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WO1993021139A1 - Procede de production d'olefines - Google Patents

Procede de production d'olefines Download PDF

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Publication number
WO1993021139A1
WO1993021139A1 PCT/GB1993/000823 GB9300823W WO9321139A1 WO 1993021139 A1 WO1993021139 A1 WO 1993021139A1 GB 9300823 W GB9300823 W GB 9300823W WO 9321139 A1 WO9321139 A1 WO 9321139A1
Authority
WO
WIPO (PCT)
Prior art keywords
zeolite
process according
member channel
intersected
alkyl
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/GB1993/000823
Other languages
English (en)
Inventor
Martin Philip Atkins
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 Chemicals Ltd
Original Assignee
BP Chemicals Ltd
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
Priority claimed from GB929208739A external-priority patent/GB9208739D0/en
Priority claimed from GB929210560A external-priority patent/GB9210560D0/en
Priority claimed from GB929210548A external-priority patent/GB9210548D0/en
Priority claimed from GB929210918A external-priority patent/GB9210918D0/en
Application filed by BP Chemicals Ltd filed Critical BP Chemicals Ltd
Priority to JP5518149A priority Critical patent/JPH06508640A/ja
Priority to EP93909070A priority patent/EP0591504A1/fr
Publication of WO1993021139A1 publication Critical patent/WO1993021139A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/65—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the ferrierite type, e.g. types ZSM-21, ZSM-35 or ZSM-38
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65

Definitions

  • the present invention relates to a process for the production of olefins by utilising a zeolite catalyst in the conversion of an oxygenate feed.
  • Olefins in particular, branched olefins such as isobutene are valuable industrial products and are often used as the starting materials for the production of other desirable chemicals.
  • Isobutene may be polymerised to provide polyisobutene which is a valuable chemical in the detergents and fuel industry.
  • polyisobutene is used as a fuel additive and a lubricant.
  • Isobutene may be produced via various reaction schemes including the catalytic conversion of oxygenates such as methanol as disclosed in our European Patent Applications 485145 and 489497.
  • isobutene may be produced from the cracking of the petroleum additive tertiary butyl alcohol (TBA) . This may be achieved using an alumina catalyst.
  • TSA tertiary butyl alcohol
  • the present invention provides a process for the production of olefins which comprises passing a feed containing an oxygenate of the general formul I
  • the present invention provides a method of producing olefins from an oxygenate containing feed which requires a lower operating temperature than known prior art processes. Furthermore, by-product yield is minimised,thus providing an improvement in the selectivity to the desired product.
  • the process of the present invention provides a method of cracking an oxygenate to produce an olefin.
  • the oxygenate is of general formula R-O-R ⁇ -.
  • R of general formula I is an alkyl of 4 or 5 carbon atoms and is preferably a secondary or tertiary alkyl. It is especially preferred that R is tertiary butyl.
  • ⁇ - of general formula. I is H or alkyl optionally substituted with an ether group.
  • ⁇ is C ⁇ to C alkyl, especially methyl or ethyl.
  • R 1 is -(CH2-) n -O 2 where R 2 is C2 to C4 alkyl
  • the process of the present invention is particularly suitable for the production of isobutene from methyl tertiary butyl ether
  • MTBE 2-methoxy butane
  • TSA tertiary butyl alcohol
  • SBA secondary butyl alcohol
  • the feed may be obtained from any suitable source and may be fed into the reaction chamber either with or without a diluent.
  • suitable diluents include steam or an inert gas, e.g. nitrogen, hydrogen, or an alkane.
  • the mole 1 of the diluent gas present may suitably be, for example, up to 50X, preferably up to 25Z, especially from 5 to 10X.
  • the feed contains an alcohol, for example TBA.
  • the percent weight of water present in the feed will affect the selectivity to isobutene.
  • the feedstream may contain from up to 30X weight of water, preferably up to 20X weight and especially up to 10X weight water.
  • Zeolites which may be used in the present invention include TON (Theta-1, Nu-10, ZSM-22, KZ-2, ISI-1) , MTT (ZSM-23, EU-13, ISI-4, KZ-1), ZSM-48, FER (FU-9, Nu-23, ISI-6, ZSM-35) and EUO (EU-1, TPZ-3, ZSM-50), all of which contain a 10- membered channel that is not intersected by another 10- or 12- membered channel.
  • MTW ZSM-12, CZH-5, Theta-3, TPZ-12
  • MOR mordenite
  • MTW ZSM-12, CZH-5, Theta-3, TPZ-12
  • MOR memory
  • MTW ZSM-12, CZH-5, Theta-3, TPZ-12
  • MOR memory
  • MTW ZSM-12, CZH-5, Theta-3, TPZ-12
  • MOR memory
  • MTW ZSM-12, CZH-5, Theta-3, TPZ-12
  • MOR memory
  • the preferred zeolite is TON. Information on zeolite structures is given in the Atlas of Zeolite Structure Types by Meier WM and Olsen DH, 1987, distributed by Polycrystal Book Service, Pittsburgh, USA. All of these known zeolite structure types can be prepared by published literature methods.
  • the synthetic zeolite immediately after synthesis contains cations which, depending upon the precise synthesis method used, may be hydrogen, aluminium, alkali metals, organic nitrogen containing cations or any combination thereof.
  • the zeolite is preferably used in the present process in the hydrogen form.
  • the hydrogen form may be achieved by, in the case of organic containing zeolite, calcination to remove the organics followed by either ammonium ion exchange followed by calcination, proton exchange with an acid solution or a combination of both.
  • the hydrogen form could, if desired, be prepared by either direct ammonium exchange followed by calcination or proton exchange with acid solution or a combination of both.
  • the hydrogen form of the zeolite also may be partially exchanged or impregnated with a metal such as Ga or Mg and used in the present process.
  • the zeolite may be modified to alter its acidity or shape selectivity in such a way to improve the catalytic performance.
  • the modifications may include a calcination regime, steam treatment, chemical treatment, e.g. with a dealu inating agent such as SiCl , EDTA, etc or an aluminating agent such as sodium aluminate, AICI3 inclusion of phosphorus compound, Lewis base, HF etc.
  • a combination of treatments may also be carried out.
  • the treatment step may be carried out during the preparation of the H-form or be carried out after preparation of the H-form.
  • the zeolite may be bound in a suitable binding material.
  • the binder may suitably be one of the conventional alumina, silica, clay or aluminophosphate binders or a combination of binders.
  • the process according to the invention may suitably be carried out at a temperature of from 100 to 400 ⁇ C, preferably 150 to 300"C, especially 150 - 200'C, and is preferably carried out at atmospheric pressure, although other pressures may be used if desired, eg up to 15 barg.
  • the oxygenate feed may be fed into the reaction chamber either with or without diluents at a rate of suitably 0.1 to 50, preferably 0.9 to 10, especially 0.9 to 4.5 liquid hourly space velocity (LHSV) .
  • LHSV liquid hourly space velocity
  • liquid hourly space velocity is defined as the volume of feed fed per volume of catalyst per hour.
  • the process of the present invention may be carried out in any suitable reactor, for example a fixed bed, fluid bed, a reactive distillation column, a slurry reactor or a continuous catalyst regeneration reactor.
  • the preferred reactor is a fixed bed reactor.
  • the reactor may be made from any suitable material, e.g. steel or quartz.
  • the product of the process of the present invention will, of course, be dependent upon the feed.
  • R is butyl
  • the product comprises butenes, e.g. n-butene and iso-butene.
  • R is pentyl
  • the product comprises pentenes, e.g. n-pentene and iso-pentene.
  • the product stream will also comprise water. Additionally, small amounts of other alkenes such as ethene, propene, hexene, octene, and the corresponding alcohols may also be present.
  • Theta-1 was synthesised using ammonia as the templating agent.
  • Sodium aluminate (19.67g, 61wtX AI2O3, 38wtX a2 ⁇ ) and sodium hydroxide (17.58g ex BDH) were dissolved in distilled water (240g) .
  • Ammonia solution (1400g, SG 0.90° containing 25% ammonia) was added with gentle mixing.
  • Ludox AS40 (Trade Mark) (1200g) silica gel which contained 40wtZ silica was added over 20 minutes with stirring to maintain a homogeneous hydrogel.
  • the molar composition of the hydro el was:
  • Example 1 The Theta-1 as synthesised in Example 1 which contained both Na + and H4 + ions was directly ion exchanged in order to remove the Na + ions.
  • the zeolite was mixed for 1 hour at room temperature with an aqueous ammonium nitrate solution (1M, zeolite to solution weight ratio of 1:20).
  • the zeolite was filtered, washed and the ion exchange treatment repeated twice.
  • the ammonium form of the zeolite was then dried at 100 ⁇ C and calcined overnight in air at 550°C to convert it to the hydrogen form.
  • the X-ray diffraction pattern of the H-form is shown in Table 1.
  • the zeolite powder (H-form) was pressed into tablets at 10 tonnes. The tablets were broken and sieved into granules to pass through 850 micron but not 600 micron sieves.
  • An 7.8ml volume of the catalyst weight 3.15 was loaded into a quartz reactor with a 35ml preheater zone in an isothermal Carbolite furnace, activated in air at a rate of 600ml per hour following the temperature profile: room temperature l°C/minutev 120°C (2 hours) l°C/minute. 500C° (14- hours.-10°C/minute-.150°C initial test temperature.
  • TBA Tertiary butyl alcohol
  • the zeolite powder (H-form) was pressed into tablets at 10 tonnes. The tablets were broken and sieved into granules to pass through 850 micron but not 600 micron sieves.
  • An 8.2ml volume of the catalyst weight 4.34g was loaded into a quartz reactor with a 25ml preheater zone in an isothermal Carbolite furnace, activated in air at a rate of 600ml per hour following the temperature profile: room temperature 2°C/minute 300 ⁇ C (12 hours)-10°C/hour >. 175°C.
  • Methyl tertiary butyl ether was pumped into the reactor using a perfusor syringe driver fitted with a 50ml syringe. On entering the reactor, the MTBE was vapourised and mixed with nitrogen (gas flow of 680ml per hour). Table 3 provides the product stream analyses obtained for the reaction. Comparative Example 1
  • Example 3 The process of Example 3 was repeated using a commercial alumina catalyst of surface area 184 ⁇ 4m'/g and mean pore volume of 19nm. A 7.8ml volume of the catalyst (weight 5.13g) was used.
  • the catalyst was purchased from ARCO under the trade name of UOP CAB 2L and came in the form of 3mm spheres. Table 3 provides the product stream analysis obtained for the reaction. It can be seen that conversion of tertiary butyl alcohol is considerably less when an alumina catalyst is used in the process. Selectivity to isobutene is also less than in the corresponding process using the zeolite catalyst. Comparative Example 2
  • Comparative Example 1 The process of Comparative Example 1 was repeated using methyl tertiary butyl ether as the feed.
  • the product stream analysis is given in Table 4. It can be seen that conversion of MTBE is considerably less when an alumina catalyst is used in the process. Selectivity to dimethyl ether is also greater than in the corresponding process using the zeolite catalyst.

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

Abstract

Un procédé de production d'oléfines consiste à faire passer une charge contenant un oxygénat de la formule générale (I): R-O-R1, dans laquelle R représente un alkyle à 4 ou 5 atomes de carbone et R1 représente H ou alkyle, le cas échéant substitué avec un groupe éther, sur un catalyseur à zéolithe, dont la structure de base comprend un canal à 10 ou 12 éléments non coupé par un autre canal à 10 ou 12 éléments, avec comme condition que, lorsque R1 représente H, la zéolithe ait une structure de base comprenant un canal à 10 éléments non coupé par un autre canal à 10 ou 12 éléments.
PCT/GB1993/000823 1992-04-22 1993-04-20 Procede de production d'olefines Ceased WO1993021139A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP5518149A JPH06508640A (ja) 1992-04-22 1993-04-20 オレフィンの製造方法
EP93909070A EP0591504A1 (fr) 1992-04-22 1993-04-20 Procede de production d'olefines

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
GB929208739A GB9208739D0 (en) 1992-04-22 1992-04-22 Process for the production of isobutene
GB9208739.4 1992-04-22
GB929210560A GB9210560D0 (en) 1992-05-18 1992-05-18 Process for the production of isobutene
GB929210548A GB9210548D0 (en) 1992-05-18 1992-05-18 Process for the production of isobutene
GB9210560.0 1992-05-18
GB9210548.5 1992-05-18
GB9210918.0 1992-05-22
GB929210918A GB9210918D0 (en) 1992-05-22 1992-05-22 Process for the production of isobutene

Publications (1)

Publication Number Publication Date
WO1993021139A1 true WO1993021139A1 (fr) 1993-10-28

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Application Number Title Priority Date Filing Date
PCT/GB1993/000823 Ceased WO1993021139A1 (fr) 1992-04-22 1993-04-20 Procede de production d'olefines

Country Status (4)

Country Link
EP (1) EP0591504A1 (fr)
JP (1) JPH06508640A (fr)
CA (1) CA2110904A1 (fr)
WO (1) WO1993021139A1 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1790627A1 (fr) * 2005-11-29 2007-05-30 BP Chemicals Limited Procédé de production d'oléfines
US7235704B2 (en) 2003-06-17 2007-06-26 Oxeno Olefinchemie Gmbh Process for preparing isobutene from tert-butanol
WO2013034708A1 (fr) * 2011-09-07 2013-03-14 Shell Internationale Research Maatschappij B.V. Procédé pour la préparation d'éthylène et de propylène à partir d'une charge de départ comprenant un éther de tert-alkyle
WO2013034699A1 (fr) * 2011-09-07 2013-03-14 Shell Internationale Research Maatschappij B.V. Procédé pour la préparation d'éthylène et de propylène à partir d'une charge de départ comprenant un éther de tert-alkyle
WO2013098198A1 (fr) * 2011-12-27 2013-07-04 Shell Internationale Research Maatschappij B.V. Catalyseur tamis moléculaire et ses procédés de formulation et d'utilisation
CN103906724A (zh) * 2011-09-07 2014-07-02 国际壳牌研究有限公司 用于制备乙烯和丙烯的方法
US8927794B2 (en) 2011-04-21 2015-01-06 Shell Oil Company Process for regenerating a coked catalytic cracking catalyst
US9115314B2 (en) 2012-04-23 2015-08-25 Shell Oil Company Process for converting a solid biomass material
US9169444B2 (en) 2011-04-21 2015-10-27 Shell Oil Company Liquid fuel composition
US9217111B2 (en) 2011-04-21 2015-12-22 Shell Oil Company Process for converting a solid biomass material
US9238779B2 (en) 2011-04-21 2016-01-19 Shell Oil Company Process for converting a solid biomass material
US20190127291A1 (en) * 2017-10-26 2019-05-02 Lyondell Chemical Technology, L.P. Methods of producing propylene and ethylene
CN111116282A (zh) * 2018-10-30 2020-05-08 中国石油化工股份有限公司 叔丁醇制烯烃的方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0054805A1 (fr) * 1980-12-19 1982-06-30 Ec Erdölchemie Gmbh Procédé de préparation d'oléfines tertiaires
EP0055529A1 (fr) * 1980-12-19 1982-07-07 Imperial Chemical Industries Plc Zéolites
GB2093721A (en) * 1981-02-02 1982-09-08 Mobil Oil Corp Selective production of olefins
EP0065400A2 (fr) * 1981-05-20 1982-11-24 Imperial Chemical Industries Plc Zéolites
US4476338A (en) * 1983-06-02 1984-10-09 Mobil Oil Corporation Olefins from methanol and/or dimethyl ether
EP0123449A1 (fr) * 1983-04-22 1984-10-31 Mobil Oil Corporation Procédé pour convertir des alcools/éthers en oléfines utilisant un catalyseur zéolithique traité à la vapeur
US5157192A (en) * 1991-11-12 1992-10-20 Mobil Oil Corporation Conversion of tertiary alcohols to C8+ olefins

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0054805A1 (fr) * 1980-12-19 1982-06-30 Ec Erdölchemie Gmbh Procédé de préparation d'oléfines tertiaires
EP0055529A1 (fr) * 1980-12-19 1982-07-07 Imperial Chemical Industries Plc Zéolites
GB2093721A (en) * 1981-02-02 1982-09-08 Mobil Oil Corp Selective production of olefins
EP0065400A2 (fr) * 1981-05-20 1982-11-24 Imperial Chemical Industries Plc Zéolites
EP0123449A1 (fr) * 1983-04-22 1984-10-31 Mobil Oil Corporation Procédé pour convertir des alcools/éthers en oléfines utilisant un catalyseur zéolithique traité à la vapeur
US4476338A (en) * 1983-06-02 1984-10-09 Mobil Oil Corporation Olefins from methanol and/or dimethyl ether
US5157192A (en) * 1991-11-12 1992-10-20 Mobil Oil Corporation Conversion of tertiary alcohols to C8+ olefins

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7235704B2 (en) 2003-06-17 2007-06-26 Oxeno Olefinchemie Gmbh Process for preparing isobutene from tert-butanol
KR101104106B1 (ko) * 2003-06-17 2012-01-12 에보니크 옥세노 게엠베하 ｔ-부탄올로부터의 이소부텐의 제조방법
WO2007063282A3 (fr) * 2005-11-29 2007-08-09 Bp Chem Int Ltd Procede de production d'olefines
RU2419596C2 (ru) * 2005-11-29 2011-05-27 Бп Кемикэлз Лимитед Способ получения олефинов
EP1790627A1 (fr) * 2005-11-29 2007-05-30 BP Chemicals Limited Procédé de production d'oléfines
US8440873B2 (en) 2005-11-29 2013-05-14 Bp Chemicals Limited Process for producing olefins
US8927794B2 (en) 2011-04-21 2015-01-06 Shell Oil Company Process for regenerating a coked catalytic cracking catalyst
US9248444B2 (en) 2011-04-21 2016-02-02 Shell Oil Company Process for regenerating a coked catalytic cracking catalyst
US9238779B2 (en) 2011-04-21 2016-01-19 Shell Oil Company Process for converting a solid biomass material
US9217111B2 (en) 2011-04-21 2015-12-22 Shell Oil Company Process for converting a solid biomass material
US9169444B2 (en) 2011-04-21 2015-10-27 Shell Oil Company Liquid fuel composition
WO2013034708A1 (fr) * 2011-09-07 2013-03-14 Shell Internationale Research Maatschappij B.V. Procédé pour la préparation d'éthylène et de propylène à partir d'une charge de départ comprenant un éther de tert-alkyle
US8779226B2 (en) 2011-09-07 2014-07-15 Shell Oil Company Process for preparing ethylene and propylene
CN103906724A (zh) * 2011-09-07 2014-07-02 国际壳牌研究有限公司 用于制备乙烯和丙烯的方法
CN103889933A (zh) * 2011-09-07 2014-06-25 国际壳牌研究有限公司 由包含叔烷基醚的给料制备乙烯和丙烯的方法
WO2013034699A1 (fr) * 2011-09-07 2013-03-14 Shell Internationale Research Maatschappij B.V. Procédé pour la préparation d'éthylène et de propylène à partir d'une charge de départ comprenant un éther de tert-alkyle
CN104125859A (zh) * 2011-12-27 2014-10-29 国际壳牌研究有限公司 分子筛催化剂、其配制和使用方法
WO2013098198A1 (fr) * 2011-12-27 2013-07-04 Shell Internationale Research Maatschappij B.V. Catalyseur tamis moléculaire et ses procédés de formulation et d'utilisation
US9115314B2 (en) 2012-04-23 2015-08-25 Shell Oil Company Process for converting a solid biomass material
US20190127291A1 (en) * 2017-10-26 2019-05-02 Lyondell Chemical Technology, L.P. Methods of producing propylene and ethylene
US10513472B2 (en) * 2017-10-26 2019-12-24 Lyondell Chemical Technology, L.P. Methods of producing propylene and ethylene
CN111116282A (zh) * 2018-10-30 2020-05-08 中国石油化工股份有限公司 叔丁醇制烯烃的方法
CN111116282B (zh) * 2018-10-30 2022-07-08 中国石油化工股份有限公司 叔丁醇制烯烃的方法

Also Published As

Publication number Publication date
EP0591504A1 (fr) 1994-04-13
JPH06508640A (ja) 1994-09-29
CA2110904A1 (fr) 1993-10-28

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