EP0642810A2 - Verfahren zur Wasserstoffbehandlung von organischen Einsätzen, die olefinische Verbindungen und einen Halogenteil enthalten - Google Patents

Verfahren zur Wasserstoffbehandlung von organischen Einsätzen, die olefinische Verbindungen und einen Halogenteil enthalten Download PDF

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Publication number
EP0642810A2
EP0642810A2 EP94308592A EP94308592A EP0642810A2 EP 0642810 A2 EP0642810 A2 EP 0642810A2 EP 94308592 A EP94308592 A EP 94308592A EP 94308592 A EP94308592 A EP 94308592A EP 0642810 A2 EP0642810 A2 EP 0642810A2
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EP
European Patent Office
Prior art keywords
compounds
hydrogen
stream
hydrogen halide
hydrogenation reaction
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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EP94308592A
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English (en)
French (fr)
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EP0642810A3 (de
Inventor
Eberhard L. Dreher
Barbara Böeheimer
Celio Lume Pereira
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Dow Chemical Co
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Dow Chemical Co
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Priority to EP94308592A priority Critical patent/EP0642810A3/de
Priority to CN94118715.2A priority patent/CN1123267A/zh
Publication of EP0642810A2 publication Critical patent/EP0642810A2/de
Publication of EP0642810A3 publication Critical patent/EP0642810A3/de
Withdrawn legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
    • A62D3/30—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
    • A62D3/37—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents by reduction, e.g. hydrogenation
    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/20—Organic substances
    • A62D2101/22—Organic substances containing halogen

Definitions

  • the field of art to which this invention pertains is the conversion of an organic feedstock which contains thermally unstable compounds and a halogen component to produce hydrocarbonaceous compounds having a reduced concentration of halogen moieties.
  • the present invention provides a process for hydrotreating an organic feedstock containing thermally unstable compounds and a halogen component by means of contacting the organic feedstock and a gaseous recycle stream containing hydrogen and a hydrogen halide compound with a hydrogenation catalyst in a hydrogenation reaction zone to produce a hydrogenated hydrocarbonaceous stream having a reduced concentration of halogen and a halide compound stream.
  • the resultant effluent from the hydrogenation zone is separated to produce a recycle stream containing a hydrogen halide compound.
  • Important elements of the improved process are the reduced formation of polymerized olefins or decomposed compounds in the processing plant, reduced coke formation or carbonaceous deposition on the hydrogenation catalyst, the ability to achieve longer run lengths and catalyst life, and higher conversion per pass.
  • the invention provides a process for hydrotreating an organic feedstock containing thermally unstable compounds and a halogen component while minimizing the thermal decomposition of the thermally unstable compounds and stabilizing the activity of the hydrotreating catalyst, which process comprises the following steps: (a) contacting the organic feedstock, containing thermally unstable compounds and a halogen component, and a gaseous recycle stream, comprising hydrogen and a hydrogen halide compound, with a hydrogenation catalyst in a hydrogenation reaction zone at hydrogenation reaction conditions to increase the hydrogen content of the organic feedstock and to produce a hydrogen halide compound; (b) condensing at least a portion of the resulting effluent from the hydrogenation reaction zone to produce a gaseous stream comprising hydrogen and a hydrogen halide compound, and a liquid stream comprising hydrocarbonaceous compounds; (c) recycling at least a portion of the gaseous stream comprising hydrogen and a hydrogen halide compound recovered in step (b) to the hydrogenation reaction zone in step (a); and (d) recovering a stream
  • Embodiments of the present invention encompass further details such as preferred feedstocks, hydrogenation catalysts and operating conditions, all of which are hereinafter disclosed in the following discussion of each of these facets of the invention.
  • the drawing is a simplified process flow diagram of a preferred embodiment of the present invention.
  • the present invention provides an improved integrated process for hydrotreating an organic feedstock containing thermally unstable compounds and a halogen component while minimizing thermal decomposition and polymerization of thermally unstable compounds and thereby stabilizing the activity of the hydrotreating catalyst.
  • halogenated organic compounds containing thermally unstable compounds are candidates for feed streams in accordance with the process of the present invention.
  • organic streams comprising halogenated organic compounds which are suitable for treatment by the process of the present invention are dielectric fluids, hydraulic fluids, heat transfer fluids, used lubricating oil, used cutting oils, used solvents, halogenated hydrocarbonaceous by-products, oils contaminated with polychlorinated biphenyls (PCB), halogenated wastes, by-products from the manufacture of vinyl chloride monomer, propylene oxide, allyl chloride, epichlorohydrin and other halogenated intermediates and final products, petrochemical by-products and other halogenated hydrocarbonaceous industrial wastes.
  • PCB polychlorinated biphenyls
  • halogenated wastes by-products from the manufacture of vinyl chloride monomer, propylene oxide, allyl chloride, epichlorohydrin and other halogenated intermediates and final products, petrochemical
  • the process of the present invention is most advantageously utilized when the feedstock contains thermally unstable compounds which have a marked tendency to polymerize or form coke or carbonaceous deposits when raised to an elevated temperature, for example olefinic or heteroatomic compounds.
  • thermally unstable compounds which have a marked tendency to polymerize or form coke or carbonaceous deposits when raised to an elevated temperature, for example olefinic or heteroatomic compounds.
  • the undesirable reactions by thermally unstable compounds presented great difficulties for those attempting to process such feed streams because of the resulting operational problem in the operating plant.
  • the halogenated organic feedstock preferably contains less than 500 ppm by weight of water and, in certain contexts, of water precursors.
  • water precursors are oxygenated compounds which, when subjected to hydrogenation conditions in the presence of certain of the contemplated catalysts, are converted into hydrogenated compounds and water.
  • the resulting hydrogen halide is conveniently recovered as an anhydrous hydrogen halide stream and as used herein, the term "anhydrous hydrogen comprising hydrogen halide" connotes a stream having less than 50 ppm by weight of water.
  • Preferred feedstocks comprise fractionation column bottoms from the production of allyl chloride, fractionation column bottoms from the production of ethylene dichloride, by-products from the manufacture of vinyl chloride monomer, fractionation column bottoms from the production of trichloroethylene or perchloroethylene, used dielectric fluids containing polychlorinated biphenyls (PCB) or halogenated benzene, used solvents, fractionation bottoms from the purification column in epichlorohydrin production, carbon tetrachloride, 1,1,1-trichloroethane, halogenated alcohols, halogenated ethers, chlorofluorocarbons or admixtures thereof.
  • PCB polychlorinated biphenyls
  • halogenated organic compounds which are contemplated as feedstocks in the present invention may contain chlorine, bromine, fluorine or iodine.
  • Preferred halogen compounds contain chlorine or fluorine.
  • the halogenated organic compounds preferably contain from 1 to 20 carbon atoms per molecule.
  • a feedstock containing halogenated organic compounds is introduced in admixture with a hydrogen-rich, gaseous recycle stream containing a hydrogen halide and, optionally, a recycle stream comprising unreacted halogenated organic compounds into a catalytic hydrogenation zone containing hydrogenation catalyst and maintained at hydrogenation conditions.
  • This catalytic hydrogenation zone may contain a fixed, ebulliated or fluidized catalyst bed.
  • the hydrogenation reaction zone may consist of multiple catalyst beds operated at various conditions. This reaction zone is preferably maintained at conditions which are chosen to dehalogenate the halogenated organic compounds which are introduced thereto.
  • the catalytic hydrogenation zone is preferably maintained under an imposed pressure from atmospheric to 2000 psig (14 MPa, gauge) and more preferably under a pressure from 100 psig (0.7 MPa, gauge) to about 1800 psig (12.5 MPa, gauge).
  • a maximum catalyst bed temperature in the range of 50 ° F. (10 ° C.) to 850 ° F. (455 ° C.) selected to perform the desired dehalogenation conversion to reduce or eliminate the concentration of halogenated organic compounds contained in the combined feed stream and to consequently increase the hydrogen content of the stream.
  • the desired hydrogenation conversion includes, for example, dehalogenation and hydrocracking.
  • the effluent from the hydrogenation zone preferably contains essentially no olefinic compounds or other thermally unstable compounds which may be deleterious to any other further processing steps.
  • Further preferred operating conditions include liquid hourly space velocities in the range from 0.05 h- 1 to 20 h- 1 and hydrogen circulation rates from 200 standard cubic feet per barrel (SCFB) (35 normal m 3 /m 3 ) to 150,000 SCFB (27,000 normal m 3 /m 3 ), preferably from 200 SCFB (35 normal m 3 /m 3 ) to 100,000 SCFB (18,000 normal m 3 / m 3).
  • SCFB standard cubic feet per barrel
  • hydrotreating or “hydrogenation” is broadly meant to include reactions whereby the organic reactants achieve an increased hydrogen content, regardless of whether this is achieved by olefin saturation, diolefin saturation, desulfurization, denitrification or dehalogenation, for example.
  • a hydrogen halide be recycled along with the hydrogen-rich gaseous recycle stream in order to achieve the unexpected result of minimizing the polymerization of olefinic compounds or decomposition of other thermally unstable compounds which are contained in the fresh feedstock.
  • the level of hydrogen halide which is recycled to the hydrogenation reaction zone is a function of the level of the thermally unstable compounds which are contained in the original feedstock.
  • the concentration of hydrogen halide in the hydrogen-rich gaseous recycle stream is preferably from 2 mole percent to 60 mole percent.
  • the hydrogen halide is present in an amount from 5 wt. percent to 200 wt. percent based upon the weight of the combined feedstock and recycle including unreacted halogenated organic compounds, if any, to the hydrogenation reaction zone.
  • the preferred catalytic composite disposed within the hereinabove described hydrogenation zone can be characterized as containing a metallic component having hydrogenation activity, which component is combined with a suitable refractory carrier material of either synthetic or natural origin, especially a refractory inorganic oxide.
  • a suitable refractory carrier material of either synthetic or natural origin, especially a refractory inorganic oxide.
  • Preferred carrier materials are alumina, silica, carbon and mixtures thereof.
  • Suitable metallic components having hydrogenation activity are those selected from the group comprising the metals of Groups VIB and VIII of the Periodic Table, as set forth in the Periodic Table of Elements, E. H. Sargent and Company, 1964.
  • the metallic components of Group VIB are generally present in an amount within the range of from 1 to 20 weight percent, the iron-group metals in an amount within the range of 0.2 to 10 weight percent, whereas the noble metals of Group VIII are preferably present in an amount within the range of from 0.1 to 5 weight percent, all of which are calculated as if these components existed within the catalytic composite in the elemental state.
  • hydrogenation catalytic composites may comprise one or more of the following components: cesium, francium, lithium, potassium, rubidium, sodium, copper, gold, silver, cadmium, mercury and zinc.
  • Preferred hydrogenation catalysts comprise alumina and palladium.
  • the hydrocarbonaceous effluent containing at least one hydrogen halide compound from the hydrogenation zone is cooled and introduced into a vapor-liquid separator to produce a hydrogen-rich, gaseous recycle stream containing hydrogen halide and a liquid stream comprising hydrogenated hydrocarbonaceous compounds and hydrogen halide.
  • One technique which may be used in order to adjust the amount of hydrogen halide which is recycled in the hydrogen-rich gaseous recycle stream is to select the operating pressure and the amount of cooling performed on the effluent and the resulting operating temperature of the vapor-liquid separator.
  • the vapor-liquid separator is operated at a pressure between 400 psig (2.75 MPa, gauge) and 1800 psig (12.5 MPa, gauge) at a temperature from -70 F. (-57 ° C.) to 60 F. (16 ° C.).
  • the resulting liquid stream comprising hydrogenated hydrocarbonaceous compounds and hydrogen halide is separated in a preferred further step to produce an anhydrous stream comprising hydrogen halide and a liquid stream comprising hydrogenated hydrocarbonaceous compounds and unreacted organic compounds.
  • This resulting liquid stream is then separated to produce a recycle stream comprising unreacted halogenated organic compounds which is introduced into the hydrogenation reaction zone and a hydrogenated hydrocarbonaceous stream having a reduced level of halogen.
  • the hydrogen halide compound is thus recovered as an anhydrous product stream. This permits the subsequent recovery and use of a desirable and valuable hydrogen halide compound.
  • the resulting hydrogenated hydrocarbonaceous effluent from the hydrogenation reaction zone is preferably separated to produce a hydrogen-rich gas phase containing a hydrogen halide compound and a liquid hydrocarbonaceous stream in a separation zone which is maintained at essentially the same pressure as the hydrogenation reaction zone and at a temperature in the range from -70 ° F. (-57 ° C.) to 60 ° F. (16 ° C.), and as a consequence, the liquid hydrocarbonaceous stream contains dissolved hydrogen, dissolved hydrogen halide and low molecular weight normally gaseous hydrocarbons if present.
  • the hydrogenated liquid phase comprising the hydrogen chloride is separated to produce an anhydrous hydrogen halide stream by separating, for example, by stripping, flashing or fractionating.
  • a resulting hydrocarbonaceous stream is separated to produce a hydrocarbonaceous stream, primarily comprising hydrogenated hydrocarbonaceous compounds and a stream primarily comprising halogenated organic compounds which may then be recycled to the hydrogenation conversion zone if desired.
  • Such a separation may be conducted in any convenient manner such as, for example, stripping, flashing or fractionating.
  • an organic feed stream containing thermally unstable compounds and a halogen component is introduced into the process via conduit 1 and is contacted with a hydrogen-rich gaseous recycle stream containing a hydrogen halide compound which is provided via conduit 7 and is hereinafter described.
  • the organic feed stream containing thermally unstable compounds, the hydrogen-rich gaseous recycle stream containing a hydrogen halide compound and an unconverted organic recycle stream provided via conduit 14 and hereinafter described are introduced into hydrogenation reaction zone 2.
  • the resulting hydrogenated organic stream is removed from the hydrogenation reaction zone 2 via conduit 3, is cooled in heat exchanger 4 and introduced into vapor liquid separator 6 via conduit 5.
  • a hydrogen-rich gaseous stream containing a hydrogen halide compound is removed from vapor-liquid separator 6 via conduit 7 and recycled as described hereinabove. Since hydrogen is lost in the process by means of a portion of the hydrogen being dissolved in the exiting liquid hydrocarbon and hydrogen being consumed during the hydrogenation reaction, it is necessary to supplement the hydrogen-rich gaseous stream with a make-up hydrogen from some suitable external source, for example, a catalytic reforming unit or a hydrogen plant. Make-up hydrogen may be introduced into the system at any convenient and suitable point but is not shown on the drawing.
  • a liquid hydrogenated hydrocarbonaceous stream containing hydrogen and a hydrogen halide in solution is removed from vapor liquid separator 6 and is introduced into fractionation zone 9 via conduit 8.
  • a product stream containing hydrogen halide is removed from fractionation zone 9 via conduit 10 and recovered in anhydrous form.
  • a liquid distillable hydrogenated hydrocarbonaceous stream is removed from fractionation zone 9 via conduit 11 and is introduced into fractionation zone 12.
  • a product stream containing hydrocarbonaceous compounds having a reduced concentration of halogen is removed from fractionation zone 12 via conduit 13 and recovered.
  • a liquid stream containing unconverted organic compounds is removed from fractionation zone 12 via conduit 14 and is recycled to hydrogenation reaction zone 2 via conduit 14 as described hereinabove.
  • Example 1 is a control experiment using an olefinic feedstock without a hydrogen halide recycle.
  • Example 2 is another control experiment with a non-olefinic feedstock having thermal instability without hydrogen halide recycle.
  • This example demonstrates a process for the conversion of a feedstock containing 70% dichloropropane and 30% dichloropropene wherein the feedstock was passed over a dechlorination catalyst containing palladium and alumina at a weight hourly space velocity (WHSV) of 0.6, a pressure of 750 psig (5.2 MPa, gauge), a hydrogen circulation of 91,000 standard cubic feet per barrel (SCFB) (16,200 normal m 3 /m 3 ) with no hydrogen halide compound recycle and an average catalyst bed temperature of about 140 ° F. (60 ° C).
  • WHSV weight hourly space velocity
  • SCFB standard cubic feet per barrel
  • This example demonstrates a process for the conversion of a feedstock having the characteristics presented in Table 1 wherein the feedstock was passed over a dechlorination catalyst containing palladium and alumina at a weight hourly space velocity (WHSV) of 0.6, a pressure of 750 psig (5.2 MPa, gauge), a gas circulation rate of 55,000 SCFB (9,800 normal m 3 /m 3 ) (>80 mole percent of hydrogen, 0 mole percent HCI and the remainder propane) and an average catalyst bed temperature in the range of 248 ° F. (120 ° C.) to 320 F. (160 ° C.). After 162 hours of operation, the run was discontinued to analyze the catalyst for coke or carbonaceous components. The catalyst at the top of the catalyst bed contained 5.63 weight percent carbonaceous deposit while the catalyst at the bottom of the catalyst bed contained 2.65 weight percent carbonaceous deposit.
  • WHSV weight hourly space velocity
  • This example is conducted in accordance with one embodiment of the present invention and the recycle of hydrogen halide reduces the carbonaceous or coke deposit.
  • a feedstock containing 91.9 weight percent dichloropropane and 7.5 percent dichloropropene was contacted with a dechlorination catalyst containing palladium and alumina at a WHSV of 0.3, an operating pressure of 750 psig (5.2 MPa, gauge), a hydrogen circulation rate of 45,000 SCFB (8,000 normal m 3 /m 3 ) and an average catalyst bed temperature of about 311 ° F. (155 ° C.).
  • the hydrogen chloride which was produced in the dechlorination reaction was recycled at an average value of 31 mole percent of the recycle gas.
  • the operation was considered good but was discontinued after 1350 hours of stable performance to analyze the catalyst for coke or carbonaceous components.
  • the catalyst at the top of the catalyst bed contained 2.93 weight percent carbonaceous deposit while the catalyst at the bottom of the catalyst bed contained only 0.14 weight percent carbonaceous deposit.

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  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
EP94308592A 1994-11-21 1994-11-21 Verfahren zur Wasserstoffbehandlung von organischen Einsätzen, die olefinische Verbindungen und einen Halogenteil enthalten. Withdrawn EP0642810A3 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP94308592A EP0642810A3 (de) 1994-11-21 1994-11-21 Verfahren zur Wasserstoffbehandlung von organischen Einsätzen, die olefinische Verbindungen und einen Halogenteil enthalten.
CN94118715.2A CN1123267A (zh) 1994-11-21 1994-11-21 加氢处理含烯烃化合物和卤素组分的有机原料的方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP94308592A EP0642810A3 (de) 1994-11-21 1994-11-21 Verfahren zur Wasserstoffbehandlung von organischen Einsätzen, die olefinische Verbindungen und einen Halogenteil enthalten.
CN94118715.2A CN1123267A (zh) 1994-11-21 1994-11-21 加氢处理含烯烃化合物和卤素组分的有机原料的方法

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EP0642810A2 true EP0642810A2 (de) 1995-03-15
EP0642810A3 EP0642810A3 (de) 1995-05-10

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EP94308592A Withdrawn EP0642810A3 (de) 1994-11-21 1994-11-21 Verfahren zur Wasserstoffbehandlung von organischen Einsätzen, die olefinische Verbindungen und einen Halogenteil enthalten.

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US5314614A (en) * 1992-06-17 1994-05-24 Uop Process for hydrotreating an organic feedstock containing olefinic compounds and a halogen component

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CN1123267A (zh) 1996-05-29

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