WO2013078035A1 - Process for the production of chlorinated alkanes - Google Patents

Process for the production of chlorinated alkanes Download PDF

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Publication number
WO2013078035A1
WO2013078035A1 PCT/US2012/064792 US2012064792W WO2013078035A1 WO 2013078035 A1 WO2013078035 A1 WO 2013078035A1 US 2012064792 W US2012064792 W US 2012064792W WO 2013078035 A1 WO2013078035 A1 WO 2013078035A1
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WO
WIPO (PCT)
Prior art keywords
tetra
tri
pentachlorinated
alkane
alkanes
Prior art date
Application number
PCT/US2012/064792
Other languages
English (en)
French (fr)
Inventor
Matthew Lee GRANDBOIS
William J. Kruper
Original Assignee
Dow Global Technologies, Llc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dow Global Technologies, Llc filed Critical Dow Global Technologies, Llc
Priority to CA2856271A priority Critical patent/CA2856271A1/en
Priority to EP12791389.5A priority patent/EP2782889B1/en
Priority to IN3748CHN2014 priority patent/IN2014CN03748A/en
Priority to CN201280057105.XA priority patent/CN104039744B/zh
Priority to JP2014542375A priority patent/JP6050372B2/ja
Priority to US14/358,079 priority patent/US9067855B2/en
Publication of WO2013078035A1 publication Critical patent/WO2013078035A1/en

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Classifications

    • 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
    • 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
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms

Definitions

  • the present invention relates to processes for the production of chlorinated alkanes, and in particular, to processes for the production of tri-, tetra- and pentachlorinated alkanes.
  • Hydrofluorocarbon (HFC) products are widely utilized in many applications, including refrigeration, air conditioning, foam expansion, and as propellants for aerosol products including medical aerosol devices. Although HFC's have proven to be more climate friendly than the chlorofluorocarbon and hydrochlorofluorocarbon products that they replaced, it has now been discovered that they exhibit an appreciable global warming potential (GWP).
  • GWP global warming potential
  • HFO hydrofluoroolefin
  • HFO compounds such as 2,3,3, 3-tetrafluoroprop-l-ene or 1,3,3,3- tetrafluoroprop-l-ene, may typically be produced utilizing feedstocks of chlorocarbons, and in particular, highly chlorinated alkanes, e.g., tri -, tetra- and pentachloroalkanes.
  • the present invention provides efficient processes for the production of chlorinated alkanes. More particularly, the processes make use of one or more mono- and/or dichloroalkanes to produce tri-, terra-, and pentachloroalkanes with high selectivity. In some embodiments, the processes advantageously make use of 1,2-dichloropropane, a by-product in the production of chlorohydrin, as a low cost starting material. Selectivity of the process is enhanced over conventional chlorination processes by employing a Lewis acid as an ionic chlorination catalyst, instead of the catalyst systems comprising multiple catalysts required by the conventional processes. Further cost savings are provided in that low intensity process conditions, e.g., low temperatures, ambient pressure and minimal reactor residence time, are utilized.
  • low intensity process conditions e.g., low temperatures, ambient pressure and minimal reactor residence time
  • the present invention provides a process for the production of tri-, tetra, and/or pentachlorinated alkanes from one or more mono and/or dichlorinated alkanes.
  • the process comprises chlorinating the one or more mono and/or dichlorinated alkane in the presence of one ionic chlorination catalyst.
  • the mono and/or dichlorinated alkane is a vicinal dichlorinated alkane, e.g., a 1,2-dichloroalkane, and in such embodiments, the corresponding trichlorinated alkane, e.g., a 1 , 1 ,2-trichloroalkane, may be produced with a regioselectivity of at least 20: 1, or at least 30: 1, or at least 40: 1, or even at least 50: 1.
  • the dichlorinated alkane may be 1,2-dichloropropane and the trichlorinated alkane may be 1, 1,2-trichloropropane.
  • the chlorinating agent is desirably a liquid, and in some embodiments, may desirably be sulfuryl chloride.
  • the ionic chlorination catalyst is desirably a Lewis acid catalyst, such as aluminum chloride, and advantageously, the process requires only the use of one such catalyst.
  • the process is desirably conducted at low intensity conditions, e.g., a reaction temperature of from 55°C to 65°C, ambient pressure, and with a reactor residence time of 1 hour or less.
  • first”, “second”, and the like, as used herein do not denote any order, quantity, or importance, but rather are used to distinguish one element from another. Also, the terms “a” and “an” do not denote a limitation of quantity, but rather denote the presence of at least one of the referenced item, and the terms “front”, “back”, “bottom”, and/or “top”, unless otherwise noted, are merely used for convenience of description, and are not limited to any one position or spatial orientation.
  • PDC 1,2-dichloropropane
  • TCP 1,2,3-trichloropropane
  • the present invention provides efficient processes for the production of chlorinated alkanes.
  • the present processes comprise reacting one or more mono-and/or dichloroalkanes to tri-, tetra- and/or pentachloroalkanes, with high regioselectivity, e.g., to 1,1,2- trichloroalkanes, 1, 2,2,3 -tetrachloropropane and/or 1,1, 2,2,3 -pentachloropropane.
  • only one catalyst is required, and desirably comprises a Lewis acid catalyst.
  • the present processes make use of sulfuryl chloride as a chlorinating agent, rather than a gaseous chlorinating agent such as chlorine gas.
  • sulfuryl chloride is not only advantageous in that it is easier to transport and utilize than gaseous chlorinating agents, but also because, since it is a liquid, it can also serve as a solvent for the reaction and desired catalyst.
  • the process uses lower intensity process conditions than at least some conventional processes, and thus, operating costs are saved.
  • the present process can make use of one or more mono-and/or dichlorinated alkanes to produce the desired tri-, tetra- and or pentachlorinated alkanes.
  • at least one of the chlorinated alkanes is a vicinal dichlorinated alkane, i.e., the chlorine atoms are present on adjacent carbon atoms.
  • the use of vicinal dichlorinated alkanes is advantageous in that it contributes to the regioselectivity provided by the process.
  • any alkane can be utilized in the process, although alkanes comprising from 2-10 carbon atoms, or from 2-8 carbon atoms, or from 2-6 carbon atoms, or from 2-5 carbon atoms, or from 2-4 carbon atoms, or from 2-3 carbon atoms, are particularly suitable.
  • one of the mono- and/or dichlorinated alkanes comprises mono- or dichlorinated propane, and in those embodiments wherein the dichlorinated alkane is desirably vicinal, comprises 1,2-dichloropropane.
  • 1,2-dichloropropane as a feedstock for the process is advantageous, since it may be available at low cost due to its production as a by-product in many chlorohydrin processes.
  • the one or more mono- and/or dichlorinated alkanes may be generated within the process, if desired, by any methods known to those of ordinary skill in the art.
  • the tri-, tetra-, and/or pentachlorinated alkane produced by the process will depend upon the mono-and/or dichlorinated alkane used as a starting material, and so, in some embodiments, and due to the commercial significance of trichlorinated ethanes, propanes and butanes, the use of one or more mono and/or dichlorinated ethanes, propanes and butanes as starting materials may be preferred.
  • 1 ,2-dichloropropane is utilized as a starting material to produce 1, 1,2-trichloropropane at high selectivity, while in others a combination of monochloropropane and 1,2-dichloropropane is utilized as a starting material to produce 1, 2,2,3 -tetrachloropropane and/or 1, 1, 1,2,3-pentachloropropane and 1, 1,2,2,3- pentachloropropane.
  • the one or more chlorinated alkane is advantageously chlorinated using a liquid chlorinating agent, such as sulfuryl chloride.
  • a liquid chlorinating agent is advantageous compared to the use of a gaseous chlorinating agent, such as chlorine gas, since a liquid is easier to transport and/or handle than a gaseous chlorinating agent.
  • Chlorine gas in particular, can present a safety hazard.
  • Liquid chlorinating agents, and in particular, sulfuryl chloride (SO 2 CI 2 ) can also act as a solvent for certain catalyst systems and/or reactions, thereby assisting in the provision of an acceptable reaction rate and/or yield. And so, in some embodiments, sulfuryl chloride may desirably be used as the chlorinating agent.
  • a Lewis acid as an ionic chlorination catalyst.
  • anhydrous aluminum chloride although known as a component of a multicatalyst system for the chlorination of alkanes, when used alone, assists in providing a high degree of specificity to the desired tri-, tetra- and/or pentachloroalkane, e.g., a 1, 1,2-trichloroalkane, 1,2,2,3- tetrachloropropane and/or 1, 1,2,2, 3-pentachloropropane.
  • aluminum chloride has conventionally been utilized with at least one other catalyst, oftentimes iodine and/or ferric chloride, as a component of a free radical initiator system that often requires the additional use of an initiator, such as ultraviolet light.
  • aluminum chloride may be used as an ionic chlorination catalyst, and in combination with sulfuryl chloride as a chlorinated agent, acts to transform one or more mono- and/or dichloroalkanes, which in some embodiments may comprise a vicinal dichloroalkane, to the corresponding 1,1,2-trichloroalkane, 1,2,2,3-tetrachloropropane and/or 1, 1,2,2, 3-pentachloropropane with regioselectivities of greater than 10: 1, or greater than 20: 1 or greater than 30: 1 or even at a 40: 1 ratio, or greater, over other tri-, tetra- and pentachloroalkane products.
  • the reaction conditions under which the process is carried out are advantageously low intensity. That is, low temperatures, e.g., of less than 100°C, or less than 90°C, or less than 80°C or less than 70°C, or less than 60°C, or less than 50°C, or even as low as 40°C may be utilized and the desired selectivities to the tri-, terra-, and/or pentachloroalkanes yet be realized. In some embodiments, temperatures of from 40°C to 70°C, or 55°C to 65°C may be utilized.
  • ambient pressure is suitable for carrying out the process, or pressures within 250, or 200, or 150, or 100, or 50, or 40, or 30, or 20, or even lOpsi, of ambient are suitable.
  • Reactor occupancy may also be minimized with the desired selectivities yet seen - for example, reactor occupancy times of less than 20 hours, or less than 15 hours, or less than 10 hours, or less than 5 hours, or less than 4, 3, 2, or even 1 hour, are possible.
  • the reactor may be any suitable liquid phase reactor, such as a batch or continuous stirred tank autoclave reactor with an internal cooling coil. A shell and multitube exchanger followed by vapor liquid disengagement tank or vessel can also be used.
  • 1,2-dichloropropane is converted to 1, 1,2- trichloropropane at selectivities of, e.g., 40: 1 over other trichloroalkane products, by reacting 1,2-dichloropropane with sulfuryl chloride in the present of aluminum chloride at a temperature of from 55°C to 65°C, ambient pressure and a reactor occupancy of less than one hour.
  • monochloropropane is converted 1, 1,2,2,3- pentachloropropane at selectivities of, e.g., 40: 1 over other trichloroalkane products, by reacting monochloropropane with sulfuryl chloride in the presence of aluminum chloride at a temperature of from 55°C to 65°C, ambient pressure, and a reactor occupancy of 24-48 hours.
  • Example 1 Ionic Chlorination of PDC to TCP using aluminum chloride as catalyst and sulfuryl chloride as chlorinating agent.
  • Liquid sulfuryl chloride and PDC (1,2-dichloropropane) are mixed in a 100ml flask heated in a water bath to maintain temperature 55°C-60°C in the presence of aluminum chloride (AICI 3 ) catalyst.
  • a reflux column is placed to return unreacted reactants as well the reaction intermediate 1 -chloropropene to the reaction liquid while the HC1 and SO 2 byproducts are released to a caustic scrubber at the top of the reflux column.
  • Gas chromatography coupled with mass spectroscopy is used to determine the product composition.
  • Example 2 Comparative. Chlorination of PDC to TCP using aluminum chloride as catalyst and chlorine gas as chlorinating agent.
  • Liquid PDC and an inert solvent, carbon tetrachloride are mixed in a 100ml flask heated in a water bath to maintain a temperature of 55°C-60°C in the presence of AICI 3 catalyst.
  • a reflux column is placed to return unreacted reactants. Gaseous chlorine is bubbled into the liquid phase. Gas chromatography coupled with mass spectroscopy is used to determine the product composition.
  • Liquid sulfuryl chloride and PDC are mixed in a 100ml flask heated in a water bath to maintain a temperature of 55°C-60°C in the presence of A1C1 3 and I 2 catalyst.
  • a reflux column is placed to return unreacted reactants.
  • Gaseous chlorine is bubbled into the liquid phase.
  • Gas chromatography coupled with mass spectroscopy is used to determine the product composition.
  • Example 4 Ionic Chlorination of monochloropropane to TPC using aluminum chloride as catalyst and sulfuryl chloride as chlorinating agent.
  • Liquid sulfuryl chloride and 2-chloropropane are mixed in a 100ml flask heated in a water bath to maintain temperature 55°C-60°C in the presence of AICI 3 catalyst.
  • a reflux column is placed to return unreacted reactants as well the reaction intermediates to the reaction liquid while the HCl and SO2 byproducts are released to a caustic scrubber at the top of the reflux column.
  • Gas chromatography coupled with mass spectroscopy is used to determine the product composition.
  • Example 5 Ionic Chlorination of PDC to 1, 1,2,2,3-pentachloropropane using aluminum chloride as catalyst and sulfuryl chloride as chlorinating agent.
  • Liquid sulfuryl chloride and PDC are mixed in a 100ml flask heated in a water bath to maintain temperature 55°C-60°C in the presence of A1C1 3 catalyst.
  • a reflux column is placed to return unreacted reactants as well the reaction intermediates to the reaction liquid while the HCl and SO2 byproducts are released to a caustic scrubber at the top of the reflux column.
  • Gas chromatography coupled with mass spectroscopy is used to determine the product composition.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
PCT/US2012/064792 2011-11-21 2012-11-13 Process for the production of chlorinated alkanes WO2013078035A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
CA2856271A CA2856271A1 (en) 2011-11-21 2012-11-13 Process for the production of chlorinated alkanes
EP12791389.5A EP2782889B1 (en) 2011-11-21 2012-11-13 Process for the production of chlorinated alkanes
IN3748CHN2014 IN2014CN03748A (OSRAM) 2011-11-21 2012-11-13
CN201280057105.XA CN104039744B (zh) 2011-11-21 2012-11-13 制备氯化烷烃的方法
JP2014542375A JP6050372B2 (ja) 2011-11-21 2012-11-13 クロロアルカンの製造方法
US14/358,079 US9067855B2 (en) 2011-11-21 2012-11-13 Process for the production of chlorinated alkanes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201161562025P 2011-11-21 2011-11-21
US61/562,025 2011-11-21

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WO2013078035A1 true WO2013078035A1 (en) 2013-05-30

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US (1) US9067855B2 (OSRAM)
EP (1) EP2782889B1 (OSRAM)
JP (1) JP6050372B2 (OSRAM)
CN (1) CN104039744B (OSRAM)
CA (1) CA2856271A1 (OSRAM)
IN (1) IN2014CN03748A (OSRAM)
WO (1) WO2013078035A1 (OSRAM)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2791092A1 (en) * 2011-12-13 2014-10-22 Dow Global Technologies LLC Process for the production of chlorinated propanes and propenes
US8889930B2 (en) 2013-01-22 2014-11-18 Axiall Ohio, Inc. Process for producing chlorinated hydrocarbons
US9139497B2 (en) 2013-10-23 2015-09-22 Axiall Ohio, Inc. Process for producing chlorinated hydrocarbons in the presence of a polyvalent bismuth compound
US9169177B2 (en) 2011-12-22 2015-10-27 Blue Cube Ip Llc Process for the production of tetrachloromethane
US9284239B2 (en) 2011-12-02 2016-03-15 Blue Cube Ip Llc Process for the production of chlorinated alkanes
US9289758B2 (en) 2013-01-22 2016-03-22 Axiall Ohio, Inc. Processes for producing chlorinated hydrocarbons and methods for recovering polyvalent antimony catalysts therefrom
US9334205B2 (en) 2011-12-13 2016-05-10 Blue Cube Ip Llc Process for the production of chlorinated propanes and propenes

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CN108929192A (zh) 2011-08-07 2018-12-04 蓝立方知识产权有限责任公司 生产氯化的丙烯的方法
CN103717557A (zh) 2011-08-07 2014-04-09 陶氏环球技术有限责任公司 生产氯化的丙烯的方法
JP6059246B2 (ja) * 2011-12-02 2017-01-11 ブルー キューブ アイピー エルエルシー 塩素化アルカンの製造方法
BR112014015123A2 (pt) 2011-12-23 2017-06-13 Dow Global Technologies Llc processo para a produção de um ou mais alcenos ou compostos aromáticos
IN2014CN04544A (OSRAM) * 2011-12-23 2015-09-18 Dow Global Technologies Llc
CA2884435A1 (en) 2012-09-20 2014-03-27 Dow Global Technologies Llc Process for the production of chlorinated propenes
EP2897930A1 (en) 2012-09-20 2015-07-29 Dow Global Technologies LLC Process for the production of chlorinated propenes
EP2900364B1 (en) 2012-09-30 2018-06-13 Blue Cube IP LLC Weir quench and processes incorporating the same
CA2887559A1 (en) 2012-10-26 2014-05-01 Dow Global Technologies Llc Mixer and reactor and process incorporating the same
EP2935165A1 (en) 2012-12-18 2015-10-28 Blue Cube IP LLC Process for the production of chlorinated propenes
EP2935166A1 (en) 2012-12-19 2015-10-28 Blue Cube IP LLC Process for the production of chlorinated propenes
US9382176B2 (en) 2013-02-27 2016-07-05 Blue Cube Ip Llc Process for the production of chlorinated propenes
US9403741B2 (en) 2013-03-09 2016-08-02 Blue Cube Ip Llc Process for the production of chlorinated alkanes
WO2018009459A1 (en) 2016-07-05 2018-01-11 Occidental Chemical Corporation Photochlorination of chloroform to carbon tetrachloride
CN113329986A (zh) 2019-01-10 2021-08-31 西方化学股份有限公司 部分氯化的氯代甲烷光氯化成四氯化碳

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