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WO2009092682A2 - Procédé et dispositif de retraitement par voie distillative de 1,5,9-cyclododécatriène et préparation de cdt à haut niveau de pureté - Google Patents

Procédé et dispositif de retraitement par voie distillative de 1,5,9-cyclododécatriène et préparation de cdt à haut niveau de pureté Download PDF

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Publication number
WO2009092682A2
WO2009092682A2 PCT/EP2009/050542 EP2009050542W WO2009092682A2 WO 2009092682 A2 WO2009092682 A2 WO 2009092682A2 EP 2009050542 W EP2009050542 W EP 2009050542W WO 2009092682 A2 WO2009092682 A2 WO 2009092682A2
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WO
WIPO (PCT)
Prior art keywords
column
dividing wall
wall column
removal
liquid
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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.)
Ceased
Application number
PCT/EP2009/050542
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German (de)
English (en)
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WO2009092682A3 (fr
Inventor
Thomas Genger
Andrea Haunert
Anton Meier
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BASF SE
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BASF SE
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Priority to DE112009000199T priority Critical patent/DE112009000199A5/de
Publication of WO2009092682A2 publication Critical patent/WO2009092682A2/fr
Publication of WO2009092682A3 publication Critical patent/WO2009092682A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • 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
    • B01D3/32—Other features of fractionating columns ; Constructional details of fractionating columns not provided for in groups B01D3/16 - B01D3/30
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
    • C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered

Definitions

  • the invention relates to a process for the distillative workup of 1, 5,9-cyclododecatriene hereinafter abbreviated as CDT, as well as a device for carrying out the method.
  • CDT is a precursor for the preparation of cyclododecanone, which is mainly used for the production of laurolactam and thus nylon 12.
  • Decisive for the quality of the secondary products cyclododecanone and laurolactam is the purity of the starting material CDT. Therefore, care must be taken at the stage of the CDT that compounds such as vinylcyclohexene, cyclooctadiene, C16 compounds, oligomers and especially oil-containing compounds are depleted as much as possible. In practice, it has been shown that CDT purity should be more than 99% in order to obtain sufficient product qualities at the subsequent stages.
  • CDT is produced by trimerization of butadiene.
  • By-products of CDT preparation are vinylcyclohexene, cyclooctadiene and oligomers of butadiene having 16, 20 or more carbon atoms.
  • the cyclizing trimerization of 1,3-butadiene to cyclododecatriene with the aid of Ziegler catalysts is industrially important because it makes the cycloaliphatic and open-chain C12 compound classes accessible, cf. G. Wilke, Angew. Chemistry 69 (1957) 397; H. Breil, P. Heimbach, M. Kröner, H. Müller, G.
  • cyclododecatriene include i.a. Cyclododecanone, cyclododecanol, decanedicarboxylic acid and laurolactam (precursor for nylon 12).
  • the synthesis is transition metal-catalyzed with Ti, Ni or Cr catalysts, which are usually reduced with a reducing agent.
  • a reducing agent for reduction, an organometallic compound from the 1.-3. Group of the periodic table used.
  • the reaction of TiCl 4 or titanium acetylacetonate with an aluminum organyl has proved to be particularly advantageous for the Ti catalysts which are widely used in industrial applications (compare US 3,878,258, US 3,655,795, DE 3021840, DE 3021791).
  • numerous other titanium salts and reducing agents have also been described as starting materials (eg DE 1946062, US Pat. No. 3,644,548).
  • the titanium catalysts are based, for example, on titanium tetrachloride / ethylaluminum sesquichloride (EASC) or diethylaluminum chloride, with an Al: Ti ratio of 4: 1 or higher being adjusted to minimize the formation of polybutadiene.
  • Typical reaction temperatures with these Ziegler catalysts are between 40 and 90 0 C.
  • the CDT arises mainly the ice, trans, trans-isomer, while with Ni and Cr-catalysts mainly is all-trans-isomer is formed.
  • the reaction can be carried out both in inert solvents such as hydrocarbons such as benzene, cyclohexane, hexane, heptane, octane, decane, cyclohexane, toluene, xylene, ect. be carried out or without solvent to give a reaction product (see JP 2003335709; DE 3021840; US 6,403,851).
  • inert solvents such as hydrocarbons such as benzene, cyclohexane, hexane, heptane, octane, decane, cyclohexane, toluene, xylene, ect.
  • the discharged catalyst is generally decomposed.
  • Polar solvents are suitable for this purpose, and alcohols are also suitable in some cases with the addition of HCl (cf DE 1212075, US 3,476,820, DE1942729).
  • HCl cf DE 1212075, US 3,476,820, DE1942729.
  • water for example: ammonium hydroxide solutions (compare JP05070377, JP 0625439), THF / water mixtures (compare JP 05070377), amines or aminoethanols (compare JP 526962, JP 6215046), ammonia Water (see DE 1618771, DE 1768067) and Ca (OH) 2 / water mixtures (see NL 6603264).
  • DE 10002460 describes the purely distillative separation of the catalyst and its recycling.
  • the reactivity and selectivity of the catalyst system can be adjusted and improved by adding one or more more promoters (eg, oxygen-containing, nitrogen, phosphorus or sulfur compounds) (see US 3,546,309, DE 2825341, JP 2004-26787, US 3,381,045). ,
  • promoters eg, oxygen-containing, nitrogen, phosphorus or sulfur compounds
  • the reaction is usually carried out in a continuous process with one or more stirred tanks.
  • unreacted butadiene can be recovered in the workup and recycled with fresh butadiene in the process.
  • the synthesis can also be carried out in a loop reactor (cf. AE 20070128).
  • oligomers and deactivated catalyst are generally first removed.
  • the liquid reaction discharge is partially evaporated in a suitable evaporator system.
  • the resulting vapors contain the valuable product. Due to the thermal sensitivity of the desired product CDT, the high-boiler separation should be carried out with the lowest possible residence times and low temperatures. Therefore, preference is given to thin-film evaporators or short-path evaporators, if appropriate in combination with an upstream falling film evaporator or forced circulation evaporator (see, for example, US Pat. No. 3,365,507).
  • the desired product is further purified, for example, another solvent separation may follow, for example via distillation.
  • the crude CDT thus obtained is purified by distillation.
  • An object of the invention is therefore to provide an improved and in particular more economical process for obtaining the pure product CDT in a purity of> 99%, or> 99.5%.
  • the solution is based on a process for the distillative workup of crude CDT, which was obtained by the trimerization of butadiene.
  • dividing wall columns are used for the distillative separation of the crude CDT obtained as a multicomponent mixture, i. Distillation columns with vertical dividing walls, which in some areas prevent cross-mixing of liquid and vapor streams.
  • the partition which may preferably consist of a sheet, divides the column in the longitudinal direction in the middle part in an inlet part and a removal part.
  • thermally coupled columns can be used, i. Arrangements of at least two columns, wherein each of the columns with each other at least two links in spatially separated locations.
  • the invention is characterized in that the workup by distillation in each case in a dividing wall column (TK) in which a dividing wall (T) in the column longitudinal direction to form an upper common column region, a lower common column region, a feed part with reinforcing part and stripping section and a removal part with stripping section and reinforcing member is arranged, with feeding of the crude product (the crude CDT mixture) in the region of the feed part, removal of the high-boiling fraction (C) from the bottom of the column, the low-boiling fraction (A) via the top of the column and the medium boiler fraction (B) from the Area of the removal part or in thermally coupled columns is performed.
  • TK dividing wall column
  • T in the column longitudinal direction to form an upper common column region, a lower common column region, a feed part with reinforcing part and stripping section and a removal part with stripping section and reinforcing member is arranged, with feeding of the crude product (the crude CDT mixture) in the region of the feed
  • the demanding distillative separation task for obtaining the pure product CDT from the crude product which is obtained from the trimerization of butadiene, can be successfully solved even in the known more difficult to control dividing wall columns or thermally coupled columns.
  • the said crude product is a complex mixture, typically having compositions as listed below;
  • low boilers substances whose boiling point below the respective main product and as high boilers substances whose boiling point is above the respective main product:
  • Crude CDT contains in addition to the main product CDT about 2-10% low boilers, thereof in particular 4-vinylcyclohexene (VCH) and 1, 5-cyclooctadiene (COD) and chlorinated C8 compounds, next about 1-10% high boilers, especially oligomers of Butadiene with 16 or 20 carbon atoms and chlorinated C12 compounds.
  • VCH 4-vinylcyclohexene
  • COD 1, 5-cyclooctadiene
  • chlorinated C8 compounds next about 1-10% high boilers, especially oligomers of Butadiene with 16 or 20 carbon atoms and chlorinated C12 compounds.
  • pure product is understood here to mean a mixture which is defined as follows: pure CDT contains at least 99%, in particular at least 99.5%, particularly preferably at least 99.7% of CDT, residual impurities. The purity is typically determined by analyzing the area fraction using gas chromatograph (GC) and medium flame ionization detection (FID).
  • GC
  • Dividing wall columns typically have a dividing wall oriented in the longitudinal direction of the column, which subdivides the column interior into the following subareas: an upper common column area, a lower common column area, and an inlet part and a removal part, each with reinforcing part and driven part.
  • the mixture to be separated is fed in the region of the feed part, a high boiler fraction is taken from the bottom of the column, a low boiler fraction via the top of the column and a medium boiler fraction from the region of the withdrawal part.
  • the distribution ratio of the liquid at the upper end of the partition wall is adjusted in such a way that the proportion of high-boiling key components in the liquid return via the stripping section of the removal part 10% to Is 80%, preferably 30% to 50%, of the permissible limit in the medium boiler fraction, and that the heating power in the bottom evaporator of the dividing wall column is adjusted in such a way that the concentration of the low-boiling key components in the liquid at the lower end of the partition 10% to 80% , preferably 30% to 50% of the limit value permitted in the medium-low flow.
  • the liquid distribution at the upper end of the partition is adjusted so that at higher levels of high-boiling key components more and at lower levels of the same less liquid is directed to the inlet part.
  • the control of the heating power is carried out to the effect that with a higher content of low-boiling key components increases the heating power and at a lower level of the same, the heating power is reduced.
  • the medium boiler fraction is preferably taken off in liquid form; this process variant is thermally advantageous and easier to implement in terms of apparatus.
  • the quantitative ratio of the vapor stream in the withdrawal section to the vapor stream in the inlet section is 0.8 to 1.2, preferably 0.9 to 1.1.
  • the selection and / or dimensioning of separable internals and / or the installation of pressure loss generating devices is selected and / or dimensioning of separable internals and / or the installation of pressure loss generating devices.
  • the return from the upper common column part can be regulated so that the ratio of the return flow in the inlet part to the return in the withdrawal part is 0.1 to 1, preferably 0.5 to 0.8.
  • the removal of the top stream can be carried out temperature-controlled, wherein the measuring point for the control temperature in the upper common portion of the column, is arranged at a position which is arranged by 1 to 8, preferably by 1 to 5 theoretical plates below the upper end of the column.
  • the removal of the average low-boiling current is carried out in a controlled manner, the liquid level in the evaporator or in the bottom of the column being used as the controlled variable.
  • the removal of the high boiler stream can be temperature-controlled, wherein the measuring point for the control temperature in the lower common column area by 1-5, preferably 2-4 theoretical plates is located above the lower end of the column.
  • the invention also provides a dividing wall column for carrying out the method according to the invention. Particularly suitable for this partition wall columns with 5 to 100, preferably with 10 to 30 theoretical plates.
  • the division of the number of separation stages on the individual sections of the dividing wall column is preferably carried out in such a way that each of the 6 column sections of the dividing wall column each 5% to 50%, preferably 15% to 30% of the total number of theoretical plates of the dividing wall column.
  • the feed point of the stream to be separated and the removal point of the medium boiler stream can be arranged at different heights in the column.
  • Ordered sheet metal packings with a specific surface area of 100 m 2 / m 3 to 500 m 2 / m 3 are particularly suitable for the packed columns.
  • the liquid distribution in the individual subregions of the dividing wall column can be set separately. As a result, the total energy required to separate the mixture can be minimized.
  • the liquid in the subregions of the feed part of the dividing wall column, the liquid can be increasingly reduced in the wall region and in partial regions of the dividing wall column in the wall region. As a result, unwanted creeps are avoided and increases the achievable product end purities.
  • the inventive use of a dividing wall column allows the separation of more than two mixture components per stage, whereby less steps the same result can be achieved. Further, the partition wall suppresses flows that would cause the mixture fed to the feed to the removal part of the medium boiler fraction (or low boiler fraction). Thus, the inventive use of a dividing wall column increases the purity of the desired product.
  • the dividing wall column can be equipped in one or more subregions with ordered packings or packing.
  • the loose partition wall can have internal manholes or removable segments which allow to pass from one side of the partition wall to the other side within the dividing wall column.
  • thermally coupled columns instead of the dividing wall column. Arrangements with thermally coupled columns are equivalent in terms of energy requirements with a dividing wall column.
  • This variant of the invention is particularly suitable for the availability of existing columns. The most suitable forms of interconnection can be selected depending on the number of separation stages of the existing columns.
  • the thermally coupled columns can thus each be equipped with its own evaporator and / or condenser.
  • the low boiler fraction and the high boiler fraction are taken from different columns.
  • men wherein the operating pressure of the column from which the high boiler fraction is taken, is set lower than the operating pressure of the column from which the low boiler fraction is removed, preferably by 0.1 to 2 bar, in particular by 0.5 to 1 bar ,
  • the inventive method can preferably be carried out both in the use of a dividing wall column and thermally coupled columns in such a way that the feed stream is partially or completely pre-evaporated and the column is fed in two phases or in the form of a gaseous and a liquid stream.
  • This pre-evaporation is particularly useful when the bottom stream of the first column contains larger amounts of medium boilers.
  • the pre-evaporation can be done at a lower temperature level and the evaporator of the second column are relieved. Furthermore, the output part of the second column is substantially relieved by this measure.
  • the pre-evaporated stream can be fed to the second column in two phases or in the form of two separate streams.
  • the tightness of the column is particularly high through the use of seals, for example comb seals and / or by welding manholes and nozzles, so that as little oxygen as possible gets into the column during the distillation.
  • seals are therefore arranged and arranged in or on the column in order to seal the internal volume of the columns in a fluid-tight manner from the environment of the column.
  • Fig. 1 is a schematic representation of a dividing wall column for carrying out the method according to the invention.
  • Fig. 1 shows schematically a dividing wall column (TK) with vertically arranged partition wall (T), the column in an upper common column area 1, a lower common column area 6, an inlet part 2, 4 with reinforcement part 2 and output part 4 and a removal part. 3 , 5 with stripping section 3 and reinforcing member 5 divides.
  • the feed of the mixture to be separated (A, B, C) takes place in the central region of the feed section 2, 4.
  • Submerged medium fraction (B) deducted.
  • COD COD
  • VCH vanadium carbide
  • high-boiling compounds each containing about 1% by weight, as well as other low-boiling and high-boiling compounds.
  • the content of chlorinated C8 and C12 compounds was between 5 and 14 ppm by weight.
  • a specification-compliant product was obtained, ie CDT with greater than 99.5% purity.
  • the chlorine content in the pure CDT was 1-2 ppm.
  • the COD content was 80 ppm.
  • C16 olefin content was about 40 ppm.
  • Further components in the colon feed were each containing about 1-2% COD by weight, VCH and high-boiling components, as well as other low-boiling and high-boiling components.
  • the content of chlorinated C8 and C12 compounds was between 8 and 15 ppm by weight.
  • a specification-compliant product was obtained, ie CDT with a purity of greater than 99.5% and a Cl content of 2 ppm.
  • the COD content was 20 ppm
  • the C16 olefin content was about 100 ppm.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Water Supply & Treatment (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de retraitement par voie distillative d'un produit brut à base de cyclododécatriène obtenu par trimérisation de butadiène, pour préparer le produit pur à base de cyclododécatriène correspondant. Le retraitement par voie distillative intervient dans chaque cas dans une colonne à paroi de séparation, dans laquelle une paroi de séparation est aménagée dans le sens longitudinal de la colonne, de manière à former une zone de colonne commune supérieure, une zone de colonne commune inférieure, une partie d'alimentation présentant une section de renforcement et une section de rectification, ainsi qu'une partie de soutirage présentant une section de rectification et une section de renforcement, le produit brut à base de cyclododécatriène étant acheminé dans la zone médiane de la partie d'alimentation, une fraction à point d'ébullition élevé étant évacuée de la phase liquide de la colonne, une fraction à faible point d'ébullition étant évacuée par la tête de colonne et une fraction à point d'ébullition moyen étant évacuée de la zone médiane de la partie de soutirage ou bien ledit traitement s'effectue dans des colonnes en couplage thermique.
PCT/EP2009/050542 2008-01-25 2009-01-19 Procédé et dispositif de retraitement par voie distillative de 1,5,9-cyclododécatriène et préparation de cdt à haut niveau de pureté Ceased WO2009092682A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE112009000199T DE112009000199A5 (de) 2008-01-25 2009-01-19 Verfahren und Vorrichtung zur destillativen Aufarbeitung von 1,5,9-Cyclododecatrien und Gewinnung von CDT mit hoher Reinheit

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP08150659 2008-01-25
EP08150659.4 2008-01-25

Publications (2)

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WO2009092682A2 true WO2009092682A2 (fr) 2009-07-30
WO2009092682A3 WO2009092682A3 (fr) 2009-10-01

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8188320B2 (en) 2009-01-28 2012-05-29 Basf Se Process for preparing pure cyclododecanone
US8212082B2 (en) 2009-01-28 2012-07-03 Basf Se Process for the isolation of dodecatrienal and its use as aroma substance
DE102012223367A1 (de) 2012-12-17 2014-06-18 Evonik Industries Ag Aufarbeitung eines CDON/CDOL-Gemisches mittels einer "gelochten" Trennwandkolonne
WO2014173604A1 (fr) * 2013-04-22 2014-10-30 Wacker Chemie Ag Procédé et dispositif de séparation par distillation d'un mélange à trois composants ou à composants multiples
DE102013214765A1 (de) 2013-07-29 2015-01-29 Wacker Chemie Ag Verfahren und Vorrichtung zur destillativen Trennung eines Drei- oder Mehrkomponentengemisches
US9382181B2 (en) 2012-12-17 2016-07-05 Evonik Degussa Gmbh Workup of a cyclododecanone cyclododecanol mixture in a sequence of side draw columns
CN108137442A (zh) * 2015-10-23 2018-06-08 沙特基础全球技术有限公司 纯化1,3-丁二烯的方法和系统
CN112512655A (zh) * 2018-07-26 2021-03-16 环球油品有限责任公司 具有蒸气分离的分隔壁塔
CN116143578A (zh) * 2023-02-17 2023-05-23 中国天辰工程有限公司 一种丁二烯低聚反应溶剂回收工艺及系统
WO2023140986A1 (fr) 2022-01-19 2023-07-27 Exxonmobil Chemical Patents Inc. Compositions contenant du tri-cyclopentadiène et leurs procédés de fabrication
WO2025244981A1 (fr) 2024-05-20 2025-11-27 ExxonMobil Technology and Engineering Company Procédés de fabrication d'exo-dicyclopentadiène et de tricyclopentadiène

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Publication number Priority date Publication date Assignee Title
US3792102A (en) * 1971-12-30 1974-02-12 Phillips Petroleum Co Preparation of 1,9-decadiene from ethylene and cyclooctene
US4761025A (en) * 1984-11-05 1988-08-02 Kennecott Corporation Method and apparatus for distributing the load between sections of a vertical column
ATE242190T1 (de) * 1999-07-13 2003-06-15 Degussa Verfahren zur herstellung von cyclododecatrienen mit rückführung des katalysators
DE10233388A1 (de) * 2002-07-23 2004-02-12 Basf Ag Verfahren zur kontinuierlich betriebenen Reindestillation des bei der koppel-produktfreien Propylenoxidsynthese verwendeten Lösungsmittels Methanol unter gleichzeitiger Abtrennung der Methoxypropanole und der Schwersieder
DE102005031316A1 (de) * 2005-07-05 2007-01-18 Basf Ag Verfahren zur Gewinnung von Cyclododecatrien durch Verdampfung

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8212082B2 (en) 2009-01-28 2012-07-03 Basf Se Process for the isolation of dodecatrienal and its use as aroma substance
US8188320B2 (en) 2009-01-28 2012-05-29 Basf Se Process for preparing pure cyclododecanone
US9278898B2 (en) 2012-12-17 2016-03-08 Evonik Degussa Gmbh Workup of a cyclododecanone cyclododecanol mixture in a dividing wall column
DE102012223367A1 (de) 2012-12-17 2014-06-18 Evonik Industries Ag Aufarbeitung eines CDON/CDOL-Gemisches mittels einer "gelochten" Trennwandkolonne
EP2742981A2 (fr) 2012-12-17 2014-06-18 Evonik Industries AG Traitement d'un mélange CDON/CDOL au moyen d'une colonne de paroi de séparation perforée
US9382181B2 (en) 2012-12-17 2016-07-05 Evonik Degussa Gmbh Workup of a cyclododecanone cyclododecanol mixture in a sequence of side draw columns
WO2014173604A1 (fr) * 2013-04-22 2014-10-30 Wacker Chemie Ag Procédé et dispositif de séparation par distillation d'un mélange à trois composants ou à composants multiples
CN105142747A (zh) * 2013-04-22 2015-12-09 瓦克化学股份公司 用于蒸馏分离三组分或多组分混合物的方法和装置
DE102013207282A1 (de) 2013-04-22 2014-11-06 Wacker Chemie Ag Verfahren und Vorrichtung zur destillativen Trennung eines Drei- oder Mehrkomponentengemisches
US10076713B2 (en) 2013-04-22 2018-09-18 Wacker Chemie Ag Method and apparatus for the separation by distillation of a three- or multi-component mixture
DE102013214765A1 (de) 2013-07-29 2015-01-29 Wacker Chemie Ag Verfahren und Vorrichtung zur destillativen Trennung eines Drei- oder Mehrkomponentengemisches
US10226718B2 (en) 2013-07-29 2019-03-12 Wacker Chemie Ag Method and device for distillative separation of a three- or multi-component mixture
CN108137442A (zh) * 2015-10-23 2018-06-08 沙特基础全球技术有限公司 纯化1,3-丁二烯的方法和系统
US10689313B2 (en) 2015-10-23 2020-06-23 Sabic Global Technologies B.V. Processes and systems for purification of 1,3-butadiene
CN112512655A (zh) * 2018-07-26 2021-03-16 环球油品有限责任公司 具有蒸气分离的分隔壁塔
CN112512655B (zh) * 2018-07-26 2023-08-22 环球油品有限责任公司 具有蒸气分离的分隔壁塔
WO2023140986A1 (fr) 2022-01-19 2023-07-27 Exxonmobil Chemical Patents Inc. Compositions contenant du tri-cyclopentadiène et leurs procédés de fabrication
CN116143578A (zh) * 2023-02-17 2023-05-23 中国天辰工程有限公司 一种丁二烯低聚反应溶剂回收工艺及系统
WO2025244981A1 (fr) 2024-05-20 2025-11-27 ExxonMobil Technology and Engineering Company Procédés de fabrication d'exo-dicyclopentadiène et de tricyclopentadiène

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DE112009000199A5 (de) 2010-12-16
WO2009092682A3 (fr) 2009-10-01

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