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WO1992003401A1 - Procede d'etherification - Google Patents

Procede d'etherification Download PDF

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Publication number
WO1992003401A1
WO1992003401A1 PCT/GB1991/001419 GB9101419W WO9203401A1 WO 1992003401 A1 WO1992003401 A1 WO 1992003401A1 GB 9101419 W GB9101419 W GB 9101419W WO 9203401 A1 WO9203401 A1 WO 9203401A1
Authority
WO
WIPO (PCT)
Prior art keywords
reactor
product
tertiary
unreacted
distillation column
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.)
Ceased
Application number
PCT/GB1991/001419
Other languages
English (en)
Inventor
Ernest V. Turner
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.)
BP PLC
Original Assignee
BP PLC
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 BP PLC filed Critical BP PLC
Publication of WO1992003401A1 publication Critical patent/WO1992003401A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/34—Separation; Purification; Stabilisation; Use of additives
    • C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
    • C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation

Definitions

  • the present invention relates to the production of blends of tertiary alkyl ethers and hydrocarbons.
  • MTBE methyl tertiary butyl ether
  • the MTBE may be made by reacting methanol and isobutene over an appropriate catalyst.
  • An example of such a process is that disclosed in GB 2 047 706.
  • Isobutene is a reactive material and it is possible to obtain very high yields of MTBE by reacting together isobutene and methanol in a single reactor. Thus conversions of 93-98% of the isobutene are mentioned in GB 2 047 706.
  • the product from the first reactor is subjected to a distillation step in which substantially pure MTBE is recovered from the bottom of the distillation column while unreacted hydrocarbons and methanol are taken overhead.
  • the conversion in the first reaction stage is very high and there would normally be little benefit in see i ⁇ s to obtain the reaction of the last few % of isobutene left in the hydrocarbon mixture which leaves the initial reactor.
  • An alternative approach to preparing blends of tertiary alkyl ethers and hydrocarbons is to use mixtures containing less reactive olefins, for example isopentenes or isohexenes.
  • tertiary alkyl ethers such as methyl tertiary pentyl ether (otherwise known as tertiary amyl ether (TAME)) and methyl isohexyl ether.
  • TAME tertiary amyl ether
  • the hydrocarbon feed to the first reactor may consist substantially only of C ⁇ and higher hydrocarbons. Alternatively it may also contain a C stream containing isobutene.
  • Processes for making MTBE and higher alkyl ethers such as TAME are well known and persons skilled in the art will be familiar with the types of hydrocarbon feed suitable for use in such processes.
  • reaction conditions for etherification reactions and for catalyst to be used are well known to those skilled in the art. In general it will be desirable to provide for a recycle of some product from the first reactor but with the major portion being taken off into the distillation column.
  • distillation technology will be readily able to design and operate a distillation column so as to leave the ethers derived from the C ⁇ and higher tertiary olefins in the bottoms product from the distillation column while the remaining products pass overhead.
  • a distillation column will be operated with a reflux stream.
  • the second reactor will be operated under conditions generally similar to those used in the first reactor. If the feed to the first reactor contained isobutene then the feed to the second reactor will contain MTBE in addition to the unreacted isoolefins (mainly C5 and higher) .
  • the feed from the second reactor may be processed so as to recover unreacted methanol and a product which is a mixture of unreacted hydrocarbons, including unreacted tertiary isoolefins, as well as tertiary alkyl ethers.
  • Figure 1 is a diagrammatic representation of a flow sheet for a process not according to the invention
  • Figure 2 is a diagrammatic representation of a flow sheet of a process according to the invention.
  • a mixture of methanol and a hydrocarbon fraction containing C ⁇ and C - isoolefins is fed into reactor (1) through line (2). Part of the product from reactor (1) is fed through line (3) to reactor (4). The remainder is recycled to reactor (1). The product from reactor (4) is recovered through line (5).
  • the catalyst was assumed to be an ion-exchange resin type catalyst as is commonly used in the production of tertiary alkyl ethers. Reaction conditions assumed were conventional reaction conditions.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Crystallography & Structural Chemistry (AREA)

Abstract

On augmente le rendement d'éthers d'alkyle tertiaire supérieurs obtenus de la réaction de méthanol et d'alcènes tertiaires C5 et C6 en distillant le produit provenant d'un premier réacteur et en alimentant un second réacteur en un distillat de tête provenant de la distillation.
PCT/GB1991/001419 1990-08-25 1991-08-22 Procede d'etherification Ceased WO1992003401A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9018719.6 1990-08-25
GB909018719A GB9018719D0 (en) 1990-08-25 1990-08-25 Etherification process

Publications (1)

Publication Number Publication Date
WO1992003401A1 true WO1992003401A1 (fr) 1992-03-05

Family

ID=10681254

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1991/001419 Ceased WO1992003401A1 (fr) 1990-08-25 1991-08-22 Procede d'etherification

Country Status (2)

Country Link
GB (1) GB9018719D0 (fr)
WO (1) WO1992003401A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0577464A1 (fr) * 1992-07-01 1994-01-05 Institut Francais Du Petrole Procédé de préparation d'un éther alkylique tertiaire comprenant une section réactionnelle de finition
US5852220A (en) * 1995-12-22 1998-12-22 Neste Oy Process for preparing a mixture of tertiary alkyl ethers
US7560607B2 (en) 2004-04-16 2009-07-14 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to liquid hydrocarbons
US7579510B2 (en) 2006-02-03 2009-08-25 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US8921625B2 (en) 2007-02-05 2014-12-30 Reaction35, LLC Continuous process for converting natural gas to liquid hydrocarbons
US9133078B2 (en) 2010-03-02 2015-09-15 Gtc Technology Us, Llc Processes and systems for the staged synthesis of alkyl bromides
US9193641B2 (en) 2011-12-16 2015-11-24 Gtc Technology Us, Llc Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems
US9206093B2 (en) 2004-04-16 2015-12-08 Gtc Technology Us, Llc Process for converting gaseous alkanes to liquid hydrocarbons
WO2022174081A1 (fr) * 2021-02-12 2022-08-18 Lummus Technology Llc Éthérification d'iso-oléfines c5 à haute concentration par distillation catalytique

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2521964A1 (de) * 1974-05-21 1975-11-27 Snam Progetti Verfahren zur herstellung von teralkylaethern
US4193770A (en) * 1977-12-22 1980-03-18 Gulf Canada Limited Preparation of gasoline containing tertiaryamyl methyl ether
GB2047706A (en) * 1979-04-24 1980-12-03 Inst Francais Du Petrole Process for producing methyl tert-butyl ether from methanol and isobutene
US4647703A (en) * 1984-07-10 1987-03-03 Institut Francais Du Petrole Process for producing a hydrocarbon cut of high octane number by etherification of olefins

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2521964A1 (de) * 1974-05-21 1975-11-27 Snam Progetti Verfahren zur herstellung von teralkylaethern
US4193770A (en) * 1977-12-22 1980-03-18 Gulf Canada Limited Preparation of gasoline containing tertiaryamyl methyl ether
GB2047706A (en) * 1979-04-24 1980-12-03 Inst Francais Du Petrole Process for producing methyl tert-butyl ether from methanol and isobutene
US4647703A (en) * 1984-07-10 1987-03-03 Institut Francais Du Petrole Process for producing a hydrocarbon cut of high octane number by etherification of olefins

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Hydrocarbon processing, Vol., March 1981 J.D. Chase et al.: "Maximize blend ethers with MTBE and TAME ", *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0577464A1 (fr) * 1992-07-01 1994-01-05 Institut Francais Du Petrole Procédé de préparation d'un éther alkylique tertiaire comprenant une section réactionnelle de finition
FR2693189A1 (fr) * 1992-07-01 1994-01-07 Inst Francais Du Petrole Procédé de préparation d'un éther alkylique tertiaire comprenant une section réactionnelle de finition.
US5364975A (en) * 1992-07-01 1994-11-15 Institut Francais Du Petrole Process for the production of a tertiary alkyl ether comprising a fractionation section
US5852220A (en) * 1995-12-22 1998-12-22 Neste Oy Process for preparing a mixture of tertiary alkyl ethers
US7560607B2 (en) 2004-04-16 2009-07-14 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to liquid hydrocarbons
US9206093B2 (en) 2004-04-16 2015-12-08 Gtc Technology Us, Llc Process for converting gaseous alkanes to liquid hydrocarbons
US7579510B2 (en) 2006-02-03 2009-08-25 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US8921625B2 (en) 2007-02-05 2014-12-30 Reaction35, LLC Continuous process for converting natural gas to liquid hydrocarbons
US9133078B2 (en) 2010-03-02 2015-09-15 Gtc Technology Us, Llc Processes and systems for the staged synthesis of alkyl bromides
US9193641B2 (en) 2011-12-16 2015-11-24 Gtc Technology Us, Llc Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems
WO2022174081A1 (fr) * 2021-02-12 2022-08-18 Lummus Technology Llc Éthérification d'iso-oléfines c5 à haute concentration par distillation catalytique
US12162825B2 (en) 2021-02-12 2024-12-10 Lummus Technology Llc Etherification of high concentration C5 ISO-olefins via catalytic distillation

Also Published As

Publication number Publication date
GB9018719D0 (en) 1990-10-10

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