US20080300432A1 - Chemical Production Processes and Systems - Google Patents

Chemical Production Processes and Systems Download PDF

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US20080300432A1
US20080300432A1 US11/661,167 US66116705A US2008300432A1 US 20080300432 A1 US20080300432 A1 US 20080300432A1 US 66116705 A US66116705 A US 66116705A US 2008300432 A1 US2008300432 A1 US 2008300432A1
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olefin
production process
chemical production
mixture
reactor
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Vicki Hedrick
Stephan Brandstadter
Janet Boggs
Mitchel Cohn
Venkat Reddy Ghojala
P.V. Ramachandran
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Great Lakes Chemical Corp
PCBU Services Inc
Purdue Research Foundation
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/20—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising free carbon; comprising carbon obtained by carbonising processes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
    • C07C17/04—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C07C17/21—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms with simultaneous increase of the number of halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/19—Halogenated dienes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/19—Halogenated dienes
    • C07C21/20—Halogenated butadienes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00002—Chemical plants
    • B01J2219/00004—Scale aspects
    • B01J2219/00006—Large-scale industrial plants
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Definitions

  • the present invention relates to the field of chemical production processes and systems and more specifically to the production of conjugated olefins and systems for producing conjugated olefins.
  • C 4 F 6 Hexafluoro-1,3-butadiene
  • C 4 F 6 is just one example of a conjugated olefin that can be prepared according to the processes and systems described herein.
  • Chemical production processes include reacting a metal comprising olefin to form a conjugated olefin; reacting a heterohalogenated olefin to form a conjugated olefin; reacting a halogenated alkane to form a conjugated olefin; and/or reacting a hydrohalogenated olefin to form a conjugated olefin.
  • Chemical production systems can include: a first reactant reservoir configured to house a perhalogenated olefin; a second reactant reservoir configured to house a catalyst mixture; a first reactor coupled to both the first and second reservoirs with the first reactor configured to house a metal-comprising mixture and receive both the perhalogenated olefin from the first reactant reservoir and the reactant mixture from the reservoir; and a product collection reservoir coupled to the first reactor and configured to house a conjugated olefin.
  • FIG. 1 is an exemplary system for preparing compositions according to an embodiment.
  • FIG. 2 is an exemplary system for preparing compositions according to an embodiment.
  • FIG. 3 is an exemplary system for preparing compositions according to an embodiment.
  • a system 10 that includes a reaction zone 11 coupled to a heterohalogenated olefin reservoir 12 , a metal-comprising mixture reservoir 13 and a reactant mixture reservoir 14 .
  • System 10 also includes a product recovery zone 16 and a recycle conduit 15 configured to return by-products separated from products in zone 16 to reaction zone 11 .
  • reaction zone 11 can include a single reactor or a plurality of reactors.
  • the reactor can be constructed of glass and/or a nickel-alloy such as Inconel® 600 (Special Metals Corporation 3200 Riverside Drive Huntington, W. Va. 25705-1771, USA). These reactors can be configured to control the temperature within the reactor via cooling coils and/or heat tape, for example, depending on the requirements of the temperature within the reactor.
  • the reactor can also be configured to control the pressure within the reactor during the combination of reactants.
  • system 10 can be configured to react a metal-comprising olefin to form a conjugated olefin.
  • the reacting can include exposing the metal-comprising olefin to a reactant mixture to form the conjugated olefin, for example.
  • This exposing can include providing the metal-comprising olefin to within the reactor and providing a reactant mixture to within the reactor.
  • Exemplary embodiments include maintaining the temperature of the contents of the reactor during the providing of the catalyst mixture.
  • the providing of the metal-comprising olefin can include reacting a heterohalogenated olefin from heterohalogenated olefin reservoir 12 to form the metal-comprising olefin.
  • the heterohalogenated olefin of heterohalogenated olefin reservoir 12 can include a C-2 olefin.
  • the heterohalogenated olefin can also include F and one or more of Cl, Br, and/or I.
  • the heterohalogenated olefin can be C 2 F 3 Br and/or
  • a metal-comprising mixture from metal-comprising mixture reservoir 13 can be provided to reaction zone 11 .
  • This mixture can be in the form of a slurry and can include one or more elements from groups 1, 2, 4, 8, 11, 12, and/or 14 of the periodic table of elements and in specific embodiments zinc, as well as, a composition including tetrahydrofuran and/or a polar aprotic solvent such as one or more of acetonitrile, methyl-ethyl-ketone, dimethylformamide, and/or dimethylsulfoxide.
  • the elements may be activated and/or unactivated, for example, unactivated Zn may be utilized.
  • compositions may be anhydrous and/or contain small amounts of water, such as amounts as high as 0.15% (wt./wt.).
  • a composition of one or more acetonitrile, tetrahydrofuran, methyl-ethyl-ketone, dimethylformamide, and dimethylsulfoxide may be provided to reaction zone 11 followed by providing a metal to zone 11 with the metal and the composition forming the metal-comprising mixture.
  • the metal-comprising mixture may be heated to a temperature of from about room temperature to about 120° C.
  • the temperature of the metal-comprising mixture can be maintained at from about 60° C. to about 70° C., and/or greater than 70° C.
  • the heterohalogenated olefin can be added from heterohalogenated olefin reservoir 12 to form the metal-comprising olefin.
  • the addition of the heterohalogenated olefin can be performed under atmospheric pressures and in other embodiments, system 10 can be closed and the addition can be performed under a vacuum such as 15 mm Hg.
  • the metal-comprising mixture may be heated to about 70° C. and a portion of the molar charge of the heterohalogenated olefin may be added to the mixture.
  • adding less than molar charge can initiate the production of the metal-comprising olefin.
  • the portion can be at least about 15% to 25% of the molar charge and combined with the metal-comprising mixture within zone 11 to produce the metal-comprising olefin.
  • adding the portion of the heterohalogenated olefin to initiate the production followed by adding the remainder of the olefin can facilitate temperature and/or pressure control of zone 11 which can also facilitate purification of the conjugated olefin where system 10 is a closed system.
  • a complete charge of the heterohalogenated olefin may be added to the metal-comprising mixture. Upon addition of the complete charge the system can be cooled to control exotherms.
  • system 10 is a closed system
  • the pressure may be controlled to regulate production and control reaction rates, as well as, efficiency.
  • the system may be maintained under vacuum.
  • the pressure of system 10 may be maintained below about 300 mm Hg and in other instances the pressure can be greater than 20 mm Hg.
  • the metal-comprising olefin can contain at least one element from groups 1, 2, 4, 8, 11, 12, and/or 14 of the periodic table of elements.
  • the element can be Zn, for example.
  • the metal-comprising olefin also can include one or more of F, Cl, Br, and/or I.
  • the metal-comprising olefin can be heterohalogenated in exemplary embodiments and/or perhalogenated.
  • the metal-comprising olefin can be a C-2 olefin and/or, according to exemplary embodiments, the metal-comprising olefin can include both F and Br. According to other embodiments, the metal-comprising olefin can include F, Br, and/or Zn.
  • the metal-comprising olefin is
  • the metal-comprising olefin can be prepared and, in exemplary embodiments, is stable for up to 4 days. As such, according to exemplary embodiments, the reactions can be performed in stages, at separate facilities and/or locations.
  • the metal-comprising olefin can be reacted to form a conjugated olefin by providing a reactant mixture from reactant mixture reservoir 14 to reactor zone 11 .
  • the reactant mixture can include one or more of Fe, Cu, Ni, and/or Mn.
  • the reactant mixture can also include a metal-halide composition and the metal-halide composition can comprise one or more of Fe, Cu, Ni, Mn, F, Cl, Br, and/or I.
  • the reactant mixture can also include one or both of polar aprotic solvents and/or non-polar solvents.
  • compositions that can be a component of the reactant mixture can include one or more of acetonitrile, tetrahydrofuran, methyl-ethyl-ketone, dimethylformamide, and dimethylsulfoxide.
  • the reactant mixture includes FeCl 3 .
  • Exemplary reactant mixtures can be stable for use for up to 4 days.
  • a product mixture including the conjugated olefin can be formed while providing the reactant mixture to zone 11 while maintaining the contents of the reaction zone at less than about 70° C., for example.
  • heating zone 11 to temperatures as high and or greater than 70° C. can facilitate efficient production of the conjugated olefin.
  • the product mixture can include approximately 60% conjugated olefin when zone 11 is maintained below 70° C., however when zone 11 is maintained above 70° C. product mixtures including as high as 90% conjugated olefin can be obtained.
  • the conjugated olefin formed can include one or more of F, Cl, Br, and/or I.
  • the conjugated olefin can be perhalogenated and/or homohalogenated.
  • the olefin can be perhalogenated with F, for example.
  • the conjugated olefin is a C-4 olefin.
  • the conjugated olefins can be
  • the conjugated olefin can be removed from reaction zone 11 and transferred to product recovery zone 16 .
  • the conjugated olefin can be removed by increasing the maintained temperature of the contents of the reaction zone 11 , for example. In exemplary embodiments, this can include increasing the temperature at least 15% above the maintained temperature; and/or from about 15% to about 30% above the maintained temperature. For example, where the maintained temperature is about 70° C. the conjugated olefin can be removed by increasing the temperature within reaction zone 11 to about 120° C.
  • the metal-comprising olefin can include
  • the reactant mixture can include FeCl 3 , and the temperature within the reaction zone upon addition of the reactant mixture to the metal-comprising olefin can be less than about 70° C.
  • the conjugated olefin can include
  • the temperature of the reactor can be increased to a temperature greater than about 80° C. to remove the conjugated olefin from the reactor.
  • the conjugated olefin within the product recovery zone 16 , can be purified.
  • This purification can include distilling and drying the conjugated olefin, for example.
  • the distilling can include providing a product mixture that includes the conjugated olefin and by-products to a distillation apparatus. At least a portion of the mixture can be converted to the gas phase with the portion being converted to the gas phase including at least a portion of the conjugated olefin within the product mixture. A distillate can be recovered comprising the portion of the conjugated olefin with the distillate comprising less by-products than the product mixture.
  • the conjugated olefin can be dried by exposing a product mixture including the conjugated olefin to one or both of a 3 ⁇ absorbent and/or a 13 ⁇ molecular sieve, for example. During this exposing to the 3 ⁇ absorbent and/or the 13 ⁇ molecular sieve, the product mixture can be in a liquid phase, for example.
  • reaction mixture in a separate flask that can be coupled with the reaction flask and equipped with a supplying tube having a needle valve (Teflon), an agitator, and a reflux condenser, 1038 grams (6.4 moles) of ferric chloride (FeCl 3 ) and 1971 grams of DMF can be added to form an addition mixture. An exotherm can be observed when the DMF and FeCl 3 are combined.
  • the addition mixture can be added dropwise through the feeding tube to the surface of the organometallic mixture to form a reaction mixture.
  • a vacuum of about 10 cm Hg can be applied to the entire reaction system to assist in the delivering of the addition mixture to the organometallic mixture and subsequent removal of the product dimer.
  • the reaction mixture temperature can be held at about 70° C.
  • reaction mixture can be allowed to warm to from about 80° C. to about 85° C. (feed time range from 9-582 minutes) to facilitate removal of hexafluoro-1,3-butadiene product from reaction mixture into the product collecting container chilled by a dry ice and acetone bath.
  • product collecting container 384 grams (2.37 moles) of hexafluoro-1,3-butadiene product can be collected having a purity by gas chromatography of about 93 percent.
  • a reaction flask that can be equipped with an agitator, jacketing, a thermocouple, reflux condenser, a product collecting container, a vacuum pump, and a feeding tube which can be slidably coupled to a neck of the flask
  • 100 grams of acetonitrile and 20 grams (0.31 mole) of zinc can be placed to form a mixture.
  • the mixture can be heated to from about 47° C. to about 78° C. and bromotrifluoroethylene can be fed into the reactor over a period of about 95 minutes to form a reaction mixture.
  • the reaction mixture can be observed to change from having a grey color to having a greenish color.
  • the reaction mixture can be heated to about 60° C. and held for from about 15 hours to about 21 hours, and/or about 18 hours whereupon a color change can be observed from greenish to brownish.
  • the flask can be equipped with an addition funnel containing a reactant mixture.
  • the reactant mixture can be prepared by mixing 26.7 grams (0.165 mole) of ferric chloride and 48.1 grams of acetonitrile whereupon an exotherm can be observed.
  • the reactant mixture can be added dropwise to the reaction mixture over a period of about 20 minutes to form a product mixture.
  • the product mixture can contain hexafluoro-1,3-butadiene, which can be collected in the product collecting container.
  • the reactant mixture can be added to the reaction mixture while removing the hexafluoro-1,3-butadiene product from the product mixture, for example.
  • the remainder of product can be driven out of the product mixture by heating to about 80° C. until no more gas evolution can be observed.
  • a total of 4.6 grams of the product can be collected.
  • the product structure as well as reaction efficiency can be confirmed by GC/MS analysis.
  • reaction flask that can be equipped with an agitator, jacketing, a thermocouple, reflux condenser, a product collecting container, a vacuum pump, and a feeding tube which can be slidably coupled to a neck of the flask
  • 101 grams of tetrahydrofuran (THF) and 20 grams (0.31 mole) of zinc can be placed to form a mixture.
  • the mixture can be heated to from about 60° C. to about 70° C. and a total of 23.37 grams (0.145 mole) of bromotrifluoroethylene can be fed into the reactor over a period of about 90 minutes to form a reaction mixture.
  • the reaction mixture can be observed to change from having a grey color to having a greenish color.
  • the reaction mixture can be heated to about 60° C. and held for from about 15 hours to about 21 hours, and/or about 18 hours.
  • the flask can be equipped with an addition funnel containing a reactant mixture.
  • the reactant mixture can be prepared by mixing 27.6 grams (0.17 mole) of ferric chloride and 68 grams of tetrahydrofuran (THF).
  • THF tetrahydrofuran
  • the reactant mixture can be added dropwise to the reaction mixture over a period of about 20 minutes to form a product mixture.
  • the product, hexafluoro-1,3-butadiene can be collected from the product mixture in the product collecting container.
  • While adding the reactant mixture to the reaction mixture product can be recovered from the product mixture.
  • the remainder of product can be driven out of the product mixture by heating to about 60° C. until no more gas evolution can be observed affording about 6 grams total.
  • the product structure, as well as, reaction efficiency can be confirmed by GC/MS analysis.
  • a reaction flask that can be equipped with an agitator, jacketing, a thermocouple, reflux condenser, a product collecting container, a vacuum pump, and a feeding tube which can be slidably coupled to a neck of the flask
  • 100 grams of methyl-ethyl-ketone (MEK) and 20 grams (0.31 mole) of zinc can be placed to form a mixture.
  • MEK methyl-ethyl-ketone
  • the mixture can be heated to from about 50° C. to about 70° C. and a total of 20.42 grams (0.13 mole) of bromotrifluoroethylene can be fed into the reactor over a period of about 90 minutes to form a reaction mixture.
  • the reaction mixture can be heated to about 60° C.
  • the flask can be equipped with an addition funnel containing a reactant mixture.
  • the reactant mixture can be prepared by mixing 27.8 grams (0.171 mole) of ferric chloride and 48.4 grams of MEK whereupon an exotherm can be observed.
  • the reactant mixture can be added dropwise to the reaction mixture over a period of about 5 minutes to form a product mixture.
  • the product, hexafluoro-1,3-butadiene can be collected from the product mixture in the product collecting container. While adding the reactant mixture, the product can collected from the product mixture. A remainder of product can be driven out of the product mixture by heating the mixture to about 80° C. until no more gas evolution can be observed. A total of 2.0 grams of the product can be collected.
  • the product structure, as well as, reaction efficiency can be confirmed by GC/MS analysis.
  • a reaction flask that can be equipped with an agitator, jacketing, a thermocouple, reflux condenser, a product collecting container, a vacuum pump, and a feeding tube which can be slidably coupled to a neck of the flask
  • DMSO dimethyl sulfoxide
  • the mixture can be heated to from about 57° C. to about 85° C. and a total of 20.2 grams (0.125 mole) of bromotrifluoroethylene can be fed into the reactor over a period of about 45 minutes to form a reaction mixture.
  • the reaction mixture can be observed to change from having a grey color to having a greenish color.
  • the reaction mixture can be heated to about 60° C. and held for from about 15 hours to about 21 hours, and/or about 18 hours.
  • the flask can be equipped with an addition funnel containing a reactant mixture.
  • the reactant mixture can be prepared by mixing 28 grams (0.174 mole) of ferric chloride and 52 grams of DMSO.
  • the reactant mixture can be added dropwise to the reaction mixture over a period of about 10 minutes to form a product mixture.
  • the product, hexafluoro-1,3-butadiene, can be collected from the product mixture in the product collecting container.
  • the product While adding the reactant mixture, the product can be removed from the product mixture. The remainder of product can be driven out of the product mixture by heating the product mixture to about 80° C. until no more gas evolution can be observed. A total of 1.7 grams of the product can be collected. The product structure, as well as, reaction efficiency can be confirmed by GC/MS analysis.
  • the initial mixture can be observed to turn brown and can be stirred further for 1 hour at room temperature to form the trifluorovinylzinc bromide.
  • the flask can be fitted with an addition funnel containing a reactant mixture.
  • the initial mixture can be cooled to 0-5° C., a vacuum of approximately 100 mm Hg can be applied, and 0.033 mole of the reactant mixture including, for example ferric salt [FeCl 3 (in some embodiments, added as a solution in dimethylformamide), FeBr 3 , Fe(OAc) 3 ] and/or cupric salt [Copper triflate, CuBr 2 , Cu(OAc) 2 ] can be added slowly to the initial mixture while maintaining the reaction temperature at less than about 5° C.
  • reaction mixture containing the hexafluoro-1,3-butadiene product.
  • Most of the product can be collected in the cold (dry ice-acetone) trap. A remainder of the product can be collected by warming the product mixture to about 40° C. and stirring for 2 hours while maintaining the vacuum.
  • a yield of the reactions can range from about 60-68% as confirmed by GC/MS. Yields can be correlated with the catalysts utilized in accordance with Table 1, below.
  • Lithium diisopropyl amine (1.8 M solution in heptane/tetrahydrofuran (THF), 0.064 mole) can be added slowly via a syringe to the slurry, while maintaining the temperature at less than about 15° C. to form a reaction mixture.
  • the tip of the needle of the syringe can be dipped into the slurry to avoid decomposition of trifluorovinyllithium formed by a reaction of HFC-134a with lithium diisopropyl amine).
  • the reaction mixture can be stirred for 1 hour and allowed to warm to room temperature.
  • the reaction mixture can then be cooled to from about 0° C. to about 5° C. while applying vacuum (100 mm Hg).
  • Ferric salt FeCl 3 , FeBr 3 , 0.033 mole
  • cupric salt Copper triflate, Cu(OAc) 2
  • Yields can be from about 65-70%.
  • the reaction mixture can be stirred at room temperature for over night.
  • the product can be distilled at 30-42° C. under nitrogen to obtain 34 grains (62%) of the trifluorovinyl iodide product.
  • Similar reaction chemistries can be used to prepare compounds such as trifluorovinyl chloride and trifluorovinyl bromide as well.
  • 8.5 grams (0.132 mole) of activated copper powder and 50 mL of dry dimethylformamide can be added to a 100 mL round bottom flask having a side arm and fitted with a reflux condenser to form a slurry.
  • the activated copper powder can be prepared according to A. I. Vogel, Textbook of Practical Organic Chemistry, 5th Ed. Page No. 426, herein incorporated by reference.
  • 20 grams of copper powder can be exposed to 200 mL of 2% solution of iodine in acetone for 10 minutes to form a grayish colored mixture.
  • the mixture can be filtered and washed with 100 mL of a 1:1 solution of concentrated HCl in acetone.
  • the filtrate of the filtered mixture can be dried under vacuum at 40-50° C.
  • trifluorovinyl iodide 25 grams (0.120 mole) can be added slowly and kept stirring at room temperature to form a reaction mixture.
  • the reaction mixture can be stirred at room temperature for one hour and the product can be collected in a cold trap ( ⁇ 78° C.) with the following results: yield: 6.5 g (67%); conversion 77%; selectivity 74%; mass balance >99%; crude reaction mixture can contain 57% C 4 F 6 , 23% iodotrifluoroethylene (starting material), and 20% trifluoroethylene (by-product).
  • Qualitative and quantitative analyses can be determined by gas chromatography mass spectrometry utilizing total area counts.
  • System 20 includes at least two reaction zones, reaction zone 11 as previously described and coupled to reaction zone 21 .
  • System 20 also includes a heterohalogenated alkane reservoir 12 which also can be considered a portion of the product recovery zone of reaction zone 21 .
  • System 20 also includes a recycling conduit 15 that can be coupled between reactors 11 and 21 , as well as, product recovery zone 16 .
  • the halogenated alkane within halogenated alkane reservoir 22 can include one or more of F, Cl, Br, and I.
  • the halogenated alkane can be a C-2 alkane and/or the halogenated alkane can be heterohalogenated.
  • the halogenated alkane can have the general formula C 2 HF 3 Br 2 and in specific embodiments can be
  • the reducing-reagent mixture can include a base.
  • the base can be NaOH and/or KOH, for example.
  • that base can be KOH and water.
  • Other mixtures can include NaOH and/or KOH and methanol.
  • the reducing-reagent mixture can include a 40% (wt./wt.) mixture of KOH and water.
  • Reaction zone 21 can be configured to expose the halogenated olefin from halogenated olefin reservoir 22 to the reducing-reagent mixture from reducing-reagent mixture reservoir 23 .
  • the reducing-reagent mixture can be provided from reservoir 23 to the reaction zone and then the halogenated olefin exposed to the reducing reagent mixture within the reaction zone to form a heterohalogenated olefin.
  • the halogenated alkane can be reacted to form a heterohalogenated olefin and the heterohalogenated olefin can be reacted to form a conjugated olefin, for example, by transferring the heterohalogenated olefin produced in reaction zone 21 to reaction zone 11 and reacting the olefin as described above.
  • the heterohalogenated olefin can be prepared from the halogenated alkane in accordance with scheme 6 below, for example.
  • a mixture including 40 (wt/wt) % KOH in water can be provided to a glass-lined reactor equipped with an agitating apparatus.
  • Dibromodifluoroethane can be added to the reactor above the surface of the mixture at about 76° C., ambient pressure, and flow rates of from about 1.3 grams per minute to about 5.1 grams per minute.
  • reaction zone 31 can be configured to be a plurality of reactors and in exemplary embodiments reaction zone 31 can be configured as system 20 previously described or as system 10 previously described. In such configurations, reaction zone 31 can be coupled to a halogenated alkane reservoir 33 , which can form a portion of the product recovery reservoir of reaction zone 32 .
  • the halogenated alkane can be produced within reaction zone 32 by reacting a hydrohalogenated olefin from a hydrohalogenated olefin reservoir 34 to form the halogenated alkane.
  • the hydrohalogenated olefin within hydrohalogenated olefin reservoir 34 can comprise one or more of F, Cl, Br, and/or I.
  • the hydrohalogenated olefin can be a C-2 olefin such as C 2 HF 3 and in exemplary embodiments can be
  • System 30 also includes a halogenating reagent reservoir 35 coupled to reaction zone 32 .
  • the halogenating reagent of the halogenating reagent reservoir can comprise one or more of F, Cl, Br, and/or I.
  • the halogenating reagent can include Br 2 .
  • a hydrohalogenated olefin can be reacted to form a halogenated alkane and the halogenated alkane can be reacted to form a conjugated olefin.
  • the hydrohalogenated olefin can be reacted to form a conjugated olefin.
  • the reacting of the hydrohalogenated olefin to form the halogenated alkane can include configuring reaction zone 32 to expose the hydrohalogenated olefin to the halogenating reagent from halogenating reagent reservoir 35 .
  • the hydrohalogenated olefin from hydrohalogenated olefin reservoir 34 can be provided to within reaction zone 32 and the hydrohalogenated olefin provided therein can be exposed to the halogenating reagent to form the halogenated alkane.
  • System 30 can also include recycle conduit 15 that can be coupled to reaction zone 31 and 32 as well as halogenated product recovery zone 16 .
  • the recycled conduits of systems 10 , 20 , and 30 can be configured to receive at least one by-product from product reservoirs of those systems and convey those by-products to previous points in the systems for conversion of those by-products to the sought after products such as the conjugated olefin. Exemplary aspects of system 30 are described with reference to scheme (7) below.
  • the mixture can be observed to turn from deep red to semi-clear in color whereupon the incandescent light can be removed and the crude mixture can be charged to a separation funnel where it can be washed sequentially with saturated sodium bicarbonate solution and water.
  • the resulting clear oil can be dried over magnesium sulfate, filtered, and distilled to afford the 1,2-dibromo-1,1,2-trifluoroethane product.
  • a metal (Inconel® or Hastelloy®) tube reactor can be charged with the appropriate amount of activated carbon and heated by a furnace to about 150° C.
  • equal molar amounts of 1,1,2-trifluoroethene and elemental bromine can be fed at such a rate that they are consumed resulting in a semi-clear (reddish) liquid which can be collected in a flask cooled with dry ice.
  • the liquid can be charged to a separation funnel where it can be washed sequentially with saturated sodium bicarbonate solution and water.
  • the resulting clear oil can be dried over magnesium sulfate, filtered, and distilled to afford the 1,2-dibromo-1,1,2-trifluoroethane product.
  • Chemical production processes can include providing a heterohalogenated olefin and a reducing reagent to within a reactor and reacting the olefin with the reducing agent within the reactor with at least the olefin being in the liquid phase during the reacting.
  • the heterohalogenated olefin can include C 2 CIF 3 and the reducing reagent can include H, such as H 2 .
  • a catalyst composition may also be provided to the reactor, the catalyst composition can include one or both of Pd and/or C, such as activated carbon.
  • An organic media may be provided to the reactor as well. The media can include methanol, for example.
  • methanol can be added and cooled to about ⁇ 10° C.
  • a sufficient amount of a 10% (wt./wt.) palladium on activated carbon (Pd/AC) composition To the methanol can be added a sufficient amount of a 10% (wt./wt.) palladium on activated carbon (Pd/AC) composition.
  • Pd/AC palladium on activated carbon
  • CTFE chlorotrifluoroethylene
  • the reactor can then be sealed, evacuated, and purged with hydrogen (H 2 ) twice.
  • the reactor can then be heated to from about 30 to about 40° C. and then pressurized to 6 Kg/cm 2 of H 2 .
  • CTFE and H 2 can then be fed simultaneously to the reactor using a 20% molar ratio excess of H 2 to CTFE.
  • the reactor pressure may increase, and when the pressure within the reactor reaches the desired operating pressure (1-12 Kg/cm 2 ), the product trifluoroethylene (TriFE), CTFE, and H 2 can be removed which can result in a 50% conversion of CTFE to TriFE.
  • TriFE trifluoroethylene
  • a crude reaction mixture can assay as high as 70% TriFE by GC.
  • the crude reaction mixture can then be fed into another reactor (equipped with an agitator), and the reactor can be charged with elemental bromine (Br 2 ) at 50° C. while H 2 can be removed via a column connected to the reactor and fitted with a cooled condenser.
  • Another crude reaction mixture can then be separated by distillation giving the desired 1,2-dibromo-1,1,2-trifluoroethylene (DBTFE) as a overhead condensate.
  • DBTFE 1,2-dibromo-1,1,2-trifluoroethylene
  • the perhalogenated olefin can be produced according to scheme (9) below from the starting material perchloroethene.

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  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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US9902672B2 (en) 2014-08-25 2018-02-27 Asahi Glass Company, Limited Method for producing hydrofluoroolefin
US9988327B2 (en) 2014-08-25 2018-06-05 Asahi Glass Company, Limited Process for producing hydrofluoroolefin
US11046629B2 (en) 2018-02-02 2021-06-29 Kanto Denka Kogyo Co., Ltd. Method of producing compound having butadiene skeleton containing hydrogen and fluorine and/or chlorine
TWI818190B (zh) * 2019-08-13 2023-10-11 日商大金工業股份有限公司 1,1,2-三氟乙烯、六氟-1,3-丁二烯或1,2-二氯六氟環丁烷的製造方法、含有1,2-二氯六氟環丁烷與六氟-1,3-丁二烯之組成物，以及含有1,1,2-三氟乙烯與六氟-1,3-丁二烯之組成物

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JP5738021B2 (ja) * 2010-08-26 2015-06-17 国立大学法人大阪大学 ヘキサフルオロ−１，３−ブタジエンの製造方法
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FR2987358B1 (fr) * 2012-02-28 2016-10-21 Arkema France Procede de synthese du trifluoroethylene a partir du chlorotrifluoroethylene
JP5738486B2 (ja) * 2012-05-14 2015-06-24 国立大学法人大阪大学 ハロゲン化含フッ素（シクロ）アルケニル亜鉛化合物の製造方法
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JP2016128415A (ja) * 2014-12-18 2016-07-14 国立大学法人大阪大学 含フッ素（シクロ）アルケニル基を有するフッ素化合物の製造方法
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JP6963263B2 (ja) * 2019-12-27 2021-11-05 ダイキン工業株式会社 ハロゲン化含フッ素（シクロ）アルケニル亜鉛化合物の製造方法
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KR102701981B1 (ko) * 2021-09-23 2024-09-05 주식회사 진성이엔지 1,4-디브로모-2,3-디클로로헥사플루오로부탄 제조 방법 및 이를 이용한 헥사플루오로-1,3-부타디엔 제조 방법
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120302804A1 (en) * 2010-02-16 2012-11-29 Central Glass Company, Limited Method for Producing 3,3,3-Trifluoro Propene
EP2514735A4 (en) * 2010-02-16 2013-09-04 Central Glass Co Ltd PROCESS FOR THE PREPARATION OF 3,3,3-TRIFLUOR PROPENES
US8664457B2 (en) * 2010-02-16 2014-03-04 Central Glass Company, Limited Method for producing 3,3,3-trifluoropropene
US9902672B2 (en) 2014-08-25 2018-02-27 Asahi Glass Company, Limited Method for producing hydrofluoroolefin
US9988327B2 (en) 2014-08-25 2018-06-05 Asahi Glass Company, Limited Process for producing hydrofluoroolefin
US10781151B2 (en) 2014-08-25 2020-09-22 AGC Inc. Process for producing hydrofluoroolefin
US11046629B2 (en) 2018-02-02 2021-06-29 Kanto Denka Kogyo Co., Ltd. Method of producing compound having butadiene skeleton containing hydrogen and fluorine and/or chlorine
TWI818190B (zh) * 2019-08-13 2023-10-11 日商大金工業股份有限公司 1,1,2-三氟乙烯、六氟-1,3-丁二烯或1,2-二氯六氟環丁烷的製造方法、含有1,2-二氯六氟環丁烷與六氟-1,3-丁二烯之組成物，以及含有1,1,2-三氟乙烯與六氟-1,3-丁二烯之組成物

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