US3366568A - Recovery of aromatics by extraction or extractive distillation with solvent mixtures - Google Patents

Recovery of aromatics by extraction or extractive distillation with solvent mixtures Download PDF

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US3366568A
US3366568A US490818A US49081865A US3366568A US 3366568 A US3366568 A US 3366568A US 490818 A US490818 A US 490818A US 49081865 A US49081865 A US 49081865A US 3366568 A US3366568 A US 3366568A
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solvent
mixture
aromatics
phase
solvents
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Eisenlohr Karl-Heinz
Muller Eckart
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GEA Group AG
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Metallgesellschaft AG
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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
    • C10G21/12—Organic compounds only
    • C10G21/20—Nitrogen-containing compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0488—Flow sheets
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/04—Purification; Separation; Use of additives by distillation
    • C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
    • C07C7/08—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by extractive distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
    • 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
    • C10G21/12—Organic compounds only
    • C10G21/16—Oxygen-containing compounds

Definitions

  • the present invention provides an improved process for the recovery of aromatic hydrocarbons, especially benzene, toluene and xylene, from hydrocarbon mixtures containing the same, by extraction with water free solvent mixtures selective for aromatics which as a whole boil over the boiling point rangeof the aromatics to be recovered.
  • the extraction with the solvent mixtures concerned is either a liquid-liquid extraction or an extractive distillation.
  • non-aqueous solvent mixtures such as, for example, mixtures of SO2, ethylene glycol and formamide or mixtures which consist of a primary solvent which contains glycol derivatives and a secondary solvent such as methanol, ethanol and y
  • solvents include, for example, (l) the combination of various glycol derivatives, (2) mixtures of two solvents of which the iirst contains l or 2 hydroxyl groups and the second contains 2 or more hydroxyl groups, (3) ethylene carbonate with additions of glycerol, ethylene glycol, pentaerythritol, formamide, forrnic acid, ethanol amines, monochlorohydrin, acetamide, resorcinol or hydroquinone as diluent, (4) alkane dinitriles, dimethyl hydantoin, N-alkylpyrrolidones, butyrolactone, cyan ethers of diethylene glycol, trior tetraethylene glycol
  • the third namely, the aromatics range is especially suited as the classifying principle for dividing the solvents into certain groups. If the solvents are arranged according to increasing aromatics range they can be divided into three groups:
  • a low aromatics range is one of less than 50% and preferably less than 35% is the maximum of the twophase region.
  • FIGS. 1-6 show phase diagrams for 3 component systems of benzene, n-heptane and the selective solvent concerned;
  • FIG. 7 is a diagram showing the maximum quantity of benzene in the heavy phase (solvent phase) with respect to the composition of the solvent mixture N-methyl pyrrolidone (hereinafter referred to as NMP) and ethylene glycol;
  • NMP N-methyl pyrrolidone
  • FIG. 8 is a diagram showing the dependency of the selectivity of the composition of solvent mixture NMI and ethylene glycol
  • FIG. 9 is a diagram in which the selectivity is plotted against the partition-coefficient in dependence on the composition of solvent mixture NMP ⁇ and ethylene glycol;
  • FIG. l is a phase diagram for the 3 component system NMF-ethylene glycol-benzene
  • FIG. ll is a diagram showing the dependency of the viscosity of solvent mixture -NMP and ethylene glycol on its composition
  • FIG. l2 schematically shows an apparatus for carrying out a liquid-liquid extraction according to the invention.
  • FIG. 13 schematically shows an apparatus for carrying out an extractive distillation according to the invention.
  • FIGS. l and 2 Two typical phase diagrams are shown in FIGS. l and 2 for two typical solvents of the rst group (low aromatics range), namely, for N-methyl pyrrolidone and furfural, with indication of the partition equilibriums in the system solvent-benzene-n-heptane.
  • the solvents of this group are characterized by their high capacity, low selectivity and high solubility of the solvent in the hydrocarbon phase. In view of their low selectivity the solvents of this group normally are only employed in combination with water whereby the above mentioned disadvantages must be accepted.
  • Solvents with a high .aromatics range that is, solvents with an aromatic range of at least 50% in the maximum of the two phase system belong to the second group. They are therefore near the solubility limit with aromatics, for example so that they are miscible in .all proportions with benzene but not with xylene.
  • Phase diagrams as in FIGS. l and 2 are given in FIGS. 3 and 4 for sulfolane and ethylene carbonate which are representatives of this group.
  • solvents of this group which have very high selectivity with good capacity, the latter, nevertheless, being lower than that of the solvents of Uroup A.
  • solvents of group B would be the ideal solvents for the extraction of aromatics insofar as only the selectivity and capacity is taken into consideration, but remarkably they without exception possess other physical properties of such unfavorable values that they must be considered substantial disadvantages.
  • representatives of this group all have the disadvantages that they are no longer stable at their boiling point and have a high viscosity.
  • their melting points in some instances are above normal temperat-ure.
  • Compounds with double bonded oxygen and dinitriles such as, for example, sulfolane, ethylene and propylene carbonate, oxy, thioand imino-dipropionitrile, monomethyl formamide and tetraethylene glycol especially are illustrative of group B solvents.
  • the solvents of the third group have a miscibility gap with aromatics.
  • Phase diagrams of representatives of this group namely, diethylene glycol ⁇ and propylene glycol, are given in FIGS. 5 and 6.
  • Representatives of this group which dissolve less than 25% of benzene at 20 C. are preferably employed.
  • Their capacity is less than that of the solvents of both other groups.
  • Their selectivity is better than that of solvents of the iirst group and mostly less than that of solvents of the second group. Almost all have a high viscosity. Thermal stability at the boiling point is sometimes given.
  • This group mostly contains chain compounds with one or more hydroxyl groups often also compounds with amino groups, such as, for example, ethylene glycol, diethylene glycol, propylene glycol, mono, diand triethanol amine, 1.4-cyclol1exane dimethanol, diglycol amine, formamide, malondinitrile, hydrazine and others.
  • solvent mixtures could be obtained which have substantially better properties than could be expected from the rule of mixtures by mixing a solvent belonging to the first group (A) ⁇ with a solvent belonging to the third group (C).
  • the selectivity is better than could be expected from the rule of mixtures and in some instances ever higher than of each of the individual components of the mixture.
  • the ability to take up aromatics with solvents of group A is limited by their low aromatics range, and with solvents of group C by their low solvent capacity for aromatics.
  • the combination of a solvent of group A with a solvent of group C results in a mixture having an ability to take up aromatics which is always better than that of each component and which often exceeds that of the component with the best take up ability by 50% and more.
  • solvents of groups C are their high viscosity.
  • an unexpected advantage also is found in the combinations according to the invention as the viscosity of the solvent mixture is always less than could be expected from the rule of mixtures.
  • solvent A-solvent C-benzene determines the solubility limits and then the critical point (plait point) that is, the point where at the solubility limit the volumes of the light and heavier phases are equal.
  • the composition at this point is the most favorable composition for the liquid-liquid extraction or extractive distillation of aromatics.
  • Equal parts by volume of benzene and Solvent C are placed in a vessel. Two phases are formed, one of which predominantly contains benzene-generally the lighter phase-in the following designated as the IIC-phase (hydrocarbon phase) and one which predominantly contains solvent C--generally the heavy phase-designated in the following as the S-phase (solvent phase). Then small increments of solvent A are added while observing how both phases behave or change with respect to each other. When a certain quantity of solvent A has been added the phase separation line will suddenly disappear and only one phase will be present. lf by chance the volumes of the phases have been equal just before disappearance of the phase separation line the critical point would already have been determined.
  • the critical point lies between the composition where two phases are last observed and the composition at which the phase separation line disappears. Usually, however, the volumes of the phases will be different and shortly before disappearance of the phase separation line the phase present in the larger quantity will be a multiple of the other phase. The procedure which follows under such circumstances depends upon which of the two phases was the larger just before disappearance of the phase separation line. If the HC- phase is the smaller one, small increments of benzene are added to the mixture until the mixture becomes cloudy and again separates into two phases. If at this point the HC-phase is still the smaller one, then a mixture of equal parts of benzene and solvent A are added in small increments until the phase separation line again disappears so that only one phase is present.
  • the quantity of solvent C in the mixture can Ibe 5 to less than previously defined. If, on the other hand, the non-aromatics in the feed stock contains large quantities of olefins and/ or naphthenes it often is expedient to increase the quantity of solvent C in the mixture about 5 to 10%.
  • NMP N-methyl pyrrolidone
  • ethylene glycol ethylene glycol
  • FIG. 7 the ability to take up aromatics of a mixture of a solvent of group A (NMP) and a solvent of group C (ethylene glycol) is better than that which corresponds to the rule of mixtures and is represented by the broken line A-C.
  • the ability of a solvent mixture of a solvent of group A with a solvent of group C to take up aromatics is greater than that of each solvent individually.
  • the maximum take up is achieved with a mixture of 55% of ethylene glycol and 45% of NMP and amounts to 55 weight percent of benzene in the heavy phase.
  • FIG. 9 The manner in which the optimum between selectivity and capacity can be determined is shown in FIG. 9.
  • the capacities (partition coecients) and the selectivities for different mixing ratios of NMP and ethylene glycol are respectively plotted as abscissa and ordinates.
  • Solvent mixture components Weight, percent N-methylpyrrolidone 35.55 Diethanolamine 64.45 Aniline 52.1 Monoethanolamine 47.9 Butyrolactone 36.56 1.4-cyclohexanedimethanol 63.44 Phenol 38.5 Ethylene glycol 61.5 Aniline 57.0 Ethylene glycol 43.0 Phenol 50.7
  • N-methylpyrrolidone 21.2 Malonnitrile 7 8.8 Dimethylsulfoxide 47.2 Monoethanolamine 52.8 Dimethylformamide 23.4 Malonnitrile 76.6 Dimethylsulfoxide 35.1 Malonnitrile 64.9 Dimethylformamide 60.8 Formamide 39.2 N-methylpyrrolidone 58.99 Glycerine 41.01 Dimethylsulfoxide 62.3 Ethylene glycol 37.7 Dimethylformamide 74.24 Glycerine 25.76 N-methylpyrrolidone 64.24 Formamide 35.76
  • the present invention is generally suited for the recovery of aromatics from hydrocarbon mixtures containing aromatica by liquidliquid extraction or extractive distillation and also for the recovery of extracts in which the concentration of aromatics in the hydrocarbon extracts has only been increased over that in the starting mixture.
  • An especial advantage of the process according to the invention is that it also is adapted for the recovery of high purity aromatica, which in recent times have assumed considerable significance as starting materials for chemical syntheses.
  • the process according to the invention renders it possible to recover aromatics whose non-aromatics content is below 0.1% and even under 0.01% without diiculty. Even higher purity requirements such as absence of nonaromatics in quantities capable of chromatographic detection can be achieved according to the invention.
  • FIG. 12 and FIG. 13 which diagrammatically show the apparatus employed in such examples.
  • Example 2 .1000 kg./h. of the benzene cut of a hydrogenated pyrolysis gasoline of the following composition:
  • a process for separating a hydrocarbon mixture containing aromatic and non-aromatic hydrocarbons into fractions of different degrees of aromaticity by treatment with a solvent mixture and recovering a more concentrated aromatics fraction from said mixture which comprises contacting the mixture with a water free solvent mixture which as a Whole boils above the aromatics to be recovered, said solvent mixture consisting of solvent (A), N-methyl-pyrrolidone, and solvent (C), ethylene glycol, the ratio of the quantity of said solvent Ato the quantity of said solvent C in said solvent mixture being from X:Y to X:YilO Weight percent, the ratio X:Y being the ratio of solvents A and C at the critical point in the three component system solvent A, solvent C and benzene, said solvent mixture being a mixture of 45 to 65 weight percent of ethylene glycol and 55 to 35 weight .percent of N-methyl-pyrrolidone, eecting phase separation of the phases thus formed, an extract phase in which the hydrocarbons extracted from said mixture has a higher aromatic concentration than said mixture and

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
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US490818A 1964-09-29 1965-09-28 Recovery of aromatics by extraction or extractive distillation with solvent mixtures Expired - Lifetime US3366568A (en)

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US490818A Expired - Lifetime US3366568A (en) 1964-09-29 1965-09-28 Recovery of aromatics by extraction or extractive distillation with solvent mixtures
US692016A Expired - Lifetime US3415739A (en) 1964-09-29 1967-12-20 Recovery of aromatics by extraction or extractive distillation with solvent mixturesof n-methyl pyrrolidone and diglycol amine
US692019A Expired - Lifetime US3415742A (en) 1964-09-29 1967-12-20 Recovery of aromatics by extraction with solvent mixture of n-methyl-pyrrolidone andglycerol
US692018A Expired - Lifetime US3415741A (en) 1964-09-29 1967-12-20 Recovery of aromatics by extraction with solvent mixture of n-methyl pyrrolidone and monoethanolamine
US692017A Expired - Lifetime US3415740A (en) 1964-09-29 1967-12-20 Recovery of aromatics by extraction with a solvent mixture of butyrolactone and glycerol

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US692016A Expired - Lifetime US3415739A (en) 1964-09-29 1967-12-20 Recovery of aromatics by extraction or extractive distillation with solvent mixturesof n-methyl pyrrolidone and diglycol amine
US692019A Expired - Lifetime US3415742A (en) 1964-09-29 1967-12-20 Recovery of aromatics by extraction with solvent mixture of n-methyl-pyrrolidone andglycerol
US692018A Expired - Lifetime US3415741A (en) 1964-09-29 1967-12-20 Recovery of aromatics by extraction with solvent mixture of n-methyl pyrrolidone and monoethanolamine
US692017A Expired - Lifetime US3415740A (en) 1964-09-29 1967-12-20 Recovery of aromatics by extraction with a solvent mixture of butyrolactone and glycerol

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US (5) US3366568A (cs)
BE (1) BE670244A (cs)
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GB (1) GB1110855A (cs)
IL (1) IL24353A (cs)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3434936A (en) * 1966-12-19 1969-03-25 Koppers Gmbh Heinrich Method of separating aromatic compounds from hydrocarbon mixtures containing the same by extractive distillation with an n-substituted morpholine
US3546108A (en) * 1969-03-17 1970-12-08 Sun Oil Co Novel solvent for the extraction of aromatic hydrocarbons from hydrocarbon mixtures and the process for use thereof
US3617535A (en) * 1969-01-18 1971-11-02 Basf Ag Recovery of aromatic hydrocarbons from hydrocarbon mixtures by selective extraction and/or extractive distillation
US3862254A (en) * 1970-10-16 1975-01-21 Air Prod & Chem Production of aromatic hydrocarbons
US4053369A (en) * 1974-05-30 1977-10-11 Phillips Petroleum Company Extractive distillation
US4909927A (en) * 1985-12-31 1990-03-20 Exxon Research And Engineering Company Extraction of hydrocarbon oils using a combination polar extraction solvent-aliphatic-aromatic or polar extraction solvent-polar substituted naphthenes extraction solvent mixture
US4948472A (en) * 1989-07-12 1990-08-14 Phillips Petroleum Company Extractive distillation of hydrocarbon mixtures employing mixed solvent
US5055162A (en) * 1990-05-21 1991-10-08 Phillips Petroleum Company Extractive distillation of cycloalkane/alkane feeds
US5106459A (en) * 1990-12-14 1992-04-21 Lloyd Berg Separation of p-menthane from p-cymene by extractive distillation
US5160414A (en) * 1991-07-19 1992-11-03 Phillips Petroleum Company Extractive distillation of alcohol/ether/hydrocarbon mixtures

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4013549A (en) * 1972-12-01 1977-03-22 Exxon Research And Engineering Company Lube extraction with NMP/phenol/water mixtures
DE2745672A1 (de) * 1977-10-11 1979-04-12 Metallgesellschaft Ag Verfahren zur gewinnung von aromatenfreiem n-hexan
US4382855A (en) * 1981-10-28 1983-05-10 Ashland Oil, Inc. Process for removal of hydroxy- and/or mercapto-substituted hydrocarbons from coal liquids
US5092983A (en) * 1986-09-12 1992-03-03 The Standard Oil Company Process for separating extractable organic material from compositions comprising said extractable organic material intermixed with solids and water using a solvent mixture
RU2202529C2 (ru) * 2001-05-04 2003-04-20 Белорусский государственный технологический университет Способ экстракции ароматических углеводородов
CN119979215A (zh) * 2023-11-10 2025-05-13 中国石油天然气集团有限公司 萃取精馏柴油中芳烃的复合溶剂及应用

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US1976544A (en) * 1932-05-06 1934-10-09 Standard Oil Co Method of treating mineral lubricating oils
US2109476A (en) * 1934-10-17 1938-03-01 Atlantic Refining Co Hydrocarbon oil treatment
US2128958A (en) * 1933-05-05 1938-09-06 Ig Farbenindustrie Ag Refining mineral lubricating oils
US2191767A (en) * 1934-12-15 1940-02-27 Pennsylvania Petroleum Res Cor Process for treating mineral oils
US2287736A (en) * 1939-05-16 1942-06-23 Atlantic Refining Co Production of motor fuels by solvent extraction
US2396299A (en) * 1940-08-21 1946-03-12 Standard Oil Dev Co Refining hydrocarbon oils
US2663670A (en) * 1951-12-04 1953-12-22 Socony Vacuum Oil Co Inc Solvent extraction
US3092570A (en) * 1960-08-01 1963-06-04 Socony Mobil Oil Co Inc Removal of aromatic hydrocarbons from jet fuel mixtures

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1976544A (en) * 1932-05-06 1934-10-09 Standard Oil Co Method of treating mineral lubricating oils
US2128958A (en) * 1933-05-05 1938-09-06 Ig Farbenindustrie Ag Refining mineral lubricating oils
US2109476A (en) * 1934-10-17 1938-03-01 Atlantic Refining Co Hydrocarbon oil treatment
US2191767A (en) * 1934-12-15 1940-02-27 Pennsylvania Petroleum Res Cor Process for treating mineral oils
US2287736A (en) * 1939-05-16 1942-06-23 Atlantic Refining Co Production of motor fuels by solvent extraction
US2396299A (en) * 1940-08-21 1946-03-12 Standard Oil Dev Co Refining hydrocarbon oils
US2663670A (en) * 1951-12-04 1953-12-22 Socony Vacuum Oil Co Inc Solvent extraction
US3092570A (en) * 1960-08-01 1963-06-04 Socony Mobil Oil Co Inc Removal of aromatic hydrocarbons from jet fuel mixtures

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3434936A (en) * 1966-12-19 1969-03-25 Koppers Gmbh Heinrich Method of separating aromatic compounds from hydrocarbon mixtures containing the same by extractive distillation with an n-substituted morpholine
US3617535A (en) * 1969-01-18 1971-11-02 Basf Ag Recovery of aromatic hydrocarbons from hydrocarbon mixtures by selective extraction and/or extractive distillation
US3546108A (en) * 1969-03-17 1970-12-08 Sun Oil Co Novel solvent for the extraction of aromatic hydrocarbons from hydrocarbon mixtures and the process for use thereof
US3862254A (en) * 1970-10-16 1975-01-21 Air Prod & Chem Production of aromatic hydrocarbons
US4053369A (en) * 1974-05-30 1977-10-11 Phillips Petroleum Company Extractive distillation
US4909927A (en) * 1985-12-31 1990-03-20 Exxon Research And Engineering Company Extraction of hydrocarbon oils using a combination polar extraction solvent-aliphatic-aromatic or polar extraction solvent-polar substituted naphthenes extraction solvent mixture
US4948472A (en) * 1989-07-12 1990-08-14 Phillips Petroleum Company Extractive distillation of hydrocarbon mixtures employing mixed solvent
US5055162A (en) * 1990-05-21 1991-10-08 Phillips Petroleum Company Extractive distillation of cycloalkane/alkane feeds
US5106459A (en) * 1990-12-14 1992-04-21 Lloyd Berg Separation of p-menthane from p-cymene by extractive distillation
US5160414A (en) * 1991-07-19 1992-11-03 Phillips Petroleum Company Extractive distillation of alcohol/ether/hydrocarbon mixtures

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CS171199B2 (cs) 1976-10-29
US3415739A (en) 1968-12-10
GB1110855A (en) 1968-04-24
IL24353A (en) 1969-06-25
US3415740A (en) 1968-12-10
BE670244A (cs) 1966-01-17
DK116889B (da) 1970-02-23
US3415741A (en) 1968-12-10
US3415742A (en) 1968-12-10

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