Classifications

• • 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
  • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
  • B01J31/40—Regeneration or reactivation
  • B01J31/4015—Regeneration or reactivation of catalysts containing metals
  • B01J31/4061—Regeneration or reactivation of catalysts containing metals involving membrane separation
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01D—SEPARATION
  • B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
  • B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
  • B01D61/027—Nanofiltration
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01D—SEPARATION
  • B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
  • B01D61/14—Ultrafiltration; Microfiltration
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01D—SEPARATION
  • B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
  • B01D71/02—Inorganic material
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01D—SEPARATION
  • B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
  • B01D71/02—Inorganic material
  • B01D71/024—Oxides
• • 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
  • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
  • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
  • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
  • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
• • 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
  • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
  • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
  • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
  • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
  • B01J31/2419—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member
  • B01J31/2428—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member with more than one complexing phosphine-P atom
  • B01J31/2433—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
• • 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
  • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
  • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
  • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
  • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
  • B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
  • B01J31/2447—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
  • B01J31/2452—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring with more than one complexing phosphine-P atom
• • 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
  • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
  • B01J31/40—Regeneration or reactivation
  • B01J31/4015—Regeneration or reactivation of catalysts containing metals
• • 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
  • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
  • B01J31/40—Regeneration or reactivation
  • B01J31/4015—Regeneration or reactivation of catalysts containing metals
  • B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
  • B01J31/4038—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals
• • 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
  • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
  • B01J31/40—Regeneration or reactivation
  • B01J31/4015—Regeneration or reactivation of catalysts containing metals
  • B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
  • B01J31/4038—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals
  • B01J31/4046—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals containing rhodium
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01D—SEPARATION
  • B01D2325/00—Details relating to properties of membranes
  • B01D2325/02—Details relating to pores or porosity of the membranes
  • B01D2325/022—Asymmetric membranes
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01D—SEPARATION
  • B01D2325/00—Details relating to properties of membranes
  • B01D2325/02—Details relating to pores or porosity of the membranes
  • B01D2325/0283—Pore size
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01D—SEPARATION
  • B01D2325/00—Details relating to properties of membranes
  • B01D2325/38—Hydrophobic membranes
• • 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
  • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
  • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
  • B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
  • B01J2531/0266—Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
• • 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
  • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
  • B01J2531/70—Complexes comprising metals of Group VII (VIIB) as the central metal
  • B01J2531/72—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
  • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
  • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
• • 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
  • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
  • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
  • B01J2531/82—Metals of the platinum group
  • B01J2531/821—Ruthenium
• • 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
  • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
  • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
  • B01J2531/82—Metals of the platinum group
  • B01J2531/822—Rhodium
• • 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
  • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
  • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
  • B01J2531/82—Metals of the platinum group
  • B01J2531/824—Palladium

Definitions

• the invention relates to methods for separating dissolved or colloidal solids, in particular catalysts from solutions in non-aqueous solvents with the aid of a membrane.
• EP 1 118 683 AI describes the separation of metals and other partially or completely dissolved solids in aqueous solutions with membranes made of ceramic, polymeric or metallic materials.
• Membranes can be assigned, can now be produced with a pore size of less than 1 nm. Because of their chemical, mechanical and thermal stability, these microporous, ceramic membranes have great potential for use, as Puhl Subß et al. (Puhl Subß et al., J. Membr. Sci. 174 [2000] 123-133). This publication also deals with the characterization of the membrane, which has a cut off ⁇ 500g / mol and
• the catalyst In catalytic processes, the catalyst is hardly used or not at all, and could therefore theoretically be used for any length of time.
• the problem that usually arises is the loss of the catalyst over the duration of the experiment e.g. when disconnecting the
• Laid-open specification EP 0 263 953 AI describes the retention of rhodium complex compounds, which are components of the catalyst system, from aqueous solutions.
• the catalyst is separated off using a polymer membrane.
• the material of the polymer membrane is cellulose acetate.
• Polymer membranes are primarily used in the above-described processes for retaining catalysts with increased molecular weight.
• Membranes for the retention of dissolved, molecular weight-enlarged catalysts in organic solvents are stacked. Increasing the size of the catalyst increases the size difference between the product to be discharged and the catalyst to be retained. In addition, good retention can be achieved with larger pores, which is not impaired by the wetting of the solvent on the pore walls.
• a ceramic membrane can only be used really economically if a material flow through the membrane is achieved that meets industrial requirements.
• Solvent molecules not permeable. Transport takes place over larger pores and / or defects instead, which only make up a small proportion of the total pore volume. This causes the river to sink compared to the water flow. The retention due to these larger pores or defects is clearly above the average pore size of the membrane.
• the object of the invention is to provide a process which avoids the disadvantages of the known processes and can retain the dissolved and / or colloidal solid (in particular catalyst) from a reaction solution in organic solvent with the aid of an inorganic membrane, the product-containing solvent the membrane happened unhindered.
• the size of the solid (catalyst) should remain as unchanged as possible.
• the object is achieved in that in a method of the type mentioned at the outset, a membrane is used which is hydrophobized and with which a high solvent flow can be generated which is significantly above the material flow of aqueous solution through this membrane.
• a retention has been shown which, depending on the membrane, is less than 1000 g / mol, in special cases even less than 400 g / mol.
• the invention relates to a process for separating dissolved and / or colloidal solids, in particular catalyst from solutions in non-aqueous
• Solvents in particular in organic solvents with the aid of a membrane characterized in that the solution is passed through a membrane which has a hydrophobic coating and an average pore size of at most 30 nm.
• the membrane is preferably a porous membrane, particularly preferably an inorganic membrane, particularly preferably a ceramic membrane, based on A1 2 0 3 , Ti0 2 , Zr0 2 or
• the average pore size of the membrane is in particular at most 20 nm, preferably 2 nm to 10 nm, particularly preferably 2 nm to 5 nm.
• the pore size is expediently selected such that the average pore size in the active region of the membrane is below the range of the average molecular size of the membrane to be separated
• the membrane preferably has a multilayer structure. It is in particular an asymmetrical membrane that consists of at least 2, in special cases even of at least 3 layers.
• the carrier layer is in particular a few millimeters thick and roughly porous with pores with an average diameter of 1 to 10 ⁇ m, preferably 3 to 5 ⁇ m
• the intermediate layer built thereon is provided with a thickness of in particular 10 to 100 ⁇ m and has a pore size (average diameter) from 3 to 100 nm.
• the separating layer has in particular a thickness of 0.5 to 2 ⁇ m and has pores with an average diameter of 0.9 to 30 nm.
• the main advantage of this membrane is the uniform structure with very few imperfections ,
• the hydrophobic coating is preferably produced on the membrane by means of silanes.
• reactions of the membrane surface with silanes of the general formula R 2 R 3 t Si are suitable, preferably at least one but at most three of the groups R 1 to R 4 hydrolyzable groups, for example -Cl, -OCH3 or -O-CH 2 -CH 3 are and / or at least one but at most three of the groups R 1 to R 4 are non-hydrolyzable groups, for example alkyl groups or phenyl groups, the non-hydrolyzable substituents preferably being at least partially fluorinated to increase the hydrophobic effect.
• the ceramic membranes can be modified using the hydrophobizing agents described, either in the liquid phase by soaking the membrane in a solution of the hydrophobizing agent, or by flowing the membrane with the hydrophobizing agent in the gaseous phase by using a carrier gas, for example N 2 or noble gas.
• a carrier gas for example N 2 or noble gas.
• the non-aqueous solvent is in particular an organic solvent and is particularly preferably selected from the series: alcohols, in particular methanol or ethanol, ethers, in particular tetrahydrofuran, aromatic hydrocarbons, in particular chlorobenzene or toluene, or optionally halogenated aliphatic hydrocarbons, in particular dichloromethane.
• a preferred method is characterized in that the solution contains homogeneously dissolved and / or colloidally present catalysts, in particular catalysts selected from the group of organometallic complex compounds, and ligands of these complex compounds, particularly preferably Ru-B AP, Pd-BLNAP and Rh- EtDUPHOS or complex compounds of triphenylphosphine with palladium (e.g. Pd (OAc) 2 (PPh 3 ) 2 ) or rhodium.
• catalysts selected from the group of organometallic complex compounds, and ligands of these complex compounds, particularly preferably Ru-B AP, Pd-BLNAP and Rh- EtDUPHOS or complex compounds of triphenylphosphine with palladium (e.g. Pd (OAc) 2 (PPh 3 ) 2 ) or rhodium.
• suitable catalysts are selected from complex compounds of the elements of group IVA, VA, VIA, VBA, VIHA or EB of the periodic table of the elements, particularly preferably of manganese, iron, cobalt, nickel, palladium, platinum, ruthenium, rhodium or iridium.
• the ligands of these complex compounds can additionally be alkylated or arylated.
• the separation of the solids from the solution is preferably carried out at a temperature of from -20 ° C. to 200 ° C., particularly preferably from 0 ° C. to 150 ° C.
• the pressure across the membrane is 2,000 to 40,000 hPa.
• the invention is particularly suitable for catalyst retention when carrying out a reaction in which the catalyst is dissolved or colloidal and is to be kept in a reaction kettle, while the reaction product is in particular continuously removed from the kettle. In this way, losses can be minimized and the product is free from unwanted ones
• the catalyst can also be in a mixture of dissolved and undissolved fractions.
• the process is also suitable for concentrating and cleaning active ingredient solutions in the pharmaceutical industry and in biotechnology, sectors in which high purity of the products is required.
• the process can be combined with other purification processes, e.g. using chromatographic methods.
• Fig. 1 is a schematic sketch of the separation device used in the examples
• the appropriate solvent is filled into the reservoir 1 (see FIG. 1), the membrane 4 is installed in the module 3 and the solution with the pump 2 and by means of pressure superimposition in cross-flow mode is passed over the membrane 4.
• a sample is taken from permeate 5 and retentate 6 at regular intervals and the specific flow is measured in kg / (h * m 2 * bar).
• the solutions are prepared according to recipe 1 to 10 (cf. Table 1) and also filled into storage container 1.
• the test procedure corresponds to the above.
• the samples are measured for their content of the substances used using GPC analysis.
• Storage container 1 5 1, stainless steel, pressure-resistant up to 40,000 hPa
• Example 1 The experiment from Example 1 was carried out in the system described above (FIG. 1).
• the pure substance flows of different solvents are measured for different membranes (A - D).
• the membranes differ in their pore sizes and retention, as well as in their surface properties.
• the exact description of the * membranes is shown in Table 2.
• the complete test parameters are in Table 3.
• the results are listed in Table 4.
• Table 4 shows the pure substance flows of the different solvents.
• Membrane A consists of a porous carrier made of ⁇ -aluminum oxide with an average pore size of 3 ⁇ m diameter, an intermediate layer made of TiO 2 with a pore size of 5 nm and a separating layer made of Ti0 2 with a pore size of 0.9 nm without a hydrophobizing coating.
• a membrane shows a water flow of 16.37 kg / (h * m 2 * bar), a methanol flow of ll, 54 kg / (h * m 2 * bar), an ethanol flux of 3.64 kg / (h * m 2 * bar) and a toluene flow of 1.5 kg / (h * m 2 * bar).
• Membrane B with properties corresponding to membrane A and a hydrophobization with 0.5% tridecafluor 1,1,2,2 tetrahydrooctyltriethoxysilane (hereinafter referred to as F6) and an addition of the hydrophobizing agent during the membrane synthesis the water flow to 10.44 kg / (h * m 2 * bar), the methanol flow to 3.12 kg / (h * m 2 * bar) and the toluene flow to 0.51 kg / (h * m 2 * bar) down.
• F6 tridecafluor 1,1,2,2 tetrahydrooctyltriethoxysilane
• Membrane C is a membrane that consists of the same Al2O3 carrier as membrane A with an intermediate layer of Ti0 2 with a pore size of 5 nm and a separating layer of Zr0 2 with a pore size of 3 nm.
• the hydrophobization is achieved by impregnation of the finished product
• Membrane carried out in the hydrophobizing agent F6. There was a water flow of 4.48 kg / (h * m 2 * bar), a methanol flow of 16.23 kg / (h * m 2 * bar) and a toluene flow of 7.7 kg / (h * m 2 *bar).
• Membrane A shows a return of dextrans in water of 450 g / mol, PEG in water of 470 g / mol and PEG in methanol of 980 g / mol. The retention of toluene was not determined because no toluene flow through the membrane could be measured.
• Membrane B shows a return of dextrans in water of 250 g / mol, PEG in methanol of> 1000 g / mol. The retention of toluene was not determined because no toluene flow through the membrane could be measured.
• Membrane C shows no retention of dextrans in water since no water flow through the membrane could be measured.
• the retention of PEG in methanol is 1000 g / mol, the retention of toluene is 500 g / mol.
• Membrane D shows a retention of dextrans in water of> 2000 g / mol, of PEG in methanol> 2000 g / mol, the residue of toluene is 340 g / mol.
• Example 3 Measurement of catalyst retention in toluene
• Example 2 The devices and the system (FIG. 1) from Example 1 were used.
• membrane D was used in the system.
• the mixture to be separated consisted of 2.5 L toluene, dissolved therein BMAP (2,2'-bis (diphenylphosphino) -l, -binaphthyl) in a concentration of 0.132 g / L and Pd 2 (dba) 3 (tris (dibenzylidene acetone) ) dipalladium) in a concentration of 0.0929 g / L.
• BMAP 2,2'-bis (diphenylphosphino) -l, -binaphthyl
• Pd 2 (dba) 3 tris (dibenzylidene acetone) dipalladium
• Examples 1 and 2 show that a ceramic membrane has a strong hydrophilicity (see membrane A). This can be seen in the high water flows and good retention of dextrans in aqueous solutions. The flows and the retention decrease with increasing polarity of the solvent. Retentions in toluene could not be measured because the strong hydrophilicity of the membrane pore walls does not allow wetting of the toluene, so that it cannot flow through the membrane pores at all.
• polystyrene retention could not be determined again because the effective pore size decreased due to the treatment of the pore walls.
• the toluene molecule is due to its
• Example 3 one of these latter membranes (membrane D) was selected to the left
• Example 2 The devices and the system (FIG. 1) from Example 1 were used.
• a type D membrane (see Table 2) was used in the system.
• the pure flow of toluene through the membrane was measured.
• the flow is 5.66 L / (h * m 2 * bar) at a temperature of 20 ° C and a transmembrane pressure (TMP) over the membrane of 4 to 8 bar.
• TMP transmembrane pressure
• the reaction solution consisted of 2L toluene, educts p-bromotrifluoromethanobenzene (mol weight 225.01 g / mol, educt 1) used therein in a concentration of 75 g / L, aniline (mol weight 93.13 g / mol, educt 2) of 58.885 g / L, and sodium tertiary butoxide 42 g / L, also the catalyst components BINAP in a concentration of 0.8544 g / L and Pd 2 (dba) 3 in a concentration of 0.573 g / L.
• the complex compound Pd-BINAP which was the catalyst, was formed with a molecular weight of at least 729 g / mol.
• the reaction solution was filtered using the membrane mentioned above at a temperature of 19.5 ° C. and a transmembrane pressure of 10 bar.

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• Materials Engineering (AREA)
• Organic Chemistry (AREA)
• Inorganic Chemistry (AREA)
• Water Supply & Treatment (AREA)
• Nanotechnology (AREA)
• Separation Using Semi-Permeable Membranes (AREA)
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• 2003
  • 2003-02-26 DE DE10308111A patent/DE10308111A1/de not_active Withdrawn
• 2004
  • 2004-02-09 US US10/774,778 patent/US20040168981A1/en not_active Abandoned
  • 2004-02-13 WO PCT/EP2004/001419 patent/WO2004076039A1/de not_active Ceased
  • 2004-02-13 JP JP2006501848A patent/JP2006519093A/ja active Pending
  • 2004-02-13 EP EP04710858A patent/EP1599275A1/de not_active Withdrawn

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