EP0419628A1 - Procede de production d'ethers d'alkyl tertiaire et d'alcools d'alkyl tertiaire - Google Patents

Procede de production d'ethers d'alkyl tertiaire et d'alcools d'alkyl tertiaire

Info

Publication number
EP0419628A1
EP0419628A1 EP90905790A EP90905790A EP0419628A1 EP 0419628 A1 EP0419628 A1 EP 0419628A1 EP 90905790 A EP90905790 A EP 90905790A EP 90905790 A EP90905790 A EP 90905790A EP 0419628 A1 EP0419628 A1 EP 0419628A1
Authority
EP
European Patent Office
Prior art keywords
olefins
molecular weight
feedstream
hydrocarbons
higher molecular
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.)
Withdrawn
Application number
EP90905790A
Other languages
German (de)
English (en)
Inventor
Harold Set Chung
Andrew Jackson
Margaret May-Som Wu
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.)
ExxonMobil Oil Corp
Original Assignee
Mobil Oil Corp
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 Mobil Oil Corp filed Critical Mobil Oil Corp
Publication of EP0419628A1 publication Critical patent/EP0419628A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
    • C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
    • C07C2/08—Catalytic processes
    • C07C2/10—Catalytic processes with metal oxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
    • C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
    • 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
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • C07C2521/08—Silica
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • C07C2523/24—Chromium, molybdenum or tungsten
    • C07C2523/26—Chromium
    • 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

  • This invention relates to a new integrated process for the production of lower alkyl tertiary alkyl ether or alkanol. More particularly, the invention relates to a novel combined process for the selective oligomerization of 1-alkenes and etherification or hydrati ⁇ n of iso-olefins in a C 4 + hydrocarbon feedstock for the production of methyl tertiary butyl ether (MTBE) and methyl tertiary amyl ether (TAME).
  • MTBE methyl tertiary butyl ether
  • TAME methyl tertiary amyl ether
  • C 5 -C 7 methyl alkyl ethers especially tertiary alkyl ethers such as methyl tertiary butyl ether (MTBE) and tertiary amyl methyl ether (TAME) , or the corresponding tertiary alcohol, have been found particularly useful for enhancing gasoline octane. Therefore, improvements to the processes related to the production of these ethers are matters of high importance and substantial challenge to research workers in the petroleum refining arts.
  • MTBE methyl tertiary butyl ether
  • TAME tertiary amyl methyl ether
  • isobutylene may be reacted with methanol over an acidic catalyst to provide methyl tertiary butyl ether (MTBE) and isoamylenes may be reacted with methanol over an acidic catalyst to produce tertiary-amyl methyl ether (TAME).
  • MTBE methyl tertiary butyl ether
  • TAME tertiary-amyl methyl ether
  • these iso-olefins can be hydrated in the presence of an acid catalyst to give alcohols.
  • a problem of major i ⁇ portance is the separation of the reaction products and separation of unrea ⁇ ted hydrocarbons.
  • the feedstream to an etherification process can be the C 4 and/or C 5 fraction from a fluid catalytic cracking unit containing a full spectrum of isomeric alkanes and alkenes of which only the iso-olefins react with methyl or ethyl alcchol to form the preferred lower alkyl tertiary butyl or tertiary amyl ether. How unreacted materials are separated and the utility to which they are directed greatly affects process economics.
  • Olefin hydration etrploying zeolite catalysts is known. As disclosed in U. S. Patent No. 4,214,107, lower olefins, in particular propylene, are catalytically hydrated over a
  • crystalline aluminosilicate zeolite catalyst having a silica to alumina ratio of at least 12 and a Constraint Index of from 1 to 12, e.g., acidic ZSM-5 type zeolite, to provide the coi-resp ⁇ nding alcohol, essentially free of ether and hydrocarbon by-product.
  • HVT-PAO novel lubricant oompositions
  • cct prising polyalpha-olefins and methods for their preparation employing, as catalyst, reduced chromium on a silica support
  • the process comprises contacting C 6 -C 20 1-alkene feedstock with reduced valence state chromium oxide catalyst on porous silica support under oligomerizing conditions in an oligcmerization zone whereby high viscosity, high VI (viscosity index) liquid hydrocarbon lubricant is produced having a branch ratio less than 0.19 and a pour point below -15°C.
  • the process is distinguished in that internal or iso-olefins are unreactive in the oligomerization; only terminal olefinic groups participate in the coordination catalyzed oligcmerization using reduced chromium oxide on silica. Accordingly, the observation has been made that the process is potentially useful for the separation of 1-alkenes from other isomers and for the conversion of 1-alkenes, or alpha-olefins, into useful oligcroers.
  • the present invention provides an integrated process for the preparation of lower alkanol tertiary alkyl ethers
  • Figure 1 is a block diagram illustrating the instant invention embodying oligcmerization downstream of etherification.
  • Figure 2 is a block diagram illustrating the instant invention embodying oligcmerization upstream of etherification.
  • the instant invention utilizes the unique capability of the oligcmerization process described herein, referred to as the HVT-PAO process, to selectively oligemerize 1-alkene without oligemerizing those alkenes containing only internal olefin bonds.
  • the process can, therefore, preferentially convert 1-alkenes in a mixture of hydrocarbons containing other
  • unsaturated olefinic iscmers and alkanes to produce higher polymers of 1-alkene, otherwise referred to as polyalpha-olefins, in the form of valuable higher molecular weight olefins.
  • polyalpha-olefins unsaturated olefinic iscmers and alkanes to produce higher polymers of 1-alkene, otherwise referred to as polyalpha-olefins, in the form of valuable higher molecular weight olefins.
  • These oligcmers with olefinic unsaturation can be used as starting material for detergents, additives and many other chemicals.
  • hydrocarbon feedstock such as from an POC (fluid catalytic cracking) unsaturated gas plant containing 1-alkene
  • the 1-alkene is preferentially separated, enhancing the performance of the etherification or hydration processes, such as MTBE or tertiary butyl alcohol (TEA) production.
  • POC fluid catalytic cracking
  • TAA tertiary butyl alcohol
  • oxygenates comprising lower alkanol tertiary allkyl ethers and tertiary alcchols plus higher molecular weight olefins from C 4 + hycirocarbons are produced from the same feedstream.
  • the oxygenates are produced by either etherification or hydration of olefins while the higher molecular weight olefins are produced by oligomerization of 1-alkene by the method described herein.
  • oxygenates or "oxygenate” as used herein refers to C 1 -C 8 lcwer aliphatic, acyclic alcchols or alkanol and symmetrical or unsymmetrical C 2 -C 8 ethers.
  • Olefins suitable for use as starting material in the HVT-PAO process vhich are preferentially oligcroerized when included in a feedstream to an iso-olefin etherification or hydration process include those olefins containing from 2 to 20 carbon atoms such as ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 1-octene, 1-decene, 1-dodecene and 1-tetradecene and branched chain iscmers such as 4-methyl-1-pentene. Also suitable for use are refinery olefinic hydrocarbon feedstocks or effluents containing alphaolefins.
  • feedstock will also be rich in C 4 + iso-olefins and other olefin iscmers and generally is comprised of 1-butene, 2-butene, iscbutene, 1-pe ⁇ tene, 2-pentene and isoamylene and higher hydrocarbons.
  • alpha-olefin oligcmers are prepared by
  • oligcmerization reactions in which a major proportion of the double bonds of the alpha-olefins are not isomerized.
  • These reactions include alpha-olefin oligcmerization by supported metal oxide catalysts, such as Cr compounds on silica or other supported IUPAC Periodic Table Group VIB compounds.
  • the catalyst most preferred is a lcwer valence Group VIB metal oxide on an inert support.
  • Preferred supports include silica, alumina, titania, silica alumina, magnesia and the like.
  • the support material binds the metal oxide catalyst.
  • Porous substrates having a pore opening of at least 40 x 10 -7 mm (40 angstroms) are preferred.
  • the support material usually lias high surface area and large pore volumes with average pore size of 40 to 350 x 10 -7 mm
  • the high surface area is beneficial for supporting large amounts of highly dispersive, active chromium metal centers and to give maximum efficiency of metal usage, resulting in very high activity catalyst.
  • the support should have large average pore openings of at least 40 x 10 -7 mm (40 angstroms), with an average pore opening of >60 to 300 x 10 -7 mm
  • the supported metal oxide catalysts are preferably prepared by impregnatirig metal salts in water or organic solvents onto the support. Any suitable organic solvent known to the art may be used, for example, ethanol, methanol, or acetic acid.
  • the solid catalyst precursor is then dried and calcined at 200 to 900°C by air or other oxygen-cxaitaining gas. Thereafter the catalyst is reduced by any of several various and well kncwn reducing agents such as, for example, CO, H 2 , NH 3 , H 2 S, CS 2 , CE 3 SCH 3 , CH 3 SSCH 3 , metal alkyl containing compounds such as R 3 A1, R 3 B,R 2 Mg, RLi, R 2 Zn, where R is alkyl, alk ⁇ xy, aryl and the like. Preferred are CO or H 2 or metal alkyl containing ccmpounds.
  • kncwn reducing agents such as, for example, CO, H 2 , NH 3 , H 2 S, CS 2 , CE 3 SCH 3 , CH 3 SSCH 3 , metal alkyl containing compounds such as R 3 A1, R 3 B,R 2 Mg, RLi, R 2 Zn, where R is al
  • the Group VIB metal may be applied to the substrate in reduced form, such as CrII compounds.
  • the resultant catalyst is very active for oligomerizing olefins at a
  • Contact time of both the olefin and the catalyst can vary from one second to 24 hours.
  • the catalyst can be used in a batch type reactor or in a fixed bed, continuous-flow reactor.
  • the support material may be added to a solution of the metal compounds, e.g., acetates or nitrates, etc., and the mixture is then mixed and dried at room
  • the dry solid gel is purged at successively higher temperatures to 316°C (600°F) for a period of 16 to 20 hours. Thereafter the catalyst is cooled under an inert atmosphere to a terrperature of 250 to 450oC and a stream of pure reducing agent is contacted therewith for a period when enough CO has passed through to reduce the catalyst as indicated by a distinct color change from bright orange to pale blue. Typically, the catalyst is treated with an amount of 00 equivalent to a two-fold stoichicmetric excess to reduce the catalyst to a lower valence CrII state. Finally, the catalyst is cooled to rocm temperature and is ready for use. The following exairples of the H7I-PAD process
  • te ⁇ perature is then raised to 400°C for 2 hours.
  • the temperature is then set at 600°C with dry air purging for 16 hours.
  • the catalyst is cooled under N 2 to a temperature of 300°C.
  • a stream of pure CO 99.99% from Matheson is introduced for one hour.
  • the catalyst is cooled to room temperature under N 2 and ready for use.
  • Example 1 The catalyst prepared in Example 1 (3.2 g ) is packed in a 9.5 mm (3/8") stainless steel tubular reactor inside an N 2 blanketed dry box. The reactor under N 2 atmosphere is then heated to 150°C by a single-zone Lindberg furnace. Prepurified 1-hexene is pumped into the reactor at 1068 kBa (140 psi) and 20 ml/hr. The liquid effluent is collected and stripped of the unreacted starting material and the lew boiling material at 7 Pa (0.05 mm Hg). The residual clear, colorless liquid has
  • a commercial chrome/silica catalyst which contains 1% Cr on a large-pore volume synthetic silica gel is used.
  • the catalyst is first calcined with air at 800°C for 16 hours and reduced with CO at 300°C for 1.5 hours. Then 3.5 g of the catalyst is packed into a tubular reactor and heated to 100°C under the N 2 atmosphere. 1-Hexene is pumped through at 28 ml per hour at 101 kPa (1 atmosphere.) The products are collected and analyzed as follows:
  • a lower alcohol such as methanol, ethanol, 1-propanol or isopropanol, but preferably methanol
  • hydrocarbon feedstock such as C 4 and C 4 + feedstock containing olefins, particularly iso-olefins, to produce methyl tertiary alkyl ethers
  • the olefins may be hydrated by reaction with water to form the correspca ⁇ ding alcohol such as tertiary butyl alcohol, 2-butanol, 2-pentanol, 3-pentanol,
  • the alkanol, or lower alcchol such as methanol
  • the alkanol, or lower alcchol is generally present in an excess amount between 2 wt.% to 100 wt%, based upon iso-olefins.
  • Excess methanol means excess methanol above the stoichicmetric equivalent amount to convert iscolefins in the hydrocarbon feedstream to methyl tertiary alkyl ethers.
  • the etherification reaction effluent stream vhich comprises unreacted methanol, hydrocarbons including a major portion of C 4 + hydrocarbons and methyl tertiary alkyl ethers, are separated according to
  • Methanol may be readily obtained from coal by
  • the methanol may be obtained from natural gas by other conventional processes, such as steam rearming or partial oxidation to make the intermediate syngas. Crude methanol from such processes usually contains a significant amount of water, usually in the range of 4 to 20 wt%.
  • the etherificaticin catalyst employed is preferably an ion exchange resin in the hydrogen form; however, any suitable acidic catalyst may be employed. Varying degrees of success are obtained with acidic solid catalysts; such as, sulf ⁇ nic acid resins, phosphoric acid modified kieselguhr, silica alumina and acid zeolites.
  • Typical hydrocarbon feedstock materials for etherification reactions include olefinic streams, such as FCC light naphtha and butenes rich in iso-olefins. These aliphatic streams are produced in petroleum refineries by catalytic cracking of gas oil or the like.
  • a preferred catalyst is a bifuncti ⁇ nal ion exchange resin vhich etherifies and isomerizes the reactant streams.
  • a typical acid catalyst is Amberlyst 15 sulf ⁇ nic acid resin.
  • MIBE and TAME are kncwn to be high octane ethers.
  • Mto 83
  • the blending value of MTBE at the 10% level is about 103.
  • the blending value of 10% MTBE is about 114.
  • one embodiment of the instant invention is presented integrating the HVI-PAD process downstream of the etherification process producing MTBE or a hydration process producing TEA.
  • 1-alkene and iso-butene is fed to an etherification or hydration zone 115 together with methanol or water feedstream 120.
  • the etherification or hydration effluent is separated to provide a raffinate stream 125 containing hydrocarbons including 1-alkene while MTBE is recovered in stream 130 in the case of
  • etherification and TEA is recovered in the case of hydration.
  • the raffinate stream 125 is passed to HVI-PAD process
  • oligcmerization zone 135 vherein 1-alkene hydrocarbons are selectively converted to higher molecular olefins and, in particular, poly-1-butene liquids.
  • the effluent from the oligcmerization zone is separated to recover oligomeric olefins 140 ilncluding poly-1-butene and a stream 145 containing unreacted C 4 or C 4 + hydrocarbons.
  • FIG. 2 another embodiment of the instant invention is presented vzhere the HVI-PAD process is integrated upstream of etherification or hydration unit, m this embodiment the C 4 or C 4 + feedstream 210 conrtaining 1-alkene and iso-olefins is fed to the oligcmerization zone 215.
  • the effluent is separated and a raffinate stream 220 containing unreacted iso-olefins is passed to etherification or hydration zone 225 in conjunction with methanol or water feedstream 230 while oligcmerization product is recovered in stream 235.
  • the effluent from the etherification or hydration zone is separated to provide MTBE or TEA 240 and unreacted hydrocarbons 245.
  • the raffinate stream from MIBE or other etherification units, containing 1-, 2-toutenes and/or butanes, is reacted over Cr/SiO 2 type catalysts to give useful liquid products.
  • the residual C 4 stream, rich in 2-butene and/or butanes, can be used in alkylation units, or starting material for butadiene or isomerization reactor to upgrade 2-butene into mixed butenes.
  • the mixed C. stream is first reacted ever an Cr/SiO 2 type catalyst to selectively remove 1-butene.
  • the raffinate is then fed into a MTBE or etherification unit to remove i-butene.
  • the residual stream is rich in 2-butene and/or butanes.
  • the l-tutene is selectively removed and converted into useful liquid products over a Cr/SiO 2
  • the residual 2-butene streams can be isomerized into higher-value 1- or
  • iso-butenes can be used in alkylation units or dehydrogenated into butadiene. These operations separate 1- and 2-butenes without complicated distillation or sorption techniques.
  • liquid oligcmer product can be used as a starting material for additives, lubricants, gasoline or distillates.
  • a catalyst 3 grams, containing 3 wt% Cr on silica gel, calcined at 600°C with air for 16 hours and reduced with CO at 350°C for one hour, is packed in a 9.5 ram (3/8") stainless steel tube reactor.
  • 1-Butene is fed through the reactor at 160°C, 2520 kPa (350 psi) and WHSV of 2. After 21.5 hours reaction time, 134 grams of liquid product is collected. The conversion of 1-butene to liquid is 100%. The liquid product is fractionated to give 3 fractions:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

Procédé de production d'éthers d'alkyl tertiaire à alkyl inférieur ou d'alcools d'alkyl tertiaire, tels que l'éther butylique tertiaire méthyl (MTBE), l'éther d'amyl tertiaire méthylique (TAME) ou l'alcool butylique tertiaire dans lequel le composant 1-alkène du courant d'alimentation en hydrocarbures vers le processus d'esthérification ou d'hydratation oléfinique est séparé par oligomérisation sélective en contact avec un catalyseur en chrome sur support en silice réduit produisant des hydrocarbures utiles de poids moléculaire plus élevé, tel que l'essence, des hydrocarbures de la gamme de lubrification ou de distillation. On a également découvert que la séparation du composant 1-alkène du courant d'alimentation en hydrocarbures peut s'effectuer au cours d'une étape d'oligomérisation intégrée soit en amont soit en aval de l'étape d'éthérification.
EP90905790A 1989-03-20 1990-03-20 Procede de production d'ethers d'alkyl tertiaire et d'alcools d'alkyl tertiaire Withdrawn EP0419628A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US32574289A 1989-03-20 1989-03-20
US325742 1989-03-20

Publications (1)

Publication Number Publication Date
EP0419628A1 true EP0419628A1 (fr) 1991-04-03

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EP90905790A Withdrawn EP0419628A1 (fr) 1989-03-20 1990-03-20 Procede de production d'ethers d'alkyl tertiaire et d'alcools d'alkyl tertiaire

Country Status (5)

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EP (1) EP0419628A1 (fr)
JP (1) JPH03504730A (fr)
AU (1) AU624495B2 (fr)
CA (1) CA2028135A1 (fr)
WO (1) WO1990011268A1 (fr)

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Publication number Priority date Publication date Assignee Title
DE19629904A1 (de) * 1996-07-24 1998-01-29 Huels Chemische Werke Ag Verfahren zur Herstellung von Alkyl-tert.butylethern und Di-n-buten aus Feldbutanen
DE19629905A1 (de) * 1996-07-24 1998-01-29 Huels Chemische Werke Ag Verfahren zur Herstellung von Alkly-tert.butylethern und Di-n-buten aus Feldbutanen
EP2098498A1 (fr) * 2008-03-04 2009-09-09 ExxonMobil Chemical Patents Inc. Oligomérisation sélective d'isobutylène
US8999013B2 (en) 2011-11-01 2015-04-07 Saudi Arabian Oil Company Method for contemporaneously dimerizing and hydrating a feed having butene
CN110945109A (zh) 2017-07-27 2020-03-31 沙特基础工业全球技术有限公司 生产燃料添加剂的方法
EP3768802B1 (fr) 2018-03-19 2023-03-29 SABIC Global Technologies B.V. Procédé de production d'un additif de carburant
SG11202008334VA (en) 2018-03-19 2020-09-29 Sabic Global Technologies Bv Method of producing a fuel additive
SG11202008333XA (en) 2018-04-19 2020-09-29 Sabic Global Technologies Bv Method of producing a fuel additive
SG11202009410PA (en) 2018-05-07 2020-10-29 Sabic Global Technologies Bv Method of producing a fuel additive
SG11202009479UA (en) 2018-05-07 2020-10-29 Sabic Global Technologies Bv Method of producing a fuel additive
WO2019220257A1 (fr) 2018-05-18 2019-11-21 Sabic Global Technologies B.V. Procédé de production d'un additif de carburant par une unité d'hydratation
CN112739670B (zh) 2018-09-18 2023-07-28 沙特基础工业全球技术有限公司 用于有效生产一种或多种燃料添加剂的***和方法
CN113165996A (zh) 2018-11-20 2021-07-23 沙特基础工业全球技术有限公司 用于生产乙烯以及丁醇和烷基叔丁基醚中的至少一种的方法和***
EP4031279A1 (fr) * 2019-09-16 2022-07-27 Chevron Phillips Chemical Company Lp Catalyseurs à base de chrome et procédés de conversion d'alcanes en hydrocarbures aliphatiques supérieurs et inférieurs

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US4403999A (en) * 1981-06-25 1983-09-13 Chevron Research Company Process for producing oxygenated fuels
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US4820877A (en) * 1987-12-28 1989-04-11 Mobil Oil Corporation Etherification process improvement
US4827073A (en) * 1988-01-22 1989-05-02 Mobil Oil Corporation Process for manufacturing olefinic oligomers having lubricating properties
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US4827046A (en) * 1988-04-11 1989-05-02 Mobil Oil Corporation Extraction of crude methanol and conversion of raffinate
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Also Published As

Publication number Publication date
JPH03504730A (ja) 1991-10-17
CA2028135A1 (fr) 1990-09-21
AU5350790A (en) 1990-10-22
AU624495B2 (en) 1992-06-11
WO1990011268A1 (fr) 1990-10-04

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