EP2435388A2 - Production de 3-méthylbut-1-ène par déshydratation de 3-méthylbutan-1-ol - Google Patents

Production de 3-méthylbut-1-ène par déshydratation de 3-méthylbutan-1-ol

Info

Publication number
EP2435388A2
EP2435388A2 EP10716338A EP10716338A EP2435388A2 EP 2435388 A2 EP2435388 A2 EP 2435388A2 EP 10716338 A EP10716338 A EP 10716338A EP 10716338 A EP10716338 A EP 10716338A EP 2435388 A2 EP2435388 A2 EP 2435388A2
Authority
EP
European Patent Office
Prior art keywords
methylbut
ene
dehydration
catalyst
mass
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Withdrawn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
EP10716338A
Other languages
German (de)
English (en)
Inventor
Alfred Kaizik
Thomas Quandt
Michael Grass
Markus Winterberg
Wilfried Büschken
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.)
Evonik Operations GmbH
Original Assignee
Evonik Oxeno GmbH and Co KG
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 Evonik Oxeno GmbH and Co KG filed Critical Evonik Oxeno GmbH and Co KG
Publication of EP2435388A2 publication Critical patent/EP2435388A2/fr
Withdrawn legal-status Critical Current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
    • C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water

Definitions

  • the present invention relates to the preparation of 3-methylbut-1-ene by dehydration of 3-methyl-butan-1-ol in the presence of a mesoporous alumina having a uniform pore structure as a catalyst.
  • C 5 olefins in particular methylbutenes
  • 2-methyl-but-1-ene is a feedstock commonly used in the perfume industry and for the production of isoprene.
  • 3-Methyl-but-1-ene can be used as monomer or comonomer for the preparation of polymers or copolymers.
  • 3-methyl-but-1-ene in C5 fractions such.
  • the content of 3-methyl-1-butene in such fractions is only about 1 to 5 mass%.
  • the isolation of 3-methyl-but-1-ene from such fractions is relatively expensive.
  • Methylbutenes can industrially z. B. be prepared by metathesis reactions.
  • DE 199 32 060 describes the preparation of pentenes and methylbutenes starting from a C 4 -olefins-containing hydrocarbon Ström.
  • JP 62-108827 describes the preparation of 3-methylbut-1-ene by partial hydrogenation of isoprene.
  • No. 4,234,752 describes the preparation of 3-methylbut-1-ene by dehydration of 3-methylbutan-1-ol in the presence of a KOH-modified ⁇ -alumina catalyst. The dehydration is carried out in the gas phase at 330 ° C. in the presence of nitrogen as the carrier gas.
  • WO 2008/006633 describes the preparation of 3-methylbut-1-ene based on isobutene-containing olefin mixtures via three process steps. Isobutene is first hydroformylated in this process, the hydroformylation product 3-methylbutanal is hydrogenated to 3-methyl-1-butanol and then water is split off from the alcohol obtained.
  • 3-methyl-butan-1-ol to 3-methyl-but-1-ene are preferably used basic modified aluminas. In the example described dehydration at 340 0 C and 0.15 MPa in the gas phase is used as a catalyst with 1, 5 mass% barium compounds (calculated as barium oxide) modified ⁇ -alumina.
  • the product contained 94.5 mass% 3- Methylbut-1-en as desired product additionally 3-methylbut-2-ene, 2-methylbut-1-ene and di (3-methylbutyl) ether as by-products.
  • Alumina may occur in various structural forms depending on the method of preparation and the temperature treatment.
  • aluminum oxides are subdivided into three classes, according to Ullmann's Enzyklopadie der ischen Chemie (VCH Weinheim, Volume 7, 1974), namely the ⁇ -modification, the so-called ⁇ -forms and the special forms.
  • the other alumina modifications are surface-rich oxides.
  • the ⁇ -alumina forms are further divided into a ⁇ and a ⁇ group.
  • the most important member of the ⁇ group which also includes ⁇ -alumina, is ⁇ -alumina.
  • the ⁇ group includes the high temperature forms such as. B, ⁇ and p alumina
  • the most important catalytic property of alumina is based on the presence of acidic sites, which are principally found in every alumina modification. About that In addition, the conversion and selectivity of the chemical reactions are influenced by the pore structure and the internal surface of the aluminas.
  • 3-methylbut-1-ene can be prepared in a particularly simple manner by dehydration of 3-methyl-1-butanol by using as the catalyst a mesoporous aluminum oxide having a uniform pore structure.
  • the present invention accordingly provides a process for preparing 3-methylbut-1-ene by dehydration of 3-methylbutan-1-ol on an aluminum-containing oxide in a temperature range from 200 to 450 ° C. in the gas or liquid / gas mixture.
  • Mixed phase characterized in that an aluminum-containing oxide having a predominantly mesoporous pore structure, whose: a) relative proportion of macropores is less than 15%; b) distribution of pore diameter has a monomodal maximum in the mesopore range of 3.6 to 50 nm; c) mean pore diameter of all pores in the meso and macropores range from 5 to 20 nm; d) composition is greater than 80% of gamma-alumina is used.
  • a mixture comprising 3-methylbut-1-ene and 2-methylbut-1-ene and / or 3-methylbut-2-ene, wherein the mass fraction of 3-methylbut-1-ene is at least 90 mass % and the mass fraction of 2-methylbut-1-ene and / or 3-methylbut-2-ene is less than 10% by mass.
  • the process according to the invention has the following advantages: a) Low-cost, commercially available aluminum oxides, which are often already present in the desired form, b) can be used without aftertreatment.
  • the catalysts used according to the invention have a high activity and product selectivity.
  • ⁇ -aluminum oxides are used. It is preferable to use mesoporous aluminas having a uniform pore structure.
  • the ⁇ -aluminas used according to the invention have the following characteristics: the relative proportion of pore volume of macropores (pore diameter of 50 nm to 100 microns) in the pore diameter range from 3.6 nm to 100 microns, determined by Hg porosimetry, is less than 15%. (the relative pore volume of the macropores is the ratio of the pore volume over the entire macropore area to the total pore volume). In particular, this ratio is less than 10%, especially less than 5%.
  • the average pore diameter of all pores having a diameter of 3.6 nm to 100 ⁇ m is preferably between 5 and 20 nm, very particularly preferably between 6 and 12 nm.
  • the ⁇ -aluminum oxides used according to the invention preferably have a monomodal maximum in the pore diameter range of 3.6 to 50 nm (in particular in the pore diameter range of 5 to 20 nm) (determined by Hg porosimetry).
  • phase composition of the aluminum oxide used according to the invention determined by X-ray diffraction analysis consists of more than 80%, in particular more than 85%, very particularly more than 90%, of ⁇ -alumina.
  • the BET surface area of the aluminum oxide used according to the invention is in the range from 120 to 360 m 2 / g, in particular in the range from 150 to 200 m 2 / g.
  • the catalyst used consists of over 99% by mass of aluminum oxide. Furthermore, it may comprise titanium dioxide, silicon dioxide and up to 0.2% by mass of alkali metal oxides.
  • porous materials including the aluminum oxides according to the invention, according to the ILJPAC standard (Manual on Catalyst Characterization in Pure & Appl. Chem. Vol. 63, pp.1227, 1991) pores with a pore diameter smaller than 2 nm as micropores, pores with pore diameter in the range of 2 to 50 nm as mesopores and pores with a diameter greater than 50 nm referred to as macropores.
  • High-pressure mercury porosimetry is used to determine the pore radius distribution PRV and the pore volume PV of catalysts in the meso and macroporous region according to DIN 66133. This measuring method is based on the fact that liquid mercury does not wet the pore surface.
  • the N 2 adsorption heat in a relative pressure range (p / po) between 0.1 and 0.3 was used and the surface determined according to Braunauer-Emmet-Teller equation. The evaluation is based on the assumption of a monomolecular coverage of the inner surface of the particles, from which the numerical size of the surface can be calculated.
  • the determination of the BET surface area of the aluminas in the present invention was carried out using an ASAP 2400 sorption apparatus from Micrometics.
  • the pore volume PV and the pore radius distribution PRV in the meso and macroporous region was determined according to DIN 66133 with Hg porosimeter type Pascal 140/440 from Porotec.
  • the maximum Hg pressure of the measuring station is limited to 400 MPa (4000 bar).
  • the device allows to determine pore volumes PV and pore radius distribution PRV of pores with diameters Dp from 3.6 nm to 100 ⁇ m. From the measured total pore volume, the relative percentages of the mesopore volume can be determined with Dp from 3.6 to 50 nm and at the macropore volume with Dp> 50 nm.
  • the dehydration can be carried out in the gas or liquid / gas mixed phase.
  • the process can be carried out continuously or batchwise and on suspended or lumpy catalysts arranged in a fixed bed.
  • the dehydration is preferably carried out on solid catalysts in the temperature range from 200 to 450 0 C in the gas or gas / liquid mixed phase because of the simple separation of the reaction products from the reaction mixture.
  • a continuous dehydration is carried out on a catalyst arranged in a fixed bed.
  • the catalysts are preferably used in the form of spheres, tablets, cylinders, extrudates or rings.
  • the dehydration of 3-methyl-butan-1-ol can, for. B. adiabatic, polytropically or practically isothermal, ie with a temperature difference of typically less than 10 0 C, be performed.
  • the process step can be carried out in one or more stages. In the latter case, all reactors, advantageously tubular reactors, can be operated adiabatically or virtually isothermally. It is also possible to operate one or more reactors adiabatically and the other practically isothermal.
  • the dehydration is operated in a straight pass. However, it can also be operated under product return.
  • the specific catalyst loading is from 0.01 to 30, preferably from 0.1 to 10 kg of alcohol per kg of catalyst per hour.
  • the temperature in the catalyst layer is preferably 200 to 450 0 C, in particular 250 to 320 0 C.
  • the dehydration (dehydration) can be carried out under reduced pressure, overpressure or at atmospheric pressure.
  • the turnover in the straight pass is limited to 30 to 90%.
  • the 3-methylbut-1-ene according to the invention which can be obtained in particular by the process according to the invention, preferably contains less than or equal to 10% by mass, preferably less than or equal to 1% by mass, and more preferably from 0.001% to 1% by mass of 2-methylbut- 1-ene and / or 3-methylbut-2-ene.
  • a preferred mixture contains 3-methylbut-1-ene and 2-methylbut-1-ene and / or 3-methylbut-2-ene, wherein the mass fraction of 3-methylbut-1-ene is at least 90 mass% and the mass fraction is less than 10% by mass of 2-methylbut-1-ene and / or 3-methylbut-2-ene.
  • the mixture has at least 99% by mass, and more preferably from 99,000 to 99.999% by mass of 3-methylbut-1-ene and preferably less than or equal to 1% by mass, and more preferably from 0.001 to 1% by mass of 2-methylbut-1 en and / or 3-methylbut-2-en, wherein the proportions add up to 100%.
  • the aluminum oxides SP 537 and SP 538 F listed in Table 1 are examples of the catalysts used according to the invention. As can be seen from Table 1, they have a high proportion of mesopores.
  • the relative macropore content of total pore volume in the range of pore widths between 3.6 nm and 100 ⁇ m is less than 5%.
  • the two aluminas LD 350 and SA 31132 not according to the invention have small proportions of mesopores at high levels of macropores.
  • 3-Methylbutan-1-ol with a purity of 99.81% by mass was used in an electrically heated flow-fixed bed reactor on the aluminum oxide catalyst LD 350 in spherical form (2 - 3 mm ball) with a bulk density of 0.59 g / cm 3 reacted.
  • the liquid educt was evaporated in an upstream evaporator at 220 0 C.
  • Table 2 shows, in addition to the composition of the product, the 100% normalized distribution of the C 5 olefin isomers.
  • a 3-methylbut-1-ene content of approx. 41, 5 mass% achieved.
  • the reaction temperature increases, the formation of desired product 3-methylbut-1-en increases.
  • the ether of 3-methylbutan-1-ol, di-3-methylbutyl ether (diisoamyl ether) is mainly formed.
  • 3-Methylbutan-1-ol with a purity of 99.81% by mass was used in an electrically heated flow fixed bed reactor on the alumina catalyst SA 31132 (extrudates of 3 mm diameter and 3 to 4 mm length) with a bulk density of 0, 52 g / cm3 reacted.
  • the liquid educt, as in Example 1, in a upstream evaporator at 220 0 C evaporated.
  • 13.0 g of 3-methylbutan-1-ol were passed through 22.0 g of catalyst in the gas phase, corresponding to a WHSV value of 0.57 h -1 , per hour , 15 MPa
  • the gaseous product was cooled in a condenser and collected in a glass original.
  • Table 3 shows, in addition to the composition of the product, the distribution of the C5-olefin isomers normalized to 100%.
  • Table 3 shows, in addition to the composition of the product, the distribution of the C5-olefin isomers normalized to 100%.
  • SA 31,132 comparable contents of 3-methylbut-1-ene to the catalyst of the invention, SA 31,132, were obtained under comparable reaction conditions as in Example 1.
  • the selectivity of cleavage of 3-methylbutan-1-ol is reduced by the formation of di (3-methylbutyl) ether.
  • 3-Methylbutan-1-ol with a purity of 99.81 mass% was in an electrically heated flow-fixed bed reactor on the aluminum oxide catalyst SP 537 in spherical form (1, 7 to 2.1 mm beads) with a bulk density of 0, 58 g / cm 3 reacted.
  • the liquid educt was evaporated in an upstream evaporator at 220 0 C.
  • 3-Methylbutan-1-ol passed through 26.0 g of catalyst in the gas phase, corresponding to a WHSV value of 0.52 h "1.
  • the reaction pressure was 0.15 MPa as in Example 1.
  • the gaseous product was in a Cooled cooler and collected in a glass template The product had anhydrous calculated the following composition:
  • 3-Methylbutan-1-ol with a purity of 99.81% by mass was in an electrically heated flow-fixed bed reactor on aluminum oxide catalyst SP 538 F in trilobium (1, 8 mm Trilobes) with a bulk density of 0.55 g / cm 3 implemented.
  • the pore structure of the SP 587 F catalyst is largely consistent with the pore structure of Example 3 Catalyst SP 537 comparable (s.Tabellei).
  • the liquid educt was evaporated in an upstream evaporator at 220 0 C.
  • the catalytic behavior of the catalyst SP 538F is similar to the behavior of the catalyst SP 537.
  • the temperature range from 280 to 300 ° C.
  • very high contents of 3-methylbut-1-enes of more than 84% by mass were obtained under comparable load. achieved.
  • the maximum yield is at a reaction temperature of 290 0 C with a 3-methylbut-1-ene content of approx. 91, 4 mass%.
  • the 3-methylbutan-1-ol on the catalyst according to the invention SP 538 F is completely converted to C 5 -olefins and water.
  • no di (3-methylbutyl) ether is formed at temperatures above 290 0 C.

Landscapes

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

Abstract

L'invention porte sur un procédé de production de 3-méthylbut-1-ène par déshydratation de 3-méthylbutan-1-ol en présence d'un oxyde à base d'aluminium, dans une plage de température de 200 à 450 °C, en phase gazeuse ou mixte liquide/gazeuse, ce procédé étant caractérisé en ce qu'il comprend l'utilisation d'un oxyde à base d'aluminium présentant une structure de pores majoritairement mésoporeuse, dont : a) la proportion relative de macropores est inférieure à 15%, b) la distribution des diamètres de pores présente un maximum monomodal dans la plage des mésopores de 3,6 à 50 nm; c) le diamètre de pore moyen de tous les pores dans la plage des mésopores et macropores est compris entre 5 et 20 nm, et d) la composition contient plus de 80% d'oxyde d'aluminium gamma.
EP10716338A 2009-05-29 2010-04-28 Production de 3-méthylbut-1-ène par déshydratation de 3-méthylbutan-1-ol Withdrawn EP2435388A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102009026585A DE102009026585A1 (de) 2009-05-29 2009-05-29 Herstellung von 3-Methylbut-1-en durch Dehydratisierung von 3-Methylbutan-1-ol
PCT/EP2010/055670 WO2010136289A2 (fr) 2009-05-29 2010-04-28 Production de 3-méthylbut-1-ène par déshydratation de 3-méthylbutan-1-ol

Publications (1)

Publication Number Publication Date
EP2435388A2 true EP2435388A2 (fr) 2012-04-04

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EP10716338A Withdrawn EP2435388A2 (fr) 2009-05-29 2010-04-28 Production de 3-méthylbut-1-ène par déshydratation de 3-méthylbutan-1-ol

Country Status (7)

Country Link
US (1) US20120136190A1 (fr)
EP (1) EP2435388A2 (fr)
JP (1) JP5591325B2 (fr)
CN (1) CN102448912A (fr)
DE (1) DE102009026585A1 (fr)
SG (1) SG176241A1 (fr)
WO (1) WO2010136289A2 (fr)

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JP5787769B2 (ja) 2009-01-23 2015-09-30 エボニック デグサ ゲーエムベーハーＥｖｏｎｉｋ Ｄｅｇｕｓｓａ ＧｍｂＨ ３置換ｃ４−１０アルケンとのポリオレフィン気相重合
EP2382245B1 (fr) 2009-01-23 2012-12-19 Evonik Oxeno GmbH Film de pe-mib préparé à l'aide de zn/cr
US9266792B2 (en) 2009-07-29 2016-02-23 The United States Of America As Represented By The Secretary Of The Navy Process and apparatus for the selective dimerization of terpenes and alpha-olefin oligomers with a single-stage reactor and a single-stage fractionation system
US8912373B2 (en) 2009-07-29 2014-12-16 The United States Of America As Represented By The Secretary Of The Navy Process for the dehydration of aqueous bio-derived terminal alcohols to terminal alkenes
US20120209047A1 (en) 2009-07-29 2012-08-16 Wright Michael E Homogeneous metallocene ziegler-natta catalysts for the oligomerization of olefins in aliphatic-hydrocarbon solvents
US9242226B2 (en) 2009-07-29 2016-01-26 The Government Of The United States Of America As Represented By The Secretary Of The Navy Process for the dehydration of aqueous bio-derived terminal alcohols to terminal alkenes
US9649626B2 (en) 2009-07-29 2017-05-16 The United States Of America As Represented By The Secretary Of The Navy Process for the dehydration of aqueous bio-derived terminal alcohols to terminal alkenes
US8785702B2 (en) 2009-07-29 2014-07-22 The United States Of America As Represented By The Secretary Of The Navy Turbine and diesel fuels and methods for making the same
WO2016104333A1 (fr) * 2014-12-24 2016-06-30 株式会社クラレ Procédé de production de 4-méthylpentanal
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Also Published As

Publication number Publication date
US20120136190A1 (en) 2012-05-31
CN102448912A (zh) 2012-05-09
DE102009026585A1 (de) 2010-12-02
WO2010136289A3 (fr) 2011-02-10
JP5591325B2 (ja) 2014-09-17
WO2010136289A2 (fr) 2010-12-02
JP2012528096A (ja) 2012-11-12
SG176241A1 (en) 2012-01-30

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