WO2013171060A1 - Distillation de liquides ioniques par distillation moléculaire - Google Patents

Distillation de liquides ioniques par distillation moléculaire Download PDF

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Publication number
WO2013171060A1
WO2013171060A1 PCT/EP2013/058900 EP2013058900W WO2013171060A1 WO 2013171060 A1 WO2013171060 A1 WO 2013171060A1 EP 2013058900 W EP2013058900 W EP 2013058900W WO 2013171060 A1 WO2013171060 A1 WO 2013171060A1
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WO
WIPO (PCT)
Prior art keywords
evaporator
distillation
mixture
ionic liquid
short
Prior art date
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PCT/EP2013/058900
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German (de)
English (en)
Inventor
Ortmund Lang
Thomas Wisniewski
Michael Lutz
Original Assignee
Basf Se
Basf Schweiz Ag
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 Basf Se, Basf Schweiz Ag filed Critical Basf Se
Publication of WO2013171060A1 publication Critical patent/WO2013171060A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/12—Molecular distillation

Definitions

  • the invention relates to a process for the distillation of mixtures containing salts with a melting point of less than 200 ° C at 1 bar (ionic liquids), which is characterized in that the distillation in an apparatus for short path distillation with a load of 5 to 100 kg of mixture per hour and square meter evaporator surface.
  • Salts having a melting point of less than 200 ° C., in particular having a melting point of less than 100 ° C. are referred to as ionic liquids.
  • ionic liquids which are already liquid at room temperature. Such ionic liquids were considered to be non-distillable for a long time, since it was assumed that they ultimately have no vapor pressure.
  • Ionic liquids are generally not consumed in their use, but only contaminated. Since these are high-value recyclables, there is a need for particularly effective and inexpensive processes for working up and separating off the ionic liquids from the mixtures obtained during use.
  • ionic liquids are used to dissolve cellulose, e.g. Mixtures containing lignins or cellulose derivatives.
  • low-cost production processes for ionic liquids are known in which, however, low-volatility by-products arise, the resulting reaction products show a discoloration due to these by-products and generally appear black.
  • Such manufacturing methods are e.g. in WO 2005/021484 (carbonate method) or in WO 91/14678 (Arduengo method).
  • the mixtures to be distilled are often heavily contaminated and discolored by previous manufacturing or use processes.
  • the high distillation temperature required for the separation of the ionic liquid often leads to decomposition and further decomposition. discolouration. Even with a distillation of the mixtures on an industrial scale as pure as possible ionic liquids are to be obtained with little discoloration.
  • Object of the present invention was therefore a technical process for the purification of ionic liquids, with which the ionic liquid in high yield and purity, in particular with the lowest possible color number, is obtained.
  • the method should also be as effective and inexpensive as possible, especially with regard to energy requirements. Accordingly, the method defined above was found.
  • the apparatus and method implementation The principle of short path distillation is based on the fact that a substance mixture supplied to the evaporator is heated at an evaporation surface and the constituents of the substance mixture that evaporate condense on a condenser surface opposite the evaporation surface.
  • the distance between the evaporation surface and the capacitor surface is chosen to be very small in order to minimize pressure losses over the path from the evaporation surface to the capacitor surface.
  • An apparatus for short path distillation therefore contains as essential components a heated evaporator surface and a cooled condenser surface, which are located at a sufficiently short distance.
  • An essential feature of the process according to the invention is that the mixture to be distilled is supplied to the apparatus in a specific amount. The per unit time and
  • Quantity supplied to square meter of heated evaporator surface is also called load.
  • the load of the apparatus for the molecular distillation is 5 to 100 kg of mixture per hour and square meter evaporator surface, preferably the load 10 to 80 kg mixture, in particular 10 to 60 kg mixture and more preferably the load is 20 to 40 kg mixture per hour and square meter evaporator surface.
  • the apparatus arrangement of the condenser surface to the evaporator surface may be configured in any geometric shape. It is essential that they are opposite each other and that the molecules from the evaporator surface reach the condenser surface as unhindered as possible.
  • the evaporator surface is the inner surface of a cylinder which is heated from the outside.
  • internals are located in the interior of the protruding cylinder, on whose surface the distillate condenses (condenser surface).
  • Such installations can be designed in various forms.
  • a single tube which is cooled from the inside and whose outer surface is the condenser surface, which is opposite to the evaporator surface.
  • the internals are a plurality of internally cooled tubes. These are arranged in a preferred embodiment in one or more rows in a circle and form by this arrangement of a cylindrical tube shape.
  • the evaporator and condenser surface itself preferably has at least one length dimension greater than 50 cm, in general the size of the heated evaporator surface is 0.1 to 100 square meters, in particular 1 to 80, particularly preferably 5 to 60 and in particular 20 to 40 square meters; the same applies to the cooled condenser surface.
  • the evaporator surface and condenser surface can be the same size or different sizes.
  • the ratio of evaporator surface to condenser surface is in the range of 0.1 to 10.
  • the distance between the evaporator surface and the condenser surface is preferably less than 80 cm, in particular less than 50 cm, particularly preferably less than 30 cm. These distances are preferably for more than 30 area percent, in particular for more than 50 area percent, and more preferably for more than 80 area percent of the total evaporator or condenser surface.
  • the distance between the evaporator surface and the condenser surface may remain the same over the entire evaporator and condenser surface, depending on the geometric configuration of the evaporator surface and the condenser surface, or may be different. The latter is z. Example, the case when the condenser surface consists of several circularly arranged tubes (see above).
  • molecular distillation Distillation processes with a small distance between evaporator and condenser surfaces are known as molecular distillation.
  • the distance between the evaporator and condenser surfaces is generally smaller than the mean free path of the compounds to be distilled.
  • the apparatus geometry and the process parameters are selected accordingly.
  • the distance of the evaporator surface to the condenser surface is therefore less than the mean free path of the ionic liquid in the gas phase at the selected temperature and the selected pressure in a particular embodiment.
  • the mixture is preferably supplied at the upper end of the apparatus, while the supply takes place so that the mixture passes directly to the evaporator surface.
  • the ionic liquid is separated by evaporation from the mixture and withdrawn as distillate from the condenser surface.
  • the residue remains on the evaporator surface. Suitable devices are e.g. such that the residue drains from the evaporator surface and is collected, the ionic liquid accordingly drains from the condenser surface and is obtained as a distillate.
  • the distribution of the mixture to be distilled on the evaporator surface is supported by a wiper system.
  • apparatuses which have a splash guard between evaporator and condenser surface, so that an undesired transition (by entrainment or spraying) from the evaporator surface to the condenser surface is reduced or completely avoided.
  • a splash guard between the evaporator surface and the condenser surface fins are suitable, these are preferably arranged vertically.
  • the slats can z. B. made of metal or plastic.
  • the horizontal spacing of the lamellae should be selected so that a transfer of liquid droplets from the evaporator surface to the condenser surface is reduced or completely prevented.
  • the spray protection used should cause the lowest possible pressure loss in the apparatus, z. B. a pressure drop of less than 0.1 mbar, preferably less than 0.01 mbar, more preferably less than 0.001 mbar.
  • the attachment of the splash guard can be done both on the wiper system and on the internals (condenser).
  • the embodiment, material and method of attachment of the splash guard are irrelevant to the present invention as long as the passage of liquid droplets is prevented or reduced and a low pressure loss is maintained.
  • the splash guard may be attached to the internal rotor of the wiper system and may rotate (as in Figure 1), or be installed as a fixed component between the evaporator surface and the condenser surface.
  • the evaporation is carried out at a temperature of 50 ° C to 300 ° C, more preferably from 80 to 300 ° C and most preferably from 120 ° C to 300 ° C, wherein these data are based on the average temperature of the heating medium.
  • the condensation on the capacitor surface can, for. Example, at a temperature of 0 ° C to 200 ° C, preferably from 10 ° C to 150 ° C and more preferably from 20 ° C to 100 ° C, these statements are based on the average temperature of the cooling medium.
  • the evaporation is preferably carried out at reduced pressure, in particular at a pressure of 10 -4 mbar to 10 mbar, more preferably from 10 -3 mbar to 1 mbar.
  • the average residence time of the ionic liquid to be separated in the apparatus is preferably in the range of 1 second to 10 minutes, more preferably in the range of 1 second to 2 minutes.
  • the distillate obtained may e.g. to more than 95 wt .-%, more preferably to more than 97 wt .-% "very particularly preferably to more than 99 wt .-% of the ionic liquid.
  • the method also distillates are available which consist of more than 99.5 or more than 99.8 wt .-% and 99.9 wt.% From the ionic liquid.
  • the resulting distillate (ionic liquid) has in particular a very low salt content, z. B. a salt content of less than 100 ppm or less than 50 ppm.
  • the distillate obtained has no or only a very slight discoloration, in particular, the Gardner color number of the distillate is less than 50, preferably less than 20.
  • the process can also be carried out repeatedly, be it by recycling the distillate obtained for the purpose of redistillation in the same apparatus or to a corresponding distillation in one or more further apparatuses which are connected in series.
  • a plant for carrying out the process according to the invention can be made e.g. comprising one or four short path evaporators, wherein the short path evaporator are connected to each other, that the residue of the first short path evaporator in the second short path evaporator, the residue of the second short path evaporator in the third short path evaporator and the residue of the third short path evaporator in the fourth short path evaporator is passed.
  • the process is carried out continuously.
  • the ionic liquid contained in the mixture to be distilled is a salt of at least one cation and at least one anion, which at normal pressure (1 bar) has a melting point of less than 200 ° C., in particular less than 100 ° C., preferably less than 75 ° C. , Very particular preference is given to a liquid salt at room temperature (21 ° C.) and atmospheric pressure (1 bar).
  • the cation of the ionic liquid according to the invention is a heterocyclic ring system having at least one nitrogen atom as a constituent of the ring system. All nitrogen atoms of the ring system carry an organic group as substituents. Protonation of these nitrogen atoms is therefore not possible.
  • the substituent is preferably an organic group which contains 1 to 20 C atoms, in particular 1 to 10 C atoms. Particularly preferably it is a hydrocarbon group which has no further heteroatoms, for example a saturated or unsaturated aliphatic group, an aromatic group or a hydrocarbon group which has both aromatic and aliphatic constituents. With very particular preference it is a C1 to C10 alkyl group, C1 to C10 alkenyl group, for example an allyl group, a phenyl group or a
  • Benzyl group is a C1 to C10, especially a C1 to C4 alkyl group, e.g. methyl, ethyl, propyl, i-propyl, n-butyl, n-hexyl, n-octyl or n-decyl.
  • a C1 to C4 alkyl group e.g. methyl, ethyl, propyl, i-propyl, n-butyl, n-hexyl, n-octyl or n-decyl.
  • it is an aromatic heterocyclic ring system.
  • the cation is preferably a derivative of imidazolium, pyrazolium or pyridinium.
  • the cation is a derivative of imidazolium (with two nitrogen atoms in the ring system and correspondingly two of the above substituents).
  • the anion of the ionic liquid is preferably a compound having at least one carboxylate group (short carboxylate) or at least one phosphate group (short phosphate).
  • phosphates are ⁇ 0 4 3_ or organic compounds having a phosphate group, in particular dialkyl phosphates, called.
  • Particularly preferred phosphates are C 1 -C 4 dialkyl phosphates, for example dimethyl phosphate and in particular diethyl phosphate.
  • Preferred anions are the carboxylates.
  • Particularly suitable carboxylates are organic compounds having 1 to 20 C atoms, preferably 1 to 10 C atoms, which contain one to three, preferably one or two, more preferably one carboxylate group.
  • carboxylates are the anions of the C1 to C10 alkanecarboxylic acids, for example acetic acid (acetate), propionic acid (propionate) and octanoic acid (octanoate).
  • the ionic liquid is therefore particularly preferably imidazolium salts of the formula I.
  • R 1 and R 3 independently of one another represent an organic radical having 1 to 20 C atoms
  • R 2, R 4, and R 5 independently of one another represent an H atom or an organic radical having 1 to 20 C atoms,
  • R 1 and R 3 are preferably independently an organic group containing 1 to 10 C atoms. Most preferably it is a C1 to C10, in particular a C1 to C4 alkyl group, e.g. a methyl group, ethyl group, propyl group, i-propyl group, n-butyl group or octyl group. Most preferably, R 1 and R 3 independently of one another are a methyl group or an ethyl group.
  • R 2, R 4 and R 5 are preferably independently of one another an H atom or an organic group which contains 1 to 10 C atoms. Most preferably, R 2, R 4 and R 5 are an H atom or a C 1 to C 10 alkyl group, e.g. a methyl group, ethyl group, propyl group, i-propyl group or n-butyl group. R2, R4 and R5 particularly preferably represent an H atom. n is preferably 1.
  • X is preferably an abovementioned carboxylate or phosphate, in particular a C1 to C10 carboxylate.
  • the mixtures to be distilled contain the ionic liquids in any amount, e.g. consist of 10 to 95 wt .-% or 40 to 95 wt.% Of the ionic liquid.
  • the content of ionic liquid in the mixture is preferably at least 10% by weight, more preferably at least 20% by weight, very preferably at least 40% by weight and in a particular embodiment at least 60% by weight, based on the total mixture ;
  • the method is particularly suitable for mixtures with a.
  • the content of ionic liquid in the mixture is generally not greater than 95 wt .-%.
  • the mixtures used in the process according to the invention preferably contain volatile compounds only in minor amounts.
  • Volatile compounds are understood here to mean those having a boiling point of less than 200 ° C., in particular less than 150 ° C. under atmospheric pressure (1 bar).
  • highly volatile compounds are initially present in the mixture, they are preferably substantially removed before carrying out the process according to the invention, so that their content in the mixture is at most 10% by weight, in particular at most 5% by weight, in particular at most 2% by weight or is at most 1% by weight, more preferably they are completely removed.
  • the removal of the volatile compounds may preferably be carried out as evaporation with a vaporiser known to those skilled in the art.
  • suitable evaporators are natural circulation evaporators, forced circulation flash evaporators, falling film evaporators, spiral tube evaporators, thin film evaporators and short path evaporators.
  • Evaporators are particularly preferred which, for the desired achievement of the degree of evaporation, allow the evaporator surface temperature to be as low as possible and a short contact time at the evaporator surface and thus low thermal damage to the mixture, e.g. Falling film evaporator, spiral tube evaporator, thin film evaporator and short path evaporator.
  • the pressure at which the components having a lower boiling point than the ionic liquid are separated is preferably in a range from 0.01 mbar to 5 mbar, more preferably in the range from 0.01 mbar to 1 mbar.
  • the temperature at which the components having a low boiling point are separated is in the range from 50 ° C to 250 ° C, more preferably in the range from 50 ° C to 200 ° C, these figures being based on the average temperature of the heating medium are.
  • the removal of volatile compounds can also be carried out by multi-stage evaporation, with condensation after each evaporation stage followed by a renewed evaporation takes place.
  • the above evaporators can be connected in series.
  • the mixtures contain constituents having a boiling point greater than 200 ° C (1 bar) as impurities, e.g. Salts, natural or synthetic oligomers or polymeric compounds, such as lignin, hemicellulose or oligosaccharides.
  • impurities e.g. Salts, natural or synthetic oligomers or polymeric compounds, such as lignin, hemicellulose or oligosaccharides.
  • Distillation aids can be added to the mixtures, as described in WO 2010/094640.
  • Suitable distillation aids preferably have a boiling point which is at least 10 ° C., particularly preferably at least 20 ° C., higher than the boiling point of the ionic liquids contained in the mixture.
  • the distillation aid is preferably miscible with the ionic liquid present in the mixture in any proportions.
  • the distillation aid may be e.g. polyalkylene glycols or their mono- or diesters or their mono- or diethers, e.g. with their mono- or diesters with low molecular weight carboxylic acids such as C 1 -C 10 -alkanecarboxylic acids or their mono- or diethers with C 1 to C 10 -alkanols.
  • Very particularly preferred polyalkylene glycols, or polyethylene glycols are e.g. those with a number-average molecular weight greater than 200, in particular greater than 300. Particularly suitable are, for example, Polyethylene glycols having a number average molecular weight of 400 to 1000, in particular 400 to 800.
  • the mixture may be distillation aids, e.g. in amounts of 0 to 40 wt .-%, in particular in amounts of 0 to 20 wt .-%.
  • ionic liquids can be obtained from any mixtures in high yield and purity.
  • the obtained ionic liquids have a very low salt content and a very low color number.
  • the molecular distillation according to Example 2 and Comparative Example 2 was carried out in an apparatus according to Figure 1;
  • the molecular distillation according to Example 1 and Comparative Example 1 was carried out in an apparatus according to Figure 1 but without splash protection.
  • the mixtures Prior to carrying out the distillation, the mixtures were freed of volatile compounds in an evaporator (e.g., falling film evaporator or thin film evaporator) to avoid foaming and splashing during the molecular distillation.
  • an evaporator e.g., falling film evaporator or thin film evaporator
  • Example 1 In a short path evaporator, a composition having a Gardner color number> 20 was introduced which contained about 90% by weight of 1-ethyl-3-methylimidazolium octanoate and about 1000 ppm by weight of sodium salt.
  • the load of the short-path evaporator with this mixture was 20 kg / h / m 2 .
  • the pressure in the short-path evaporator was 0.001 mbar; and the temperature of the heating medium 220 ° C. Under these conditions, the 1-ethyl-3-methylimidazolium octanoate was continuously evaporated.
  • non-volatile impurities for example salts, such as alkali octanoates or natural or synthetic oligomeric or polymeric compounds, such as lignin, hemicellulose or oligosaccharides
  • salts such as alkali octanoates or natural or synthetic oligomeric or polymeric compounds, such as lignin, hemicellulose or oligosaccharides
  • the distillate thus obtained had a purity of 98% by weight of 1-ethyl-3-methylimidazolium octanoate having a Gardner color number of 12.
  • the sodium content was 65 ppm by weight.
  • a splash guard was additionally installed in the short path evaporator between the evaporator surface and the condenser surface.
  • the recovered distillate had a purity of 98% by weight of 1-ethyl-3-methylimidazolium octanoate with a Gardner color number of 6.
  • the sodium content was ⁇ 10 ppm by weight.
  • a composition having a Gardner color number> 20 which contained about 90% by weight of 1-ethyl-3-methylimidazolium octanoate and about 1000 ppm by weight of sodium salt.
  • the load of the short-path evaporator with this mixture was 1 10 kg / h / m 2 .
  • the pressure in the short-path evaporator was 0.001 mbar; and the temperature of the heating medium 250 ° C. Under these conditions, the 1-ethyl-3-methylimidazolium octanoate was continuously evaporated.
  • non-volatile impurities for example salts, such as alkali octanoates or natural or synthetic oligomeric or polymeric compounds, such as lignin, hemicellulose or oligosaccharides
  • salts such as alkali octanoates or natural or synthetic oligomeric or polymeric compounds, such as lignin, hemicellulose or oligosaccharides
  • the distillate thus obtained had a purity of 95% by weight of 1-ethyl-3-methylimidazolium octanoate with a Gardner color number of> 20.
  • the sodium content was 250 ppm by weight.
  • the purity of the recovered ionic liquid proved to be unsuitable for further use.
  • a splash guard was additionally installed in the short-path evaporator between the evaporator surface and the condenser surface.
  • the recovered distillate had a purity of 95% by weight of 1-ethyl-3-methylimidazolium octanoate with a Gardner color number of> 20.
  • the sodium content was 300 ppm by weight.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de distillation de mélanges contenant des sels présentant une température de fusion inférieure à 200°c à 1 bar (liquides ioniques). L'invention est caractérisée en ce que la distillation est réalisée dans un appareil destiné à la distillation moléculaire, avec une charge comprise entre 5 et 100 kg de mélange par heure et par mètre carré de surface d'évaporateur.
PCT/EP2013/058900 2012-05-16 2013-04-29 Distillation de liquides ioniques par distillation moléculaire WO2013171060A1 (fr)

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EP12168175.3 2012-05-16
EP12168175 2012-05-16

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH716490A1 (de) * 2019-08-12 2021-02-15 Buss Sms Canzler Gmbh Vorrichtung zur thermischen Behandlung von Material, insbesondere zur thermischen Auftrennung von im Material enthaltenen Materialkomponenten.
US11124692B2 (en) 2017-12-08 2021-09-21 Baker Hughes Holdings Llc Methods of using ionic liquid based asphaltene inhibitors
US11254881B2 (en) 2018-07-11 2022-02-22 Baker Hughes Holdings Llc Methods of using ionic liquids as demulsifiers

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991014678A1 (fr) 1990-03-29 1991-10-03 E.I. Du Pont De Nemours And Company Preparation de sels d'imidazolium 1,3-disubstitue
WO2005021484A2 (fr) 2003-08-27 2005-03-10 Proionic Production Of Ionic Substances Gmbh & Co Keg Procede pour produire des liquides ioniques, des solides ioniques ou leurs melanges
WO2009027250A2 (fr) 2007-08-31 2009-03-05 Basf Se Distillation de fluides ioniques
DE102007053630A1 (de) * 2007-11-08 2009-05-14 Basf Se Verfahren und Herstellung ionischer Flüssigkeiten durch Anionenaustausch
WO2010094640A1 (fr) 2009-02-23 2010-08-26 Basf Se Distillation de liquides ioniques à l'aide d'un agent auxiliaire de distillation
DE102010001957A1 (de) 2009-02-23 2010-08-26 Basf Se Destillation von Gemischen, welche ionischer Flüssigkeiten und Metallsalze enthalten

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991014678A1 (fr) 1990-03-29 1991-10-03 E.I. Du Pont De Nemours And Company Preparation de sels d'imidazolium 1,3-disubstitue
WO2005021484A2 (fr) 2003-08-27 2005-03-10 Proionic Production Of Ionic Substances Gmbh & Co Keg Procede pour produire des liquides ioniques, des solides ioniques ou leurs melanges
WO2009027250A2 (fr) 2007-08-31 2009-03-05 Basf Se Distillation de fluides ioniques
DE102007053630A1 (de) * 2007-11-08 2009-05-14 Basf Se Verfahren und Herstellung ionischer Flüssigkeiten durch Anionenaustausch
WO2010094640A1 (fr) 2009-02-23 2010-08-26 Basf Se Distillation de liquides ioniques à l'aide d'un agent auxiliaire de distillation
DE102010001957A1 (de) 2009-02-23 2010-08-26 Basf Se Destillation von Gemischen, welche ionischer Flüssigkeiten und Metallsalze enthalten

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11124692B2 (en) 2017-12-08 2021-09-21 Baker Hughes Holdings Llc Methods of using ionic liquid based asphaltene inhibitors
US11254881B2 (en) 2018-07-11 2022-02-22 Baker Hughes Holdings Llc Methods of using ionic liquids as demulsifiers
CH716490A1 (de) * 2019-08-12 2021-02-15 Buss Sms Canzler Gmbh Vorrichtung zur thermischen Behandlung von Material, insbesondere zur thermischen Auftrennung von im Material enthaltenen Materialkomponenten.
EP3777987A1 (fr) * 2019-08-12 2021-02-17 Buss-SMS-Canzler GmbH Dispositif de traitement thermique de matériau, en particulier de séparation thermique des composants de matériau contenus dans le matériau
CN112386934A (zh) * 2019-08-12 2021-02-23 布斯-Sms-坎茨勒有限责任公司 用于热处理材料、特别是用于热分馏材料中含有的材料成分的设备
US11241637B2 (en) 2019-08-12 2022-02-08 Buss-Sms-Canzler Gmbh Device for the thermal treatment of material, in particular for the thermal separation of material components contained in the material

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