EP2195107A1 - Procédé de production d'hydrocarbures aromatiques à partir d'un mélange d'hydrocarbures - Google Patents

Procédé de production d'hydrocarbures aromatiques à partir d'un mélange d'hydrocarbures

Info

Publication number
EP2195107A1
EP2195107A1 EP08804544A EP08804544A EP2195107A1 EP 2195107 A1 EP2195107 A1 EP 2195107A1 EP 08804544 A EP08804544 A EP 08804544A EP 08804544 A EP08804544 A EP 08804544A EP 2195107 A1 EP2195107 A1 EP 2195107A1
Authority
EP
European Patent Office
Prior art keywords
extractive
extractive solvent
distillation
mixture
aromatic hydrocarbons
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Withdrawn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
EP08804544A
Other languages
German (de)
English (en)
Inventor
Uwe Stabel
Petra Deckert
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.)
BASF SE
Original Assignee
BASF SE
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 filed Critical BASF SE
Priority to EP08804544A priority Critical patent/EP2195107A1/fr
Publication of EP2195107A1 publication Critical patent/EP2195107A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/02—Monocyclic hydrocarbons
    • C07C15/04—Benzene
    • 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
    • B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
    • B01D3/40—Extractive distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/02—Monocyclic hydrocarbons
    • C07C15/06—Toluene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/02—Monocyclic hydrocarbons
    • C07C15/067—C8H10 hydrocarbons
    • C07C15/073—Ethylbenzene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/02—Monocyclic hydrocarbons
    • C07C15/067—C8H10 hydrocarbons
    • C07C15/08—Xylenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/04—Purification; Separation; Use of additives by distillation
    • C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
    • C07C7/08—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by extractive distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids

Definitions

  • the invention relates to a process for the recovery of aromatic hydrocarbons from a hydrocarbon mixture, which in addition to the aromatic hydrocarbons non-aromatic hydrocarbons and high-boiling aromatic and non-aromatic hydrocarbons.
  • hydrocarbon fractions are used as hydrocarbon feed mixtures which contain benzene, toluene, ethylbenzene or xylene or any mixture thereof as extractable constituents
  • a number of high-boiling aromatic and non-aromatic hydrocarbons accumulate in the extractive solvent with boiling points similar to the extractive solvent, resulting in a fast deterioration of the extractive solvent quality.
  • the deterioration of the solvent quality is usually the faster the higher the proportion of high-boiling hydrocarbons. The result is a deterioration in the separation efficiency of the extractive distillation, which may necessitate rapid replacement of the extractive solvent.
  • EP-A 0 329 958 discloses a process for obtaining an aromatic mixture from a feed hydrocarbon mixture whose boiling range is between 40 and 170 0 C, and in addition to non-aromatics contains several aromatics, in particular benzene, toluene and xylene, in which the feed hydrocarbon mixture is subjected to an extractive distillation using N-substituted morpholines as a selective solvent.
  • the hydrocarbons of the extract are separated by distillation from the extractive solvent in a downstream stripping column, while the solvent is recycled to the stripping column.
  • the process according to EP-A 0 329 958 solves the problem of enrichment of high-boiling aromatics in the extractive solvent by cooling a partial stream of the extractive solvent withdrawn from the stripper column, adding water and introducing it into a phase separator, the solvent contained in the solvent high-boiling aromatics separate as a lighter upper phase of the solvent / water mixture.
  • the withdrawn from the phase separator solvent / water mixture is finally decomposed into its components and reused in the process.
  • the method is based on the fact that the high-boiling aromatics and the extractive solvent, in particular N-formylmorpholine, have different dissolution properties in water.
  • the solvent in particular N-formylmorpholine
  • the high-boiling aromatics dissolve only in very small amounts in water. Since the high-boiling aromatics also have a significant difference in density compared to the solvent / water mixture, they can be separated in a phase separator as a light phase from the solvent / water mixture.
  • the object of the invention is to provide an improved process for the recovery of aromati- see hydrocarbons from a hydrocarbon mixture, which in addition to the aromatic hydrocarbons non-aromatic hydrocarbons and high-boiling aromatic and non-aromatic hydrocarbons, hereinafter referred to as "high boiler" contains, by means of extractive distillation using of N-formylmorpholine which does not have the disadvantages of the prior art.
  • the object is achieved by a process for the recovery of aromatic hydrocarbons selected from benzene, toluene, xylene and ethylbenzene and mixtures thereof, from a hydrocarbon mixture which also contains non-aromatic hydrocarbons and high boilers, with the steps
  • step (C) distillation of the mixture b1 of extractive solvents and aromatic hydrocarbons obtained in step (B), wherein one or more fractions d are obtained from aromatic hydrocarbons and the extractive solvent c2, which contains high boilers,
  • step (E) characterized in that before carrying out step (E), a distillation is carried out in which a fraction of very high-boiling hydrocarbons is separated from the substream d1 of the extractive solvent.
  • High-boiling aromatics which may be present in the hydrocarbon mixture and can accumulate in the extractive solvent, have already been described by way of example in EP-A 0 329 958 and include, for example, hemellite, p-cymene, 1,2-diethylbenzene, indane, durene, isodurol, Trimethylbenzene, naphthalene, methylnaphtha- line, dimethylnaphthalenes and diphenyl.
  • oligomeric and polymeric aromatics with a very high boiling point hereinafter also referred to for short as "heavy ends" accumulate in the extractive solvent, which are surface-active Properties may have.
  • step (E) oligomeric and polymeric aromatics
  • the separation of the heaviest boilers is generally carried out in vacuo at a pressure of 10 to 100 mbar in a distillation column having 1 to 10 theoretical stages.
  • the head temperature is generally in the range of 100 to 170 0 C, the bottom temperature in the range of 120 to. 190 ° C.
  • the heavy-boiling components are generally obtained as a non-decomposable, highly viscous bottoms product.
  • the oligomeric and polymeric heavy-boiling components are at least 90%, preferably at least 95%, removed by this distillation step.
  • hydrocarbon mixtures of aliphatic, cycloaliphatic and aromatic hydrocarbons are used in the process according to the invention, which have boiling point in the range of 50 to 225 0 C at atmospheric pressure. These generally contain a total of 10 to 90 wt .-% of toluene and xylene or a total of 10 to 90 wt .-% benzene, toluene and xylene.
  • the hydrocarbon mixtures generally contain aliphatic hydrocarbons having 5 to 10 carbon atoms and optionally cycloaliphatic hydrocarbons having 5 to 10 carbon atoms.
  • Typical hydrocarbon mixtures which can be worked up according to the invention are, for example, reformate and pyrolysis gasolines.
  • the high boilers contained in the hydrocarbon mixture which accumulate in the extractant and difficult or impossible to economically separated from this by distillation, generally have boiling points in the range of 170 to 250 0 C.
  • the very high-boiling hydrocarbons (“heaviest boilers”) still contained therein generally have a boiling point above 240 ° C. at normal pressure or can no longer be distilled without decomposition, not even in vacuo.
  • the hydrocarbon mixture a1 is subjected to extractive distillation with N-formylmorpholine as extractant.
  • the operating conditions in the extractive distillation column are generally selected as described in: Ullmanns En- cyclopedia of Industrial Chemistry, chapter Benzene, Wiley VCH GmbH, 2002. Toluene and xylene or benzene, toluene and xylene in the extractive solvent accumulate and are generally removed therefrom from the bottom of the extractive distillation column, while those of the aromatic Hydrocarbons largely freed non-aromatic hydrocarbons are generally recovered at the top of the extractive distillation column.
  • the mixture of extractive solvent and aromatic hydrocarbons which also contains the high boilers and heavy boilers, is then by distillation into one or more aromatic fractions obtained as top and / or side draw streams, and the extractive solvent containing the heavy and heavy boilers, and in general recovered at the bottom of the distillation column, separated.
  • the hydrocarbon mixture a1 contains benzene, toluene and xylene
  • separation by distillation of the extractive / aromatic mixture b1 in step (C) may comprise a fraction c11 containing benzene as the top draw stream and a fraction c12 containing toluene and another fraction c13 containing xylene as side draw streams.
  • hydrocarbon mixture a1 contains substantially toluene and xylene as aromatic hydrocarbons, essentially toluene is obtained as the top draw stream and xylene as the side draw stream in the distillative separation of the extractive solvent / aromatic mixture b1.
  • a mixture of toluene and xylene which may optionally also contain ethylbenzene, as top draw stream.
  • a partial stream d1 of the extractive solvent is separated to separate the high boilers contained therein.
  • This partial stream is generally 0.01 to 10%, preferably 0.1 to 2%, of the total stream of the extractive solvent c2 obtained by distillation in step (C).
  • the separation of the extractive solvent from the high boilers contained therein takes place in step (E) by extraction of the extractive solvent with water.
  • the partial stream d1 of the extractive solvent containing the heavy metal can be transferred to a mixing unit and dispersed with water, forming an aqueous extract phase e1 which is essentially free from high boilers and an organic phase e2 containing the high boilers.
  • the phases are subsequently separated in a phase separation apparatus which may be identical to the mixing unit or a separate phase separation apparatus.
  • the extractant is brought into intensive contact with water, so that the thermodynamic equilibrium between the forming aqueous extract phase on the one hand and the organic phase on the other hand.
  • Suitable dispersing units are stirred tanks, static mixers, mixing pumps and dynamic mixers. It is also possible to carry out the extraction in a countercurrent column.
  • the extractive solvent is completely miscible with water.
  • the high-boiling impurities of aromatic and non-aromatic hydrocarbons have a poor water solubility, so that by adding water to the extractive solvent contaminated with the high-boiling hydrocarbons, a second liquid organic phase is formed, which consists mainly of these impurities.
  • the two phases have a sufficiently large density difference, so that they can be separated from each other in commercially available apparatuses for liquid / liquid phase separation. Suitable phase separation apparatus are phase separators, centrifuges, coalescence phase separators and others.
  • the extraction with water and subsequent phase separation can be carried out both in one stage, for example in a mixer-settler, as well as in several stages, for example in a mixer-settler cascade or a countercurrent column.
  • the temperature has an influence on the miscibility gap, which is due to the addition of water to the extractors containing the high boilers. Basically, temperatures above 100 0 C are possible when the extraction is carried out with water in a pressure apparatus. Possible temperatures in the range from 0 to 160 0 C. Preferably, however, temperatures between 10 to 90 0 C, to be particularly favorable, temperatures between 40 and 60 0 C have been found. At least a sufficient amount of water is added to form separate liquid phases.
  • the ratio of amount of water: amount of extractant is generally 0.05 to 5 kg / kg, more preferably 0.2 to 0.5 kg / kg.
  • a partial stream e2 ' is separated from the high-boiling organic phase e2 in the continuous operation of the process and recycled to the dispersing unit of step (E), the quantity of organic phase e2' thus circulated being such. is dimensioned such that when dispersing the partial stream d1 of extractive solvent containing high boilers, water and circulated stream e2 ', the aqueous extract phase e1 substantially freed from high boilers forms as a disperse phase and the organic phase e2 as a continuous phase.
  • step (E) the phase separation into the aqueous extract phase on the one hand and the organic phase from high-boiling hydrocarbons on the other hand can be significantly improved.
  • the phase separation speed is significantly increased by the reversal of the dispersion direction, and the aqueous lower phase containing the extractive solvent becomes clear.
  • the dispersing direction can be reversed by an internal recycling of the organic phase e2 accumulating in the phase separation apparatus into the mixing unit.
  • the volume ratio of organic high-boiling phase to aqueous extract phase > 0.8: 1, so that the organic phase forms as a continuous phase.
  • e2 contained NFM can in turn be recovered by extraction of the e2 phase with water.
  • the resultant aqueous extract phase e1 which has essentially been freed from high boilers, is subsequently distilled in purified form in order to recover the extractive solvent.
  • This distillation can be carried out as described in EP-A 0 329 958.
  • the extractive / water mixture is distilled together with the separated in step (B) non-aromatic hydrocarbons, wherein the water contained in the extractive / water mixture is distilled off azeotropically together with the non-aromatic hydrocarbons generally overhead of the distillation column. From this azeotropic mixture, water is separated by phase separation and optionally recycled to the high boiler separation step (E).
  • the de-watered extractive solvent can be separated by phase separation of entrained non-aromatic hydrocarbons and recycled to the extractive distillation (B).
  • FIG. 1 shows a preferred embodiment of the method according to the invention:
  • the hydrocarbon mixture 1 containing benzene, toluene, xylene and non-aromatic hydrocarbons and the extractive solvent 2 are fed to the extractive distillation column 3.
  • a mixture 4 of non-aromatic hydrocarbons and extractive solvent is withdrawn, which is separated in the downstream distillation column 5 in the non-aromatic hydrocarbons 6 and the extractive solvent 7.
  • a mixture 8 of extractive solvent and the aromatic hydrocarbons is obtained. From this mixture, the individual aromatic fractions benzene 10, toluene 11 and xylene 12 are then removed by distillation in a distillation column 9.
  • extractive solvent stream 13 which also contains the heavy and heavy ends
  • the main stream 14 is returned to the extractive distillation column 3.
  • a partial stream 15 is separated to separate the heavy particles contained therein.
  • oligomeric and polymeric heavy-boiling components with surface-active properties are separated off as residue 17 in the distillation column 16.
  • the extractive solvent stream 18, which is still free of the high-boiling components and still contains the high-boiling components, is transferred together with water 19 into the dispersion unit 20.
  • the resulting dispersion 21 is separated in the phase separation apparatus 22 into an organic upper phase 23, which contains the high boiler, and an aqueous lower phase 26, which contains the extractive solvent.
  • a part 24 of the organic upper phase is discharged from the process, the other part 25 is returned to the dispersing unit 20.
  • the aqueous lower phase 26 is separated in a downstream distillation column 27 into a water stream 28, which is discharged from the process, and the purified extractive solvent stream 29, which is recycled to the extractive distillation column 3.
  • FIG. 2 shows a further preferred embodiment of the method according to the invention.
  • FIG. 2 shows a variant of the method illustrated in FIG.
  • the aqueous lower phase 26 containing the extractive solvent which is obtained in the phase separation apparatus 22, is not distilled in a separate distillation column but is distilled in the distillation column 5 together with the fraction of nonaromatic hydrocarbons obtained as top draw stream 4.
  • a mixture of non-aromatic hydrocarbons and water is obtained as the top draw stream 6a, which is separated in the downstream phase separation apparatus 30 into an organic upper phase of non-aromatic hydrocarbons 31 and an aqueous lower phase 32.
  • the aqueous lower phase may be recycled (as stream 19) to the phase separation apparatus 20.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Water Supply & Treatment (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Extraction Or Liquid Replacement (AREA)
  • Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)

Abstract

La présente invention concerne un procédé de production d'hydrocarbures aromatiques choisis entre le benzène, le toluène, le xylène, l'éthylbenzène et leurs mélanges, à partir d'un mélange d'hydrocarbures qui contient en plus des hydrocarbures non aromatiques et des composés à point d'ébullition élevé. Le procédé comprend les opérations suivantes : (A) mise à disposition d'un mélange d'hydrocarbures a1 et d'un solvant extractif a2 contenant de la N-formylmorpholine; (B) distillation extractive du mélange d'hydrocarbures a1 avec le solvant extractif pour obtenir un mélange b1 de solvant extractif et des hydrocarbures aromatiques, le mélange contenant également des composés à point d'ébullition élevé, et un mélange b2 contenant des hydrocarbures non aromatiques; (C) distillation du mélange b1 obtenu en (B) de solvant extractif et d'hydrocarbures aromatiques pour obtenir une ou plusieurs fractions d'hydrocarbures aromatiques et de solvant extractif c2 qui contient également des composés à point d'ébullition élevé; (D) séparation d'un flux partiel d1 du solvant extractif c2 et retour du solvant extractif c2 à l'opération de distillation extractive (B); (E) extraction du flux partiel d1 du solvant extractif avec de l'eau pour obtenir une phase extrait aqueuse e1 sensiblement dépourvue de composés à point d'ébullition élevé et une phase organique e2 contenant des composés à point d'ébullition élevé; (F) distillation de la phase extrait aqueuse e1 et récupération du solvant extractif a2 sous forme purifiée, et retour du solvant extractif à l'opération de distillation extractive (B), l'exécution de l'opération (E) étant précédée d'une distillation au cours de laquelle une fraction d'hydrocarbures à point d'ébullition très élevé est séparée du flux partiel d1 du solvant extractif.
EP08804544A 2007-09-28 2008-09-22 Procédé de production d'hydrocarbures aromatiques à partir d'un mélange d'hydrocarbures Withdrawn EP2195107A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08804544A EP2195107A1 (fr) 2007-09-28 2008-09-22 Procédé de production d'hydrocarbures aromatiques à partir d'un mélange d'hydrocarbures

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP07117510 2007-09-28
EP08804544A EP2195107A1 (fr) 2007-09-28 2008-09-22 Procédé de production d'hydrocarbures aromatiques à partir d'un mélange d'hydrocarbures
PCT/EP2008/062618 WO2009043753A1 (fr) 2007-09-28 2008-09-22 Procédé de production d'hydrocarbures aromatiques à partir d'un mélange d'hydrocarbures

Publications (1)

Publication Number Publication Date
EP2195107A1 true EP2195107A1 (fr) 2010-06-16

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EP08804544A Withdrawn EP2195107A1 (fr) 2007-09-28 2008-09-22 Procédé de production d'hydrocarbures aromatiques à partir d'un mélange d'hydrocarbures

Country Status (5)

Country Link
US (1) US8362314B2 (fr)
EP (1) EP2195107A1 (fr)
JP (1) JP5566291B2 (fr)
CN (1) CN101808704B (fr)
WO (1) WO2009043753A1 (fr)

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CN101808962B (zh) 2007-09-28 2012-11-28 巴斯夫欧洲公司 从烃混合物中获得芳烃的方法
DE102010051396A1 (de) 2010-11-16 2012-05-16 Thyssenkrupp Uhde Gmbh Verfahren zur Entfernung schwersiedender Kohlenwasserstoffe aus Lösungsmittelströmen
US9005405B2 (en) * 2012-03-01 2015-04-14 Cpc Corporation, Taiwan Extractive distillation process for benzene recovery
IN2015DN03742A (fr) * 2012-10-10 2015-09-18 Gtc Technology Us Llc
DE102012111292A1 (de) * 2012-11-22 2014-05-22 Thyssenkrupp Uhde Gmbh Verfahren zur Isolierung von Benzol, Toluol und Xylol aus einem aromatenreichen Einsatzgasstrom
CN103232317A (zh) * 2013-04-05 2013-08-07 大连理工大学 用于焦化粗苯加氢精制中的芳烃提纯装置及工艺
ES2887401T3 (es) 2014-09-05 2021-12-22 Scg Chemicals Co Ltd Procedimiento para la separación mejorada de etilbenceno
US9221729B1 (en) * 2015-02-23 2015-12-29 Allnew Chemical Technology Company Extractive distillation for aromatics recovery
SG11202100544QA (en) * 2018-07-20 2021-02-25 Scg Chemicals Co Ltd Process for the separation of ethylbenzene from other c8 aromatic compounds
CN112876441A (zh) * 2019-11-29 2021-06-01 南通醋酸化工股份有限公司 一种脱氢醋酸合成中甲苯母液连续处理工艺
USD977511S1 (en) * 2021-04-30 2023-02-07 Hewlett Packard Enterprise Development Lp Display with animated graphical user interface
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BE1029920B1 (de) * 2021-11-12 2023-06-12 Thyssenkrupp Uhde Eng Services Gmbh Verfahren zur Entleerung eines Lösungsmittel-Regenerierungs-Behälters sowie Vorrichtung

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Also Published As

Publication number Publication date
JP2011511757A (ja) 2011-04-14
US20100305382A1 (en) 2010-12-02
CN101808704A (zh) 2010-08-18
CN101808704B (zh) 2012-11-28
WO2009043753A1 (fr) 2009-04-09
US8362314B2 (en) 2013-01-29
JP5566291B2 (ja) 2014-08-06

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