production d'isooctènes à partir d'isobutanol sec
WO2007149371A2 (fr) * 2006-06-16 2007-12-27 E. I. Du Pont De Nemours And Company Procédé de production d'isooctènes à partir d'isobutanol sec
WO2007149373A3 (fr) * 2006-06-16 2008-04-03 Du Pont Procédé d'obtention d'isooctènes à partir d'isobutanol aqueux
WO2007149372A3 (fr) * 2006-06-16 2008-02-28 Du Pont Procédé de production d'isooctènes à partir de 1-butanol aqueux
US9410099B2 (en) 2006-06-16 2016-08-09 Butamax Advanced Biofuels Llc Process for making isooctenes from aqueous isobutanol
WO2009038547A3 (fr) * 2006-06-16 2009-08-13 Du Pont Procédé de fabrication de butènes à partir de 1-butanol déshydraté
WO2008016428A3 (fr) * 2006-06-16 2008-11-20 Du Pont Procédé permettant de fabriquer des butènes à partir d'isobutanol sec
WO2008066578A1 (fr) * 2006-12-01 2008-06-05 E. I. Du Pont De Nemours And Company Procédé de fabrication d'isooctènes à partir de 2-butanol sec
WO2008069841A3 (fr) * 2006-12-01 2008-09-04 Du Pont Procédé de préparation de butènes à partir de 2-butanol anhydre
WO2008069841A2 (fr) * 2006-12-01 2008-06-12 E. I. Du Pont De Nemours And Company Procédé de préparation de butènes à partir de 2-butanol anhydre
WO2008066577A1 (fr) * 2006-12-01 2008-06-05 E. I. Du Pont De Nemours And Company Procédé de fabrication d'isooctènes à partir de 2-butanol aqueux

Also Published As

Publication number Publication date
FI111463B (fi) 2003-07-31
FI20011996A0 (fi) 2001-10-12
FI20011996A (fi) 2003-04-13

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