WO2016156870A1 - Procédé - Google Patents

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Publication number
WO2016156870A1
WO2016156870A1 PCT/GB2016/050933 GB2016050933W WO2016156870A1 WO 2016156870 A1 WO2016156870 A1 WO 2016156870A1 GB 2016050933 W GB2016050933 W GB 2016050933W WO 2016156870 A1 WO2016156870 A1 WO 2016156870A1
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WO
WIPO (PCT)
Prior art keywords
process according
hydro
chloro
preparing
hfo
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PCT/GB2016/050933
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English (en)
Inventor
Claire REES
Maxine DORAN
Andrew Sharratt
Original Assignee
Mexichem Fluor S.A. De C.V.
Mexichem Uk Limited
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 Mexichem Fluor S.A. De C.V., Mexichem Uk Limited filed Critical Mexichem Fluor S.A. De C.V.
Publication of WO2016156870A1 publication Critical patent/WO2016156870A1/fr

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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

Definitions

  • the present invention relates to a process for preparing (hydro)haloalkenes and particularly to a process for preparing C3-7 (hydro)haloalkenes by the catalytic dehydrohalogenation of C3-7 hydrohaloalkanes.
  • C3-7 (hydro )fluoroalkenes such a hydrofluoropropenes can be conveniently prepared from corresponding hydro(halo)fluoroalkanes by dehydrohalogenation.
  • the transformation can be effected thermally, i.e. by pyrolysis, catalytically, by contacting a hydro(halo)fluoroalkane with a catalyst under suitable conditions, or chemically, typically by contacting a hydro(halo)fluoroalkane with strong bases such as alkali metal hydroxides.
  • catalytic dehydrohalogenation is believed to be preferred, and is discussed in more detail below.
  • the hydrofluoropropene 1 ,1 ,1 ,2,3-pentafluoropropene can be prepared by contacting and dehydrofluorinating 1 ,1 ,1 ,2,3,3-hexafluoropropane in the gaseous state with trivalent chromium oxide or partially fluorinated trivalent chromium oxide, optionally in the presence of oxygen (see US 5,679,875).
  • EP-A-1900716 describes the use of a variety of catalysts, including fluorinated chromia, fluorinated alumina, metal fluorides, metal fluorides and carbon-supported transition metals, in the dehydrofluorination of 1 ,1 ,3,3,3-pentafluoropropane (HFC-245fa) to 1 ,3,3,3- tetrafluoropropene (HFO-1234ze).
  • HFC-245fa 1 ,3,3,3-pentafluoropropane
  • HFO-1234ze 1 ,3,3,3- tetrafluoropropene
  • WO 2008/040969 describes the use of a zinc/chromia catalyst for the preparation of various (hydro )fluoropropenes, including HFO-1225ye and 2,3,3,3-tetrafluoropropene (HFO-1234yf) by dehydrohalogenation of corresponding hydro(halo)fluoropropanes.
  • catalytic dehydrohalogenation has its problems, one of which is because the chemistry is thought to inherently foul the catalyst.
  • Catalyst fouling typically is controlled by one or more of (a) using the mildest conditions possible, (b) increasing the concentration of hydrogen fluoride, and (c) limiting the exposure of the catalyst to high partial pressure of unsaturates.
  • the use of measures (b) and (c) above is very limited in the preparation of C3-7 (hydro)fluoroalkenes by the catalytic dehydrohalogenation (particularly dehydrofluorination) of C3-7 hydro(halo)fluoroalkanes.
  • operating cycles and catalyst life are believed generally to be relatively short compared to (hydro)fluorination chemistry. Short operating cycles and catalyst life require more frequent catalyst regeneration, or simply more catalyst, each of which have cost implications. Some catalysts, particularly certain alumina-supported catalysts and/or zirconia-based catalysts, can be difficult to regenerate. This is believed to be because the coke in a used dehydrohalogenation catalyst can be difficult to combust.
  • catalysts can be temperamental in that selectivity for the preferred reaction product may be diminished or lost following an unexpected event in the process, including a deactivation of the process, or through, say, the presence and/or build-up of impurities in the reaction vessel and/or on the catalyst.
  • the invention addresses the foregoing and other deficiencies by the provision of a process for preparing a (hydro)haloalkene comprising dehydrohalogenating a hydrohaloalkane in the presence of a catalyst comprising a ceramic material.
  • Ceramic materials such as those described herein surprisingly provide catalysts of highly stable performance for use in dehydrohalogenation processes.
  • the process comprises the preparation of a (hydro)(chloro)fluoroalkene comprising dehydrohalogenating a hydro(chloro)fluoroalkane in the presence of a catalyst comprising a ceramic material.
  • the process comprises the preparation of a C3-7 (hydro)haloalkene comprising dehydrohalogenating a C3-7 hydrohaloalkane in the presence of a catalyst comprising a ceramic material.
  • the process comprises the preparation of a C3-7 (hydro )fluoroalkene comprising dehydrohalogenating a C3-7 hydro(halo)fluoroalkane in the presence of a catalyst comprising a ceramic material.
  • the ceramic catalysts of the present invention are nonmetallic solids comprising metal, nonmetal or metalloid atoms primarily held in ionic and covalent bonds.
  • the metalloid and non metalloid species being selected from the elements Al, Si, B, C, N, Ti, Zr, Ce, Y, W.
  • Particularly useful ceramic catalysts include but are not limited to metal and non-metal carbides, nitrides, silicides and borides, for example silicon carbide and nitride, boron carbide and nitride, titanium carbide and tungsten carbide.
  • the ceramic materials may also include ceramic alloys. Ceramic alloys comprise combinations of materials that include ceramics and additional materials such as metal alloys or indeed other ceramics.
  • a ceramic alloy can be prepared by combining the metal alloy of boron, aluminium and magnesium (AIMgBi4) with titanium boride (T1B2).
  • the catalyst comprises at least one ceramic material selected from the group silicon carbide, silicon nitride, metal and/or non-metal silicides and metal and/or non-metal borides. Most preferably, the catalyst comprises silicon carbide.
  • the catalyst further comprises a metal, metal halide and/or a metal oxide.
  • the metal, the metal halide or the metal oxide may be one or more of aluminium, calcium, magnesium, chromium, iron, nickel, copper, potassium, titanium, vanadium, manganese, cobalt, tin and cerium, preferably copper or nickel.
  • the metal may be deposited or embedded on the surface of the ceramic material, with the ceramic material acting as a support or as a co-catalyst.
  • the catalysts of the invention typically have a surface area of between 0.001 m 2 /g and 50 m 2 /g, for example from 0.1 to about 10 or 20 m 2 /g.
  • the ceramic catalysts of the present invention may be subject to various pre-treatments and conditioning steps before and during use. For example, they may be pre-treated with hydrogen fluoride, hydrogen chloride, chlorine, air, water or hydrogen. Such treatment typically has the effect of improving some aspect of the physical and catalytic properties of the catalyst for dehydrohalogenation reactions.
  • the catalysts of the invention may be provided in any suitable form known in the art.
  • the catalysts may form at least part of the internal surface of the or a reaction vessel.
  • the catalyst may be regenerated or reactivated periodically by heating in air at a temperature of from about 300°C to about 1000°C.
  • Air may be used as a mixture with an inert gas such as nitrogen or with hydrogen fluoride, which emerges hot from the catalyst treatment process and may be used directly in fluorination processes employing the reactivated catalyst.
  • an inert gas such as nitrogen or with hydrogen fluoride
  • the spent catalyst from the process of the invention typically is unexpectedly easy to regenerate because of their high thermal stability compared to known catalysts such as those based on chromia which suffer thermochemical damage and activity loss during regeneration steps, especially regeneration steps requiring prolonged treatment at high temperatures.
  • the process of the invention comprises contacting the hydrohaloalkane (e.g. a C3-7 hydrohaloalkane such as a C3-7 hydro(chloro)fluoroalkane) with the catalyst with or without added hydrogen fluoride (HF) in the vapour or liquid phase (preferably the vapour phase) and may be carried out at a temperature of from 0 to 700 °C, e.g. 50 to 500 °C, for example from about 300 to about 500°C.
  • the process may be carried out with no co-feed of HF.
  • the process may be carried out at atmospheric, sub- or super atmospheric pressure, preferably up to about 30 bara, for example from about 1 to about 25 bara.
  • the hydrohaloalkane e.g. hydro(halo)fluoroalkane
  • HF e.g. without a HF feed
  • the process is conducted at a pressure of from 1 to 20 bara.
  • the preferred conditions e.g. temperature, pressure for conducting the process of the invention may vary (even outside the above ranges) depending on the nature of the hydrohaloalkane and (hydro)haloalkene, and the catalyst being employed.
  • the process of the invention can be carried out in any suitable apparatus, such as a static mixer, a stirred tank reactor or a stirred vapour-liquid disengagement vessel.
  • the process may be carried out batch-wise, or continuously. Either the batch-wise process or the continuous process may be carried out in a "one-pot” fashion, or using two or more discrete reaction zones and/or reaction vessels.
  • a continuous process the skilled person will appreciate that the process will need to paused periodically, e.g. for maintenance and/or catalyst regeneration.
  • the dehydrohalogenation can be carried out in the absence of an HF feed but it may be desirable in certain embodiments to use some HF in order to prevent and/or retard excessive decomposition of the organic feed and/or coking of the catalyst.
  • the HF:organics ratio in the process of the invention if an HF feed is utilised will range from about 0.01 :1 to about 1 :1 , preferably from about 0.1 :1 to about 1 :1 , more preferably from about 0.5: 1 to about 1 :1.
  • a (hydro)haloalkene is an alkene in which at least one of the hydrogen atoms has been replaced by a halogen selected from one or more of fluorine, chlorine, bromine and iodine (preferably fluorine and/or chlorine).
  • the (hydro)haloalkene is a (hydro)(chloro)fluoroalkene.
  • (hydro)(chloro)fluoroalkene we include hydrochlorofluoroalkenes, hydrofluoroalkenes and perfluoroalkenes.
  • a (hydro)fluoroalkene is an alkene in which at least one of the hydrogen atoms has been replaced by fluorine, i.e. a hydrofluoroalkene or a perfluoroalkene.
  • hydro(halo)fluoroalkane is an alkane in which at least one but not all hydrogen atom has been replaced by a fluorine atom and optionally at least one hydrogen atom has been replaced by a halogen selected from chlorine, bromine and iodine.
  • hydro(halo)fluoroalkanes contain at least one hydrogen, at least one fluorine and optionally at least one halogen selected from chlorine, bromine and iodine.
  • hydro(halo)fluoroalkane includes, for example, a hydrofluoroalkane, i.e., an alkane in which at least one but not all of the hydrogen atoms have been replaced by fluorine, and a hydrochlorofluoroalkane.
  • any reference to a C3-7 (hydro)haloalkene, (hydro )fluoroalkene, (hydro)(chloro)fluoroalkene, hydrofluoroalkane, hydro(chloro)fluoroalkane or hydro(halo)fluoroalkane refers to a (hydro)haloalkene, (hydro )fluoroalkene, (hydro)(chloro)fluoroalkene, hydrofluoroalkane, hydro(chloro)fluoroalkane or hydro(halo)fluoroalkane having from 3 to 7 carbon atoms.
  • the (hydro)haloalkenes produced by the process of the invention contain a double bond and may thus exist as E (ent ought) and Z (zusammen) geometric isomers about each individual double bond. All such isomers and mixtures thereof are included within the scope of the invention.
  • dehydrohalogenation or dehydrohalogenating
  • hydrogen halide e.g. HF, HCI, HBr or HI
  • hydrohaloalkane e.g. hydro(halo)fluoroalkane
  • the process of the invention is suitable for preparing any hydrohaloalkene, such as a C3-7 (hydro)fluoroalkene or C3-7 (hydro)(chloro)fluoroalkene, by dehydrohalogenating (e.g. dehydrofluorinating or dehydrochlorinating) a hydrohaloalkane, such as a C3-7 hydro(halo)fluoroalkane.
  • dehydrohalogenating e.g. dehydrofluorinating or dehydrochlorinating
  • a hydrohaloalkane such as a C3-7 hydro(halo)fluoroalkane.
  • the or a C3-7 hydro(halo)fluoroalkane or C3-7 hydro(chloro)fluoroalkane may first be fluorinated to a C3-7 hydrofluoroalkane which may then be dehydrofluorinated to a C3-7 (hydro )fluoroalkene.
  • a preferred group of (hydro)haloalkenes prepared by the process of the invention is (hydro)(chloro)fluoroalkenes, of which C3-7 (hydro)(chloro)fluoroalkenes are more preferred.
  • the process of the invention is particularly suited to the preparation of C3-7 hydrochlorofluoroalkenes and C3-7 hydrofluoroalkenes.
  • the invention is particularly suited to the preparation of (hydro)(chloro)fluoropropenes and (hydro)(chloro)fluorobutenes, especially (hydro)(chloro)fluoropropenes.
  • (Hydro )fluoropropenes prepared by the process of the invention may contain 0, 1 , 2, 3, 4 or 5 hydrogen atoms and 1 , 2, 3, 4, 5 or 6 fluorine atoms.
  • Preferred (hydro )fluoropropenes are those having from 3 to 5 fluorine atoms (and thus from 1 to 3 hydrogen atoms), particularly 4 or 5 fluorine atoms (and thus 1 or 2 hydrogen atoms).
  • preferred (hydro)fluoropropenes are trifluoropropenes, tetrafluoropropenes and pentafluoropropenes, particularly tetrafluoropropenes and pentafluoropropenes, and especially tetrafluoropropenes.
  • a preferred trifluropropene prepared by the process of the invention is 3,3,3- trifluoropropene (HFO-1243zf).
  • HFO-1243zf can be conveniently prepared by dehydrohalogenation of compounds of the type CF3CH2CH2X, where X is a halogen (F, CI, Br, I).
  • X is F or CI, namely CF3CH2CH2F (HFC-254fb) or CF 3 CH 2 CH 2 CI (HCFC-253fb).
  • a preferred pentafluoropropene prepared by the process of the present invention is 1 ,2,3,3,3-pentafluoropropene (HFO-1225ye) prepared by dehydrofluorination of 1 ,1 ,1 ,2,3,3-hexafluoropropane (HFC-236ea).
  • Preferred tetrafluoropropenes prepared by the process of the present invention include Z and/or E-1 ,3,3,3-tetrafluoropropene (HFO-1234ze, both E and Z isomers) and 2,3,3,3- tetrafluoropropene (HFO-1234yf).
  • HFO-1234ze is preferably prepared by dehydrofluorination of 1 ,1 ,1 ,3,3- pentafluoropropane (245fa) or dehydrochlorination of 1 ,1 ,1 ,3-tetrafluoro-3-chloropropane (244fa).
  • HFO-1234yf can be prepared by dehydrofluorination of 1 ,1 ,1 ,2,2-pentafluoropropane (HFC-245cb) or 1 ,1 , 1 ,2,3-pentafluoropropane (HFC-245eb).
  • HFO-1234yf by the present invention is especially preferred by dehydrochlorination of 1 ,1 ,1 ,2-tetrafluoro-2-chloropropane (HCFC-244bb).
  • HCFO-1233zd can be prepared in the accordance with the process of the invention by, for example, dehydrochlorinating 1 ,2-dichloro-3,3,3-trifluoropropane (HCFC-243db) and/or
  • HCFO-1233xf can be prepared in the accordance with the process of the invention by, for example, dehydrochlorinating 1 ,2-dichloro-3,3,3-trif!uoropropane (HCFC-243db) and/or
  • HCFO-1233xf is prepared by dehydrochlorinating HCFC-243db.
  • Preferred hydrofluorobutenes prepared by the process of the invention include Z,E or Z&E- 1 ,1 ,1 ,4,4,4-hexafluorobutene (HFO-1336mzz) and all possible fluorobutene isomers prepared by the dehydrohalogenation of 3-chloro-1 ,1 ,1 ,3-tetrafluorobutane, for example Z/E-3-chloro-1 ,1 ,1-trif!uorobut-2-ene, 3-chloro-1 , 1 ,1-trifluorobut-3-ene, Z/E-1 , 1 ,1 ,3- tetrafluorobut-2-ene and 1 ,1 ,1 ,3-tetrafluorobut-3-ene.
  • Figure 1 shows a plot of the results of Example 1
  • Figure 2 shows a plot of the results of Example 2.
  • a 1 ⁇ 2" diameter empty silicon carbide reactor tube was sealed with graphite ferrules and an Inconel thermocouple inside a Monel Thermowell was placed inside the tube.
  • the tube was pre-dried at 450°C under 60ml/min N2 overnight prior to feeding organics to the reactor.
  • the tube was heated to an internal temperature of 350°C and a supply of 244bb (5ml/min) with N2 dilution (30ml/min) was provided for around 5 minutes before diverting the N2 stream to the bottom of the reactor. Reactions were carried out at a temperature ranges of 400 to 525°C with a 244bb flow at 5ml/min.
  • An empty glass lined reactor (with & without a thermo-well) with no catalyst was tested first to form a baseline for other catalyst screening. The reaction was monitored by manually withdrawing samples from the reactor outlets and examining them via gas chromatography, the peak areas of the chromatographs being used to calculate the quantity of HCFC-244bb, HFO-1234yf and HCFO-1233xf in the product stream.
  • Figure 1 shows a plot of raw conversion data against time, while the conversion figures in Table 1 are adjusted to account for the effects of thermal conversion.
  • Figure 1 and Table 1 below the silicon carbide reactor showed extremely high stability with an excellent selectivity towards 1234yf that was maintained across a range of temperatures.
  • Example 2 Example 1 was repeated with 1.8 g of silicon nitride in pellet form (0.5 to 1 mm) in a stainless steel glass-lined reactor tube. The pellet were obtained by crushing and sieving silicon nitride powder (a-Si3N 85% minimum) to obtain pellets of the correct size.
  • Example 3 Samples of residue found in the reaction tube used in Example 1 were subjected to X-ray fluorescence spectroscopy (XRF) to determine its elemental composition. The results are shown in Table 3, below.
  • XRF X-ray fluorescence spectroscopy
  • metallic material and/or compounds such as may be deposited from fittings and the thermocouple, may collect on the ceramic material and provide some catalytic activity.
  • Copper chloride or nickel chloride represent an examples of such materials.
  • metallic material and/or compounds such as may be deposited from fittings and the thermocouple, may collect on the ceramic material and provide some catalytic activity.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Un procédé de préparation d'un (hydro)haloalcène comprenant la déshydrohalogénation d'un hydrohaloalcane en présence d'un catalyseur comprenant un matériau céramique.
PCT/GB2016/050933 2015-04-02 2016-04-01 Procédé WO2016156870A1 (fr)

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GBGB1505712.8A GB201505712D0 (en) 2015-04-02 2015-04-02 Process
GB1505712.8 2015-04-02

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018165624A1 (fr) * 2017-03-10 2018-09-13 The Chemours Company Fc, Llc Procédé amélioré de préparation de 3,3,3-trifluoroprop-1-ene
CN110343029A (zh) * 2019-07-26 2019-10-18 西安近代化学研究所 一种制备3-氯-1,1,1,3-四氟丙烷的方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB832425A (en) * 1956-09-28 1960-04-13 Diamond Alkali Co Improvements in or relating to chemical reactions employing catalysts
GB989254A (en) * 1961-01-11 1965-04-14 Sinclair Research Inc Production of monoolefins
GB1059653A (en) * 1963-07-08 1967-02-22 Daikin Ind Ltd Preparation of vinyl fluoride
WO2011099605A2 (fr) * 2010-02-12 2011-08-18 Daikin Industries, Ltd. Procédé pour la production d'un composé alcène contenant du fluor

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB832425A (en) * 1956-09-28 1960-04-13 Diamond Alkali Co Improvements in or relating to chemical reactions employing catalysts
GB989254A (en) * 1961-01-11 1965-04-14 Sinclair Research Inc Production of monoolefins
GB1059653A (en) * 1963-07-08 1967-02-22 Daikin Ind Ltd Preparation of vinyl fluoride
WO2011099605A2 (fr) * 2010-02-12 2011-08-18 Daikin Industries, Ltd. Procédé pour la production d'un composé alcène contenant du fluor

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018165624A1 (fr) * 2017-03-10 2018-09-13 The Chemours Company Fc, Llc Procédé amélioré de préparation de 3,3,3-trifluoroprop-1-ene
CN110494411A (zh) * 2017-03-10 2019-11-22 科慕埃弗西有限公司 制备3，3，3-三氟丙-1-烯的改进方法
US10577296B2 (en) 2017-03-10 2020-03-03 The Chemours Company Fc, Llc Process for preparing 3,3,3-trifluoroprop-1-ene
US11028028B2 (en) 2017-03-10 2021-06-08 The Chemours Company Fc, Llc Process for preparing 3,3,3-trifluoroprop-1-ene
US11447438B2 (en) 2017-03-10 2022-09-20 The Chemours Company Fc, Llc Process for preparing 3,3,3-trifluoroprop-1-ene
US11584701B2 (en) 2017-03-10 2023-02-21 The Chemours Company Fc, Llc Process for preparing 3,3,3-trifluoroprop-1-ene
EP4155284A1 (fr) * 2017-03-10 2023-03-29 The Chemours Company FC, LLC Compositions contenant 3-chloro-1,1,1-trifluoropropane
US11780794B2 (en) 2017-03-10 2023-10-10 The Chemours Company Fc, Llc Process for preparing 3,3,3-trifluoroprop-1-ene
CN110343029A (zh) * 2019-07-26 2019-10-18 西安近代化学研究所 一种制备3-氯-1,1,1,3-四氟丙烷的方法
CN110343029B (zh) * 2019-07-26 2022-03-15 西安近代化学研究所 一种制备3-氯-1,1,1,3-四氟丙烷的方法

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