US2549372A - Extractive fractionation process - Google Patents

Extractive fractionation process Download PDF

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US2549372A
US2549372A US74167647A US2549372A US 2549372 A US2549372 A US 2549372A US 74167647 A US74167647 A US 74167647A US 2549372 A US2549372 A US 2549372A
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complexes
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compounds
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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
    • C10G31/00—Refining of hydrocarbon oils, in the absence of hydrogen, by methods not otherwise provided for
    • C10G31/06—Refining of hydrocarbon oils, in the absence of hydrogen, by methods not otherwise provided for by heating, cooling, or pressure treatment

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  • This invention relates to a process' forv the ex' tractive fractionation of organi compounds'. More particularly, it relates to improvements 'in the process of fractonally electingorg'anic conpounds from mixtures thereof by the use of such complex-forming agents as urea and thiourea.
  • VInv'most of such conversion reactions an equi- -librium mixture is generally obtained'comprising -ixedratios of unconverted feed stock and the desired product. -If the feed. stock initially con tains some of. the conversion preduct, such as from a previous cycle through the converter,- the amount'of conversion is correspondingly reduced.
  • thiourea is the complex-forming agent employed the complexes formed therebyare usually of ⁇ a substantially different character in that thiorea forms complexes With organic' cmpounds having either a branched configuration or a cycloaliphatic structure.
  • thiourea forms only minor amounts of complexes With organic compounds of Straight chain Stllctll, Such as the nofl'al parans, Mixtures of 'these complex-forming agents have been employed 'to' extract' normal and' branched non-aromatic compounds as Well as naphthe'nes -rom mixtures containing other t'yes o'mpounds usually in excess. This latter process is usually employed for the purification of aromatics such as benzene, toluene, etc.
  • K aromatics
  • the fractionation of mixtures of organic compounds by the subject extractive fractionation processes may be improved by recycling part of the complexes back to the mixture prior to the separation step.
  • part of the complexes is meant a portion of the organic compounds extractively fractionated from the original mixtures, either in the form of the unaltered complex or in its regenerated form free of any complex-forming agent.
  • the efficiency of separating complexes from their mixtures with other compounds may be raised by the step described above.
  • the feed may be enriched in a desired fraction by employing the above step as more fully described hereinafter.
  • mixtures of organic compounds are con*- tacted with a complex-forming agent (suitably either urea or thiourea) and passed to a separator wherein the complexes are separated from the rainate.
  • ranate is meant that portion of the original mixture which fails to form complexes with the agent present under the conditions employed.
  • the process according to the present invention comprises two alternative steps: the complexes may be passed to a regenerator or part of the complexes may be recycled to the mixer and the remainder sent to the regenerator.
  • mixer is meant that apparatus wherein the mixture of organic compounds is contacted with a complex-forming agent.
  • the fraction to be returned to the mixer is predetermined by the conditions which it is desired to maintain in the mixture as well as by the desired composition of the nal product.
  • the complexes may be fractionated into any type of desired fractions, either according to molecular weight, chemical type, structural type, solubility, etc.
  • the fractionation may be conducted by fractional crystallization from a lean solvent wherein only one part of the complexes will dissolve while the remainder are unaffected.
  • the complexes may be fractionated by melting point, the temperature being raised until a particular fraction of the complexes are liquid and the remainder are unaffected at which Ypoint one phase or the other is recycled to the mixer.
  • Other types of fractionating the complexes will be more or less obvious to those familiar with the art of fractionation.
  • the fraction of the complexes returned to the mixer enrich the feed in regard to that particular type of organic compound returned in complex form.
  • the total amount of complexes separated thereafter from the enriched feed will be altered to the extent of this addition.
  • This recycling of a fraction of the complexes may be conducted to the point at which the complexes finally separated have a desired composition. From the standpoint of eiciency this should be effected in a minimum number of recycling operations.
  • a heavier cake of crystals can be built up on the filter (if such is the separating means). It has been found that a relatively thick cake of such crystals is structurally more porous than a thin densely formed layer such as is obtained when the original mixture contains only a small amount of complex-forming .organic compounds.
  • one means of regenerating organic compounds from their complexes comprises simple distillation, whereby the complex decomposes and at least part of the organic compounds are distilled leaving residual compounds and complex-forming agents behind.
  • the conditions of distillation may be adjusted to the point that a fraction of a desired boiling range may be recovered either as a distillate or as a bottoms from a distillation step.
  • Other means of regeneration are more fully described hereinafter at which point other types of fractionation of the products recovered will be described.
  • the fraction of the regenerated compounds recycled to the feed enriches the latter in that particular type of compound. Since the material returned to the feed is of a type which will form a complex with the agents employed, a suiiicient amount of such agents must be possible to form complexes not only with the active material already in the feed but also with the recycled compounds. It is undesirable to recycle at this stage if the fractionation as described hereinabove can be effectively conducted. This is due to the fact that it is necessary to form and regenerate complexes more than once thus, decreasing the eiliciency of the operation. However, if the regenerated compounds can be fractionated in a particular way to arrive at a desired fraction more effectively than when in complex form, then such multiple complex formation and regeneration becomes necessary.
  • a mixture of petroleum hydrocarbons comprises isoparafiins, normal paraflins, and naphthenes which would be contacted with thiourea.
  • the mixture of hydrocarbons and a saturated alcoholic solution of thiourea are introduced to a mixer I at room temperature.
  • the mixture 1s stirred for a short length of time to permit maximum contact of the thiourea solution with the hydrocarbons.
  • Crystalline complexes form between thiourea and the hydrocarbons of naphthenic and isoparaifmic structure.
  • the total mixture is Sent to a separator 2, wherein the rainate is ltered away from the crystalline complexes.
  • a nal product is desired which is to be a mixture of naphthenes and isoparaflins having a minimum boiling point of about C.
  • the mixture of complexes separated as described above is too unstable to fractionate by distillation. Therefore, it is sent directly from the separator 2 to the regenerator 4 wherein the comasiasva plexes are heated to their decomposition temperature and are fractionally distilled, the temy perature of distillation being adjusted to the point whereat the hydrocarbons which distill have boiling points below the minimum desired final product.
  • the bottoms from this distillation comprise isoparafin and naphthenic hydrocarbons having a minimum boiling point of the desired range in admixture with regenerated thiourea. 'Ihe latter separates from the hydrof carbons and may be recycled for further complex formation.
  • part of the latter regenerated hydrocarbons are recycled to the mixer l while the remainder is passed to storage.
  • the feed is enriched in the type of hydrocarbon having thev predetermined boiling range thereafter the complex for mation and separation are conducted as described above.
  • the separation step constituted the formation of a relatively heavy lter cake of crystalline complexes which was highly porous and allowed faster liltration than was possible during the initial separation described above.
  • the mixtures of organic compounds which may be treated with urea by the process of the present invention comprise compounds having substantially normal structure and/or compounds having a predominating substituent of substantially normal structure. Conditions may be employed whereby certain normal organic compounds are separated from other normal organic compounds, or from the other organic compounds such as isoparaiiins, aromatics, naphthenes, etc.
  • the organic compounds of normal structure which may be formed intocomplexes by the process of the present invention include both saturated and unsaturated compounds, especially the parains, and olens.
  • the normal compounds may be of a number of types, such as hydrocarbons, alcohols, ketones, aldehydes, esters, amines, amides,
  • Suitable hydrocarbons which form crystallineY complexes with urea include the paraiiinic hy'- drocarbons such as; butano, pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane,Y tridecane, tetradecane, pentadecane, hexadecane, heptadecane, octadecane, nonadecane, eicosane, etc;
  • Olen hydrocarbons which may be treated by the process of the present invention include l-butene, 2-butene, l-pentene, 2pentene, l-hexene, Z-hexene, 3-hexene, 1-heptene, Z-heptene, 3heptene, l-octene, 2-octene, 3-octene, 4-octene, 2nonene, 3-nonene, 4-nonene, 1-decene, 2-decene, 3-decene, 5-decene, 1-undecene, 2-undecene, 5undecene, 1-dodecene6dodecene, l-tridecene, G-tridecene, 1pentadecene, 8-heptadecene, 13- heptacosene, etc.
  • VAnother class of hydrocarbons which may be formed into complexes with urea, according to the process of the present invention are the normal oliolelins such as 1,2-butadiene, 1,3- butadiene, 1,2-pentadiene, 1,3-pentadiene, 1,4- pentadiene, 1,2-hexadiene, 1,3-hexadiene, 1,4- hexadiene, 1,5 -hexadiene, 2,3 -hexadiene, 2,4- hexadiene, 1,3-heptadiene, 1,6-heptadiene, 2,4- heptadiene, 1,4 octadiene, 1,5'- octad'iene, 1,7- octadiene, 2,6.-octadiene,3,5foctadiene, L-none ad'iene, L-nonadiene, 2,6-nonadiene, 1,3-d'eca
  • Normal hydrocarbons of a greater degree of unsaturation which form crystalline complexes with urea by the process or the present invention include the trioleiines,v acetylenes, diacetyl enes, oleiin-acetylenes and the dioleiin-acetyl* enes, I including 1,3,5 hexatriene, 1,3,5 e heptatriene, 2,3,6-octatriene, ethylacetylene', propyl-4 acetylene, butylacetylene, amylacetylene, caprylidene, 4-octyne, diacetyl'ene, propyl-dacety-lene,
  • Normal alcohols especially those having six or more carbon atoms, may be treated by theJ present process to form complexes with urea.' These include the aliphatic monohydric alcohols' such as hexyl alcohol, heptyl alcohol, octyl alcohol, nonyl alcohol, decyl alcohol, dodecyl alcohol, cetyl alcohol, carnaubyl alcohol, and the polyhydric alcohols, such as ethylene glycol', diethylene glycol, propylene glycol and hexitol.
  • aliphatic monohydric alcohols' such as hexyl alcohol, heptyl alcohol, octyl alcohol, nonyl alcohol, decyl alcohol, dodecyl alcohol, cetyl alcohol, carnaubyl alcohol
  • polyhydric alcohols such as ethylene glycol', diethylene glycol, propylene glycol and hexitol.
  • Ethers of normal structure forming complexes with urea include acetal, dioxane, paraldehyde, crotonyl ether,A etc.
  • Aldehydes of normal structure also respond' to the process oi this invention, including butyraldehyde, valeraldehyde, caproaldehyde, palmitic aldehyde, citral adipaldehyde, etc.
  • Ketones which form urea complexes are exemplified by 3-hexanone, palmitone, 2,3' pentanedione, etc. Acids also may be treated according to the subject process. Typical.
  • normal acids forming urea complexes are the nor-v mal fatty acids, especially those having four or more carbon atoms, such as butyric; valerio; caproic, enanthylic, capryli'c, pela'rgonic, capric," undecylic, lauric,A tridecoic, myristic, pentad'e'canoie, palmitic, margaric, stearic, etc., acid.
  • Acrylic acidsV also respond, su'ch as methylacrylic' acid, tiglic acid, oleic acid, etc.
  • the acetylene acids form urea complexes. These. include sorbicand Linoleic acids.
  • esters such as: amyl acetate, ethyl steal-ate,y etc; amines such' as nedecyl amine.v dbutyl amine and triethyl amine.; amid'es, such as stea'rarnide; ⁇ mercapta'ns, such as heptyl mercaptan; and other organic compounds.
  • esters such as: amyl acetate, ethyl steal-ate,y etc; amines such' as nedecyl amine.v dbutyl amine and triethyl amine.; amid'es, such as stea'rarnide; ⁇ mercapta'ns, such as heptyl mercaptan; and other organic compounds.
  • normal structure including halot geriated derivatives of the above compounds, thioalcohols, alkyl hydrazines, thioaldehydea amino acids, nitropar
  • the mixtures containing the organic conipounds of normal structure maybe composed vsolely of mixed normal compounds, or they may contain, materials substantially inert. toward urea, such as branched parains, isoclens, arc-V m-atics, cycloparains, etc.
  • materials substantially inert. toward urea such as branched parains, isoclens, arc-V m-atics, cycloparains, etc.
  • materials substantially inert. toward urea such as branched parains, isoclens, arc-V m-atics, cycloparains, etc.
  • Y whenv treating natural products such as petroganic com-pounds in order to modify theV type and degree oi crystallization of the latter with urea.
  • the reasonory and use of' diluents is discussed hereinafter.
  • Hydrocarbons which form complexes with thioureaare those having a pre'dominating member which is' a substantially branched radical or a naphthene radical, such as alkaryl hydrocarbons wherein at least one alkyl group is an isoparain radical of about six or more carbon atoms.
  • Isoparaflins which form complexes with thiourea include isobutane, isopentane, 2,2- dimethylpropane, isohexane, 2,3-dimethylbutane, 2- methylpentane, 3-methylpentane, Z-ethylbutane, 2 ethylpropane, 1,1 dimethylpentane, 1,2 dimethylpentane, 1,3 dimethylpentane, 1,4 dimethylpentane, Z-ethylpentane, B-ethylpentane, 2npropylbutane, 2-isopropylbutane, 2-methylhexane, 3methylhexane, 2,2-dimethylpentane, 2,3-dimethylpentane, 2,4-dimethylpentane, 3,3- dimethylpentane, 2,2,3-trimethylbutane, Z-methylheptane, B-methylheptane, 4-methylhept
  • Typical species of this group include cyclopropane, methylcyclopropane, 1,1 dimethylcyclopropane, 1,2 dimethylpropane, ethylcyclopropane, 1,1,2- trimethylcyclopropane, 1,2,3 trimethylcyclopropane, l-methyl-Z-ethylcyclopropane, propylcyclopropane, 1-methy1-2-propylcyclopropane, cyclobutane, methylcyclobutane, ethylcyclobutane, 1,2-dimethylcyc1obutane, propylcyclobutane, isopropylcyclobutane, 1,2 diisopropylcyclobutane, 1,2 dimethyl 3,4 diethylcyclobutane, 1,1,2,2 tetramethyl 3,4 diisopropylcyclobut
  • the ratio of theA complex-forming agent to active organic compounds will Vary with the type of mixture toV be treated and with the conditions of complex formation.
  • the extractive fractionation may be carried out With the intention of removing from the mixture the maximum amount possible of the compounds of normal structures present. In this particular case, it is preferred practice to Contact the mixture with urea employed in an amount in excess of that necessary for complete complex formation.
  • Complexes may be formed having varying amounts of the complex-forming agent combined with the active organic compound.
  • the temperature or other conditions during complex formation are such that about 3 mols of the agent combined with about every 4 carbon atoms of the active organic compound, it is preferred prac- 9 tice to contact the active organic compound with an amount of the agent somewhat inexcess of this ratio.
  • Steam distillation is a refinement of the above process and the principle of regeneration and fractionation applies here as well. Steam distillation is preferable where the organic compounds to be regenerated are of such high boiling point that their distillation would be accomplished by substantial decomposition.
  • a further type of regeneration comprises addition of a solvent for the complex-forming agent such as water or alcohol to the complex and the application of heat to facilitate the regeneration.
  • a solvent for the complex-forming agent such as water or alcohol
  • the regenerated organic compounds separate from the solution of the complex-forming agent and subsequently may be fractionated by normal purification or fractionation procedures.
  • a more preferred type of regeneration comprises the addition of a solvent for one or more fractions of the organic compounds to be regenerated from the complexes.
  • a solvent for one or more fractions of the organic compounds to be regenerated from the complexes.
  • Fractionation by simple heating is satisfactory plex- 10 for some purposes. Following the regeneration by such means it is usually necessary to purify or fractionate thev regeneratedcompounds and the regenerated complex-forming agent for further use.
  • the process of the present invention is .useful for the preparation of high octane gasoline or of high Diesel index fuel as well as for the preparation of internal combustion engine fuels having a narrow boiling range.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
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US74167647 US2549372A (en) 1947-04-15 1947-04-15 Extractive fractionation process
NL139931A NL72935C (is") 1947-04-15 1948-04-14
GB10496/48A GB671459A (en) 1947-04-15 1948-04-15 Extractive fractionation process
FR964694D FR964694A (is") 1947-04-15 1948-04-15

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Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2658887A (en) * 1949-06-07 1953-11-10 Process for forming urea complexes
US2666048A (en) * 1954-01-12 Separation of low molecular weight
US2681333A (en) * 1954-06-15 Gorin
US2681335A (en) * 1954-06-15 Gorin
US2681303A (en) * 1954-06-15 separation of hydrocarbons and hydrocarbon
US2681904A (en) * 1954-06-22 Separation process
US2691009A (en) * 1954-10-05 Atent office
US2700664A (en) * 1950-11-17 1955-01-25 Phillips Petroleum Co Separation of organic compounds by adduct formation
US2739144A (en) * 1956-03-20 Iio hsvm
US2756222A (en) * 1952-06-17 1956-07-24 Swern Daniel Purification of long-chain vinyl esters and ethers
US2773858A (en) * 1950-03-27 1956-12-11 Manuel H Gorin Method of preparing expanded urea
US2801993A (en) * 1953-08-11 1957-08-06 Rosenstein Ludwig Expanded thiourea
US2804451A (en) * 1957-08-27 Urea adducts of organic sulfur
US2812373A (en) * 1951-08-02 1957-11-05 Monsanto Chemicals Vulcanization of rubber with crystalline adducts of urea
US2890161A (en) * 1959-06-09 Production of low cold-test oils using urea
US2926206A (en) * 1958-02-24 1960-02-23 Union Oil Co Separation of c-8 aromatic hydrocarbon isomers utilizing werner complexes
US3082228A (en) * 1959-12-18 1963-03-19 Escambia Chem Corp Method for producing monoesters of polyunsaturated fatty acids
US3158541A (en) * 1959-12-18 1964-11-24 Escambia Chem Corp Product for reduction of blood cholesterol concentration
US4006081A (en) * 1974-01-08 1977-02-01 Sumitomo Durez Company, Ltd. Method for preventing gelation of thermosetting resins in waste water
US4044052A (en) * 1972-11-03 1977-08-23 Sumitomo Chemical Company, Limited Process for recovery of urea from its phenolic solution
CN101157871B (zh) * 2007-11-20 2013-02-13 济南钢铁股份有限公司 煤气精脱萘废柴油再生工艺方法

Families Citing this family (4)

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Publication number Priority date Publication date Assignee Title
US3164579A (en) * 1965-01-05 Tffiourea abducts of dimethyl-
US2849511A (en) * 1953-05-25 1958-08-26 Union Oil Co Separation of organic compounds
US2813851A (en) * 1953-06-22 1957-11-19 Phillips Petroleum Co Organic separation with urea and thiourea
DE1040730B (de) * 1955-12-21 1958-10-09 Chem Fab Dueren G M B H Verfahren zur Herstellung von Waschmitteln

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US1830859A (en) * 1927-09-14 1931-11-10 Schering Kahlbaum Ag Process for separating meta-cresol from phenolic mixtures
GB467749A (en) * 1935-02-27 1937-06-23 Theodor Rotta Manufacture of urea compounds useful for the treatment of textiles
US2248668A (en) * 1939-02-11 1941-07-08 Texas Co Dewaxing hydrocarbon oil
US2300134A (en) * 1939-01-17 1942-10-27 Schering Corp Process for the separation of transoestradiol and product obtained thereby

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US2109895A (en) * 1934-11-19 1938-03-01 Standard Oil Co Lubricating oil refining
GB459189A (en) * 1935-07-08 1937-01-04 Ig Farbenindustrie Ag Improvements in the recovery of aromatic compounds from liquid hydrocarbons
US2246257A (en) * 1938-07-02 1941-06-17 Shell Dev Separation of organic mixtures
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US2221301A (en) * 1939-02-13 1940-11-12 Herman B Kipper Treatment of unsaturated hydrocarbon oils
US2396303A (en) * 1940-12-07 1946-03-12 Standard Oil Dev Co Refining hydrocarbon oils
US2374102A (en) * 1940-12-31 1945-04-17 Standard Oil Co Conversion of hydrocarbons
US2342888A (en) * 1940-12-31 1944-02-29 Standard Oil Co Conversion of hydrocarbons
US2410166A (en) * 1941-05-14 1946-10-29 Sinclair Refining Co Process of separating toluene
US2386335A (en) * 1942-04-06 1945-10-09 Phillips Petroleum Co Process for the separation of hydrocarbons
US2376008A (en) * 1942-08-15 1945-05-15 Pittsburgh Coke & Iron Company Production of lutidine-urea compounds
US2423414A (en) * 1943-04-07 1947-07-01 United Gas Improvement Co Process for recovering diolefins from hydrocarbon mixtures

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1830859A (en) * 1927-09-14 1931-11-10 Schering Kahlbaum Ag Process for separating meta-cresol from phenolic mixtures
GB467749A (en) * 1935-02-27 1937-06-23 Theodor Rotta Manufacture of urea compounds useful for the treatment of textiles
US2300134A (en) * 1939-01-17 1942-10-27 Schering Corp Process for the separation of transoestradiol and product obtained thereby
US2248668A (en) * 1939-02-11 1941-07-08 Texas Co Dewaxing hydrocarbon oil

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2890161A (en) * 1959-06-09 Production of low cold-test oils using urea
US2739144A (en) * 1956-03-20 Iio hsvm
US2666048A (en) * 1954-01-12 Separation of low molecular weight
US2681333A (en) * 1954-06-15 Gorin
US2681335A (en) * 1954-06-15 Gorin
US2681303A (en) * 1954-06-15 separation of hydrocarbons and hydrocarbon
US2681904A (en) * 1954-06-22 Separation process
US2691009A (en) * 1954-10-05 Atent office
US2804451A (en) * 1957-08-27 Urea adducts of organic sulfur
US2658887A (en) * 1949-06-07 1953-11-10 Process for forming urea complexes
US2666020A (en) * 1949-06-07 1954-01-12 Sepaeation of wax-like constituents
US2773858A (en) * 1950-03-27 1956-12-11 Manuel H Gorin Method of preparing expanded urea
US2700664A (en) * 1950-11-17 1955-01-25 Phillips Petroleum Co Separation of organic compounds by adduct formation
US2812373A (en) * 1951-08-02 1957-11-05 Monsanto Chemicals Vulcanization of rubber with crystalline adducts of urea
US2756222A (en) * 1952-06-17 1956-07-24 Swern Daniel Purification of long-chain vinyl esters and ethers
US2801993A (en) * 1953-08-11 1957-08-06 Rosenstein Ludwig Expanded thiourea
US2926206A (en) * 1958-02-24 1960-02-23 Union Oil Co Separation of c-8 aromatic hydrocarbon isomers utilizing werner complexes
US3082228A (en) * 1959-12-18 1963-03-19 Escambia Chem Corp Method for producing monoesters of polyunsaturated fatty acids
US3158541A (en) * 1959-12-18 1964-11-24 Escambia Chem Corp Product for reduction of blood cholesterol concentration
US4044052A (en) * 1972-11-03 1977-08-23 Sumitomo Chemical Company, Limited Process for recovery of urea from its phenolic solution
US4006081A (en) * 1974-01-08 1977-02-01 Sumitomo Durez Company, Ltd. Method for preventing gelation of thermosetting resins in waste water
CN101157871B (zh) * 2007-11-20 2013-02-13 济南钢铁股份有限公司 煤气精脱萘废柴油再生工艺方法

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FR964694A (is") 1950-08-22
NL72935C (is") 1953-08-15
US2588506A (en) 1952-03-11
GB671459A (en) 1952-05-07

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