WO2001040150A1 - Procede d'extraction de composes aromatiques d'une phase aliphatique par utilisation d'un liquide ionique non neutre - Google Patents

Procede d'extraction de composes aromatiques d'une phase aliphatique par utilisation d'un liquide ionique non neutre Download PDF

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Publication number
WO2001040150A1
WO2001040150A1 PCT/US2000/032500 US0032500W WO0140150A1 WO 2001040150 A1 WO2001040150 A1 WO 2001040150A1 US 0032500 W US0032500 W US 0032500W WO 0140150 A1 WO0140150 A1 WO 0140150A1
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Prior art keywords
ionic liquid
alkyl
metal halide
group
liquid
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PCT/US2000/032500
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English (en)
Inventor
Lieh-Jiun Shyu
Zongchao Zhang
Qinglin Zhang
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Akzo Nobel N.V.
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Publication of WO2001040150A1 publication Critical patent/WO2001040150A1/fr

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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
    • C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
    • C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B63/00—Purification; Separation; Stabilisation; Use of additives
    • 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

  • Transition metals species such as V, Ni, Ti or Fe porphyrin
  • nitrogen- and sulfur-containing (such as dibenzothiophene) compounds are normally present in crude oils.
  • concentration level of nitrogen and sulfur in gasoline and diesel fuel has been projected to be reduced to what cannot be achieved with existing technology without a large increase in cost.
  • the current practice of employing a hydrodesulfurization catalyst has been found to be not effective for the desulfurization of dialkyl-substituted dibenzothiophene.
  • the petroleum industry is under increasing pressure to reduce N and S level from fuels. In fluidized catalytic cracking units, heavy crude fractions are cracked using a zeolite catalyst.
  • a moisture stable ionic liquid such as imidazolium hexafluorophosphate, is known to also be a solvent for the extraction of metal ions from aqueous solutions.
  • An ionic liquid comprising a metal halide and an organic salt, such as imidazolium chloride, pyridinium chloride and alkyl ammonium chloride, is known to be an effective catalyst for benzene alkylation.
  • a preferred catalyst of this type is trimethylamine hydrochloride which is described in U.S. Patent Nos. 5,731,101 and 5,824,832, which are each incorporated herein in their entirety.
  • the present invention relates to the use of a non- neutral ionic liquid that comprises a metal halide-derived anion for the extraction of aromatic compounds that may also contain heteroatoms such as sulfur, nitrogen, and metals from an aliphatic hydrocarbon fluid, such as a lubricant oil or a petroleum oil.
  • a non- neutral ionic liquid that comprises a metal halide-derived anion for the extraction of aromatic compounds that may also contain heteroatoms such as sulfur, nitrogen, and metals from an aliphatic hydrocarbon fluid, such as a lubricant oil or a petroleum oil.
  • the present invention relates to the use of non-neutral ionic liquids that comprise a metal halide-derived anion (either a moisture stable or moisture sensitive ionic liquid, or mixture thereof) to extract aromatic compounds, for example those containing N, S, and metals, from such oil and fuel sources.
  • the ionic liquid phase is immisible with the saturated lubricant oil or crude oil.
  • the oil or fuel can be effectively cleaned using this ionic liquid treatment.
  • non-neutral is to be construed on the basis of the definition of Lewis acid and Lewis base.
  • the Figure gives a plot of such acidity or basicity as a function of the anion fraction as a function of aluminum trichloride in an ionic liquid comprising a nitrogen atom-containing cation and such an anion.
  • the resulting composition is neither acidic nor basic. It is neutral in the sense that that term is used herein.
  • the metal halides useful in the ionic liquid component used in the process of this invention are those compounds which can form anions containing polyatomic chloride bridges in the presence of the alkyl-containing a ine hydrohalide salt.
  • Preferred metal halides are covalently bonded metal halides.
  • Suitable metals that can be selected for use herein include those from Groups VIII and IB, IIB and IIIA of the Periodic Table of the Elements.
  • Especially preferred metals are selected from the group comprising aluminum, gallium, iron, copper, zinc, and indium, with aluminum being most preferred.
  • the corresponding most preferred halide is chloride and therefore, the most preferred metal halide is aluminum trichloride.
  • metal halides include those of copper (e.g., copper monochloride) , iron (e.g., ferric trichloride), and zinc (e.g., zinc dichloride) .
  • Copper trichloride is most preferred because it is readily available and can form the polynuclear ion having the formula A1 2 C1 7 " .
  • the molten compositions comprising this polynuclear ion are useful as described hereinbefore. Mixtures of more than one of these metal halides can be used.
  • Granular aluminum trichloride (+4 -14 mesh or having a particle size between 1.41 mm and 4.76 mm) can be an especially preferred metal halide to employ.
  • alkyl-containing amine hydrohalide salt is intended to cover monoamines, as well as diamines, triamines, other oligoamines and cyclic amines which comprises one or more "alkyl” groups and a hydrohalide anion.
  • alkyl is intended to cover not only conventional straight and branched alkyl groups of the formula - (CH 2 ) n CH 3 where n is from 0 to about 18, preferably 0 to about 8, in particular 0 to 3 , but other structures containing heteroatoms (such as oxygen, sulfur, silicon, phosphorus, or nitrogen) . Such groups can carry substituents .
  • Representative structures include ethylenediamine, ethylenetriamine, morpholino, and poloxyalkylamine substituents.
  • Alkyl includes "cycloalkyl” as well.
  • the preferred alkyl-containing amine hydrohalide salts useful in the present invention have at least one alkyl substituent and can contain as many as three alkyl substituents.
  • the preferred compounds that are contemplated herein have the generic formula R 3 N.HX, where at least one of the "R" groups is alkyl, preferably alkyl of from one to eight carbon atoms (preferably, lower alkyl of from one to four carbon atoms) and X is halogen, preferably chloride.
  • each of the three R groups is designated R 1 R 2 and R 3 , respectively, the following possibilities exist in certain embodiments: each of R ;L -R 3 can be lower alkyl optionally interrupted with nitrogen or oxygen or substituted with aryl; R x and R 2 can form a ring with R 3 being as previously described for R-; R 2 and R 3 can either be hydrogen with R x being as previously described; or R 1 R 2 and R 3 can form a bicyclic ring. Most preferably, these groups are methyl or ethyl groups. If desired the di- and trialkyl species can be used. One or two of the R groups can be aryl, but this is not preferred.
  • the alkyl groups, and aryl, if present, can be substituted with other groups, such as a halogen. Phenyl and benzyl are representative examples of possible aryl groups to select. However, such further substitution may undesirably increase the size of the group, and correspondingly increase the viscosity of the melt. Therefore, it is highly desirable that the alkyl groups, and aryl, if present, be comprised of carbon and hydrogen groups, exclusively. Such short chains are preferred because they form the least viscous or the most conductive melts. Mixtures of these alkyl-containing amine hydrohalide salts can be used.
  • the mole ratio of alkyl-containing amine hydrohalide salt which is to be combined with the metal halide is preferably, in general, range from above about 1:1 to about 1:2.5 so as to yield an acidic melt.
  • the low temperature molten composition in the process of this invention consists essentially of the metal halide and the alkyl-containing amine hydrohalide salt.
  • the most preferred, acidic, low temperature molten composition is a mixture consisting essentially of a mole ratio of trimethylamine hydrochloride to aluminum trichloride of from about 1:1.5 to about 1:2, preferably about 1:2.
  • the metal halide and the alkyl-containing amine hydrohalide salt are solids at low temperature, i.e., below about 100° C. at standard pressure. After mixing the two solids together, the mixture can be heated until the mixture becomes a liquid. Alternatively, the heat generated by the addition of the two solids will result in forming a liquid without the need for additional external heating. Upon cooling, the mixture remains a liquid at low temperature, i.e., below about 70°C, preferably below about 50°C, and more preferably below about 30°C.
  • the advantages of using the type of low temperature ionic liquid described for use herein include having an easy-to-pump liquid employed in the reaction vessel and an extraction performance that does not depend upon the dissolution rate of a solid in the extracting liquid phase.
  • the extraction capability is much greater using an ionic liquid rather than a composition that is a solid phase material (as demonstrated in Example 4 and 5) .
  • the minimum amount of ionic liquid that is preferably used to remove the aromatic compound component from the aliphatic fluid will be substantially equivalent to the stoichiometric amount of the target aromatic compound or compounds that are present in the fluid.
  • the use of an excess of the ionic liquids is within the contemplation of the present invention since any excess ionic liquids can be recycled and reused.
  • the ionic liquid used herein to be supported, for example, by a metal oxide support, including those of silica, alumina or a zeolite, carbon, graphite, fibers, or porous polymers.
  • a representative microporous polymeric support that can be used is described in U.S. Patent No. 4,519,909 to A.J. Castro (which is incorporated herein by reference in its entirety) . This particular microporous polymer is commercially available under the ACCUREL. This invention is further illustrated by the Examples that follow.
  • Dodecane (10 gm) and 0.05 gm of naphthalene were weighed into a glass bottle. The resulting clear solution was then analyzed by GC and was shown to contain 4713 ppm of naphthalene. Then, 5.4 gm of an ionic liquid comprising trimethylamine hydrochloride (TMAC) /A1 2 C1 7 ionic liquid into the glass bottle containing the dodecane and naphthalene- containing solution. The solution was stirred for one half hour at room temperature, and a sample of the clear solution above the ionic liquid layer was withdrawn and was analyzed by GC. The analysis showed that the naphthalene level in the clear solution had decreased 70% to 1496 ppm.
  • TMAC trimethylamine hydrochloride
  • This Example illustrates a multiple step treatment in accordance with the present invention.
  • Dodecane (10 gm) and 0.05 gm of dibenzothiophene were weighed into a glass bottle. The clear solution was then analyzed by GC that showed that there was 4772 ppm of dibenzothiophene in the background sample. Then, 3 gm of trimethylamine hydrochloride (TMAC) /A1 2 C1 7 ionic liquid was added into the glass bottle holding the sample containing the dodecane and dibenzothiophene. The resulting sample was stirred for one half hour at room temperature, and a sample of the clear solution above the ionic liquid layer was than withdrawn and was analyzed by GC. Analysis showed that the dibenzothiophene level in the clear solution had decreased 88% to 573 ppm.
  • TMAC trimethylamine hydrochloride
  • Decane (10 gm) and 0.05 gm of dibenzothiophene were weighed into a glass bottle. The resulting clear solution was then analyzed by GC and was shown to contain 5211 ppm of dibenzothiophene. Then, 3 gm of an ionic liquid comprising trimethylamine hydrochloride (TMAC) /A1 2 C1 7 ionic liquid was placed into the glass bottle containing the dodecane and dibenzothiophene-containing solution. The solution was stirred for one half hour at room temperature, and a sample of the clear solution above the ionic liquid layer was withdrawn and was analyzed by GC. The analysis showed that the dibenzothiophene level in the clear solution had decreased 89% to 564 ppm.
  • TMAC trimethylamine hydrochloride
  • This Comparative Example illustrates that the selection of tetrachloroaluminate as an anion, which produced a neutral composition in regard to either Lewis acidity or basicity does not remove aromatics from an aliphatic liquid.
  • Decane (10 gm) and 0.05 gm of dibenzothiophene were weighed into a glass bottle. The resulting clear solution was then analyzed by GC and was shown to contain 6049 ppm of dibenzothiophene. Then, 3 gm of an ionic "liquid” comprising trimethylamine hydrochloride (TMAC)/A1C1 4 ionic "liquid” was placed into the glass bottle containing the dodecane and dibenzothiophene-containing solution. The trimethylamine hydrochloride (TMAC) /A1C1 4 ionic "liquid” was made from one mole of trimethylamine hydrochloride and one mole of A1C1 3 . It is a solid at room temperature.
  • TMAC trimethylamine hydrochloride
  • A1C1 4 ionic "liquid was made from one mole of trimethylamine hydrochloride and one mole of A1C1 3 . It is a solid at room temperature.
  • the solution containing the solid phase ionic "liquid” was stirred for one half hour at room temperature, and a sample of the clear solution above the ionic "liquid” layer was withdrawn and was analyzed by GC. The analysis showed that the dibenzothiophene content in the clear solution had remained at the same level. The solid phase ionic "liquid” did not show any extraction capability.
  • the clear decane solution containing the solid phase ionic "liquid” was then heated to 90°C with stirring for one half hour.
  • the dibenzothiophene level in the clear solution was analyzed by GC again. It showed that the dibenzothiophene level had remained the same after treatment at 90°C.
  • the solid phase ionic "liquid” did not show any extraction capability even when the system had been heated to 90°C.
  • A. A1C1 3 /TMAC 2:1
  • the absorption capacity for each model compound was given in table 1:
  • Table 1 lists the sulfur content of gasoline and diesel samples received for the testing in Examples
  • Example 11 Treatment of Low-S Level Naphtha
  • X-ray fluorescence analysis of the treated sample indicated a 40.9% total sulfur reduction (from 220 ppm to 130 ppm) .
  • Example 12 Treatment of Low S Level Naphtha
  • Example 15 Treatment of Low S Gas-Oil

Abstract

L'invention concerne l'extraction de composés aromatiques d'un fluide d'hydrocarbure aliphatique par mise en contact dudit fluide avec un liquide ionique non neutre qui comprend un anion dérivé d'un halogénure métallique.
PCT/US2000/032500 1999-12-01 2000-11-29 Procede d'extraction de composes aromatiques d'une phase aliphatique par utilisation d'un liquide ionique non neutre WO2001040150A1 (fr)

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US60/168,343 1999-12-01

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Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003037835A2 (fr) * 2001-11-02 2003-05-08 Solvent Innovation Gmbh Procede d'elimination d'impuretes polarisables contenues dans des hydrocarbures et melanges d'hydrocarbures
DE10154052A1 (de) * 2001-11-02 2003-07-10 Carl V Ossietzky Uni Oldenburg Einsatz ionischer Flüssigkeiten als selektive Lösungsmittel für die Trennung aromatischer Kohlenwasserstoffe von nichtaromatischen Kohlenwasserstoffen durch extraktive Rektifikation und Extraktion
WO2003070667A1 (fr) * 2002-02-19 2003-08-28 Oxeno Olefinchemie Gmbh Procede de separation de substances par extraction ou lavage par des liquides ioniques
FR2861084A1 (fr) * 2003-10-15 2005-04-22 Arkema Procede d'elimination de composes benzothiopheniques contenus dans un melange d'hydrocarbures
US7001504B2 (en) * 2001-11-06 2006-02-21 Extractica, Llc. Method for extraction of organosulfur compounds from hydrocarbons using ionic liquids
US7303607B2 (en) 2004-06-14 2007-12-04 Air Products And Chemicals, Inc. Liquid media containing Lewis acidic reactive compounds for storage and delivery of Lewis basic gases
WO2008034880A1 (fr) * 2006-09-21 2008-03-27 Universite Claude Bernard Lyon I Utilisation d'un liquide ionique pour extraire des composes polyaromatiques ou azotes neutres d'un melange d'hydrocarbures de la gamme d'ebullition du diesel
US7404845B2 (en) 2004-09-23 2008-07-29 Air Products And Chemicals, Inc. Ionic liquid based mixtures for gas storage and delivery
US7563308B2 (en) 2004-09-23 2009-07-21 Air Products And Chemicals, Inc. Ionic liquid based mixtures for gas storage and delivery
US7605297B2 (en) 2003-07-21 2009-10-20 Basf Aktiengesellschaft Method for extracting impurities using ionic liquids
US7619129B2 (en) 2003-12-22 2009-11-17 Shell Oil Company Process for the separation of olefins and paraffins
US7645438B2 (en) 2006-06-27 2010-01-12 Akzo Nobel N.V. Process for the production of hydrogen peroxide
EP2292572A1 (fr) 2009-09-07 2011-03-09 Shell Internationale Research Maatschappij B.V. Procédé pour la séparation de composés aromatiques d'un mélange
WO2011026972A1 (fr) 2009-09-07 2011-03-10 Shell Internationale Research Maatschappij B.V. Procédé pour l'élimination de composés aromatiques dans un mélange
CN103666550A (zh) * 2012-09-10 2014-03-26 中国石油化工股份有限公司 一种焦化汽油蒸汽裂解增产低碳烯烃和芳烃的方法
CN113046176A (zh) * 2019-12-27 2021-06-29 丰益(上海)生物技术研发中心有限公司 去除流体物料中塑化剂的方法

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US4359596A (en) * 1981-08-03 1982-11-16 Exxon Research And Engineering Co. Liquid salt extraction of aromatics from process feed streams
US4496744A (en) * 1980-02-28 1985-01-29 University Of Alabama Multidentate macromolecular complex salt clathrates
US5220106A (en) * 1992-03-27 1993-06-15 Exxon Research And Engineering Company Organic non-quaternary clathrate salts for petroleum separation

Patent Citations (3)

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US4496744A (en) * 1980-02-28 1985-01-29 University Of Alabama Multidentate macromolecular complex salt clathrates
US4359596A (en) * 1981-08-03 1982-11-16 Exxon Research And Engineering Co. Liquid salt extraction of aromatics from process feed streams
US5220106A (en) * 1992-03-27 1993-06-15 Exxon Research And Engineering Company Organic non-quaternary clathrate salts for petroleum separation

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10154052A1 (de) * 2001-11-02 2003-07-10 Carl V Ossietzky Uni Oldenburg Einsatz ionischer Flüssigkeiten als selektive Lösungsmittel für die Trennung aromatischer Kohlenwasserstoffe von nichtaromatischen Kohlenwasserstoffen durch extraktive Rektifikation und Extraktion
WO2003037835A2 (fr) * 2001-11-02 2003-05-08 Solvent Innovation Gmbh Procede d'elimination d'impuretes polarisables contenues dans des hydrocarbures et melanges d'hydrocarbures
US7001504B2 (en) * 2001-11-06 2006-02-21 Extractica, Llc. Method for extraction of organosulfur compounds from hydrocarbons using ionic liquids
US7553406B2 (en) 2001-11-08 2009-06-30 Merck Patent Gmbh Process for removing polar impurities from hydrocarbons and mixtures of hydrocarbons
WO2003037835A3 (fr) * 2001-11-08 2003-12-24 Solvent Innovation Gmbh Procede d'elimination d'impuretes polarisables contenues dans des hydrocarbures et melanges d'hydrocarbures
US7304200B2 (en) 2002-02-19 2007-12-04 Oxeno Olefinchemie Gmbh Method for separation of substances by extraction or by washing them with ionic liquids
WO2003070667A1 (fr) * 2002-02-19 2003-08-28 Oxeno Olefinchemie Gmbh Procede de separation de substances par extraction ou lavage par des liquides ioniques
US7605297B2 (en) 2003-07-21 2009-10-20 Basf Aktiengesellschaft Method for extracting impurities using ionic liquids
FR2861084A1 (fr) * 2003-10-15 2005-04-22 Arkema Procede d'elimination de composes benzothiopheniques contenus dans un melange d'hydrocarbures
US7619129B2 (en) 2003-12-22 2009-11-17 Shell Oil Company Process for the separation of olefins and paraffins
US7303607B2 (en) 2004-06-14 2007-12-04 Air Products And Chemicals, Inc. Liquid media containing Lewis acidic reactive compounds for storage and delivery of Lewis basic gases
US8202446B2 (en) 2004-09-23 2012-06-19 Air Products And Chemicals, Inc. Ionic liquid based mixtures for gas storage and delivery
US7404845B2 (en) 2004-09-23 2008-07-29 Air Products And Chemicals, Inc. Ionic liquid based mixtures for gas storage and delivery
US7563308B2 (en) 2004-09-23 2009-07-21 Air Products And Chemicals, Inc. Ionic liquid based mixtures for gas storage and delivery
US7645438B2 (en) 2006-06-27 2010-01-12 Akzo Nobel N.V. Process for the production of hydrogen peroxide
WO2008034880A1 (fr) * 2006-09-21 2008-03-27 Universite Claude Bernard Lyon I Utilisation d'un liquide ionique pour extraire des composes polyaromatiques ou azotes neutres d'un melange d'hydrocarbures de la gamme d'ebullition du diesel
WO2011026975A1 (fr) 2009-09-07 2011-03-10 Shell Internationale Research Maatschappij B.V. Procédé pour la séparation de composés aromatiques à partir d'un mélange
WO2011026972A1 (fr) 2009-09-07 2011-03-10 Shell Internationale Research Maatschappij B.V. Procédé pour l'élimination de composés aromatiques dans un mélange
EP2292572A1 (fr) 2009-09-07 2011-03-09 Shell Internationale Research Maatschappij B.V. Procédé pour la séparation de composés aromatiques d'un mélange
CN103666550A (zh) * 2012-09-10 2014-03-26 中国石油化工股份有限公司 一种焦化汽油蒸汽裂解增产低碳烯烃和芳烃的方法
CN103666550B (zh) * 2012-09-10 2015-11-25 中国石油化工股份有限公司 一种焦化汽油蒸汽裂解增产低碳烯烃和芳烃的方法
CN113046176A (zh) * 2019-12-27 2021-06-29 丰益(上海)生物技术研发中心有限公司 去除流体物料中塑化剂的方法

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