EP0602302A1 - Process for the recovery of a polymerisable fraction - Google Patents

Process for the recovery of a polymerisable fraction Download PDF

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Publication number
EP0602302A1
EP0602302A1 EP93106219A EP93106219A EP0602302A1 EP 0602302 A1 EP0602302 A1 EP 0602302A1 EP 93106219 A EP93106219 A EP 93106219A EP 93106219 A EP93106219 A EP 93106219A EP 0602302 A1 EP0602302 A1 EP 0602302A1
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EP
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Prior art keywords
fraction
valuable
gas column
styrene
fractions
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EP93106219A
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German (de)
French (fr)
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EP0602302B1 (en
Inventor
Uwe Dr. Stabel
Gerd Dr. Wunsch
Helmut Dr. Woerz
Andreas Dr. Fried
Ruediger Dr. Kotkamp
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G70/00—Working-up undefined normally gaseous mixtures obtained by processes covered by groups C10G9/00, C10G11/00, C10G15/00, C10G47/00, C10G51/00
    • C10G70/04—Working-up undefined normally gaseous mixtures obtained by processes covered by groups C10G9/00, C10G11/00, C10G15/00, C10G47/00, C10G51/00 by physical processes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G9/00—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G7/00—Distillation of hydrocarbon oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L7/00—Fuels produced by solidifying fluid fuels
    • C10L7/02—Fuels produced by solidifying fluid fuels liquid fuels
    • C10L7/04—Fuels produced by solidifying fluid fuels liquid fuels alcohol

Definitions

  • the description relates to a process for obtaining a polymerizable fraction of valuable materials, consisting of styrene, methylstyrenes, vinyltoluenes, indenes, methylenes and fractions, the boiling points of which are between styrene and methylindenes, from the cracking gases of a steam cracker plant.
  • the above valuable fraction is a starting product for various adhesive resins.
  • Japanese Patent 87-190136 shows a process in which a polymerizable fraction of C9-C10 cuts is obtained from residual oil by distillation.
  • US Pat. No. 4,371,428 describes a process for separating vinyltoluene from other alkenyl aromatics by means of an extraction distillation.
  • indene a method is described in US Pat. No. 4,827,078 which shows the extraction from a petrochemical mixture by means of adsorption with zeolites.
  • the task therefore was to extract the valuable material fraction by means of a simple, economical process step.
  • This object is achieved in that a side stream of the cracked gas column is divided by means of a distillation unit into the valuable fraction and into fractions which are returned to the cracked gas column.
  • the higher-boiling products such as naphthalene and undesirable C10 and higher components are withdrawn from the column at the bottom and the cracked gas column advantageously returned below the bottom.
  • the valuable fraction is advantageously removed from the gas phase of the column and condensed.
  • the process according to the invention is characterized by a high yield of the valuable material fraction. Another advantage is that a lower energy consumption is necessary if the enriched side stream of the cracked gas column is worked up for the valuable fraction than to obtain the valuable fraction by distillation of pyrolysis gasoline. In the event of faults in the column for obtaining the valuable material fraction, the pyrolysis gasoline processing of the steam cracker is not affected and the availability of the steam cracker is not impeded.
  • the valuable fraction does not contain any dicyclopentadiene, which changes the properties of the valuable fraction, and, on the other hand, when cyclopentadiene / dicyclopentadiene is obtained from pyrolysis gasoline from the steam cracker, which components which impair the purity of the dicyclopentadiene, such as indene, already separate vinyl toluene are.
  • the recyclable material fraction obtained according to the method according to the invention contains, for example, 4% by weight of styrene, 20% by weight of methylstyrene and vinyltoluenes, 20% by weight of indene and 11% by weight of methylindene.
  • the products 3 boiling lower than the valuable material fraction are drawn off overhead and returned to the cracked gas column.
  • the products 4 boiling higher than the valuable material fraction are drawn off and fed back to the cracking gas column.
  • the column is equipped with approx. 14-18 practical exchange trays, such as dual-flow trays, sieve or valve trays.
  • the operating data of the column are: Print: ⁇ 1.9 bar on the head Head temperature: ⁇ 125 ° C Temperature at the swamp: ⁇ 193 ° C Temperature at the point of withdrawal of the valuable material fraction: ⁇ 176 ° C
  • the removal point 5 of the valuable material fraction takes place between the 9th and 13th Exchange tray, calculated from the top of the column.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Abstract

Verfahren zur Gewinnung einer polymerisierbaren Wertstofffraktion, bestehend aus Styrol, Methylstyrolen, Vinyltoluolen, Inden, Methylindenen und Fraktionen, deren Siedepunkte zwischen Styrol und Methylindenen liegen, aus den Crackgasen einer Steamcrackeranlage, wobei ein Nebenstrom der Spaltgaskolonne mittels einer Destillationseinheit in die Wertstofffraktion und in Fraktionen, die in die Spaltgaskolonne zurückgeführt werden, aufgeteilt wird.Process for obtaining a polymerizable fraction of valuable materials, consisting of styrene, methylstyrenes, vinyltoluenes, indene, methylindene and fractions, the boiling points of which are between styrene and methylindene, from the cracked gases of a steam cracker plant, whereby a bypass flow of the cracked gas column by means of a distillation unit into the valuable substance fraction and in fractions, which are returned to the cracking gas column.

Description

Die Beschreibung betrifft ein Verfahren zur Gewinnung einer polymerisierbaren Wertstofffraktion, bestehend aus Styrol, Methylstyrolen, Vinyltoluolen, Inden, Methylindenen und Fraktionen, deren Siedepunkte zwischen Styrol und Methylindenen liegen, aus den Crackgasen einer Steamcrackeranlage.The description relates to a process for obtaining a polymerizable fraction of valuable materials, consisting of styrene, methylstyrenes, vinyltoluenes, indenes, methylenes and fractions, the boiling points of which are between styrene and methylindenes, from the cracking gases of a steam cracker plant.

Obige Wertstofffraktion ist ein Ausgangsprodukt für verschiedene Klebeharze.The above valuable fraction is a starting product for various adhesive resins.

Verfahren zur Gewinnung ähnlicher Wertstofffraktionen sind bekannt und in der Patentliteratur beschrieben. So ist beispielsweise in der japanischen Patentschrift 87-190136 ein Verfahren aufgezeigt, bei dem eine polymerisierbare Fraktion an C₉-C₁₀-Schnitten aus Rückstandöl mittels Destillation gewonnen wird. In der US-Patentschrift 4 371 428 ist ein Verfahren zur Abtrennung von Vinyltoluol aus anderen Alkenyl-Aromaten mittels einer Extraktionsdestillation beschrieben. Zur Gewinnung von Inden ist in der US-Patentschrift 4 827 078 ein Verfahren beschrieben, das die Gewinnung aus einem petrochemischen Gemisch mittels Adsorption mit Zeolithen aufzeigt.Methods for obtaining similar fractions of valuable substances are known and are described in the patent literature. For example, Japanese Patent 87-190136 shows a process in which a polymerizable fraction of C₉-C₁₀ cuts is obtained from residual oil by distillation. US Pat. No. 4,371,428 describes a process for separating vinyltoluene from other alkenyl aromatics by means of an extraction distillation. For the production of indene, a method is described in US Pat. No. 4,827,078 which shows the extraction from a petrochemical mixture by means of adsorption with zeolites.

Die beschriebenen Verfahren haben verschiedene Nachteile, so beispielsweise, daß die gewünschte Wertstofffraktion erst aus dem Rückstandöl gewonnen wird, und somit hohen thermischen Belastungen ausgesetzt ist. Des weiteren sind die beschriebenen Verfahren energieaufwendig.The processes described have various disadvantages, for example that the desired fraction of valuable material is only obtained from the residual oil and is therefore exposed to high thermal loads. Furthermore, the methods described are energy-intensive.

Es stellte sich daher die Aufgabe, die Wertstofffraktion mittels eines einfachen, wirtschaftlichen Verfahrensschrittes zu gewinnen.The task therefore was to extract the valuable material fraction by means of a simple, economical process step.

Diese Aufgabe wird erfindungsgemäß dadurch gelöst, daß ein Nebenstrom der Spaltgaskolonne mittels einer Destillationseinheit in die Wertstofffraktion und in Fraktionen, die in die Spaltgaskolonne zurückgeführt werden, aufgeteilt wird.This object is achieved in that a side stream of the cracked gas column is divided by means of a distillation unit into the valuable fraction and into fractions which are returned to the cracked gas column.

Gemäß dem erfindungsgemäßen Verfahren wird aus der Spaltgaskolonne der Steamcrackeranlage an einem geeigneten Boden ein Produktstrom abgezogen, der beispielsweise die gewünschten Komponenten = Wertstofffraktion in einer Anreicherung von ca. 5-55 Gew.-% enthält. Überraschenderweise zeigte sich nun, daß die Abtrennung der unerwünschten Produkte und die Gewinnung der Wertstofffraktion mittels einer Destillationseinheit = einer Kolonne möglich ist. Die niederer als das Wertprodukt siedenden Produkte, wie beispielsweise Benzol, Toluol und Teile des Styrols werden bei der Kolonne am Kopf abgezogen und der Spaltgaskolonne vorteilhafterweise oberhalb des Entnahmebodens wieder zugefahren. Die höher als das Wertprodukt siedenden Produkte, wie beispielsweise Naphthalin und unerwünschte C₁₀- und höhere Komponenten werden bei der Kolonne am Sumpf abgezogen und der Spaltgaskolonne vorteilhafterweise unterhalb des Entnahmebodens wieder zugefahren. Die Wertstofffraktion wird vorteilhafterweise aus der Gasphase der Kolonne entnommen und kondensiert. Das erfindungsgemäße Verfahren ist gekennzeichnet durch eine hohe Ausbeute an der Wertstofffraktion. Ein Vorteil besteht außerdem darin, daß ein geringerer Energieverbrauch notwendig ist, wenn für die Wertstofffraktion der angereicherte Seitenstrom der Spaltgaskolonne aufgearbeitet wird, als die Wertstofffraktion durch Destillation von Pyrolysebenzin zu gewinnen. Bei Störungen der Kolonne zur Gewinnung der Wertstofffraktion ist die Pyrolysebenzinaufarbeitung des Steamcrackers nicht betroffen und die Verfügbarkeit des Steamcrackers ist nicht behindert. Letztendlich ist ein weiterer Vorteil, daß einerseits die Wertstofffraktion kein Dicyclopentadien enthält, das die Eigenschaften der Wertstofffraktion verändert, und andererseits bei der Gewinnung von Cyclopentadien/Dicyclopentadien aus Pyrolysebenzin des Steamcrackers, die die Reinheit des Dicyclopentadiens beeinträchtigenden Komponenten, wie Inden, Vinyltoluol, bereits abgetrennt sind.According to the process of the invention, a product stream is drawn off from the cracking gas column of the steam cracker plant on a suitable tray and contains, for example, the desired components = valuable fraction in an enrichment of about 5-55% by weight. Surprisingly, it has now been found that the removal of the undesired products and the extraction of the Valuable fraction by means of a distillation unit = a column is possible. The products boiling lower than the product of value, such as benzene, toluene and parts of the styrene, are drawn off at the top of the column and advantageously returned to the cracking gas column above the removal tray. The higher-boiling products, such as naphthalene and undesirable C₁₀ and higher components are withdrawn from the column at the bottom and the cracked gas column advantageously returned below the bottom. The valuable fraction is advantageously removed from the gas phase of the column and condensed. The process according to the invention is characterized by a high yield of the valuable material fraction. Another advantage is that a lower energy consumption is necessary if the enriched side stream of the cracked gas column is worked up for the valuable fraction than to obtain the valuable fraction by distillation of pyrolysis gasoline. In the event of faults in the column for obtaining the valuable material fraction, the pyrolysis gasoline processing of the steam cracker is not affected and the availability of the steam cracker is not impeded. Ultimately, it is a further advantage that, on the one hand, the valuable fraction does not contain any dicyclopentadiene, which changes the properties of the valuable fraction, and, on the other hand, when cyclopentadiene / dicyclopentadiene is obtained from pyrolysis gasoline from the steam cracker, which components which impair the purity of the dicyclopentadiene, such as indene, already separate vinyl toluene are.

Die gemäß dem erfindungsgemäßen Verfahren gewonnene Wertstofffraktion enthält beispielsweise 4 Gew.-% Styrol, 20 Gew.-% Methylstyrol und Vinyltoluole, 20 Gew.-% Inden und 11 Gew.-% Methylindene.The recyclable material fraction obtained according to the method according to the invention contains, for example, 4% by weight of styrene, 20% by weight of methylstyrene and vinyltoluenes, 20% by weight of indene and 11% by weight of methylindene.

Das erfindungsgemäße Verfahren wird nachstehend anhand eines vereinfachten Verfahrensschemas näher erläutert.The process according to the invention is explained in more detail below with the aid of a simplified process scheme.

Gemäß dem Verfahrensschema bildet beispielsweise 1 den Produktstrom = Seitenstrom aus der Spaltgaskolonne, der ca. 5 - 55 Gew.-% der Wertstofffraktion enthält. Dieser Produktstrom wird einer Destillationseinheit 2 = reine Abtriebskolonne, ausgerüstet mit Verdampfer, Kondensator, etc. am Kopf zugefahren. Über Kopf werden die niederer als die Wertstofffraktion siedenden Produkte 3 abgezogen und der Spaltgaskolonne wieder zugeführt. Am Sumpf werden die höher als die Wertstofffraktion siedenden Produkte 4 abgezogen und der Spaltgaskolonne wieder zugeführt.According to the process scheme, 1 forms, for example, the product stream = side stream from the cracking gas column, which contains about 5 to 55% by weight of the valuable material fraction. This product stream is fed to a distillation unit 2 = pure stripping column, equipped with an evaporator, condenser, etc. at the top. The products 3 boiling lower than the valuable material fraction are drawn off overhead and returned to the cracked gas column. At the bottom, the products 4 boiling higher than the valuable material fraction are drawn off and fed back to the cracking gas column.

Die Kolonne ist mit ca. 14-18 praktischen Austauschböden, wie beispielsweise Dual-Flow-Böden, Sieb- oder Ventilböden, ausgerüstet. Die Betriebsdaten der Kolonne sind: Druck: ∼1,9 bar am Kopf Temperatur am Kopf: ∼125°C Temperatur am Sumpf: ∼193°C Temperatur an der Entnahmestelle der Wertstofffraktion: ∼176°C The column is equipped with approx. 14-18 practical exchange trays, such as dual-flow trays, sieve or valve trays. The operating data of the column are: Print: ∼1.9 bar on the head Head temperature: ∼125 ° C Temperature at the swamp: ∼193 ° C Temperature at the point of withdrawal of the valuable material fraction: ∼176 ° C

Die Entnahmestelle 5 der Wertstofffraktion erfolgt zwischen dem 9.-13. Austauschboden, gerechnet vom Kopf der Kolonne.The removal point 5 of the valuable material fraction takes place between the 9th and 13th Exchange tray, calculated from the top of the column.

Claims (1)

Verfahren zur Gewinnung einer polymerisierbaren Wertstofffraktion, bestehend aus Styrol, Methylstyrolen, Vinyltoluolen, Inden, Methylindenen und Fraktionen, deren Siedepunkte zwischen Styrol und Methylindenen liegen, aus den Crackgasen einer Steamcrackeranlage, dadurch gekennzeichnet, daß ein Nebenstrom der Spaltgaskolonne mittels einer Destillationseinheit in die Wertstofffraktion und in Fraktionen, die in die Spaltgaskolonne zurückgeführt werden, aufgeteilt wird.A process for obtaining a polymerizable fraction of valuable materials, consisting of styrene, methylstyrenes, vinyltoluenes, indene, methylindene and fractions, the boiling points of which are between styrene and methylindene, from the cracked gases of a steam cracker plant, characterized in that a bypass flow of the cracking gas column is carried out by means of a distillation unit in the valuable material fraction and is divided into fractions which are returned to the cracked gas column.
EP93106219A 1992-12-14 1993-04-16 Process for the recovery of a polymerisable fraction Expired - Lifetime EP0602302B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4242054 1992-12-14
DE4242054A DE4242054C1 (en) 1992-12-14 1992-12-14 Process for obtaining a polymerizable recyclable fraction

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EP0602302A1 true EP0602302A1 (en) 1994-06-22
EP0602302B1 EP0602302B1 (en) 1996-12-27

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US (1) US5326927A (en)
EP (1) EP0602302B1 (en)
JP (1) JPH08504456A (en)
KR (1) KR950704449A (en)
BR (1) BR9307637A (en)
CA (1) CA2151602A1 (en)
CZ (1) CZ64093A3 (en)
DE (2) DE4242054C1 (en)
ES (1) ES2095510T3 (en)
FI (1) FI931712A (en)
MX (1) MX9307879A (en)
PL (1) PL298637A1 (en)
TW (1) TW273558B (en)
WO (1) WO1994013757A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005016483A1 (en) * 2003-08-05 2005-02-24 Basf Aktiengesellschaft Distillative method for separating narrow boiling or azeotropic mixtures using ionic liquids
EP3489330A1 (en) 2017-11-23 2019-05-29 Linde Aktiengesellschaft Method and assembly for polymerisable aromatic compounds

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4848112B2 (en) * 2001-09-28 2011-12-28 住友化学株式会社 Distillation method of easily polymerizable substances

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2370948A (en) * 1942-05-05 1945-03-06 Lummus Co Styrene fractionation
US3408263A (en) * 1966-11-22 1968-10-29 Universal Oil Prod Co Single column distillation of mixture of aromatics containing styrene
US3629076A (en) * 1970-09-08 1971-12-21 Universal Oil Prod Co Distillation of styrene containing a polymerization inhibitor and contacting the bottoms stream with an alcohol
DE2914226A1 (en) * 1978-07-18 1980-10-23 Cosden Technology METHOD FOR DISTILLING EASILY POLYMERIZABLE AROMATIC VINYL COMPOUNDS

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5090977A (en) * 1990-11-13 1992-02-25 Exxon Chemical Patents Inc. Sequence for separating propylene from cracked gases

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2370948A (en) * 1942-05-05 1945-03-06 Lummus Co Styrene fractionation
US3408263A (en) * 1966-11-22 1968-10-29 Universal Oil Prod Co Single column distillation of mixture of aromatics containing styrene
US3629076A (en) * 1970-09-08 1971-12-21 Universal Oil Prod Co Distillation of styrene containing a polymerization inhibitor and contacting the bottoms stream with an alcohol
DE2914226A1 (en) * 1978-07-18 1980-10-23 Cosden Technology METHOD FOR DISTILLING EASILY POLYMERIZABLE AROMATIC VINYL COMPOUNDS

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005016483A1 (en) * 2003-08-05 2005-02-24 Basf Aktiengesellschaft Distillative method for separating narrow boiling or azeotropic mixtures using ionic liquids
EP3489330A1 (en) 2017-11-23 2019-05-29 Linde Aktiengesellschaft Method and assembly for polymerisable aromatic compounds
WO2019101957A1 (en) 2017-11-23 2019-05-31 Linde Aktiengesellschaft Method and system for obtaining polymerizable aromatic compounds
US11203723B2 (en) 2017-11-23 2021-12-21 Linde Gmbh Method and system for obtaining polymerizable aromatic compounds

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CA2151602A1 (en) 1994-06-23
FI931712A0 (en) 1993-04-15
KR950704449A (en) 1995-11-20
WO1994013757A1 (en) 1994-06-23
MX9307879A (en) 1994-06-30
CZ64093A3 (en) 1994-06-15
EP0602302B1 (en) 1996-12-27
US5326927A (en) 1994-07-05
DE59304893D1 (en) 1997-02-06
PL298637A1 (en) 1994-06-27
FI931712A (en) 1994-06-15
BR9307637A (en) 1999-08-31
DE4242054C1 (en) 1994-01-13
JPH08504456A (en) 1996-05-14
ES2095510T3 (en) 1997-02-16
TW273558B (en) 1996-04-01

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