EP2629869A1 - Procédé permettant de simplifier la séparation d'un produit de réaction présent dans des mélanges de gaz de réaction au moyen d'au moins deux condensations partielles - Google Patents

Procédé permettant de simplifier la séparation d'un produit de réaction présent dans des mélanges de gaz de réaction au moyen d'au moins deux condensations partielles

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Publication number
EP2629869A1
EP2629869A1 EP11776731.9A EP11776731A EP2629869A1 EP 2629869 A1 EP2629869 A1 EP 2629869A1 EP 11776731 A EP11776731 A EP 11776731A EP 2629869 A1 EP2629869 A1 EP 2629869A1
Authority
EP
European Patent Office
Prior art keywords
reaction
partial condensation
reaction product
stream
condensation
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Withdrawn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
EP11776731.9A
Other languages
German (de)
English (en)
Inventor
Amgad Salah Moussa
Peter Lehner
Knut Sommer
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.)
Bayer Intellectual Property GmbH
Original Assignee
Bayer Intellectual Property GmbH
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 Bayer Intellectual Property GmbH filed Critical Bayer Intellectual Property GmbH
Publication of EP2629869A1 publication Critical patent/EP2629869A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/09—Purification; Separation; Use of additives by fractional condensation
    • 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
    • B01D3/14—Fractional distillation or use of a fractionation or rectification column
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D5/00—Condensation of vapours; Recovering volatile solvents by condensation
    • B01D5/0033—Other features
    • B01D5/0036—Multiple-effect condensation; Fractional condensation

Definitions

  • the present invention relates to a process for the simplified separation of a reaction product (P) from reaction gas mixtures by at least two partial condensation of the reaction gas mixture consisting of the reaction product (P) at least one high boiler (H) and at least one low boilers (L), and non-condensable Reaktinosgasen (G ).
  • the reaction gas in addition to the desired gaseous reaction product aniline, the reaction gas also produces ammonia as a by-product.
  • a reaction gas mixture is obtained the desired gaseous reaction product aniline, as well as the reaction gases ammonia, nitrobenzene, the excess hydrogen, and further such as introduced by the F.duct gases nitrobenzene and hydrogen gaseous impurities such as inert gases (eg nitrogen, carbon dioxide and water vapor).
  • diphenylamine is also formed as a high boiler (H) by side reactions (addition reaction).
  • reaction product (P) to be separated according to the invention described below is not necessarily identical to the desired reaction product of the reaction carried out before the separation described here, but can also be a starting material, by-product or even a mixture of starting material and desired reaction product and / or by-product of the reaction in question.
  • the affiliation of the reaction gases to one or the other group results in the specific case of the ratio between the respective boiling point of the desired reaction product (P) and the boiling point of the respective further reaction gas.
  • non-condensable reaction gases G
  • non-condensable reaction gases G are understood to mean those low-boiling components (L) which have a boiling point below room temperature (23 ° C.) under ambient pressure (1013 hPa).
  • Typical representatives of the low boilers (L) which fall into the group of non-condensable reaction gases according to the present invention are, for example, the so-called inert gases, as are generally known to the person skilled in the art under this term, ie. Gases such as so-called noble gases (argon, helium, etc.) carbon dioxide, nitrogen. Also included in the group of non-condensable reaction gases are e.g. Hydrogen, which is given in about the context of hydrogenation reactions in excess of the previous reaction, and carbon monoxide. These are, depending on the composition of the reaction gas mixture optionally together with other reaction gases, hereinafter summarized as non-condensable reaction gases (G).
  • Reaction gases in the context of the present invention, denote all compounds which are gaseous from the gas phase reaction and which are not the reaction product (P). Reaction gases thus include gaseous impurities, inert gases, non-condensable reaction gases (G), low boilers (L) and high boilers (H).
  • reactant gases or educt gas mixtures designate gaseous compounds which are fed to the abovementioned gas-phase reaction.
  • Such reactant gases or reactant gas mixtures either leave the gas phase reaction as reaction gases or are chemically converted to them or are chemically converted to the reaction product product (P).
  • Reaction gas mixture referred to according to the present invention, a mixture consisting of reaction product and reaction gases.
  • reaction product (P) In order to separate the reaction product (P) from the reaction gas mixture of the reaction gases comprising the aforementioned high boilers (H), low boilers and non-condensable reaction gases (G), the process technology practice almost always relies on the generally known technique of rectification or distillation.
  • the rectification or distillation are based on the basic physical principle that a mixture of substances at a certain pressure and at a certain temperature in its gaseous portion has a different composition than in its liquid portion. This is generally made use of by condensing and evaporating such reaction gas mixtures, which takes place repeatedly in the process engineering practice in so-called rectification or distillation columns.
  • the quality and the effort of separation Of the substances that form the reaction gases of the reaction product (P) is not least determined by the distance between the respective boiling points of the substances at each pressure to each other. The farther they are apart, ie the farther the boiling points of low boilers (L) and high boilers (H) are from the boiling point of the reaction product (P), the easier and better is the separation of the reaction product (P).
  • the rectificative or distillative separation based on the condensation and evaporation of the reaction gas mixture the output of the gas phase reaction is completely gaseous.
  • reaction gas mixture must be repeatedly condensed and vaporized according to the commonly operated processes for separating the reaction product (P) in which the reaction gas mixture is fed to a rectification or distillation column in its entirety.
  • reaction gas mixtures in which the boiling points of reaction product (P) and reaction gases are close to each other follows that the entire reaction gas mixture for good separation and thus purity of the reaction product (P) must be correspondingly often condensed and evaporated in a rectification column with reflux ,
  • reaction gas mixture consists of reaction product (P) and a large proportion of reaction gases which in turn are to a large extent high-boiling components (H), then the energy expenditure which must be expended for the separation is considerable. In general, however, it is always the case that for the abovementioned separation always a large
  • EP 2 028 176 A1 discloses a process in which first the reaction gas mixture is completely condensed, the complete condensate from the water which separates automatically by phase separation up to Solubility concentration of the aromatic amine herein is separated, and then the thus-obtained "crude” aromatic amine is reacted with an aqueous solution of an alkali hydroxide, whereby the reaction gases in the form of compounds having phenolic hydroxy groups are largely converted into the corresponding alkali salts the method disclosed therein boiling so high that they accumulate below in the bottom of the rectification column and essentially do not get into the remaining portions of the rectification column, which eliminates the need for multiple evaporation and condensation while saving energy for this.
  • the process described therein involves the preparation and purification of the reaction product styrene obtained by the dehydrogenation of ethylbenzene.
  • the reaction gas mixture is first cooled, but not condensed, and fed to a scrubber under reflux.
  • the cooling is used in the method according to US 6 388 1 55 B l especially the energy recovery from the reaction sgasgemi sch.
  • the gas stream leaving the above scrubber is fed to the single condenser of the process wherein the gases are partially condensed.
  • the condensed portion of the gases is fed to a phase separation. A part of the liquids is then subjected to distillation.
  • the scrubber can be any gas-liquid contact apparatus according to US 6,388,155 Bl.
  • the combination of scrubber, condenser and phase separator is to be regarded as a unit for carrying out a partial condensation, this partial condensation by the reflux in more as a theoretical step.
  • an evaporator is added to the bottom of the aforementioned scrubber, whereby the scrubber is no longer regarded as a scrubber, but rather as a special form of rectification column, since now both a condensation of the overhead stream and recycling the resulting condensate to the scrubber, as well as evaporating the bottom stream and returning the vapor to the scrubber.
  • reaction step described, for example, in EP 2 028 176 A1 is achieved either by the abovementioned partial, multistage
  • the entire reaction gas mixture in the sense of a multiple evaporation and condensation of the entire reaction gas mixture is treated again in US 6,388,155 Bl either in the case of the particular embodiment as a rectification step, which brings the already described energetic disadvantages, or it is in the case of once performed partial multi-stage condensation reached no optimal utilization of the enthalpy of the reaction gas mixture, which could have been dispensed with at least one of the distillation columns described in this case according to US 6,388,155 B l with appropriate energy conservation.
  • the distillation columns in turn, the aforementioned disadvantageous vol l continuous condensation and evaporation of the total supplied Antei le of the reaction gas mixture.
  • reaction product (P) a reaction product (P) from reaction gas mixtures at a temperature above room temperature (23 ° C.) consisting of the abovementioned reaction product (P), at least one low boiler (L) and / or non-condensable reaction gas (G) and at least one high boiler (H) comprising at least one distillation and / or rectification step, characterized in that prior to the at least one distillation and / or rectification step, the reaction gas mixture is subjected to at least two partial condensation steps in which at least one
  • the abovementioned partial condensations according to the invention can be carried out in simple devices which are generally known to the person skilled in the art. Theoretically, it is sufficient for this cooled, or even in special cases, in which the reaction product (P) has a boiling point in the range of ambient temperature (23 ° C) or above, uncooled containers with a supply line for the reaction gas mixture, a derivative for the condensate and a derivative for the remaining gas stream. Usually, however, it will be safe to use condensation heat exchangers generally known to those skilled in the art in order to carry out the partial condensations according to the invention. In the context of the preferred embodiments of the method according to the invention described below, additionally preferred variations of such devices will be explained.
  • the first partial condensation according to step a) and the second partial condensation according to step b) of the process according to the invention are carried out directly after one another, wherein the gas stream from the first partial condensation of the second partial condensation is fed directly ,
  • the gas stream comprising the second partial condensation and also the reaction product (P) is fed to a third partial condensation in which at least 80% by weight of the reaction product (P) fed to the third partial condensation condenses become.
  • This third partial condensation is particularly advantageous if the gas stream from the second partial condensation, in addition to the low-boiling components (L) and / or non-condensable reaction gases (G), also comprises significant portions of the reaction product (P), for example because the phase equilibrium of remaining reaction gas mixtures exit the second partial condensation is unfavorable, or if in the process according to the invention, the low boilers (L) and / or non-condensable reaction gases (G) should also be separated from each other.
  • At least one of the partial condensations is carried out with reflux of the condensate of this partial condensation.
  • a part or the entirety of the recycled condensate is preferably removed and led out of this partial condensation as a further liquid stream.
  • a part or the entirety of the recycled condensate is preferably removed and led out of this partial condensation as a further liquid stream.
  • the reflux ratio and / or proportion of the derived condensate results in a different composition then one or two led out of the partial condensation
  • a design under reflux with the aforementioned department of a further liquid stream is particularly advantageous if the gas stream fed to such partial condensation low boilers (L), non-condensable reaction gases (G) and reaction product (P), or high boilers (H), reaction product (P) and Low boilers (L), since in such a design with reflux with discharge and the simultaneous separation of low boilers (L) and Reakti on s. (P) or high boilers (H) and reaction product (P) in two different liquid streams, and non-condensable Reaction gases (G) or low boilers (L) in a remaining gas stream is possible.
  • a derivative is usually realized by providing a derivative with control valve of the return line tion of the condensate in the wash column.
  • At least one of the partial condensations also comprises a phase separation between two liquid phases which are incompletely miscible with each other under the conditions of partial condensation, so that from the partial condensation according to this preferred development as well as in the case of the above described in the second preferred development in derivation of two liquid streams and a gas stream can be obtained.
  • the components of the reaction gas mixture that may already have been pre-fractionated by the at least one partial condensation may be fractionated again without any further energy expenditure.
  • these two liquid streams are then a first liquid stream comprising substantially nonpolar constituents of the partially condensed reaction gas mixture and a second liquid stream comprising essentially polar constituents of the partially condensed reaction gas mixture.
  • the partial condensation according to this third preferred further development can also be combined with the partial condensation according to the second preferred development and its preferred embodiments with dissipation. This may optionally be up to three Liquid streams of different composition from a partial condensation step can be obtained.
  • a device for carrying out the partial condensation according to the third preferred development is about a condensing heat exchanger connected with a calming tank, lead out of the two discharges for liquids, one at the bottom of this container and one above the phase boundary of the liquids in the container, and a discharge for the remaining reaction gases at the top of the container.
  • the first partial condensation according to step b) according to the invention is carried out directly after a partial condensation according to step a) according to the invention and after step b) a partial condensation under reflux of the condensate of this partial condensation wherein a part of this recycled condensate is discharged and is led out as a further liquid stream from this third partial condensation.
  • the first partial condensation according to the inventive step b) is carried out directly after a partial condensation according to the inventive step a) and this first partial condensation is carried out under reflux of the condensate of this partial condensation, wherein also a portion of this recycled condensate is discharged and is led out as a further liquid stream from this first condensation, while the second partial condensation according to step b) also includes a phase separation between two liquid, with each other under the conditions of partial condensation incompletely miscible phases, so that a liquid stream comprising substantially polar constituents of the partially condensed reaction gases and a liquid stream comprising substantially non-polar constituents of the partially condensed reaction Are led out of this second partial condensation of gas.
  • the first partial condensation according to step b) according to the invention is carried out directly after a partial condensation according to step a) according to the invention and this first partial condensation is carried out under reflux of the condensate of this partial condensation, wherein a Part of this recycled condensate is discharged and is led out as a further liquid stream from this first condensation, while the second partial condensation according to step b) is also carried out under reflux of the condensate of this second partial condensation and wherein also a part of this recycled condensate is derived and as a further Liquid stream is led out of this second partial condensation.
  • the first partial condensation according to step b) according to the invention is carried out directly after a partial condensation according to step a) according to the invention and this first partial condensation takes place with complete reflux of the condensate of this partial condensation and with phase separation between carried out two liquid, with each other under the conditions of partial condensation incompletely miscible phases, so that another liquid stream is led out of this first condensation, while the second partial condensation according to step b) only a phase separation between two liquid, with each other under the Conditions of partial condensation incompletely miscible phases, so that a liquid stream comprising substantially polar constituents of the partially condensed reaction gases and a liquid stream comprising substantially nonpolar constituents of the partially condensed reaction gases can be led out of this second partial condensation.
  • the reaction gas mixture comprises the reaction product (P) toluenediamine, the noncondensable reaction gases (G) hydrogen and nitrogen, the low boilers (L) water and high boilers having a boiling point of more than 3OO ° C at ambient pressure (1013 hPa) and that this reaction gas mixture of a first partial condensation is supplied, from which a first liquid stream comprising the entirety of the high boilers (H) and a proportion of not more than 10 wt .-% of the toluenediamine is obtained , and a first gas stream comprising all of the hydrogen and nitrogen and all the water, and at least 90 wt .-% of the toluenediamine is obtained.
  • the aforementioned first gas stream of the second partial condensation is supplied, from which a second gas stream is obtained, the total hydrogen and nitrogen and all the water of the second partial condensation supplied first gas stream in addition to a maximum of 20 wt. % of the toluene diamine fed thereto. Furthermore, from this second partial condensation, containing a second liquid stream, only the toluenediamine is obtained.
  • the second gas stream is fed to the third partial condensation with reflux and with the discharge of a third and a fourth liquid stream from the third partial condensation.
  • the third partial condensation leaves a third gas stream comprising not more than 30% by weight of the water supplied to it with the second gas stream and all of the nitrogen and hydrogen.
  • the third liquid stream comprises the water and the fourth liquid stream alone contains the toluenediamine.
  • the aforesaid first liquid stream is fed in the middle between the stripping and enrichment sections in the middle between the stripping section and the enrichment section in accordance with the particularly preferred embodiment of the first preferred embodiment described herein.
  • the first distillation column is treated with pure toluene diamine at the top and the high boilers (H). taken from the ground.
  • the abovementioned second and optionally also the fourth liquid stream are in particular preferably fed to a second distillation column in the enrichment section thereof and the pure toluene diamine is removed there between the stripping section and the enrichment section, as well as the water at the top.
  • All partial condensations according to the above-described particularly preferred embodiment of the first particularly preferred further development of the invention are in this case usually operated at a pressure in the range from 2 to 5 bar, preferably at a pressure of about 3 bar.
  • the first partial condensation is usually operated at a temperature in the range of 200 ° C to 220 ° C and the second partial condensation at a temperature in the range of 160 ° C to 200 ° C.
  • the third partial condensation is preferably operated in the region of the wash column at a temperature in the range from 85 ° C. to 160 ° C., and condensation heat exchangers and downstream collection vessels are operated at a temperature in the range from 50 ° C. to 90 ° C.
  • the reaction gas mixture comprises the reaction product (P) methanol, the non-condensable reaction gases (G) carbon monoxide, carbon dioxide, hydrogen, nitrogen and methane, the low-boiling components (L ) Dimethyl ether and the high boilers (H) comprises water and ethanol and in that this reaction gas mixture is subjected to a first partial condensation under reflux from the first liquid stream comprising the entirety of the water, a portion of the ethanol and a proportion of not more than 30 wt.
  • % of the methanol, a second liquid stream comprising methanol and ethanol, and a first gas stream comprising all of the hydrogen and nitrogen and all of the carbon monoxide, and at least 90 wt .-% of the carbon dioxide, methane and dimethyl ether is obtained.
  • the aforementioned first gas stream of the second partial condensation is supplied, from which a second gas stream is obtained, the total hydrogen and nitrogen and the total carbon monoxide of the second partial condensation supplied first gas stream together with at least each 95 wt .-% of the second partial condensation supplied first gas stream of carbon dioxide, methane and dimethyl ether in addition to a maximum of 50 wt .-% of the methanol supplied to it comprises.
  • a third liquid stream comprising methanol, ethanol and not more than 5% by weight of the first gas stream of dimethyl ether and carbon dioxide fed to the second partial condensation.
  • the aforesaid first liquid stream is supplied to the combination of the first and second preferred developments of a first distillation column in the middle between the stripping and enrichment sections, and the first distillation column becomes pure dimethyl ether on the top, water and ethanol on the bottom, and methanol removed in the region of the stripping section.
  • the abovementioned second and optionally also the third liquid stream are in particular preferably fed to a second distillation column and this at the top of the dimethyl ether, as well as methanol at the bottom optionally taken together with remaining ethanol, or alternatively a so-called stripper, as the skilled person generally knows supplied from the methanol may also be taken off at the bottom together with any remaining ethanol and dimethyl ether at the top.
  • the two partial condensations according to the above-described particularly preferred embodiment of the invention are in this case usually operated at a pressure in the range of 50 to 90 bar, preferably at a pressure of about 75 bar.
  • the first partial condensation is preferably operated and in the region of the wash column at a temperature in the range of I20 ° C to 1 60 Ü C condensation heat exchanger and a downstream collection vessel be operated at a temperature ranging from 70 ° C to 120 ° C.
  • the second partial condensation is usually operated at a temperature in the range of 40 ° C to 80 ° C.
  • the reaction gas mixture comprises the reaction product (P) benzene, the non-condensable reaction gases (G) hydrogen, nitrogen and methane and the high boiler (H) toluene and in that this reaction gas mixture is fed to a first partial reflux under reflux, from which a first liquid stream comprising the entirety of the toluene and a proportion of not more than 50% by weight of the benzene is obtained, a second liquid stream comprising benzene is obtained, and a first gas stream comprising all of the hydrogen and nitrogen and all of the methane, and benzene is obtained.
  • the abovementioned first gas stream is fed to the second partial condensation, from which a second gas stream is obtained, which comprises all of the hydrogen and nitrogen and all the methane of the first gas ion supplied to the second partial condensation. Furthermore, from this second partial condensation it is particularly preferred to obtain a third liquid stream comprising at least 95% by weight of the benzene supplied to the second partial condensation.
  • the aforesaid first liquid stream is fed to a first distillation column in the middle between the stripping and enrichment sections, and pure benzene is removed from the first distillation column at the top and pure toluene is removed from the bottom ,
  • the abovementioned second and optionally also the third liquid stream are in particular preferably fed to a second distillation column and taken from this at the head of pure benzene, or alternatively a so-called stripper, as the skilled person generally knows supplied, is taken from the pure benzene at the top.
  • the two partial condensations according to the above-described particularly preferred embodiment of the invention are in this case usually operated at a pressure in the range of 30 to 40 bar, preferably at a pressure of about 35 bar.
  • the first partial condensation is preferably operated in the region of the wash column at a temperature in the range from 140 ° C. to 220 ° C., and condensation heat exchangers and downstream collection vessels are operated at a temperature in the range from 70 ° C. to 150 ° C.
  • the second partial condensation is usually carried out at a temperature in the range of
  • reaction gas mixture as reaction product (?) Is a mixture of aniline and phenol, as non-condensable reaction gases (G) hydrogen, nitrogen and ammonia, as low boilers ( L) comprises water and benzene and as high boilers (H) diphenylamine and in that this reaction gas mixture is fed to a first partial reflux under reflux with a discharge comprising a first liquid stream comprising the entirety of the diphenylamine and a proportion of not more than 50% by weight of the Reaction product (P) is obtained, a second liquid stream comprising the reaction product (P) is obtained, and a first gas stream comprising all the hydrogen and nitrogen and the total ammonia, and at least each 95 wt .-% of benzene and water is obtained.
  • the aforementioned first gas stream is fed to the second partial condensation with phase separation, from which a second gas stream is obtained which contains all the hydrogen and nitrogen and at least 80% by weight of ammonia of the second partial condensation includes first gas stream. Further, from the second partial condensation, a third liquid stream comprising at least 95% by weight of the benzene fed to the second partial condensation and a fourth liquid stream comprising at least 95% by weight of the water fed to the second partial condensation are obtained.
  • the aforesaid first and second liquid streams are fed to a distillation column according to the particularly preferred embodiment of the second preferred embodiment described herein.
  • the first liquid stream in the stripping section of the column is supplied and fed to the second liquid stream in the enrichment section of the column.
  • the reaction product (P) is removed.
  • the two partial condensations according to the above-described particularly preferred embodiment of the invention are in this case usually operated at a pressure in the range of 2 to 10 bar, preferably at a pressure of about 5 bar.
  • the first partial condensation is preferably operated in the region of the wash column at a temperature in the range from 140 ° C. to 150 ° C., and condensation heat exchangers and downstream collection vessels are operated at a temperature in the range from 110 ° C. to 150 ° C.
  • the second partial condensation is usually operated at a temperature in the range of 60 ° C to 120 ° C.
  • the reaction gas mixture comprises the reaction product (P) isopropylbenzene, the noncondensable reaction gases (G) propylene and propane, the low boilers (L) benzene and the high boilers (H ) Diisopropylbenzene and when this reaction gas mixture is fed to a first partial reflux under reflux, from which a first liquid stream comprising the entirety of the diisopropylbenzene and a proportion of not more than 10% by weight of the isopropylbenzene is obtained, a second liquid stream comprising the isopropylbenzene and a first gas stream comprising all the propylene and more than 95% by weight of the propane and more than 90% by weight of the benzene is obtained.
  • first gas stream of the second partial condensation is fed under reflux with discharge, from which a second gas stream is obtained which comprises at least 70% by weight of propylene and propane of the first partial second condensation Gas stream includes. Furthermore, except for this second partial condensation, a third liquid stream comprising at least 70% by weight of the benzene fed to the second partial condensation and a fourth liquid stream comprising at least 60% by weight of the isopropylbenzene fed to the second partial condensation are obtained.
  • the aforesaid first and second liquid streams are fed to a distillation column in accordance with the particularly preferred embodiment described here for the third particularly preferred further development.
  • the first liquid stream in the stripping section of the column is supplied and fed to the second liquid stream in the enrichment section of the column.
  • the reaction product (P) is removed.
  • the two partial condensations according to the above-described particularly preferred embodiment of the invention are in this case usually operated at a pressure in the range of 1 to 5 bar, preferably at a pressure of about 2 bar.
  • the first partial condensation is preferably operated in the region of the wash column at a temperature in the range from 150 ° C. to 190 ° C. and condensation heat exchangers and downstream collection vessels are operated at a temperature in the range from 140 ° C. to 160 ° C.
  • the second partial condensation is preferably operated in the region of the wash column at a temperature in the range from 100 ° C. to 150 ° C., and condensation heat exchangers and downstream collection vessels are operated at a temperature in the range from 60 ° C. to 110 ° C.
  • the reaction gas mixture, the reaction product (P) ethylbenzene, the non-condensable reaction gases (G) ethylene, propylene and ethane, the low boilers (L) benzene and the High boilers (H) comprises diethylbenzene and when this reaction gas mixture of a first partial reflux under reflux is supplied from a first liquid stream comprising the entirety of the diethylbenzene and a proportion of not more than 10 wt .-% of ethylbenzene, a second liquid stream comprising the ethylbenzene, and a first gas stream comprising more than 95 wt .-% of ethylene, propylene and ethane, and more than 20 wt .-% of the benzene is obtained.
  • the aforementioned first gas stream of the second partial condensation is supplied under reflux with discharge, from which a second gas stream is obtained, the at least 90 wt .-% of ethylene, propylene and ethane of the second partial condensation comprises supplied first gas stream.
  • a third liquid stream comprising at least 70% by weight of the benzene fed to the second partial condensation and a fourth liquid stream comprising at least 60% by weight of the ethylbenzene fed to the second partial condensation are obtained.
  • the aforesaid first and second liquid streams are fed to a distillation column in accordance with the particularly preferred embodiment described here for the third particularly preferred further development.
  • the first liquid stream in the stripping section of the column fed and fed the second liquid stream in the enrichment section of the column. Between the stripping and enrichment section of the column, the reaction product (P) is removed.
  • the two partial have condensations according to the above-described particularly preferred embodiment of the invention are in this case usually operated at a pressure in the range of 1 to 3 bar, preferably at a pressure of about 1, 1 bar.
  • the first partial condensation is preferably operated in the region of the wash column at a temperature in the range from 110 ° C. to 170 ° C., and condensation heat exchangers and downstream collection vessels are operated at a temperature in the range from 90 ° C. to 115 ° C.
  • the second partial condensation is preferably operated in the region of the wash column at a temperature in the range of 70 ° C to 100 ° C and condensation heat exchanger, and downstream collection container are operated at a temperature in the range of 50 ° C to 80 ° C.
  • reaction gas mixture comprises as reaction product (P) a mixture of benzene and toluene, noncondensable reaction gases (G) ethylene, hydrogen and methane, and high boilers (H).
  • the aforementioned first gas stream of the second partial condensation is fed under phase separation, from which a second gas stream is obtained, the at least 90 wt .-% of hydrogen, methane and ethylene of the second partial condensation supplied first Gas stream includes.
  • a third liquid stream comprising at least 70% by weight of the second partial condensation reaction product (P) and a fourth liquid stream comprising the remaining water of the second partial condensation gas stream is obtained.
  • the aforesaid first liquid stream is fed to a distillation column in accordance with the particularly preferred embodiment described here for the fourth particularly preferred further development.
  • the first liquid stream is supplied between the stripping section and the reinforcing section of the column.
  • the reaction product (P) is removed, styrene is removed at the bottom of the column.
  • FIG. 1 a process flow diagram according to embodiment 1
  • FIGS. 2 is a process flow diagram according to embodiment 2 (FIG. 2 a) and 3 (FIG. 2 b)
  • FIG. 3 e is a process flowchart according to embodiment 4
  • FIG. 4 is a process flow diagram according to exemplary embodiments 5 and 6
  • FIG F ig. 5 ei n process flowchart according to the embodiment 7th
  • FIG. 6 shows an embodiment of a capacitor for the partial condensation according to the invention.
  • a condenser is supplied with a gas stream (FS), which is partially condensed in a condensation heat exchanger and leaves it again as stream (PCS) comprising at least one liquid phase and one gas phase.
  • This stream (PCS) is separated in a receiver with mist eliminator into a liquid stream (OS u ) and a gas stream (OSQ).
  • a condenser possibly carried out in this form is designated by (Ci).
  • FIG. 7 shows a further embodiment of a capacitor for the partial condensation according to the invention.
  • This condenser allows the teilwei e condensation with return and discharge of a second liquid stream.
  • a condenser is supplied with a gas flow (FS).
  • This gas stream (FS) enters a wash column with packing, where it is partially condensed with reflux of the condensate (RS).
  • the wash column leaves a first liquid stream (OSu) and your gas stream (GS).
  • the gas flow is in turn partially condensed as a condensation heat exchanger and exits as a stream (PCS) comprising at least one liquid phase and one gas phase.
  • PCS stream
  • This stream (PCS) is separated in a receiver with droplet separator into a liquid stream and a gas stream (OS G ), the liquid stream being separated and leaving the condenser for this fraction (OS L2 ). The other portion of this liquid flow is recycled as condensate (RS) to the wash column.
  • a condenser possibly carried out in this form is denoted by (C 22 ), respectively.
  • FIG. 8 shows yet another embodiment of a capacitor for the partial condensation according to the invention.
  • Such a condenser is supplied with a gas stream (FS) which is partially condensed in a condensation heat exchanger and re-circulated as a stream (PCS) comprising two liquid phases and one gas phase.
  • This current (PCS) is in a collecting vessel with mist into a first separated liquid stream (OS L i) and second liquid stream (OS) 2) and a gas stream (OS G).
  • the separation between the first liquid stream (OS u ) and the second liquid stream (OSu) in the collecting container is effected by the gravitational phase separation of a polar and non-polar liquid phase of different density.
  • a capacitor possibly carried out in this form is designated by (C 12 ).
  • FIG. 9 shows yet another embodiment of a capacitor for the partial condensation according to the invention.
  • a gas stream FS
  • a scrubbing column as in FIG. 7, which is partially condensed with reflux of the condensate (RS).
  • the scrubber leaves a first fluid stream (OSu) and a gas stream (GS), which is partially condensed in a condensation heat exchanger and leaves it again as stream (PCS) comprising two liquid phases and one gas phase.
  • This stream (PCS) is separated in a catch tank with mist eliminator into a first liquid stream (RS) and second liquid stream (OS L2 ) and a gas stream (OS G ).
  • the separation between the first liquid stream (RS) and the second liquid stream (OS L 2) in the collecting container is effected by the gravitational phase separation of a polar and nonpolar liquid phase of different density.
  • the first fluid flow (RS) is the fluid flow comprising the higher density phase. This is returned to the wash column.
  • the second liquid stream (OSu) comprising the liquid phase of lower density is led out of the condenser.
  • a capacitor possibly carried out in this form is designated by (C2).
  • Fig. 10 shows a capacitor of the type and operation, as already described with reference to Fig. 7, but with the difference that no discharge of a second liquid flow is provided.
  • Fig. 11 shows a capacitor of the type and operation, as already described with reference to Fig. 9, but with the difference that a derivative of a third liquid flow (OSu) is additionally provided.
  • OSu third liquid flow
  • Example 1 Process according to the first particularly preferred further development applied to reaction gas mixtures comprising the reaction product (P) toluenediamine (TDA)
  • the first gas stream (2) was then a second partial condensation in a second
  • the second gas stream (4) was subjected to a third partial condensation in a third condenser (C 22 ) according to FIG.
  • This partial condensation was called partial condensation carried out under reflux and with discharge of a partial flow of the condensate, so that from the third partial condensation, a third (7) and a fourth liquid stream (8) was obtained.
  • a third gas stream (6) was obtained from the third partial condensation.
  • the third and fourth liquid streams (7, 8), as well as the third gas stream (6) were in turn assembled according to Table 2.
  • the temperature in the wash column was in the range of 86 ° C to 160 ° C
  • the temperature in the condensation heat exchanger and receiver was in the range of 50 ° C to 86 ° C. The above ranges were due to an adjusting temperature distribution in the individual devices.
  • the first liquid stream (3) was fed to a rectification column (D) between the stripping section and the enrichment section, from which a top stream (9) and a bottom stream (10) were taken, again in accordance with Table 2.
  • a reaction gas mixture according to Table 3 was subjected to the procedure described below.
  • This reaction gas mixture was subjected to a process as shown in the flow chart of Fig. 2a.
  • first the stream of the reaction gas mixture (1) was assembled according to Table 3 in a first capacitor (C 22 ) according to FIG. 7 subjected to a first partial condensation.
  • This first partial condensation was carried out under reflux and with removal of part of the condensate, so that a first liquid stream (3) and a second liquid stream (10) were obtained.
  • the first condenser (C 22 ) was operated in the scrubbing column at a temperature in the range of 128 ° C to 160 ° C and in the condensation heat exchanger and receiver in the range of 78 ° C to 1 16 ° C.
  • a first gas stream (2) was obtained, which was a second partial condensation in a second capacitor (Ci) shown in FIG. 6 was supplied.
  • This second partial condensation was carried out at temperatures in the range of 40 ° C to 78 ° C and from this a second gas stream (4) and a third liquid stream (5) were obtained.
  • the liquid streams (5) and (10) were fed together to a stripper (V), from which a gas stream (6) and a liquid stream (7) was obtained.
  • the liquid stream (3) was fed to a rectification column (D) between the stripping and enrichment section, which was removed in the stripping section of pure methanol.
  • the respective streams (2-12) are composed according to Table 4.
  • the process was carried out with the exception of the aforementioned stripper (V) and the rectification column (D) at pressures of about 50-100 bar.
  • the stripper (V) and the rectification column (D) were operated at a pressure below 50 bar at about ambient pressure (1013 hPa). Ie. it For example, the pressures were not lowered above a level that would otherwise result from the general pressure drop in the streams and / or condensers.
  • This process variant according to the invention avoids the necessity of complete condensation and evaporation of the methanol contained in the reaction gas mixture (1), which leads to significant energy savings by using the enthalpy of the reaction gas mixture at most within the aforementioned partial condensations for the separation of the components.
  • Example 3 Process according to the first and second preferred further developments, applied to reaction gas generants comprising the reaction product (F) benzene
  • a reaction gas mixture according to Table 5 was subjected to the procedure described below.
  • This reaction gas mixture was also subjected to a process as shown in the flow chart of FIG. 2b.
  • first the stream of the reaction gas mixture (1) was assembled according to Table 5 in a first capacitor (C 22 ) according to FIG. 7 subjected to a first partial condensation.
  • This first partial condensation was carried out under reflux and with removal of part of the condensate, so that a first liquid stream (3) and a second liquid stream (10) were obtained.
  • the first condenser (C 22 ) was operated in the scrubbing column at a temperature in the range of 1 6 ° C to 220 ° C and in the condensation heat exchanger and receiver in the range of 75 ° C to 146 ° C.
  • a first gas stream (2) was obtained, which was a second partial condensation in a second capacitor (Ci) shown in FIG. 6 was supplied.
  • This second partial condensation was at temperatures in the range of 50 ° C to 75 ° C and from this, a second gas stream (4) and a third liquid stream (5) were obtained.
  • the liquid streams (5) and (10) were fed together to a stripper (V), from which a gas stream (6) and a liquid stream (7) was obtained.
  • the liquid stream (3) was fed to a rectification column (D) between the stripping and enrichment section, which was removed in the stripping section of pure methanol.
  • the respective streams (2-10) are composed according to Table 4.
  • the process was carried out at pressures of about 75 bar except for the aforementioned stripper. That the pressures were not lowered beyond a level that would otherwise result from the general pressure drop in the streams and / or condensers.
  • Table 6 Composition of the streams according to FIG. 2b in mass process of electricity (1)
  • reaction gas mixture (1) This process variant according to the invention avoids the need for complete condensation and vaporization of benzene contained in the reaction gas mixture (1), which leads to significant energy savings by the enthalpy of the reaction gas mixture is used as a maximum within the aforementioned partial condensations for the separation of the components.
  • Example 4 Process according to the second particularly preferred further development applied to reaction gas mixtures comprising as reaction product (F) a mixture of aniline and phenol.
  • a reaction gas mixture according to Table 7 was subjected to the procedure described below.
  • This reaction gas mixture was subjected to a process as shown in the flow chart of FIG. 3.
  • first the stream of the reaction gas mixture (1) was assembled according to Table 7 in a first condenser (C22) according to FIG. 7 subjected to a first partial condensation.
  • This first partial condensation was carried out under reflux and with removal of part of the condensate, so that a first liquid stream (3) and a second liquid stream (4) were obtained.
  • the first condenser (C 22 ) was operated in the scrubbing column at a temperature in the range 145 ° C to 147 ° C and in the condensation heat exchanger and receiver in the range of 1 18 ° C to 145 ° C.
  • a first gas stream (2) was also obtained which is fed to a second partial condensation with phase separation in a second condenser (C i2 ) according to FIG. 8 together with the top stream (12) from a second rectification column (D 2 ) has been.
  • This second partial condensation was carried out at temperatures in the range of 60 ° C to 1 18 ° C and from this a second gas stream (5) and a third (7) and fourth liquid stream (1) was obtained.
  • the third liquid stream (7) essentially contained the nonpolar components and the fourth liquid stream (11) the polar components.
  • the fourth liquid stream (11) is fed to a second rectification column (D 2 ) from which a further liquid stream (6) comprising essentially water and a top stream (12) comprising essentially ammonia and water was obtained.
  • Table 8 Composition of the streams according to Kg. 3 in mass percent of current (1)
  • the liquid streams (3), (4) and (7) were fed separately from one another at different points of a first rectification column (D).
  • the liquid streams (4) and (7) were fed to the rectifying section and the liquid stream (3) to the stripping section of the rectification column (D). It was found that it is irrelevant whether the streams (4) and (7) were fed separately or together to the first rectification column (Di). The only thing was that they were the first Recti fication column (Di) were supplied in the reinforcing part, while the current (3) was supplied to the driven part. Between the stripping and enrichment section, a pure mixture (10) of aniline and phenol was taken.
  • the respective streams (2-1 1) are composed according to Table 8.
  • the process was carried out with the exception of the rectification columns (DD 2 ) at pressures of about 5 bar.
  • the rectification columns (Di, D 2 ) were operated at absolute pressures in the range of 100 to 600 mbar. Ie. essentially, the pressures were not lowered beyond a level that would otherwise result from the general pressure drop in the streams and / or condensers.
  • This Anlagensvariame according to the invention avoids the need for complete condensation and evaporation of aniline contained in the reaction gas mixture (1), which leads to significant energy savings by the enthalpy of the reaction gas mixture is used as a maximum in the aforementioned partial condensations for the separation of the components.
  • Example 5 Process according to the third particular preferred further development applied to reaction gas mixtures comprising the reaction product (P) isopropylbenzene
  • a reaction gas mixture according to Table 9 was subjected to the procedure described below.
  • This reaction gas mixture was subjected to a process as shown in the flow chart of FIG. 4.
  • first the stream of the reaction gas mixture (1) was assembled according to Table 9 in a first capacitor (IC 22 ) according to FIG. 7 subjected to a first partial condensation.
  • This first partial condensation was carried out under reflux and with removal of part of the condensate, so that a first liquid stream (3) and a second liquid stream (4) were obtained.
  • the first condenser (IC 22 ) was operated in the scrubbing column at a temperature in the range of 156 ° C to 190 ° C and in the condensation heat exchanger and receiver in the range of 145 ° C to 156 ° C.
  • a first gas stream (2) was obtained, which is a second partial condensation under reflux with discharge in a second capacitor (2C22). was supplied as shown in FIG. From this second partial condensation, a third (6) and a fourth (7) liquid stream were obtained in addition to a second gas stream (5).
  • the second condenser (2C22) was operated in the scrubbing column at a temperature in the range of 102 ° C to 145 ° C and in the condensation heat exchanger and receiver in the range of 65 ° C to 102 ° C.
  • Table 10 Composition of the streams according to Kg. 4 in mass percent of stream (1) in Ex. 5
  • the liquid streams (3), (4) and (7) were fed together to a rectification column (D).
  • the liquid streams (4) and (7) were fed to the rectifying section and the liquid stream (3) to the stripping section of the rectification column.
  • pure isopropylbenzene (10) was removed.
  • a top stream (8) and bottom stream (9) were taken from the column.
  • the respective streams (2-10) are composed according to Table 10.
  • the process was carried out at pressures of about 2 bar. Ie. the pressures were not lowered beyond a level that would otherwise result from the general pressure drop in the streams and / or condensers.
  • Reaction gas mixture is used as a maximum in the context of the aforementioned partial condensations for the separation of the components.
  • Example 6 Process according to the third particularly preferred development applied to reaction gas mixtures comprising the reaction product (P) ethylbenzene
  • a reaction gas mixture according to Table 11 was subjected to the process described below.
  • This reaction gas mixture was also subjected to a process as shown in the flow chart of FIG. 4.
  • first the stream of the reaction gas mixture (1) was assembled according to Table 11 in a first capacitor (IC 22 ) according to FIG. 7 subjected to a first partial condensation.
  • This first partial condensation was carried out under reflux and with removal of part of the condensate, so that a first liquid stream (3) and a second liquid stream (4) were obtained.
  • the first condenser (IC 22 ) was operated in the scrubbing column at a temperature in the range of 1 1 ° C to 170 ° C and in the condensation heat exchanger and receiver in the range of 90 ° C to 1 1 1 ° C. From this first partial condensation, a first gas stream (2) was obtained, which was a second partial condensation under reflux with discharge in a second capacitor (2C22) shown in FIG. 7 was supplied. From this second partial condensation, a third (6) and a fourth (7) liquid stream were obtained in addition to a second gas stream (5).
  • the second capacitor (2C K) was operated in the scrubbing column at a temperature in the range 78 ° C to 90 C C and the condensation heat exchanger and the collecting container in the region of 55 ° C to 78 ° C.
  • Table 12 Composition of the streams according to Flg. 4 In mass percent of electricity (1) in Ex. 6
  • the liquid streams (3), (4) and (7) were fed together to a rectification column (D).
  • the liquid streams (4) and (7) were fed to the rectifying section and the liquid stream (3) to the stripping section of the rectification column.
  • pure isopropylbenzene (10) was removed.
  • the column was a top stream (8) and
  • the respective streams (2-10) are composed according to Table 12.
  • the process was carried out at pressures of about 1.1 bar. Ie. the pressures were not lowered beyond a level that would otherwise result from the general pressure drop in the streams and / or condensers.
  • This process variant of the invention avoids the need for complete condensation and evaporation of benzene and ethylbenzene contained in the reaction gas mixture (1), which leads to significant energy savings by the enthalpy of the reaction gas mixture is maximally used in the context of the aforementioned partial condensations for the separation of the components.
  • Example 7 Process according to the fourth particularly preferred development applied to reaction gas mixtures comprising as reaction product (P) a mixture of benzene and toluene.
  • a reaction gas mixture according to Table 13 was subjected to the procedure described below.
  • This reaction gas mixture was subjected to a process as shown in the flow chart of FIG. 5.
  • first of all the stream of the reaction gas mixture (1) was combined according to Table 13 in a first condenser (C24) according to FIG. 9 subjected to a first partial condensation.
  • the first partial condensation was carried out under reflux and with phase separation, so that a first liquid stream (3) and a second liquid stream (4) were obtained.
  • the first liquid stream (3) essentially contained the non-polar components
  • the second liquid stream (4) essentially comprised the polar components, ie the water together with entrained gas residues of methane and ethylene.
  • the first condenser (C24) was operated in the scrubbing column at a temperature in the range 72 ° C to 250 ° C and in the condensation heat exchanger and receiver in the range of 65 ° C to 72 ° C.
  • a first gas stream (2) was also obtained, which was fed to a second partial condensation with phase separation in a second condenser (C12) according to FIG. 8.
  • Table 14 Composition of the streams according to FIG. 5 in mass percent of stream (1)
  • This second partial condensation was carried out at temperatures in the range of 35 ° C to 65 ° C and from this, a second gas stream (5) and a third (6) and fourth liquid stream (7) were obtained.
  • the third liquid stream (6) essentially contained the non-polar components and the fourth liquid stream (7) contained the polar components in the form of pure water.
  • the liquid stream (3) was fed to a rectification column (D) between the stripping section and the reinforcing section.
  • pure reaction product (8) was removed in the form of a mixture of benzene and toluene.
  • pure ethylbenzene was removed in a further stream (10) and pure styrene (9) was removed from the bottom of the column.
  • the respective streams (2-10) are composed according to Table 14. The process was carried out at pressures of about 1.5 bar. Ie. the pressures were not lowered above a level that would otherwise result from the overall loss of traction in the streams and / or condensers.
  • This process variant of the invention avoids the need for complete condensation and evaporation of benzene and toluene and also allows the further separation of the components benzene and toluene without further Destilatioaskolonne. This leads to significant energy savings by using the enthalpy of the reaction gas mixture as much as possible in the context of the abovementioned partial condensations for separating the components.

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Abstract

La présente invention concerne un procédé permettant de simplifier la séparation d'un produit de réaction (P) présent dans des mélanges de gaz de réaction au moyen d'une condensation partielle du mélange de gaz de réaction composé du produit de réaction (P), d'au moins un constituant à point d'ébullition élevé (H) et d'au moins un constituant à bas point d'ébullition (L).
EP11776731.9A 2010-10-21 2011-10-17 Procédé permettant de simplifier la séparation d'un produit de réaction présent dans des mélanges de gaz de réaction au moyen d'au moins deux condensations partielles Withdrawn EP2629869A1 (fr)

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PCT/EP2011/068127 WO2012052411A1 (fr) 2010-10-21 2011-10-17 Procédé permettant de simplifier la séparation d'un produit de réaction présent dans des mélanges de gaz de réaction au moyen d'au moins deux condensations partielles

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DE102010042731A1 (de) * 2010-10-21 2012-04-26 Bayer Materialscience Aktiengesellschaft Verfahren zur Reinigung von Anilin aus Gasphasenhydrierungen
TWI652257B (zh) * 2014-01-07 2019-03-01 德商林德股份有限公司 藉由分離技術處理二甲醚反應器之產物流的方法
JP6509234B2 (ja) * 2014-01-07 2019-05-08 リンデ アクチエンゲゼルシャフトＬｉｎｄｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ ジメチル反応器の生成物ストリームから形成されたガス混合物の分離技術による加工処理
US11402155B2 (en) 2016-09-06 2022-08-02 Lummus Technology Inc. Pretreatment of natural gas prior to liquefaction
EP3960265A1 (fr) * 2020-08-31 2022-03-02 Linde GmbH Procédé et installation de fabrication d'éther diméthylique

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GB775274A (en) * 1953-04-30 1957-05-22 Bataafsche Petroleum Process for condensing vapours
US2794515A (en) * 1954-01-12 1957-06-04 Schmalenbach Adolf Process for the recovery of benzene
GB832939A (en) 1957-11-27 1960-04-21 Ici Ltd Improved reduction process
NL232050A (fr) * 1958-10-07
US4640743A (en) * 1985-04-24 1987-02-03 Shell Oil Company Multi-stage condensation process
US6388155B1 (en) 2000-08-01 2002-05-14 Abb Lummus Global Inc. Styrene dehydrogenation reactor effluent treatment
DE102007001658A1 (de) * 2007-01-11 2008-07-17 Linde Ag Verfahren und Vorrichtung zur fraktionierten Kryokondensation
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