US3684665A - Process for recovering styrene and xylenes from cracked oil by extractive distillation with a dealkyl acetamide - Google Patents

Process for recovering styrene and xylenes from cracked oil by extractive distillation with a dealkyl acetamide Download PDF

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US3684665A
US3684665A US10640A US3684665DA US3684665A US 3684665 A US3684665 A US 3684665A US 10640 A US10640 A US 10640A US 3684665D A US3684665D A US 3684665DA US 3684665 A US3684665 A US 3684665A
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styrene
xylene
distillation
cracked oil
column
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Hisao Abe
Masanori Tatsumi
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Toray Industries Inc
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Toray Industries Inc
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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
    • C10G7/00—Distillation of hydrocarbon oils
    • C10G7/08—Azeotropic or extractive distillation
    • 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

Definitions

  • the present invention relates to a process for recovering aromatic hydrocarbons contained in cracked oil obtained as by-products from the production of ethylene by thermal degradation (cracking) of naphtha. Further, the present invention relates to a process for obtaining styrene and Xylene from the cracked oil directly by extractivedistillation using solvents defined hereunder.
  • Ethylene being one of the most important intermediate products of the petro-chemical industry, is produced by heat-degradation of a refinery gas, a natural gas, or a naphtha.
  • cracking of naphtha is the main method for producing ethylene in most locations in the world, other than those having an abundance of natural gas.
  • cracked oil consists of many different components, Because it contains a large amount of unsaturated hydrocarbons such as oleins, dienes, acetylene derivatives and the like, it is very difcult to separate and rene a specific component directly from the cracked oil.
  • unsaturated hydrocarbons means unsaturated hydrocarbons having an oleiinic double bond or an acetylenic triple bond, but does not mean the double 'bond of an aromatic ring.
  • unsaturated hydrocarbons it is a very important matter to utilize these aromatic hydrocarbons for reducing the cost of ethylene.
  • hydrocarbons having up to carbon atoms and hydrocarbons having more than 9 carbon atoms were removed by distillation from the cracked oil, the resulting mixture was hydrogenated to convert unsaturated hydrocarbons such as olens, dienes and acetylene derivatives, and then aromatic hydrocarbons were separated from the mixture by extraction using solvents such as diethyleneglycol, sulfolane and N-methylpyrrolidone.
  • solvents such as diethyleneglycol, sulfolane and N-methylpyrrolidone.
  • Benzene, toluene, xylene and other aromatic hydrocarbons were separated by further distillation of the resulting hydrocarbons. Benzene and toluene thus recovered did not have any problem as to quality; however,
  • a novel and advantageous process is provided for recovering aromatic hydrocarbons particularly styrene and xylene from the cracked oil, which consists of, in order to concentrate C-8 aromatic hydrocarbon, separating hydrocarbons having up to about 5, more preferably 7, carbon atoms and more than 9 carbon atoms from the cracked oil by fractional distillation, producing a fraction containing Xylene at the top of the distillation column and a residue containing styrene at the bottom of the distillation column by extraetive-distillation, and, in necessity, hydrogenating the fraction containing the Xylene.
  • the present invention relates to a process for recovering aromatic hydrocarbons from cracked oil which consists of (l) removing hydrocarbons having up to about 5, more preferably about 7, carbon atoms and more than 9 carbon atoms from the cracked oil by fractional dis tillation, (2) obtaining the fraction mainly consisting of Xylene from the top of the distillation column and the residue substantially consisting of styrene and solvent from the bottom of the distillation column by extractivedistillation of the middle fraction of step (l), and (3) in necessity, hydrogenating the fraction containing xylenes obtained from step (2).
  • the present invention be carried out by: (1) separating hydrocarbons having about 5 carbon atoms or less from the cracked oil by fractional distillation, (2) separating benzene, toluene (as a fraction having a lower boiling temperature than Xylenes or styrene) and hydrocarbons having at least about 9 carbon atoms (as a residue having a higher boiling temperature than xylenes or styrene) by fractional distillation, (3) obtaining the fraction of xylenes from the top of the distillation column and styrene from the bottom of the distillation column by extractive-distillation of the fraction containing xylenes and styrene obtained from step (2) and (4) hydrogenating the fraction of xylenes.
  • benzene, toluene, Xylene and styrene can be recovered from the cracked oil eiciently and economically.
  • the cracked oil employed according to the present invention may consist of by-products from a plant producing ethylene by heat degradation (cracking) of naphtha at about 700-l000 C. Since the cracked oil consists of multiple components, it is diflcult to state its composition critically because various compositions are created under different cracking conditions. However, in the present invention, all cracked oils from which have been removed hydrocarbons having up to 5 carbon atoms are considered to be useful. It is not necessary to remove these hydrocarbons completely, but the total retained contents of these hydrocarbons should not be in excess of about 1% by weight. As above mentioned, t is not possible to set forth the composition of the cracked oil critically, however, normally a cracked oil containing about 30-80% by weight aromatic hydrocarbons may be used. Of course, there is no intention to limit the present invention with respect to the contents above mentioned.
  • the cracked oils are readily available commercially as by-products from plants producing olefins (ethylene) by cracking of naphtha.
  • the step of removing hydrocarbons having up to 5 (7) carbon atoms and more than 9 carbon atoms from the cracked oil is usually carried out by fractional distillation. All of the known distillation operations are useful in the present invention. Normally, the distillation operation is carried out at a temperature of about 70 C., under a normal atmospheric pressure, with a reux ratio of about 2, preferably at a temperature of 135 C. and 150 C. of the converted value of normal atmospheric pressure, and with a reflux ratio of 3. In this distillation procedure, two distillation columns are preferably used.
  • the operating condition of the distillation step is set up and controlled at the discretion of the operator.
  • this fraction contains a few parts of an aromatic hydrocarbon having 8 carbon atoms and that the residue consists of hydrocarbons having at least 9 carbon atoms.
  • distillation operation when one distillation column is used, the fraction having a lower boiling temperature is recovered from the top of the column, the fraction of desired aromatic hydrocarbons is recovered from the middle of the column, and the residue is re- I covered from the bottom of the column.
  • the distillation is carried out under atmospheric pressure or reduced pressure. Normally, the distillation operation 1s carried out at a temperature of 70 C. under a normal atmospheric pressure, and with a reux ratio of 2. However, these operating conditions are not intended to limit the scope of the present invention.
  • the desired product fraction thus obtained consists of aromatic hydrocarbons having 8 carbon atoms as its main components.
  • benzene and toluene are separable easily from the fraction, it is possible to include a great amount of benzene and toluene in the fraction, although these amounts may be greater than the amounts of Xylene and styrene.
  • the total amount of benzene and toluene should not exceed 10% by weight.
  • any great amount of hydrocarbons having at least 9 carbon atoms be contained in this fraction, because they are an obstacle to subsequent extractive-distillation.
  • the total amount of these hydrocarbons should be less than about 1% by weight.
  • the separation of xylene and styrene from the fraction is successfully carried out by eXtractive-distillation.
  • the extractive-distillation step is carried out by feeding the fraction obtained from the above mentioned operations into a column at the middle of the column and also feeding a solvent, hereunder dened, into the column near the top of the column, and then the fraction containing concentrated xylene is recovered from the top of the column and concentrated styrene is recovered from the bottom of the column with solvent.
  • One or more distillation columns are used in the extract-ive-distillation, however, it is preferable to use two distillation columns.
  • Suitable solvents include a dialkyl acetamide such as dimethylacetamide, a dialkylsulfoxide such as dimethylsulfoxide, an alkylene carbonate such as ethylene carbonate and propylene carbonate, a lactone such as 'ybutyrolactone and methyl-fy-butyrolactone, a lactum such as e-caprolactum, phenol, an alkylphenol, a salicylic acid alkylester, aniline, an alkylaniline, a phthalic acid alkylester, a tetraalkylurea, an N,Ndialkyl carbamicester, a glycol monoalkylether such as diethyleneglycol monoalkylether and triethyleneglycol monoalkylether and N- methylpyrrolidone.
  • a dialkyl acetamide such as dimethylacetamide
  • a dialkylsulfoxide such as dimethylsulfoxide
  • an alkylene carbonate
  • alkyl substituted compounds it is preferable to use compounds having alkyl group of 1 to 3 carbon atoms.
  • One to 50 mol of solvent preferably 2-10 mol of solvent, is used as an extractive-distillation solvent based on one mol of styrene contained in the feed.
  • the temperature and pressure should be controlled in the extractive-distillation step; it may be below 120 C. at the bottom (boiler) of the distillation column, preferably within the range of about -110 C.
  • the pressure should be determined according to the structure of the distillation column and the nature of the solvent. However, the pressure may usually be within the range of about 10-200 mm. Hg absolute, preferably within the range of about 20-100 rnm. 'Hg absolute at the top of the column.
  • any known inhibitor may be used, such as hydroquinone, tert-butylcatechol, phenothiozine, sulfur, etc.
  • the amount of inhibitor employed in the distillation step may be 10-500 p.p.m. based on the weight of the feed, or even more.
  • the preferable reux ratio is within the range of 10-20.
  • a solvent selected from the group consisting of a dialkyl acetamide such as dimethylacetamide, a dialkylsulfoxide such as dimethylsulfoxide, an alkylene carbonate such as ethylene carbonate and propylene carbonate, a lactone such as q/-butyrolactone and methyl-'ybutyrolactone, a lactum such as e-caprolactum, phenol, an alkylphenol, a salicylic acid alkylester, aniline, an alkylaniline, a phthalic acid alkylester, a tetraalkylurea, an N,N-dialkyl carbamicester, a glycol monoalkylether such as diethyleneglycol monoalkylether and triethyleneglycol monoalkylether and N-methylpyrrolidone styrene can be obtained at a high purity and at a high yield ratio.
  • a solvent selected from the group consisting of a dialkyl ace
  • styrene has been produced by dehydrogenation of ethylbenzene of high purity and distillation of the resulting products under reduced pressure.
  • Ethylbenzene has been obtained by reaction of ethylene and benzene, or separated from fractions of Xylenes by distillation. It would be thought to be particularly advantageous to recover ethylbenzene from the xylene fraction since great quantities of the xylene fraction can be readily obtained from the patro-chemical industry.
  • the method (l) is expensive because of the silver salt; the method (2) has a low separation etlciency; the method (3) is troublesome because styrene and xylene respectively form azeotropics with dimethylformamide and so it is virtually impossible to recover styrene and xylene from solvent by distillation; the method (4) is actually impractical.
  • styrene can be -obtained from the xylene fraction easily by the extractive-distillation using the above mentioned solvents.
  • the residue thus obtained consists essentially of styrene and solvent.
  • Styrene can be separated easily by normal distillation of the residue under reduced pressure. It is preferable that the pressure be controlled within the range of about 20-100 mm. Hg absolute at the top of the column. In order to prevent thermal polymerization of the styrene, it is preferable that the temperature be kept below 120 C. at any plate of the column. It is also preferable to use an inhibitor in this distillation as well as in the extractive-distillation. Styrene can be recovered from the top of the column as a fraction.
  • the fraction taken from the top of the column consists mainly of xylene but toluene, benzene and other saturated and unsaturated aliphatic hydrocarbons may be present.
  • the fraction, as it is or after washing with Water, may be hydrogenated by using a catalyst such as Mo, Co, Ni and combinations thereof.
  • the hydrogenation reaction may be carried out under a pressure of -200 kg./cm.2 absolute and at a temperature of 10D-400 C. In this hydrogenation procedure it may be advisable to use a mixture with xylene fraction of extractive-distillation and the lower fraction and/or the residue obtained from the distillation of the cracked oil.
  • aromatic hydrocarbons such as benzene, toluene, xylene and styrene can be recovered from the cracked oil successfully.
  • xylene having good quality containing a high concentration of P-xylene and a low concentration of ethylbenzene
  • styrene having high purity can be obtained from cracked oil directly.
  • P-xylene is an important raw material of terephthalic acid
  • styrene is also important as a raw material in plastics. The present invention should contribute to reduce the costs of these products greatly.
  • Example l Cracked oil of depentanized bottom product containmg 7 .5% by weight styrene was obtained from the commercial plants of naphtha cracking. Lower fractions whose boiling temperatures of up to 130 C. and higher fractions of beyond '150 C. were removed by fractional distillation of said cracked oil.
  • the remaining oil was extractively distilled, using two distillation columns.
  • the first column which has plates number of 50 was operated under 70 mm. Hg absolute at 60 C. using a reflux ratio of l2, and the second column which has plates number 60 was operated under 20 mm. Hg absolute at 45 C. using a redux ratio of 15.
  • the oil was fed into the middle plate of the first column and dimethylacetamide in the same amount of the oil (containing 300 ppm. of tert-butylcatechol) was supplied from the top of the column.
  • the residue from the bottom of the first column was fed into the middle plate of the second column, and dimethylacetamide in a quantity of ⁇ 0.5 times the amount of the residue was supplied to the top of the secondl column.
  • the fractions from the top of the second column were recycled to the middle of the irst column, and the mixture of styrene and the solvent was obtained from the bottom cf the second column.
  • Xylene contained in the reaction mixture thus obtained was composed of 21% by weight ethylbenzene, 18% by Weight P-xylene, 36% by weight m-xylene, and 25% by Weight O-xylene.
  • xylene without separating styrene contained 47% by weight ethylbenzene and 12% P-xylene.
  • Example 2 The same operation as Example 1 was carried out, except using 4-methyl-y-butylolactone instead of using dimethylacetamide of Example 1 as the solvent.
  • Styrene was recovered at 98% purity and with a 75% yield ratio based on the cracked oil.
  • Xylenes contained in the reaction mixture were composed of 25% by weight ethylbenzene, 17% by weight P-xylene, 34% by weight m-xylene and 24% by weight O-Xylene.
  • Example 3 A cracked oil containing 7% by weight styrene was obtained by fractional distillation of by-product of a plant producing ethylene after removing hydrocarbons having up to 5 carbon atoms.
  • the lower fractions having boiling temperatures of up to C. under 150 rnm. Hg absolute were separated from the cracked oil by fractional distillation and the higher fractions having boiling temperatures of at least 80 C. under 43 mm. Hg were separated by fractional distillation. Fractions of hydrocarbons having 8 carbon atoms as the main portion were obtained.
  • the fractions from the top of the rst column were hydrogenated under 50 atm. pressure at 380 C. in the presence of Co-Mo catalysts.
  • the xylene fraction thus obtained was composed of 20% by weight ethylbenzene, 18% by weight P-xylene, 36% by weight rnxylene and 26% by vweight O-xylene.
  • the xylenes contained in the reaction mixture hydrogenated without separating styrene by extractive-distillation contained 48% by weight ethylbenzene and 12% by weight P-xylene.
  • Example 7 The same operation of Example 6 was applied except using 'y-butylolactone instead of dimethylacetamide as the solvent.
  • Styrene was recovered with 99.2% purity and at an 85% yield ratio.
  • Xylene contained in the reaction mixture were composed of 21% by weight ethylbenzene, 18% by weight P- xylene, 36% by weight m-xylene and 25% by weight O-xylene.
  • Examples 8-24 Styrene and xylene were separated from each other and from various compositions consisting of styrene and xylene by extractive-distillation using various solvents.
  • each distillation column had a capacity of 2.5 meters height and 30 mm. inner diameter, ⁇ and was filled up with 3 x 3 mm. wire nettings.
  • Each composition was supplied from a feed plate set up at 1.8 meter height of each column, and also each solvent was supplied from a feed plate set up at 2.4 meters height of each column.
  • Xylene was recovered from the top of the column as a fraction, and styrene was recovered from the bottom of the column as residue.
  • each percentage of purity of hydrocarbon represents the concentrate ratio except of solvent.
  • the method for separating xylene and styrene from a C3 fraction containing primarily xylene and styrene 10 comprising extractively distilling said C3 fraction with a dialkyl acetamide; recovering a xylene fraction in the form of a vapor, removing the styrene in a solvent solution of the dialkyl acetamide and rectifying the solvent solution to separate the styrene from the dialkyl acetamide.
  • dialkyl acetamide is dimethyl acetamide.
  • said inhibitor is a member selected from the class consisting of hydroquinone, tert-butylcatechol, phenothiozine, sulfur and mixtures thereof.

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US10640A 1969-02-17 1970-02-11 Process for recovering styrene and xylenes from cracked oil by extractive distillation with a dealkyl acetamide Expired - Lifetime US3684665A (en)

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JP1110469A JPS4813099B1 (fr) 1969-02-17 1969-02-17
JP6688669 1969-08-26

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NL (1) NL7001959A (fr)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3884769A (en) * 1972-03-20 1975-05-20 Inst Francais Du Petrole Process for purifying benzene and toluene by extractive azeotropic distillation
US4031153A (en) * 1975-09-25 1977-06-21 Phillips Petroleum Company Separation of styrene from xylenes
US4050993A (en) * 1972-09-11 1977-09-27 Cosden Oil & Chemical Company Distillation of readily polymerizable ethylenically unsaturated compounds
US4115208A (en) * 1975-08-25 1978-09-19 Stamicarbon, B.V. Recovery of styrene from cracked hydrocarbon fractions
US4129605A (en) * 1977-01-28 1978-12-12 Phillips Petroleum Company Recovering styrene by complexing with copper(I) sulfonates
US4379027A (en) * 1981-12-24 1983-04-05 Mobil Oil Corporation Selective hydrogenation of vinyltoluene
US4959128A (en) * 1990-02-26 1990-09-25 Lloyd Berg Separation of styrene from ethyl benzene by extractive distillation
US5039380A (en) * 1991-04-03 1991-08-13 Lloyd Berg Separation of m-xylene from p-xylene or o-xylene by azeotropic distillation
US5091059A (en) * 1991-10-22 1992-02-25 Lloyd Berg Separation of p-xylene from m-xylene by extractive distillation
US5094725A (en) * 1991-04-04 1992-03-10 Lloyd Berg Separation of m-xylene from o-xylene by extractive distillation with esters
US5849982A (en) * 1996-05-21 1998-12-15 Hfm International, Inc. Recovery of styrene from pyrolysis gasoline by extractive distillation
US5877385A (en) * 1996-05-21 1999-03-02 Hfm International, Inc. Process including extractive distillation and/or dehydrogenation to produce styrene from petroleum feedstock including ethyl-benzene/xylene mixtures
DE102005029643B3 (de) * 2005-06-23 2006-07-20 Uhde Gmbh Verfahren zur Gewinnung von Reinstyrol aus einer Pyrolysebenzinfraktion
US20110015462A1 (en) * 2009-07-17 2011-01-20 Amy Sealey Methods for inhibiting polymerization of vinyl aromatic compounds during extractive distillation
WO2016036392A1 (fr) * 2014-09-05 2016-03-10 Scg Chemicals Company Limited Procédé de séparation améliorée d'éthylbenzène
WO2016036388A1 (fr) * 2014-09-05 2016-03-10 Scg Chemicals Company Limited Procédé de séparation pour un mélange de composés aromatiques c8
US9353024B2 (en) 2013-02-06 2016-05-31 Exxonmobil Chemical Patents Inc. Selective hydrogenation of styrene to ethylbenzene
US20220306555A1 (en) * 2020-06-16 2022-09-29 Lg Chem, Ltd. Method of producing aromatic hydrocarbons
US20220306950A1 (en) * 2020-06-16 2022-09-29 Lg Chem, Ltd. Method of producing aromatic hydrocarbons

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7509991A (nl) * 1975-08-25 1977-03-01 Stamicarbon Werkwijze voor het winnen van styreen uit gekraakte koolwaterstoffen.
DE2911394B1 (de) * 1979-03-23 1980-04-30 Basf Ag Verfahren zur Gewinnung eines konjugierten Diolefins aus einem C4- oder C5- Kohlenwasserstoffgemisch
DE10038349C1 (de) * 2000-08-05 2002-01-31 Basf Ag Verfahren zur Destillation von vinylaromatischen Monomeren

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3884769A (en) * 1972-03-20 1975-05-20 Inst Francais Du Petrole Process for purifying benzene and toluene by extractive azeotropic distillation
US4050993A (en) * 1972-09-11 1977-09-27 Cosden Oil & Chemical Company Distillation of readily polymerizable ethylenically unsaturated compounds
US4115208A (en) * 1975-08-25 1978-09-19 Stamicarbon, B.V. Recovery of styrene from cracked hydrocarbon fractions
US4031153A (en) * 1975-09-25 1977-06-21 Phillips Petroleum Company Separation of styrene from xylenes
US4129605A (en) * 1977-01-28 1978-12-12 Phillips Petroleum Company Recovering styrene by complexing with copper(I) sulfonates
US4379027A (en) * 1981-12-24 1983-04-05 Mobil Oil Corporation Selective hydrogenation of vinyltoluene
US4959128A (en) * 1990-02-26 1990-09-25 Lloyd Berg Separation of styrene from ethyl benzene by extractive distillation
US5039380A (en) * 1991-04-03 1991-08-13 Lloyd Berg Separation of m-xylene from p-xylene or o-xylene by azeotropic distillation
US5094725A (en) * 1991-04-04 1992-03-10 Lloyd Berg Separation of m-xylene from o-xylene by extractive distillation with esters
US5091059A (en) * 1991-10-22 1992-02-25 Lloyd Berg Separation of p-xylene from m-xylene by extractive distillation
US5849982A (en) * 1996-05-21 1998-12-15 Hfm International, Inc. Recovery of styrene from pyrolysis gasoline by extractive distillation
US5877385A (en) * 1996-05-21 1999-03-02 Hfm International, Inc. Process including extractive distillation and/or dehydrogenation to produce styrene from petroleum feedstock including ethyl-benzene/xylene mixtures
US8648227B2 (en) * 2005-06-23 2014-02-11 Thyssenkrupp Uhde Gmbh Method for extracting pure styrene from a pyrolysis benzine fraction
US20090306445A1 (en) * 2005-06-23 2009-12-10 Helmut Gehrke Method for Extracting Pure Styrene From a Pyrolysis Benzine Fraction
DE102005029643B3 (de) * 2005-06-23 2006-07-20 Uhde Gmbh Verfahren zur Gewinnung von Reinstyrol aus einer Pyrolysebenzinfraktion
WO2006136255A2 (fr) 2005-06-23 2006-12-28 Uhde Gmbh Procede d'extraction de styrene pur d'une fraction de pyrolyse-benzine
US20110015462A1 (en) * 2009-07-17 2011-01-20 Amy Sealey Methods for inhibiting polymerization of vinyl aromatic compounds during extractive distillation
US8771476B2 (en) * 2009-07-17 2014-07-08 Gtc Technology Lp Methods for inhibiting polymerization of vinyl aromatic compounds during extractive distillation
US9353024B2 (en) 2013-02-06 2016-05-31 Exxonmobil Chemical Patents Inc. Selective hydrogenation of styrene to ethylbenzene
US9416072B1 (en) 2013-02-06 2016-08-16 Exxonmobil Chemical Patents Inc. Selective hydrogenation of styrene to ethylbenzene
KR20170058953A (ko) * 2014-09-05 2017-05-29 에스씨지 케미컬스 컴퍼니, 리미티드. 에틸벤젠의 향상된 분리를 위한 방법
WO2016036388A1 (fr) * 2014-09-05 2016-03-10 Scg Chemicals Company Limited Procédé de séparation pour un mélange de composés aromatiques c8
KR20170056580A (ko) * 2014-09-05 2017-05-23 에스씨지 케미컬스 컴퍼니, 리미티드. C8 방향족 혼합물을 위한 분리 방법
WO2016036392A1 (fr) * 2014-09-05 2016-03-10 Scg Chemicals Company Limited Procédé de séparation améliorée d'éthylbenzène
TWI670259B (zh) * 2014-09-05 2019-09-01 泰商Ｓｃｇ化學股份有限公司 用於ｃ８芳香族混合物之分離製程
US10427994B2 (en) 2014-09-05 2019-10-01 Scg Chemicals Co., Ltd. Separation process for C8 aromatics mixture
US10435340B2 (en) 2014-09-05 2019-10-08 Scg Chemicals Co., Ltd. Process for the enhanced separation of ethylbenzene
KR102275314B1 (ko) 2014-09-05 2021-07-12 에스씨지 케미컬스 컴퍼니, 리미티드. 에틸벤젠의 향상된 분리를 위한 방법
KR102329813B1 (ko) 2014-09-05 2021-11-23 에스씨지 케미컬스 컴퍼니, 리미티드. C8 방향족 혼합물을 위한 분리 방법
US20220306555A1 (en) * 2020-06-16 2022-09-29 Lg Chem, Ltd. Method of producing aromatic hydrocarbons
US20220306950A1 (en) * 2020-06-16 2022-09-29 Lg Chem, Ltd. Method of producing aromatic hydrocarbons
US11667855B2 (en) * 2020-06-16 2023-06-06 Lg Chem, Ltd Method of producing aromatic hydrocarbons
US11976039B2 (en) * 2020-06-16 2024-05-07 Lg Chem, Ltd. Method of producing aromatic hydrocarbons

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GB1274784A (en) 1972-05-17
DE2006863B2 (de) 1973-06-20
DE2006863A1 (de) 1971-09-09
DE2006863C3 (de) 1974-01-31
BE745743A (fr) 1970-07-16
NL7001959A (fr) 1970-08-19

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