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WO2018046323A1 - Utilisation de polyalkylène-glycoldialkyléthers en tant qu'antioxydants pour des catalyseurs hétérogènes réduits - Google Patents

Utilisation de polyalkylène-glycoldialkyléthers en tant qu'antioxydants pour des catalyseurs hétérogènes réduits Download PDF

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Publication number
WO2018046323A1
WO2018046323A1 PCT/EP2017/071483 EP2017071483W WO2018046323A1 WO 2018046323 A1 WO2018046323 A1 WO 2018046323A1 EP 2017071483 W EP2017071483 W EP 2017071483W WO 2018046323 A1 WO2018046323 A1 WO 2018046323A1
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WO
WIPO (PCT)
Prior art keywords
reduced
catalyst
use according
polyalkylene glycol
glycol dialkyl
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/EP2017/071483
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German (de)
English (en)
Inventor
Thomas Heidemann
Regine Helga BEBENSEE
Christian Gruenanger
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BASF SE
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BASF SE
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Filing date
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Publication of WO2018046323A1 publication Critical patent/WO2018046323A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J33/00—Protection of catalysts, e.g. by coating
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/74—Iron group metals
    • B01J23/75—Cobalt
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/835—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with germanium, tin or lead
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/889—Manganese, technetium or rhenium
    • B01J23/8892—Manganese
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/185—Phosphorus; Compounds thereof with iron group metals or platinum group metals
    • B01J27/1853—Phosphorus; Compounds thereof with iron group metals or platinum group metals with iron, cobalt or nickel
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J27/187—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with manganese, technetium or rhenium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
    • B01J37/0018—Addition of a binding agent or of material, later completely removed among others as result of heat treatment, leaching or washing,(e.g. forming of pores; protective layer, desintegrating by heat)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
    • C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
    • C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J25/00—Catalysts of the Raney type
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the present invention relates to the use of polyalkylene glycol dialkyl ethers as oxidation protection for reduced, heterogeneous catalysts.
  • polyalkylene glycol alkyl ether also referred to below as “polyglycol ether”
  • R2 is hydrogen or methyl
  • Alkyl radicals for R 1 are linear or branched C 1 -C 6 -alkyl chains, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, iso Pentyl, sec-pentyl, neo-pentyl, 1,2-dimethyl-propyl, iso-amyl, n-hexyl, iso-hexyl, sec-hexyl, n-heptyl, and n-octy.
  • Preferred alkyl radicals are C 1 -C 4 -alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, particularly preferably methyl, ethyl and n-butyl.
  • n represents an integer of not less than 2, preferably 2 to 10, more preferably 2 to 4.
  • Particularly preferred polyglycol ethers are the following compounds selected from the group consisting of diglyme [CH 3 -0- (CH 2 CH 2 0) 2 CH 3], Proglyme [CH 3 -0- (CH 2 -CHCH 3 0) 2 - CH 3 ], triglyme [CH 3 -O- (CH 2 -CH 2 O) 3-CH 3 ], tetraglyme [CH 3 -O- (CH 2 -CH 2 O) 4 -CH 3 ], ethyl diglyme [C 2 H5-0- (CH2-CH20) 2-C2H 5], butyl diglyme Polyglyme [CH 3 -O- (CH 2 - CH 2 O) n-CH 3 ] and Higlyme [CAS 366009-01-0] or mixtures thereof.
  • Very particularly preferred polyglycol ethers are preglyme, butyl diglyme, polyglyme and higlyme or mixtures thereof.
  • a further preferred embodiment of the use according to the invention is characterized in that the hydroxyl number (OHN) of the polyglycol ether is less than 100 mg KOH / g, more preferably less than 50 mg KOH / g, most preferably less than 10 mg KOH / g.
  • OPN hydroxyl number
  • a likewise preferred embodiment of the use according to the invention is characterized in that the polyglycol ether is a compound which is in liquid form at a temperature in the range from 10 ° C. to 100 ° C. (at normal pressure).
  • the melting temperature of the polyglycol ether is generally lower than the temperature at which the catalyst is stored prior to use.
  • the melting temperature of the polyglycol ether is in the range of -5 ° C to -75 ° C, more preferably in the range of -5 ° C to -60 ° C.
  • the melting temperature of the polyglycol ether to which the catalyst is added is preferably lower than the temperature at which the hydrogenation is carried out, so as to facilitate the separation of the polyglycol ether from the catalyst at the beginning of a hydrogenation process.
  • the boiling point of the polyglycol ether used in the invention is> 170 ° C, preferably in the range of 170 ° C to 280 ° C, more preferably in the range of 175 ° C to 275 ° C.
  • polyglycol ethers used according to the invention are also distinguished by the fact that they have a flash point above 100 ° C., preferably in the range from 110 ° C. to 160 ° C.
  • the use according to the invention of polyglycol ethers as oxidation protection generally applies to those catalysts which are suitable for chemical reactions with hydrogen as reactant, e.g. Hydrogenations or aminations are suitable.
  • These include, for example, heterogeneous catalysts containing as active component at least one element from the group consisting of iron, cobalt, nickel, ruthenium, rhodium, palladium and platinum or mixtures thereof.
  • heterogeneous catalysts are preferred, mentioning as the active component at least one element selected from the group consisting of nickel, cobalt, ruthenium, iron and copper or mixtures thereof, particularly preferably such catalysts, the nickel and / or cobalt contain.
  • the catalysts may also contain other elements as promoters.
  • the use of the polyglycol ethers according to the invention is further characterized in that the catalyst to be protected is reduced by means of thermal treatment of its active component present in oxidic form with hydrogen.
  • the catalysts are purged at room temperature with nitrogen and under nitrogen atmosphere, a pressure of 2 to 10 bar, preferably 4 to 8 set bar.
  • the temperature usually within 2 to 24 h, preferably 5 to 15 h, from room temperature to 80 to 200 ° C, preferably 120 to 160 ° C, increased
  • a further part of the nitrogen stream is replaced by hydrogen , so that a total hydrogen content of 30 to 70%, preferably 40 to 60% is achieved
  • the temperature is usually within 2 to 24 hours, preferably 5 to 15 hours, to 200 to 400 ° C, preferably 250 to 350 ° C increased This final temperature is usually kept until no more reducing water is detectable in the gas stream leaving the catalyst.
  • the hydrogen content in the gas stream is usually exchanged for nitrogen again and allowed to cool the reduced catalyst in a stream of nitrogen to room temperature.
  • full catalysts moldings which are completely permeated by the active component
  • supported catalysts solid catalysts, consisting of the active component, which is responsible for the actual catalytic reaction, and a support material
  • Raney catalysts finely divided hydrogenation and dehydrogenation catalysts [ nickel and cobalt in particular], which are prepared by alloying the metals, for example, with aluminum, magnesium or zinc and then dissolving away the alloying metals with alkalis.
  • the catalyst may be present, for example, as a powder, grit or shaped article.
  • the amount of active components, based on the total mass of the catalyst is preferably 30 to 100% by weight, more preferably 50 to 99% by weight and most preferably 55 to 98% by weight.
  • the content of the active components, based on the total mass of the catalyst preferably 0.01 to 30 wt .-%, wherein in the case of precious metals Ru, Rh, Pd and Pt their content is more in the range 0.01 to 10 Wt .-%, preferably 0.05 to 5 wt .-%, and in the case of the remaining metals whose content is more in the range 1 to 30 wt .-%, preferably 5 to 20 wt .-%
  • Raney catalysts for example, they may contain 0 to 15% by weight of aluminum and 50 to 100% by weight of nickel or cobalt.
  • the use according to the invention is advantageously carried out in the form of a dispersion which contains the reduced, heterogeneous catalyst as the disperse phase and at least one polyalkylene glycol dialkyl ether of the general formula I as the dispersion medium.
  • the amount of polyglycol ether used as the protective material in the dispersion is preferably at least 40% by weight, preferably at least 55% by weight, particularly preferably at least 60% by weight. Very good results were achieved with an amount of polyglycol ether of at least 65 wt .-%. (All wt .-% data based on the total weight of the mixture of catalyst and protective material).
  • the amount of polyglycol ether is preferably at most 95% by weight, preferably at most 90% by weight, particularly preferably at most 85% by weight. Very good results were with a Weight fraction of polyglycol ether used of at most 80 wt .-% achieved. (All wt .-% data based on the total weight of the mixture of catalyst and protective material).
  • Polyglycol ethers are to be regarded as inert solvents. Targeted adjustment of the chain lengths and alkyl fragments according to GHS (Globally Harmonized System for Classification and Labeling of Chemicals) does not require labeling of polyethers which are non-flammable as well as liquid in a wide temperature range.
  • GHS Globally Harmonized System for Classification and Labeling of Chemicals
  • the polyglycol ethers can either be expelled at elevated temperature with an inert gas stream or be dissolved out with suitable process constituents. Due to their inertness, the catalyst is in its active form after removal of the ether and can be used directly for the desired reaction without undergoing a complicated drying or activation procedure.
  • Example B3 a NiO / CuO / Co 3 04 / SnO / Al 2 O 3 -containing catalyst was prepared.
  • Catalyst added (catalyst II: reduced / Butyldiglyme).
  • catalyst III reduced / passivated.
  • a cobalt-containing catalyst was prepared in the form of 2 mm extrudates.
  • the cobalt catalyst was transferred to a rotary flask and heated in an N 2 / H 2 stream (95% / 5%) to 150 ° C, then the H2 content was gradually increased to 50%.
  • the mixture was then carefully heated to a temperature of 280 ° C (thereby controlling that the product temperature is always ⁇ 300 ° C) and reduced as long as without pressure until no more water attack in the gas discharge was detected.
  • Table 3 shows the results obtained after 3 h and 5 h running time.
  • MEG monoethylene glycol
  • MEOA monoethanolamine
  • EDA ethylenediamine
  • the reaction was carried out in four continuously operated tubular reactors connected in series.
  • the imination of isophorone nitrile (IPN) with ammonia to give isophorone nitrilimine (I PNI) in the first reactor was carried out at 60 ° C. on T1O2 (75 ml).
  • the feed amount of IPN was 80 g / h, the NH3 amount 165 g / h.
  • the effluent from the reactor was fed to the second reactor along with hydrogen and along with a recycle stream from the fourth reactor.
  • the effluent from the second reactor was passed to the third reactor.
  • the discharge of the third reactor was passed to the fourth reactor.
  • the temperature of the second reactor was 70 ° C, that of the third reactor 1 10 ° C and that of the fourth reactor 140 ° C.
  • the amount of hydrogen supplied was 87 Nl / h.
  • the recycle stream from the fourth reactor to the inlet of the second reactor was 1100 g / hr.
  • the system was operated at 195 bar.
  • the proportion of IPDA was 96.2 GC area%. It can be seen from these comparative examples that the prereduced catalyst, which was stored according to the invention in the presence of a polyglycol ether, has a comparable activity to a catalyst which has been freshly reduced in the reactor.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

L'invention concerne l'utilisation d'au moins un polyalkylène-glycoldialkyléther de la formule générale (I) : R1-O-CH2-CHR2O)n-R1, dans laquelle les substituants ont la signification suivante indépendamment les uns des autres : R1 est C1-C8-alkyle ; R2 est hydrogène ou méthyle ; n est 2 à 10, en tant qu'antioxydant pour des catalyseurs hétérogènes réduits, notamment pour des catalyseurs hétérogènes réduits qui contiennent en tant que composant actif au moins un élément choisi dans le groupe composé de nickel, cobalt, ruthénium, fer et cuivre ou de mélanges de ceux-ci.
PCT/EP2017/071483 2016-09-06 2017-08-28 Utilisation de polyalkylène-glycoldialkyléthers en tant qu'antioxydants pour des catalyseurs hétérogènes réduits Ceased WO2018046323A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP16187424 2016-09-06
EP16187424.3 2016-09-06

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WO2018046323A1 true WO2018046323A1 (fr) 2018-03-15

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10774034B2 (en) 2017-05-03 2020-09-15 Basf Se Process for the conversion of ethylene oxide to monoethanolamine and ethylenediamine employing a zeolite
US11091425B2 (en) 2016-11-30 2021-08-17 Basf Se Process for the conversion of ethylene glycol to ethylenediamine employing a zeolite catalyst
US11104637B2 (en) 2016-11-30 2021-08-31 Basf Se Process for the conversion of monoethanolamine to ethylenediamine employing a copper-modified zeolite of the MOR framework structure

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0636409A1 (fr) 1993-07-31 1995-02-01 BASF Aktiengesellschaft Catalyseurs au cobalt
JPH0824665A (ja) * 1994-07-08 1996-01-30 Kuraray Co Ltd 安定化触媒
EP0742045A1 (fr) * 1995-05-09 1996-11-13 Basf Aktiengesellschaft Catalyseurs à base de cobalt
DE19516845A1 (de) 1995-05-09 1996-11-14 Basf Ag Kobaltkatalysatoren
DE19909175A1 (de) 1999-03-03 2000-09-07 Kataleuna Gmbh Catalysts Verfahren zur Passivierung pyrophorer Katalysatoren
US20060100452A1 (en) 2002-10-18 2006-05-11 Engelhard Corporation Nickel catalyst for hydrogenation reactions
EP1779928A2 (fr) 2005-09-30 2007-05-02 Sued-Chemie Catalysts Japan, Inc. Méthode de stabilisation d'un catalyseur à base de nickel
WO2013072289A1 (fr) 2011-11-17 2013-05-23 Basf Se Procédé pour la production des catalyseurs contenant sn

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0636409A1 (fr) 1993-07-31 1995-02-01 BASF Aktiengesellschaft Catalyseurs au cobalt
JPH0824665A (ja) * 1994-07-08 1996-01-30 Kuraray Co Ltd 安定化触媒
EP0742045A1 (fr) * 1995-05-09 1996-11-13 Basf Aktiengesellschaft Catalyseurs à base de cobalt
DE19516845A1 (de) 1995-05-09 1996-11-14 Basf Ag Kobaltkatalysatoren
DE19909175A1 (de) 1999-03-03 2000-09-07 Kataleuna Gmbh Catalysts Verfahren zur Passivierung pyrophorer Katalysatoren
US20060100452A1 (en) 2002-10-18 2006-05-11 Engelhard Corporation Nickel catalyst for hydrogenation reactions
EP1779928A2 (fr) 2005-09-30 2007-05-02 Sued-Chemie Catalysts Japan, Inc. Méthode de stabilisation d'un catalyseur à base de nickel
WO2013072289A1 (fr) 2011-11-17 2013-05-23 Basf Se Procédé pour la production des catalyseurs contenant sn

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11091425B2 (en) 2016-11-30 2021-08-17 Basf Se Process for the conversion of ethylene glycol to ethylenediamine employing a zeolite catalyst
US11104637B2 (en) 2016-11-30 2021-08-31 Basf Se Process for the conversion of monoethanolamine to ethylenediamine employing a copper-modified zeolite of the MOR framework structure
US10774034B2 (en) 2017-05-03 2020-09-15 Basf Se Process for the conversion of ethylene oxide to monoethanolamine and ethylenediamine employing a zeolite

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