WO2015147046A1 - Solvant d'extraction pour la distillation extractive et procédé de séparation d'hydrocarbures l'utilisant - Google Patents

Solvant d'extraction pour la distillation extractive et procédé de séparation d'hydrocarbures l'utilisant Download PDF

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WO2015147046A1
WO2015147046A1 PCT/JP2015/059103 JP2015059103W WO2015147046A1 WO 2015147046 A1 WO2015147046 A1 WO 2015147046A1 JP 2015059103 W JP2015059103 W JP 2015059103W WO 2015147046 A1 WO2015147046 A1 WO 2015147046A1
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extraction solvent
hydrocarbon
hydrocarbon mixture
separating
hydrocarbons
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PCT/JP2015/059103
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English (en)
Japanese (ja)
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東洋藏 藤岡
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出光興産株式会社
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Priority to CN201580015895.9A priority Critical patent/CN106573878A/zh
Priority to JP2016510418A priority patent/JPWO2015147046A1/ja
Publication of WO2015147046A1 publication Critical patent/WO2015147046A1/fr

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    • 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
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the present invention relates to an extraction solvent for extractive distillation and a method for separating hydrocarbons using the same.
  • Extractive distillation is an important separation method in the chemical industry as a method for separating a target component from a hydrocarbon mixture.
  • aromatic compounds such as benzene, toluene and xylene, which are important raw materials such as plastics and chemical fibers, are produced by separating them from raw materials such as crude oil, naphtha and modified naphtha.
  • raw materials such as crude oil, naphtha and modified naphtha.
  • there are saturated hydrocarbons and unsaturated hydrocarbons whose boiling points are very close to those of the aromatic compounds to be separated, so separation is difficult by simple distillation purification, and extractive distillation is used. It has been.
  • Extractive distillation adds a third component, an extraction solvent (hereinafter also referred to as “extraction solvent”), to the mixture containing at least two components to change the relative volatility of the components to be separated. And separating by distillation. That is, the extraction solvent needs to be a solvent having a different affinity for each component in the mixture.
  • extraction solvent from the viewpoint of versatility, conventionally, N-methyl-2-pyrrolidone (hereinafter also referred to as “NMP”), N, N-dimethylformamide (hereinafter also referred to as “DMF”), Etc. are used.
  • NMP which has been widely used as an extraction solvent
  • ECHA European Chemicals Agency
  • SSC number: 0457 Designated as a candidate substance (SVHC).
  • ISC number: 0457 DMF has been shown in the International Chemical Safety Card (ICSC number: 0457) that long-term or repeated exposure may affect the liver and cause dysfunction. It is also designated as a guideline substance related to virulence.
  • extraction solvents are required to have high safety in addition to the ability to efficiently separate the target components, and NMP and DMF substitute solvents that are concerned about health effects are strong. It has been demanded.
  • the present inventors have found that a specific compound that has not been restricted in use from the viewpoint of safety and that has not been examined for use is extracted by distillation.
  • the present invention was completed by finding that it can be used as an extraction solvent having excellent extraction efficiency and high safety. That is, the present invention provides the following [1] to [8].
  • R 1 is a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms
  • R 2 and R 3 are each independently a linear or branched alkyl group having 1 to 6 carbon atoms.
  • N is an integer of 0 to 2
  • the mass ratio [(a) / (b)] of the component (a) and the component (b) in the hydrocarbon mixture is 20/80 to 95/5 The extraction solvent as described.
  • the mass ratio [(a) / (c)] of the component (a) to the component (c) is 20/80 to 95/5, or The extraction solvent according to [2].
  • the present invention can provide an extraction solvent for extractive distillation having high safety and high extraction efficiency, and a method for separating hydrocarbons using the same.
  • the extraction solvent of the present invention comprises a hydrocarbon mixture containing at least two kinds selected from a saturated aliphatic hydrocarbon (a), an unsaturated aliphatic hydrocarbon (b) and an aromatic hydrocarbon (c).
  • a saturated aliphatic hydrocarbon
  • b unsaturated aliphatic hydrocarbon
  • c aromatic hydrocarbon
  • To (c) is an extraction solvent for extractive distillation represented by the following general formula (1).
  • R 1 is a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms
  • R 2 and R 3 are each independently a linear or branched alkyl group having 1 to 6 carbon atoms. It is.
  • n is an integer of 0-2.
  • the carbon number of R 1 is 1 to 6, preferably 1 to 5, more preferably 1 to 4, from the viewpoint of improving extraction efficiency and safety.
  • the extraction solvent can be purified at a lower temperature after being used for extractive distillation, so that the extraction solvent is excellent in energy efficiency.
  • R 1 is a linear, branched or cyclic alkyl group, preferably a linear or branched alkyl group, and more preferably a linear alkyl group.
  • linear alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-heptyl group, and an n-hexyl group.
  • branched alkyl group examples include isopropyl group, s-butyl group, isobutyl group, t-butyl group, 2-methylbutyl group, 3-methylbutyl group, isopentyl group, 2-ethylpropyl group, neopentyl group and the like.
  • cyclic alkyl group examples include a cyclopentyl group and a cyclohexyl group.
  • it is preferably a methyl group, ethyl group, n-propyl group, n-butyl group, more preferably a methyl group, n -A butyl group.
  • the carbon numbers of R 2 and R 3 are each independently 1 to 6, preferably 1 to 3, more preferably, from the viewpoint of improving extraction efficiency and safety. 1 to 2, more preferably 1.
  • the extraction solvent can be purified at a lower temperature after being used for extractive distillation, so that the extraction solvent is excellent in energy efficiency.
  • R 2 and R 3 are each independently a linear or branched alkyl group, preferably a linear alkyl group, from the viewpoint of improving extraction efficiency.
  • linear alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-heptyl group, and an n-hexyl group.
  • branched alkyl group examples include isopropyl group, s-butyl group, isobutyl group, t-butyl group, 2-methylbutyl group, 3-methylbutyl group, isopentyl group, 2-ethylpropyl group, neopentyl group and the like. Can be mentioned.
  • it is preferably a methyl group, an ethyl group, or an n-propyl group, more preferably a methyl group, an ethyl group, and still more preferably. It is a methyl group.
  • n is an integer of 0 to 2, preferably an integer of 1 to 2, more preferably 2, from the viewpoint of improving extraction efficiency.
  • Specific examples of the compound represented by the general formula (1) include, for example, those in which R 2 and R 3 are methyl groups, 3-methoxy-N, N-dimethylpropionamide, 3-ethoxy-N, N— Dimethylpropionamide, 3-n-propoxy-N, N-dimethylpropionamide, 3-isopropoxy-N, N-dimethylpropionamide, 3-n-butoxy-N, N-dimethylpropionamide, 3-sec-butoxy -N, N-dimethylpropionamide, 3-t-butoxy-N, N-dimethylpropionamide, 3-n-pentyloxy-N, N-dimethylpropionamide, 3-cyclopentyloxy-N, N-dimethylpropionamide 3-n-hexyloxy-N, N-dimethylpropionamide, 3-cyclohexyloxy-N, N- Methylpropionamide, and the like.
  • Examples of the compound represented by the general formula (1) in which R 2 and R 3 are ethyl groups include 3-methoxy-N, N-diethylpropionamide, 3-ethoxy-N, N-diethylpropionamide, 3 -N-propoxy-N, N-diethylpropionamide, 3-isopropoxy-N, N-diethylpropionamide, 3-n-butoxy-N, N-diethylpropionamide, 3-sec-butoxy-N, N- Diethylpropionamide, 3-t-butoxy-N, N-diethylpropionamide, 3-n-pentyloxy-N, N-diethylpropionamide, 3-cyclopentyloxy-N, N-diethylpropionamide, 3-n- Hexyloxy-N, N-diethylpropionamide, 3-cyclohexyloxy-N, N-diethylpropio Amide.
  • Examples of the compound represented by the general formula (1) in which R 2 and R 3 are n-propyl groups include 3-methoxy-N, N-di-n-propylpropionamide, 3-ethoxy-N, N -Di-n-propylpropionamide, 3-n-propoxy-N, N-di-n-propylpropionamide, 3-isopropoxy-N, N-di-n-propylpropionamide, 3-n-butoxy- N, N-di-n-propylpropionamide, 3-sec-butoxy-N, N-di-n-propylpropionamide, 3-t-butoxy-N, N-di-n-propylpropionamide, 3- n-pentyloxy-N, N-di-n-propylpropionamide, 3-cyclopentyloxy-N, N-di-n-propylpropionamide, 3-n-hexyloxy-N, N Di -n- propyl propionamide, 3-
  • Examples of the compound represented by the general formula (1) in which R 2 and R 3 are isopropyl groups include 3-methoxy-N, N-diisopropylpropionamide, 3-ethoxy-N, N-diisopropylpropionamide, 3 -N-propoxy-N, N-diisopropylpropionamide, 3-isopropoxy-N, N-diisopropylpropionamide, 3-n-butoxy-N, N-diisopropylpropionamide, 3-sec-butoxy-N, N- Diisopropylpropionamide, 3-t-butoxy-N, N-diisopropylpropionamide, 3-n-pentyloxy-N, N-diisopropylpropionamide, 3-cyclopentyloxy-N, N-diisopropylpropionamide, 3-n- Hexyloxy-N, N-diisopropyl Pion'amido, 3-cyclohexyloxy
  • Examples of the compound represented by the general formula (1) in which one of R 2 and R 3 is an ethyl group and the other is a methyl group include, for example, 3-methoxy-N, N-methylethylpropionamide, 3- Ethoxy-N, N-methylethylpropionamide, 3-n-propoxy-N, N-methylethylpropionamide, 3-isopropoxy-N, N-methylethylpropionamide, 3-n-butoxy-N, N- Methylethylpropionamide, 3-sec-butoxy-N, N-methylethylpropionamide, 3-t-butoxy-N, N-methylethylpropionamide, 3-n-pentyloxy-N, N-methylethylpropionamide 3-cyclopentyloxy-N, N-methylethylpropionamide, 3-n-hexyloxy-N, N-methyl ester Le propionamide, 3-cyclohexyloxy -N, like N- methyl
  • Examples of the compound represented by the general formula (1) in which one of R 2 and R 3 is an n-propyl group and the other is a methyl group include, for example, 3-methoxy-N, N-methylpropylpropionamide, 3-ethoxy-N, N-methylpropylpropionamide, 3-n-propoxy-N, N-methylpropylpropionamide, 3-isopropoxy-N, N-methylpropylpropionamide, 3-n-butoxy-N, N-methylpropylpropionamide, 3-sec-butoxy-N, N-methylpropylpropionamide, 3-t-butoxy-N, N-methylpropylpropionamide, 3-n-pentyloxy-N, N-methylpropyl Propionamide, 3-cyclopentyloxy-N, N-methylpropylpropionamide, 3-n-hexyl Carboxymethyl -N, N- methylpropyl propionamide, 3-cyclohexyloxy -N, like N- methylpropyl pro
  • Examples of the compound represented by the general formula (1) in which one of R 2 and R 3 is an n-propyl group and the other is an ethyl group include, for example, 3-methoxy-N, N-ethylpropylpropionamide, 3-ethoxy-N, N-ethylpropylpropionamide, 3-n-propoxy-N, N-ethylpropylpropionamide, 3-isopropoxy-N, N-ethylpropylpropionamide, 3-n-butoxy-N, N-ethylpropylpropionamide, 3-sec-butoxy-N, N-ethylpropylpropionamide, 3-t-butoxy-N, N-ethylpropylpropionamide, 3-n-pentyloxy-N, N-ethylpropyl Propionamide, 3-cyclopentyloxy-N, N-ethylpropylpropionamide, 3-n-hexyl Carboxymethyl -N, N-
  • Examples of the compound represented by the general formula (1) in which R 2 and R 3 are n-butyl groups include 3-methoxy-N, N-dibutylpropionamide, 3-ethoxy-N, N-dibutylpropionamide 3-n-propoxy-N, N-dibutylpropionamide, 3-isopropoxy-N, N-dibutylpropionamide, 3-n-butoxy-N, N-dibutylpropionamide, 3-sec-butoxy-N, N-dibutylpropionamide, 3-t-butoxy-N, N-dibutylpropionamide, 3-n-pentyloxy-N, N-dibutylpropionamide, 3-cyclopentyloxy-N, N-dibutylpropionamide, 3- n-hexyloxy-N, N-dibutylpropionamide, 3-cyclohexyloxy-N, N-dibutylpro On'amido, and the like.
  • Examples of the compound represented by the general formula (1) in which R 2 and R 3 are n-heptyl groups include 3-methoxy-N, N-diheptylpropionamide, 3-ethoxy-N, N-diheptyl Propionamide, 3-n-propoxy-N, N-diheptylpropionamide, 3-isopropoxy-N, N-diheptylpropionamide, 3-n-butoxy-N, N-diheptylpropionamide, 3-sec -Butoxy-N, N-diheptylpropionamide, 3-t-butoxy-N, N-diheptylpropionamide, 3-n-pentyloxy-N, N-diheptylpropionamide, 3-cyclopentyloxy-N, N-diheptylpropionamide, 3-n-hexyloxy-N, N-diheptylpropionamide, 3-cyclohexyloxy N, N-di-heptyl pro
  • Examples of the compound represented by the general formula (1) in which R 2 and R 3 are n-hexyl groups include 3-methoxy-N, N-dihexylpropionamide, 3-ethoxy-N, N-dihexylpropionamide 3-n-propoxy-N, N-dihexylpropionamide, 3-isopropoxy-N, N-dihexylpropionamide, 3-n-butoxy-N, N-dihexylpropionamide, 3-sec-butoxy-N, N-dihexylpropionamide, 3-t-butoxy-N, N-dihexylpropionamide, 3-n-pentyloxy-N, N-dihexylpropionamide, 3-cyclopentyloxy-N, N-dihexylpropionamide, 3- n-hexyloxy-N, N-dihexylpropionamide, 3-cyclohexyloxy N, N-dihexyl propionamide
  • the compounds represented by the general formula (1) may be used alone or in combination of two or more.
  • the hydrocarbon mixture used for the extractive distillation using the extraction solvent of the present invention is at least selected from a saturated aliphatic hydrocarbon (a), an unsaturated aliphatic hydrocarbon (b) and an aromatic hydrocarbon (c). Contains 2 types.
  • saturated aliphatic hydrocarbon (a) examples include cyclic or chain saturated aliphatic hydrocarbons.
  • Specific examples of the cyclic saturated aliphatic hydrocarbon include cyclopentane, cyclohexane, methylcyclohexane, 1,2-dimethylcyclohexane, 1,3-dimethylcyclohexane, 1,4-dimethylcyclohexane, cyclooctane, cyclodecane, cyclododecane, Preferable examples include methylcyclopentane, ethylcyclohexane, dimethylcyclohexane, and ethylcyclopentane.
  • chain saturated aliphatic hydrocarbon examples include n-pentane, 2-methylbutane, 2,2-dimethylpropane, n-hexane, 2-methylpentane, 3-methylpentane, 2,2-dimethylbutane, 2,3-dimethylbutane, 3-ethylbutane, n-heptane, 2-methylhexane, 3-methylhexane, 2,2-dimethylpentane, 2,3-dimethylpentane, 2,4-dimethylpentane, 3-ethylpentane N-octane, 2-methylheptane, 3-methylheptane, 4-methylheptane, 2,2-dimethylhexane, 2,3-dimethylhexane, 3,3-dimethylhexane, 3,4-dimethylhexane, 3- Ethylhexane, n-nonane, 2-methyloctane, 3-methyloctane,
  • the carbon number of the saturated aliphatic hydrocarbon (a) is preferably 4 to 10, more preferably 5 to 8, still more preferably 6 to 7, and still more preferably 6.
  • the saturated aliphatic hydrocarbon (a) has a carbon number within the above range, it can be efficiently separated.
  • Examples of the unsaturated aliphatic hydrocarbon (b) include cyclic or chain unsaturated aliphatic hydrocarbons.
  • Specific examples of the cyclic unsaturated aliphatic hydrocarbon include cyclopentene, cyclohexene, methylcyclohexene, dimethylcyclohexene, cyclooctene, cyclodecene, cyclododecene, ethylcyclohexene, methylcyclopentene, ethylcyclopentene, cyclopentadiene, cyclohexadiene, methylcyclohexadiene, Preferred examples include cycloheptadiene, cyclooctaneene, cyclodecadiene, cyclododecadiene and the like.
  • chain unsaturated aliphatic hydrocarbon examples include an internal olefin or a terminal olefin, and these may have one or more unsaturated bonds in one molecule. Furthermore, when having a plurality of unsaturated bonds, they may be conjugated or non-conjugated.
  • chain unsaturated aliphatic hydrocarbon examples include n-pentene, 2-n-pentene, 3-n-pentene, 2-methylbutene, 2,2-dimethylpropene, n-hexene, 2-n- Hexene, 3-n-hexene, 2-methylpentene, 3-methylpentene, 2,2-dimethylbutene, 2,3-dimethylbutene, 3-ethylbutene, n-heptene, 2-methylhexene, 3-methylhexene, 2,2-dimethylpentene, 2,3-dimethylpentene, 2,4-dimethylpentene, 3-ethylpentene, n-octene, 2-methylheptene, 3-methylheptene, 4-methylheptene, 2,2-dimethylhexene, 2 , 3-dimethylhexene, 3,3-dimethylhexene, 3,4-dimethylhexene, 3-ethylhex
  • the number of carbon atoms of the unsaturated aliphatic hydrocarbon (b) is preferably 4 to 10, more preferably 5 to 8, still more preferably 6 to 7, and still more preferably 6.
  • the unsaturated aliphatic hydrocarbon (b) has a carbon number within the above range, it can be efficiently separated.
  • Aromaatic hydrocarbon (c) Preferred examples of the aromatic hydrocarbon (c) include benzene, toluene, o-xylene, m-xylene, p-xylene, ethylbenzene, diethylbenzene, isopropylbenzene, and trimethylbenzene.
  • the number of carbon atoms of the aromatic hydrocarbon (c) is preferably 6 to 10, more preferably 6 to 8, still more preferably 6 to 7, and still more preferably 6. When the carbon number of the aromatic hydrocarbon (c) is within the above range, it can be separated efficiently.
  • a hydrocarbon mixture containing hydrocarbon (c) is preferred, a cyclic saturated aliphatic hydrocarbon having 6 to 10 carbon atoms (a) and a cyclic unsaturated aliphatic hydrocarbon having 6 to 10 carbon atoms (b).
  • a hydrocarbon mixture containing (c) is more preferred, a cyclic saturated aliphatic hydrocarbon having 6 or 7 carbon atoms (a), a cyclic unsaturated aliphatic hydrocarbon having 6 or 7 carbon atoms (b), and Or a hydrocarbon mixture containing a cyclic unsaturated aliphatic hydrocarbon having 6 or 7 carbon atoms (b) and an aromatic hydrocarbon having 6 or 7 carbon atoms (c) is even more preferable. .
  • the components (a) to (c) may have a substituent such as a carbonyl group, an ether group, a hydroxyl group, or a carboxyl group as long as the effects of the present invention are not impaired.
  • the hydrocarbon mixture to be subjected to extractive distillation using the extraction solvent of the present invention is at least 2 selected from saturated aliphatic hydrocarbons (a), unsaturated aliphatic hydrocarbons (b) and aromatic hydrocarbons (c).
  • saturated aliphatic hydrocarbons a
  • unsaturated aliphatic hydrocarbons b
  • aromatic hydrocarbons c
  • it is a hydrocarbon mixture containing seeds, it is not particularly limited, and it may contain components other than the above (a) to (c).
  • the hydrocarbon mixture is a hydrocarbon mixture containing a saturated aliphatic hydrocarbon (a) and an unsaturated aliphatic hydrocarbon (b), or a saturated aliphatic hydrocarbon (a) and A hydrocarbon mixture containing an aromatic hydrocarbon (c) is preferred.
  • Mass ratio [(a) / (b)] of said (a) component and said (b) component in the hydrocarbon mixture containing saturated aliphatic hydrocarbon (a) and unsaturated aliphatic hydrocarbon (b) Is preferably 20/80 to 95/5, more preferably 40/60 to 90/10, and still more preferably 60/40 to 80/20 from the viewpoint of efficient separation.
  • the mass ratio [(a) / (c)] of the component (a) and the component (c) is: From the viewpoint of efficient separation, it is preferably 20/80 to 95/5, more preferably 40/60 to 90/10, and still more preferably 60/40 to 80/20.
  • the method for separating hydrocarbons of the present invention comprises a hydrocarbon mixture containing at least two selected from saturated aliphatic hydrocarbons (a), unsaturated aliphatic hydrocarbons (b) and aromatic hydrocarbons (c).
  • the saturated aliphatic hydrocarbon (a), the unsaturated aliphatic hydrocarbon (b), the aromatic hydrocarbon (c), and the hydrocarbon mixture containing these used in the separation method of the present invention are the above extraction solvents. It is the same as that described in the description section, and the preferred embodiment is also the same.
  • the separation method of the present invention has high safety and can separate target components with high extraction efficiency. Moreover, when isolate
  • polar solvents examples include sulfone compounds such as sulfolane, aliphatic dinitrile compounds such as adiponitrile, N-alkylpyrrolidone compounds such as N-methylpyrrolidone, lactone compounds such as ⁇ -butyrolactone, and dialkyl sulfoxides such as dimethyl sulfoxide.
  • sulfone compounds such as sulfolane
  • aliphatic dinitrile compounds such as adiponitrile
  • N-alkylpyrrolidone compounds such as N-methylpyrrolidone
  • lactone compounds such as ⁇ -butyrolactone
  • dialkyl sulfoxides such as dimethyl sulfoxide.
  • a combination with a lactone compound such as ⁇ -butyrolactone and water is preferable from the viewpoint of safety.
  • the amount of these other extraction solvents used is preferably such that the molar ratio of the compound represented by the general formula (1) to the other polar solvent is 0.1: 0.9 from the viewpoint of extraction efficiency and cost. ⁇ 1: 0, more preferably 0.3: 0.7 to 1: 0, still more preferably 0.5: 0.5 to 1: 0.
  • the molar ratio of the hydrocarbon mixture to the extraction solvent is preferably 1: 0.5 to 1:10, more preferably 1: 0.75 to 1. : 7, more preferably 1: 1 to 1: 5, and still more preferably 1: 1 to 1: 2.
  • the separation efficiency of the target hydrocarbon can be increased.
  • the size of the apparatus can be reduced, and the solvent recovery cost can be reduced.
  • a conventionally known system As a system for carrying out the separation method of the present invention, a conventionally known system can be used, which may be either batch distillation or continuous distillation, and can be appropriately selected according to the purpose. .
  • the apparatus for carrying out the separation method of the present invention can be carried out using a conventionally known distillation apparatus such as a distillation column.
  • a distillation column When the separation method of the present invention is carried out in a multistage continuous distillation column, the number of stages between the extraction solvent introduction stage and the raw material supply stage, the number of stages between the tower top and the extraction solvent introduction stage, and the bottom and raw material supply The number of stages between the stages can be appropriately selected by preliminarily examining the relationship between the purity of the distillate component, the recovery rate, and the like.
  • the temperature at which the separation method of the present invention is carried out can be appropriately selected according to the boiling point of the component intended for separation.
  • the pressure at which the separation method of the present invention is carried out may be any of normal pressure, pressurization, and reduced pressure, and can be appropriately determined in consideration of extraction efficiency.
  • Example 1 As shown in FIG. 1, the extraction solvent shown in Table 1 and carbonized in a 1 L glass container equipped with a sample collecting cock (cock A) with a cooling pipe and a two-way cock (cock C). Hydrogen compounds (a and b) were added to obtain a mixture.
  • the cock of the dropping funnel (cock B) is opened, the reflux liquid is set so as to return to the glass container, the temperature of the oil bath is increased while stirring the interior with a magnetic stirrer and a stirrer, and the mixture is heated. Refluxed. Next, the temperature of the oil bath was adjusted and maintained so that the number of droplets falling from the cooling tube was about 2 to 3 droplets per second.
  • the cock (cock B) of the dropping funnel was closed, and the distillate was collected in the dropping funnel.
  • the distillate in the dropping funnel is collected from the sample collection cock (cock A) using a syringe, and the two-way cock (cock C) attached to a glass container in the same manner. ) From the bottom.
  • the collected liquid was subjected to gas chromatographic analysis (detector) to calculate the concentration (mass%) of cyclohexane and cyclohexene, and the relative volatility ⁇ ab was calculated according to the following formula.
  • ⁇ ab (Y (a) / X (a)) / (Y (b) / X (b)) Y (a) and Y (b) respectively represent the moles of hydrocarbon compound a and hydrocarbon compound b relative to the sum of hydrocarbon compound a and hydrocarbon compound b in the gas phase (distillate) in the vapor-liquid equilibrium state. It is a fraction.
  • X (a) and X (b) are respectively the mole fractions of hydrocarbon compound a and hydrocarbon compound b relative to the sum of hydrocarbon compound a and hydrocarbon compound b in the liquid phase (bottom liquid) in the vapor-liquid equilibrium state. Rate.
  • Example 2 Comparative Examples 1 to 4
  • Example 1 the separation operation was performed in the same manner as in Example 1 except that the extraction solvent to be used, the distillate, and the amounts used thereof were changed as shown in Tables 1 and 2.

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Abstract

L'invention concerne un solvant d'extraction pour la distillation extractive représenté par la formule générale (1) utilisé lors de la séparation de l'une quelconque de (a)-(c) par distillation extractive à partir d'un mélange d'hydrocarbures contenant au moins deux éléments sélectionnés parmi les hydrocarbures aliphatiques saturés (a), les hydrocarbures aliphatiques insaturés (b), et les hydrocarbures aromatiques (c), et un procédé de séparation d'hydrocarbures l'utilisant. R1: groupe alkyle en C1-6 linéaire/ramifié/cyclique ; R2, 3: groupe alkyle en C1-6 linéaire/ramifié ; n: 0-2
PCT/JP2015/059103 2014-03-28 2015-03-25 Solvant d'extraction pour la distillation extractive et procédé de séparation d'hydrocarbures l'utilisant WO2015147046A1 (fr)

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CN201580015895.9A CN106573878A (zh) 2014-03-28 2015-03-25 萃取蒸馏用的萃取溶剂以及使用所述溶剂的烃类的分离方法
JP2016510418A JPWO2015147046A1 (ja) 2014-03-28 2015-03-25 抽出蒸留用の抽出溶剤、及びそれを用いた炭化水素類の分離方法

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CN114751826B (zh) * 2022-04-21 2023-02-28 厦门大学 一种分离乙酸乙酯和甲基环己烷恒沸物的萃取精馏方法

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