US20220112226A1 - Trifluoroacetyl iodide compositions useful for making trifluoroiodomethane - Google Patents
Trifluoroacetyl iodide compositions useful for making trifluoroiodomethane Download PDFInfo
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- US20220112226A1 US20220112226A1 US17/495,506 US202117495506A US2022112226A1 US 20220112226 A1 US20220112226 A1 US 20220112226A1 US 202117495506 A US202117495506 A US 202117495506A US 2022112226 A1 US2022112226 A1 US 2022112226A1
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- trifluoroacetyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 138
- MTRCYRVBLMQHPZ-UHFFFAOYSA-N 2,2,2-trifluoroacetyl iodide Chemical compound FC(F)(F)C(I)=O MTRCYRVBLMQHPZ-UHFFFAOYSA-N 0.000 title claims abstract description 100
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 title claims description 47
- 239000012535 impurity Substances 0.000 claims abstract description 83
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims abstract description 21
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000011630 iodine Substances 0.000 claims abstract description 19
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 19
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- -1 hydrogen triiodide Chemical class 0.000 claims abstract description 15
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims abstract description 14
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 claims abstract description 13
- UXPOJVLZTPGWFX-UHFFFAOYSA-N pentafluoroethyl iodide Chemical compound FC(F)(F)C(F)(F)I UXPOJVLZTPGWFX-UHFFFAOYSA-N 0.000 claims abstract description 13
- CPLSOYONVLSMGL-UHFFFAOYSA-N 1,1-difluorobutane Chemical compound CCCC(F)F CPLSOYONVLSMGL-UHFFFAOYSA-N 0.000 claims abstract description 10
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 claims abstract description 10
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 claims abstract description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 claims abstract description 10
- YSLFMGDEEXOKHF-UHFFFAOYSA-N difluoro(iodo)methane Chemical compound FC(F)I YSLFMGDEEXOKHF-UHFFFAOYSA-N 0.000 claims abstract description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 10
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 9
- 235000013847 iso-butane Nutrition 0.000 claims abstract description 9
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims abstract description 9
- VMVNZNXAVJHNDJ-UHFFFAOYSA-N methyl 2,2,2-trifluoroacetate Chemical compound COC(=O)C(F)(F)F VMVNZNXAVJHNDJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims abstract description 9
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000002894 organic compounds Chemical class 0.000 claims description 65
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 claims description 26
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 25
- DCEPGADSNJKOJK-UHFFFAOYSA-N 2,2,2-trifluoroacetyl fluoride Chemical compound FC(=O)C(F)(F)F DCEPGADSNJKOJK-UHFFFAOYSA-N 0.000 claims description 12
- CYXIKYKBLDZZNW-UHFFFAOYSA-N 2-Chloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)CCl CYXIKYKBLDZZNW-UHFFFAOYSA-N 0.000 claims description 7
- 238000004817 gas chromatography Methods 0.000 description 81
- 238000000034 method Methods 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000004519 manufacturing process Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- 239000000376 reactant Substances 0.000 description 11
- 238000004821 distillation Methods 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 8
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 7
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 description 5
- 238000010586 diagram Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000012264 purified product Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- WMIYKQLTONQJES-UHFFFAOYSA-N hexafluoroethane Chemical compound FC(F)(F)C(F)(F)F WMIYKQLTONQJES-UHFFFAOYSA-N 0.000 description 3
- PDJAZCSYYQODQF-UHFFFAOYSA-N iodine monofluoride Chemical group IF PDJAZCSYYQODQF-UHFFFAOYSA-N 0.000 description 3
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- DTJIBVSGNIAPCX-UHFFFAOYSA-N 2,2,2-trifluoroacetyl bromide Chemical compound FC(F)(F)C(Br)=O DTJIBVSGNIAPCX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 229910020323 ClF3 Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 229910001182 Mo alloy Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910006080 SO2X Inorganic materials 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- DIYMOBFUCJGKFJ-UHFFFAOYSA-N butane;hydroiodide Chemical compound I.CCCC DIYMOBFUCJGKFJ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- OGSYQYXYGXIQFH-UHFFFAOYSA-N chromium molybdenum nickel Chemical compound [Cr].[Ni].[Mo] OGSYQYXYGXIQFH-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000623 nickel–chromium alloy Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
- C07C17/363—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms by elimination of carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/16—Acyclic saturated compounds containing halogen atoms containing fluorine and iodine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
Definitions
- the present disclosure relates to trifluoroacetyl iodide compositions. Specifically, the present disclosure relates to trifluoroacetyl iodide compositions useful for producing trifluoroiodomethane.
- Trifluoroiodomethane (CF 3 I), also known as perfluoromethyliodide, trifluoromethyl iodide, or iodotrifluoromethane, is a useful compound in commercial applications as a refrigerant or a fire suppression agent, for example.
- Trifluoroiodomethane is a low global warming potential molecule with negligible ozone depletion potential. Trifluoroiodomethane can replace more environmentally damaging materials.
- U.S. Pat. No. 7,196,236 discloses a catalytic process for producing trifluoroiodomethane using reactants comprising a source of iodine, at least a stoichiometric amount of oxygen, and a reactant CF 3 R, where R is selected from the group consisting of —COOH, —COX, —CHO, —COOR 2 , AND —SO 2 X, where R 2 is alkyl group and X is a chlorine, bromine, or iodine.
- Hydrogen iodide which may be produced by the reaction, can be oxidized by the at least a stoichiometric amount of oxygen, producing water and iodine for economic recycling.
- U.S. Pat. No. 7,132,578 (Mukhopadhyay et al.) also discloses a catalytic, one-step process for producing trifluoroiodomethane from trifluoroacetyl chloride.
- the source of iodine is iodine fluoride (IF).
- IF iodine fluoride
- iodine fluoride is relatively unstable, decomposing above 0° C. to I 2 and IF 5 . Iodine fluoride may also not be available in commercially useful quantities.
- compositions of trifluoroacetyl iodide are needed that allow more economical operation because the production of trifluoroiodomethane from trifluoroacetyl iodide may be subject to undesirable side reactions.
- compositions including trifluoroacetyl iodide (CF 3 COI), at least one organic impurity and at least one inorganic impurity that are suitable for the manufacture trifluoroiodomethane (CF 3 I).
- CF 3 COI trifluoroacetyl iodide
- organic impurity at least one organic impurity
- inorganic impurity that are suitable for the manufacture trifluoroiodomethane (CF 3 I).
- the present invention provides a composition comprising trifluoroacetyl iodide, at least one organic impurity comprising at least one of: difluoroiodomethane, pentafluoroiodoethane, iodomethane, iodopropane, dichlorotetrafluoroethane, dichlorotrifluoroethane, trichlorotrifluoroethane, methyltrifluoroacetate, trifluoroacetic anhydride, difluorobutane and methyl propane, and at least one inorganic impurity comprising at least one of: hydrogen iodide, hydrogen chloride, iodine and hydrogen triiodide.
- FIG. 1 is a process flow diagram showing a gas-phase process for manufacturing trifluoroacetyl iodide compositions.
- FIG. 2 is a process flow diagram showing a gas-phase process for manufacturing trifluoroiodomethane from trifluoroacetyl iodide compositions.
- the present disclosure describes trifluoroacetyl iodide compositions including at least one impurity organic impurity and at least one inorganic impurity. Even with the impurities, the compositions have been found to be suitable for the manufacture of trifluoroiodomethane.
- the trifluoroacetyl iodide is provided as a composition including organic and inorganic impurities because pure trifluoroacetyl iodide can be too costly to permit the economically efficient manufacture of trifluoroiodomethane. It has been found that some impurities can have a more detrimental impact on the overall efficiency of process than other impurities. For example, it is believed that some hydrogen-containing impurities and some halogen-containing impurities in the trifluoroacetyl iodide composition can result in increased formation of byproducts, such as methyl trifluoride (CF 3 H) and iodine (I 2 ).
- CF 3 H methyl trifluoride
- I 2 iodine
- hydrogen-containing impurities include trifluoroacetic acid (TFA), hydrogen iodide (HI), hydrogen chloride (HCl) and hydrogen triiodide (HI 3 ).
- halogen-containing impurities include trifluoroacetyl fluoride (CF 3 COF), trifluoroacetyl chloride (CF 3 COCl), difluoroiodomethane (CF 2 HI), pentafluoroiodoethane (CF 3 CF 2 I), iodomethane (CH 3 I), iodine (I 2 ), iodopropane (C 3 H 7 I) and trifluoroiodomethane (CF 3 I). While the trifluoroiodomethane is the desired product, trifluoroiodomethane in the trifluoroacetyl iodide composition feeding the reaction can react to produce undesired byproducts.
- iodine-containing impurities such as iodine (I 2 ) and hydrogen triiodide (HI 3 )
- I 2 iodine
- HI 3 hydrogen triiodide
- organic impurities in the trifluoroacetyl iodide composition have relatively little effect on the efficiency of the process. Such impurities generally pass through the reactor without reacting and do not corrode the processing equipment.
- organic impurities include dichlorotetrafluoroethane (C 2 Cl 2 F 4 ), dichlorotrifluoroethane (C 2 HCl 2 F 3 ), chlorotrifluoroethane (C 2 H 2 ClF 3 ), trichlorotrifluoroethane (C 2 Cl 3 F 3 ), methyltrifluoroacetate (CF 3 COOCH 3 ), trifluoroacetic anhydride ((CF 3 CO) 2 O), difluorobutane (C 4 H 8 F 2 ) and methyl propane (CH 3 CH(CH 3 )CH 3 ).
- Trifluoroacetyl iodide compositions useful as a feed stock for producing trifluoroiodomethane according to the process of Equation 1 above include trifluoroacetyl iodide, at least one organic impurity comprising at least one of: difluoroiodomethane, pentafluoroiodoethane, iodomethane, iodopropane, dichlorotetrafluoroethane, dichlorotrifluoroethane, trichlorotrifluoroethane, methyltrifluoroacetate, trifluoroacetic anhydride, difluorobutane and methyl propane, and at least one inorganic impurity comprising at least one of: hydrogen iodide, hydrogen chloride, iodine and hydrogen triiodide.
- the organic compounds in the trifluoroacetyl iodide compositions may be measured by gas chromatography (GC) and gas chromatography-mass spectroscopy (GC-MS) analyses. Peak areas provided by the GC analysis for each of the organic compounds can be combined to provide a GC area percentage (GC area %) of the total organic compounds for each of the organic compounds as a measurement of the relative concentrations of the organic compounds in the compositions.
- the GC area % may be interpreted as equivalent to a weight %.
- the concentration of organic impurities in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, may be as low as about 0.05%, about 0.1%, about 0.5%, or about 1% or may be as high as about 2%, about 3%, about 4%, or about 5%, or within any range defined between any two of the foregoing values, such as about 0.05% to about 5%, about 0.1% to about 4%, about 0.5% to about 3%, about 1% to about 2%, about 0.05% to about 2%, about 0.5% to about 2%, about 2% to about 5%, or about 0.05% to about 1%, for example.
- the concentration of inorganic impurities in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds may be from about 0.05% to about 3%. More preferably, the concentration of inorganic impurities in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, may be from about 0.05% to about 2%. Most preferably, the concentration of inorganic impurities in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, may be from about 0.05% to about 1%.
- the concentration of difluoroiodomethane, iodopropane, dichlorotetrafluoroethane, dichlorotrifluoroethane, difluorobutane and methyl propane in total in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, may be as low as about 0.0001%, about 0.001%, about 0.005%, about 0.01%, about 0.02% or about 0.03%, or may be as high as about 0.05%, about 0.1%, about 0.2%, about 0.3% or about 0.5%, or within any range defined between any two of the foregoing values, such as about 0.0001% to about 0.5%, about 0.001% to about 0.3%, about 0.005% to about 0.2%, about 0.01% to about 0.1%, about 0.001% to about 0.2%, about 0.001% to about 0.03%, about 0.05% to about 0.5%, or about 0.1% to about 0.3%, for example.
- the concentration of trifluoroacetic anhydride when present in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, may be as low as about 0.001%, about 0.005%, about 0.01%, about 0.02% or about 0.03%, or may be as high as about 0.05%, about 0.1%, about 0.2%, about 0.3%, about 0.5% or about 1%, or within any range defined between any two of the foregoing values, such as about 0.001% to about 1%, about 0.005% to about 0.5%, about 0.01% to about 0.3%, about 0.02% to about 0.2%, about 0.03% to about 0.1%, about 0.01% to about 0.05%, about 0.1% to about 1%, or about 0.01% to about 0.3%, for example.
- the concentration of pentafluoroiodoethane when present in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, may be as low as about 0.0001%, about 0.001%, about 0.005%, about 0.01%, about 0.02% or about 0.03%, or may be as high as about 0.05%, about 0.1%, about 0.2%, about 0.3% or about 0.5%, or within any range defined between any two of the foregoing values, such as about 0.0001% to about 0.5%, about 0.001% to about 0.3%, about 0.005% to about 0.2%, about 0.01% to about 0.1%, about 0.001% to about 0.2%, about 0.001% to about 0.03%, about 0.05% to about 0.5%, or about 0.1% to about 0.3%, for example.
- the concentration of pentafluoroiodoethane in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds is from about 0.0001% to about 0.2%. More preferably, the concentration of pentafluoroiodoethane in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, is from about 0.0001% to about 0.1%. Most preferably, the concentration of pentafluoroiodoethane in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, is from about 0.0001% to about 0.05%.
- the concentration of iodomethane when present in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, may be as low as about 0.0001%, about 0.001%, about 0.005%, about 0.01%, about 0.02% or about 0.03%, or may be as high as about 0.05%, about 0.1%, about 0.2%, about 0.3% or about 0.5%, or within any range defined between any two of the foregoing values, such as about 0.0001% to about 0.5%, about 0.001% to about 0.3%, about 0.005% to about 0.2%, about 0.01% to about 0.1%, about 0.001% to about 0.2%, about 0.001% to about 0.03%, about 0.05% to about 0.5%, or about 0.1% to about 0.3%, for example.
- the concentration of iodomethane in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds is from about 0.0001% to about 0.2%. More preferably, the concentration of iodomethane in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, is from about 0.0001% to about 0.1%. Most preferably, the concentration of iodomethane in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, is from about 0.0001% to about 0.05%.
- the concentration of methyltrifluoroacetate, when present, in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, may be as low as about 0.001%, about 0.005%, about 0.01%, about 0.02%, about 0.03% or about 0.05%, or may be as high as about 0.1%, about 0.2%, about 0.3%, about 0.5%, about 1%, or about 2%, or within any range defined between any two of the foregoing values, such as about 0.001% to about 2%, about 0.005% to about 1%, about 0.01% to about 0.5%, about 0.02% to about 0.3%, about 0.03% to about 0.2%, about 0.05% to about 0.1%, about 0.1% to about 1%, or about 0.02% to about 0.1%, for example.
- trifluoroacetyl iodide compositions described above may further include at least one additional organic impurity comprising at least one of: trifluoroacetic acid, trifluoroacetyl fluoride, trifluoroacetyl chloride, trifluoroiodomethane and chlorotrifluoroethane.
- the concentration of trifluoroacetic acid when present in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, may be as low as about 0.001%, about 0.005%, about 0.01%, about 0.02%, about 0.03% or about 0.05%, or may be as high as about 0.1%, about 0.2%, about 0.3%, about 0.5%, about 1%, or about 2%, or within any range defined between any two of the foregoing values, such as about 0.001% to about 2%, about 0.005% to about 1%, about 0.01% to about 0.5%, about 0.02% to about 0.3%, about 0.03% to about 0.2%, about 0.05% to about 0.1%, about 0.1% to about 1%, or about 0.02% to about 0.1%, for example.
- the concentration of trifluoroacetic acid in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds is from about 0.001% to about 1%. More preferably, the concentration of trifluoroacetic acid in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, is from about 0.001% to about 0.5%. Most preferably, the concentration of trifluoroacetic acid in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, is from about 0.001% to about 0.2%.
- the concentration of trifluoroacetyl fluoride when present in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, may be as low as about 0.0001%, about 0.0005%, about 0.001%, about 0.002% or about 0.003%, or may be as high as about 0.005%, about 0.01%, about 0.02%, about 0.03% or about 0.05%, or within any range defined between any two of the foregoing values, such as about 0.0001% to about 0.05%, about 0.0005% to about 0.03%, about 0.001% to about 0.02%, about 0.002% to about 0.01%, about 0.003% to about 0.005%, about 0.0005% to about 0.02%, about 0.005% to about 0.05%, or about 0.001% to about 0.01%, for example.
- the concentration of trifluoroacetyl fluoride in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds is from about 0.0001% to about 0.02%. More preferably, the concentration of trifluoroacetyl fluoride in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, is from about 0.0001% to about 0.01%. Most preferably, the concentration of trifluoroacetyl fluoride in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, is from about 0.0001% to about 0.005%.
- the concentration of trifluoroacetyl chloride when present in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, may be as low as about 0.001%, about 0.005%, about 0.01%, about 0.02%, about 0.03% or about 0.05%, or may be as high as about 0.1%, about 0.2%, about 0.3%, about 0.5%, about 1%, or about 2%, or within any range defined between any two of the foregoing values, such as about 0.001% to about 2%, about 0.005% to about 1%, about 0.01% to about 0.5%, about 0.02% to about 0.3%, about 0.03% to about 0.2%, about 0.05% to about 0.1%, about 0.1% to about 1%, or about 0.02% to about 0.1%, for example.
- the concentration of trifluoroacetyl chloride in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds is from about 0.001% to about 1%. More preferably, the concentration of trifluoroacetyl chloride in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, is from about 0.001% to about 0.5%. Most preferably, the concentration of trifluoroacetyl chloride in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, is from about 0.001% to about 0.2%.
- the concentration of trifluoroiodomethane when present in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, may be as low as about 0.0001%, about 0.001%, about 0.01%, about 0.02% or about 0.05%, or may be as high as about 0.1%, about 0.5%, about 1%, or about 2% or within any range defined between any two of the foregoing values, such as about 0.0001% to about 2%, about 0.001% to about 1%, about 0.01% to about 0.5%, about 0.02% to about 0.1%, about 0.001% to about 0.05%, about 0.1% to about 0.5%, about 0.05% to about 0.3%, or about 0.001% to about 0.03%, for example.
- the concentration of trifluoroiodomethane in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds is from about 0.0001% to about 1%. More preferably, the concentration of trifluoroiodomethane in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, is from about 0.0001% to about 0.5%. Most preferably, the concentration of trifluoroiodomethane in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, is from about 0.0001% to about 0.1%.
- the concentration of chlorotrifluoroethane when present in the trifluoroacetyl iodide compositions, in GC area % of total organic compounds, may be as low as about 0.0001%, about 0.001%, about 0.005%, about 0.01%, about 0.02% or about 0.03%, or may be as high as about 0.05%, about 0.1%, about 0.2%, about 0.3% or about 0.5%, or within any range defined between any two of the foregoing values, such as about 0.0001% to about 0.5%, about 0.001% to about 0.3%, about 0.005% to about 0.2%, about 0.01% to about 0.1%, about 0.001% to about 0.2%, about 0.001% to about 0.03%, about 0.05% to about 0.5%, or about 0.1% to about 0.3%, for example.
- the concentration of iodine (I 2 ) in the trifluoroacetyl iodide compositions may be measured via titration, as is known in the art.
- concentration of hydrogen iodide, hydrogen chloride, hydrogen triiodide and other hydrogen-containing inorganic compounds may be measured by H-NMR, as is known in the art.
- the concentration of inorganic impurities in the trifluoroacetyl iodide compositions may be as low as about 0.01 weight percent (wt. %), about 0.02 wt. %, about 0.03 wt. % or about 0.05 wt. %, or as high as about 0.1 wt. %, about 0.2 wt. %, about 0.3 wt. %, about 0.5 wt. %, about 1 wt. %, or about 1.5 wt. %, or within any range defined between any two of the foregoing values, such as about 0.01 wt. % to about 1.5 wt. %, about 0.02 wt. % to about 1 wt.
- the concentration of inorganic impurities in the trifluoroacetyl iodide compositions is from about 0.01 wt. % to about 0.5 wt. %.
- the concentration of inorganic impurities in the trifluoroacetyl iodide compositions is from about 0.01 wt. % to about 0.1 wt. %. Most preferably, the concentration of inorganic impurities in the trifluoroacetyl iodide compositions is from about 0.01 wt. % to about 0.05 wt. %.
- the concentration of hydrogen iodide when present in the trifluoroacetyl iodide compositions may be as low as about 0.0001 wt. %, 0.001 wt. %, about 0.005 wt. %, about 0.01 wt. %, about 0.02 wt. %, or about 0.03 wt. %, or as high as about 0.05 wt. %, about 0.1 wt. %, about 0.2 wt. %, about 0.3 wt. % or about 0.5 wt. %, or within any range defined between any two of the foregoing values, such as about 0.0001 wt. % to about 0.5 wt.
- % about 0.001 wt. % to about 0.5 wt. %, about 0.005 wt. % to about 0.3 wt. %, about 0.01 wt. % to about 0.2 wt. %, about 0.02 wt. % to about 0.1 wt. %, about 0.03 wt. % to about 0.05 wt. %, about 0.01 wt. % to about 0.3 wt. %, about 0.005 wt. % to about 0.03 wt. %, about 0.05 wt. % to about 0.5 wt. %, or about 0.05 wt. % to about 0.3 wt. %, for example.
- the concentration of hydrogen iodide in the trifluoroacetyl iodide compositions is from about 0.0001 wt. % to about 0.3 wt. %. More preferably, the concentration of hydrogen iodide in the trifluoroacetyl iodide compositions is from about 0.0001 wt. % to about 0.1 wt. %. Most preferably, the concentration of hydrogen iodide in the trifluoroacetyl iodide compositions is from about 0.0001 wt. % to about 0.05 wt. %.
- the concentration of iodine (I 2 ) when present in the trifluoroacetyl iodide compositions may be as low as about 0.001 wt. %, about 0.005 wt. %, about 0.01 wt. %, about 0.02 wt. %, or about 0.03 wt. %, or as high as about 0.05 wt. %, about 0.1 wt. %, about 0.2 wt. %, about 0.3 wt. % or about 0.5 wt. %, or within any range defined between any two of the foregoing values, such as about 0.001 wt. % to about 0.5 wt. %, about 0.005 wt.
- % to about 0.3 wt. % about 0.01 wt. % to about 0.2 wt. %, about 0.02 wt. % to about 0.1 wt. %, about 0.03 wt. % to about 0.05 wt. %, about 0.01 wt. % to about 0.3 wt. %, about 0.005 wt. % to about 0.03 wt. %, about 0.05 wt. % to about 0.5 wt. %, or about 0.05 wt. % to about 0.3 wt. %, for example.
- the concentration of iodine in the trifluoroacetyl iodide compositions is from about 0.001 wt. % to about 0.3 wt. %. More preferably, the concentration of iodine in the trifluoroacetyl iodide compositions is from about 0.001 wt. % to about 0.1 wt. %. Most preferably, the concentration of iodine in the trifluoroacetyl iodide compositions is from about 0.001 wt. % to about 0.05 wt. %.
- the concentration of hydrogen triiodide when present in the trifluoroacetyl iodide compositions may be as low as about 0.0001 wt. %, about 0.001 wt. %, about 0.005 wt. %, about 0.01 wt. %, about 0.02 wt. %, or about 0.03 wt. %, or as high as about 0.05 wt. %, about 0.1 wt. %, about 0.2 wt. %, about 0.3 wt. % or about 0.5 wt. %, or within any range defined between any two of the foregoing values, such as about 0.0001 wt. % to about 0.05 wt.
- % about 0.001 wt. % to about 0.5 wt. %, about 0.005 wt. % to about 0.3 wt. %, about 0.01 wt. % to about 0.2 wt. %, about 0.02 wt. % to about 0.1 wt. %, about 0.03 wt. % to about 0.05 wt. %, about 0.01 wt. % to about 0.3 wt. %, about 0.005 wt. % to about 0.03 wt. %, about 0.05 wt. % to about 0.5 wt. %, or about 0.05 wt. % to about 0.3 wt. %, for example.
- the concentration of hydrogen triiodide in the trifluoroacetyl iodide compositions is from about 0.0001 wt. % to about 0.3 wt. %. More preferably, the concentration of hydrogen triiodide in the trifluoroacetyl iodide compositions is from about 0.0001 wt. % to about 0.1 wt. %. Most preferably, the concentration of hydrogen triiodide in the trifluoroacetyl iodide compositions is from about 0.0001 wt. % to about 0.05 wt. %.
- FIG. 1 is a process flow diagram showing an exemplary gas-phase process 10 for manufacturing trifluoroacetyl iodide.
- the trifluoroacetyl iodide may be produced by processes other than those described below.
- the process 10 comprises material flows of hydrogen iodide (HI) 12 and trifluoroacetyl chloride (CF 3 COCl) 14 .
- HI hydrogen iodide
- CF 3 COCl trifluoroacetyl chloride
- trifluoroacetyl chloride is used to illustrate the processes of FIG. 1 , it is understood that trifluoroacetyl bromide or trifluoroacetyl fluoride may be used instead of trifluoroacetyl chloride.
- the flow of hydrogen iodide 12 and the flow of trifluoroacetyl chloride 14 are combined in a mixer valve 16 to form a reactant stream 18 .
- the reactant stream 18 may be provided directly to a reactor 20 .
- the reactant stream 18 may pass through a preheater 22 to heat the reactant stream 18 before the reactant stream 18 is provided to the reactor 20 .
- the trifluoroacetyl chloride and the hydrogen iodide in the reactant stream 18 react in the presence of a catalyst 24 contained within the reactor 20 to produce a product stream 26 comprising trifluoroacetyl iodide (CF 3 COI) and various organic and inorganic impurities, including unreacted trifluoroacetyl chloride and hydrogen iodide.
- a catalyst 24 contained within the reactor 20 to produce a product stream 26 comprising trifluoroacetyl iodide (CF 3 COI) and various organic and inorganic impurities, including unreacted trifluoroacetyl chloride and hydrogen iodide.
- the product stream 26 may proceed directly to a distillation column 28 .
- the product stream 26 may pass through a heat exchanger 30 before the product stream 26 is provided to the distillation column 28 , as shown in FIG. 1 .
- the heat exchanger 30 is configured to cool the product stream 26 before it enters the distillation column 28 .
- the distillation column 28 is configured for the separation of some of the by-products, reactants, and organic compounds from the trifluoroacetyl iodide to produce a purified product stream 32 . As shown in FIG.
- the distillation column 28 can be configured to separate and return the unreacted hydrogen iodide to the flow of hydrogen iodide 12 for use in the reactant stream 18 in a hydrogen iodide flow 36 and to separate and return the unreacted trifluoroacetyl chloride to the flow of trifluoroacetyl chloride 14 for use in the reactant stream 18 in a trifluoroacetyl chloride flow 34 .
- the distillation column 28 can also be configured to separate the hydrogen chloride into a hydrogen chloride stream 38 for sale, reuse elsewhere, or disposal.
- the purified product stream 32 directed to a storage tank 40 comprises a trifluoroacetyl iodide composition as described above.
- the purified product stream 32 may be further purified before being directed to the storage tank 40 .
- FIG. 2 is a process flow diagram showing a process 110 for manufacturing trifluoroiodomethane from any of the trifluoroacetyl iodide compositions described above.
- a feed stream 132 including any of the trifluoroacetyl iodide compositions described above is provided to a vapor-phase reactor 140 , as shown in FIG. 2 .
- the trifluoroacetyl iodide reacts at a reaction temperature within the reactor 140 to produce a product stream 144 .
- the product stream 144 comprises trifluoroiodomethane and reaction by-product carbon monoxide according to Equation 1 above.
- the reaction temperature may be as low as about 200° C., about 250° C., about 300° C., about 310° C., about 320° C., about 325° C., about 330° C., about 340° C., about 350° C., or about 360° C., or as high as about 370° C., about 380° C., about 390° C., about 400° C., about 425° C., about 450° C., about 475° C., about 500° C., about 525° C., about 550° C., about 575° C., about 600° C., about 700° C. or about 800° C., or any range defined between any two of the foregoing values, such as about 200° C.
- the reaction temperature is from about 300° C. to about 500° C. More preferably, the reaction temperature is from about 350° C. to about 450° C. Most preferably, the reaction temperature is from about 375° C. to about 425° C.
- the reaction may take place in the presence of a catalyst 142 contained within the reactor 140 .
- the catalyst 142 may comprise stainless steel, nickel, nickel-chromium alloy, nickel-chromium-molybdenum alloy, nickel-copper alloy, copper, alumina, silicon carbide, platinum, palladium, rhenium, activated carbon, such as such as Norit-PK35, Calgon or Shirasagi carbon, or combinations thereof.
- the surfaces of the reactor 140 itself in contact with the trifluoroacetyl iodide compositions may provide the catalytic effect.
- the reaction may proceed by pyrolysis, or thermal decomposition, of the trifluoroacetyl iodide.
- the reaction may be conducted at a reaction operating pressure as low as about atmospheric pressure, about 5 psig (34 kPaG), about 10 psig (69 kPaG), about 15 psig (103 kPaG), about 20 psig (138 kPaG), about 25 psig (172 kPaG), about 30 psig (207 kPaG), about 35 psig (241 kPaG), about 40 psig (276 kPaG) or about 50 psig (345 kPaG), or as high as about 60 psig (414 kPaG), about 70 psig (483 kPaG), about 80 psig (552 kPaG), about 100 psig (689 kPaG), about 120 psig (827 kPaG), about 150 psig (1,034 kPaG), about 200 psig (1,379 kPaG), 225 psig (1551 kPaG), about 250 psig (1
- the reaction is conducted at a reaction operating pressure from about 5 psig (34 kPaG) to about 275 psig (1896 kPaG). More preferably, the reaction is conducted at a reaction operating pressure from about 10 psig (69 kPaG) to about to about 250 psig (1,724 kPaG). Most preferably, the reaction is conducted at a reaction operating pressure from about 20 psig (138 kPaG) to about 225 psig (1551 kPaG).
- the trifluoroacetyl iodide composition may be in contact with the catalyst 142 (and/or the surface of the reactor 140 ) for a contact time as short as about 0.01 second, about 0.05 second, about 0.1 second, about 1 second, about 2 seconds, about 3 seconds, about 5 seconds, about 8 seconds, about 10 seconds, about 12 seconds, or about 15 seconds, or as long as about 18 seconds, 20 seconds, about 25 seconds, about 30 seconds, about 35 seconds, about 40 seconds, about 50 seconds, about 60 seconds, about 300 seconds, or about 600 seconds, or for any contact time within any range defined between any two of the foregoing values, such as about 0.01 seconds to about 600 seconds, about 0.1 seconds to about 600 seconds, about 1 second to about 60 seconds, about 3 seconds to about 50 seconds, about 5 seconds to about 40 seconds, about 8 seconds to about 35 seconds, about 10 seconds to about 30 seconds, about 12 seconds to about 25 seconds, about 15 seconds to about 20 seconds, about 20 seconds to about 25 seconds, about 10 seconds to about 40 seconds, or about 10 seconds to about 30
- the trifluoroacetyl iodide composition is in contact with the catalyst 142 (and/or the surface of the reactor 140 ) for a contact time from about 0.1 seconds to about 100 seconds. More preferably, the trifluoroacetyl iodide composition is in contact with the catalyst 142 (and/or the surface of the reactor 140 ) for a contact time from about 0.1 second to about 60 seconds. Most preferably, the trifluoroacetyl iodide composition is in contact with the catalyst 142 (and/or the surface of the reactor 140 ) for a contact time from about 0.1 second to about 10 seconds.
- the product stream 144 may proceed directly to a distillation column 146 , as shown in FIG. 2 .
- the product stream 144 comprises unreacted trifluoroacetyl iodide and other by-products, such as trifluoromethane (CHF 3 ), hexafluoroethane (C 2 F 6 ), and hexafluoroacetone ((CF 3 ) 2 CO).
- CHF 3 trifluoromethane
- C 2 F 6 hexafluoroethane
- hexafluoroacetone (CF 3 ) 2 CO).
- the distillation column 146 is configured for the separation of unreacted trifluoroacetyl iodide and by-products, such as carbon monoxide, trifluoromethane and hexafluoroethane, from the trifluoroiodomethane to produce a purified product stream 148 , comprising trifluoroiodomethane.
- the distillation column 146 may be configured to separate and return the unreacted trifluoroacetyl iodide to the feed stream 132 in an unreacted trifluoroacetyl iodide flow 150 .
- the distillation column 146 may also be configured to separate the carbon monoxide into a carbon monoxide stream 152 for sale, reuse elsewhere, or disposal.
- any range defined between any two of the foregoing values literally means that any range may be selected from any two of the values listed prior to such phrase regardless of whether the values are in the lower part of the listing or in the higher part of the listing.
- a pair of values may be selected from two lower values, two higher values, or a lower value and a higher value.
- the modifier “about” used in connection with a quantity is inclusive of the stated value and has the meaning dictated by the context (for example, it includes at least the degree of error associated with the measurement of the particular quantity).
- the modifier “about” is also considered as disclosing the range defined by the absolute values of the two endpoints.
- Aspect 1 is a composition comprising trifluoroacetyl iodide, at least one organic impurity and at least one inorganic impurity.
- the at least one organic impurity comprises at least one of difluoroiodomethane, pentafluoroiodoethane, iodomethane, iodopropane, dichlorotetrafluoroethane, dichlorotrifluoroethane, trichlorotrifluoroethane, methyltrifluoroacetate, trifluoroacetic anhydride, difluorobutane and methyl propane.
- the at least one inorganic impurity comprises at least one of: hydrogen iodide, hydrogen chloride, iodine and hydrogen triiodide.
- Aspect 2 is the composition of Aspect 1, wherein the at least one organic impurity is present, in GC area % of total organic compounds, in an amount from about 0.05 GC area % to about 5.0 GC area %.
- Aspect 3 is the composition of Aspect 1, wherein the at least one organic impurity is present, in GC area % of total organic compounds, in an amount from about 0.05 GC area % to about 2.0 GC area %.
- Aspect 4 is the composition of Aspect 1, wherein the at least one organic impurity is present, in GC area % of total organic compounds, in an amount from about 0.05 GC area % to about 1.0 GC area %.
- Aspect 5 is composition of any of Aspects 1-4, wherein the at least one organic impurity comprises trifluoroacetic anhydride present, in GC area % of total organic compounds, in amount from about 0.001 GC area % to about 1.0 GC area %.
- Aspect 6 is the composition of any of Aspects 1-5, wherein the at least one organic impurity comprises pentafluoroiodoethane present, in GC area % of total organic compounds, in amount from about 0.0001 GC area % to about 0.5 GC area %.
- Aspect 7 is the composition of any of Aspects 1-6, wherein the at least one organic impurity comprises iodomethane present, in GC area % of total organic compounds, in amount from about 0.0001 GC area % to about 0.5 GC area %.
- Aspect 8 is the composition of any of Aspects 1-7, wherein the at least one organic impurity comprises methyltrifluoroacetate present, in GC area % of total organic compounds, in amount from about 0.001 GC area % to about 2.0 GC area %.
- Aspect 9 is the composition of any of Aspects 1-8, wherein the at least one organic impurity comprises at least one of: difluoroiodomethane, dichlorotetrafluoroethane, dichlorotrifluoroethane, trichlorotrifluoroethane, iodopropane, difluorobutane and methyl propane present, in GC area % of total organic compounds, in total in an amount from about 0.0001 GC area % to about 0.5 GC area %.
- Aspect 10 is the composition of any of Aspects 1-9, further comprising at least one additional organic impurity comprising at least one of: trifluoroacetic acid, trifluoroacetyl fluoride, trifluoroacetyl chloride, trifluoroiodomethane and chlorotrifluoroethane.
- Aspect 11 is the composition of Aspect 10, wherein the at least one additional organic impurity comprises trifluoroacetic acid present, in GC area % of total organic compounds, in amount from about 0.001 GC area % to about 2.0 GC area %.
- Aspect 12 is the composition of Aspect 10 or Aspect 11, the at least one additional organic impurity comprises trifluoroacetyl fluoride present, in GC area % of total organic compounds, in amount from about 0.0001 GC area % to about 0.05 GC area %.
- Aspect 13 is the composition of any of Aspects 10-12, wherein the at least one additional organic impurity comprises trifluoroacetyl chloride present, in GC area % of total organic compounds, in amount from about 0.001 GC area % to about 2.0 GC area %.
- Aspect 14 is the composition of any of Aspects 10-13, wherein the at least one additional organic impurity comprises trifluoroiodomethane present, in GC area % of total organic compounds, in amount from about 0.0001 GC area % to about 2.0 GC area %.
- Aspect 15 is the composition of any of Aspects 10-14, wherein the at least one additional organic impurity comprises chlorotrifluoroethane present, in GC area % of total organic compounds, in amount from about 0.0001 GC area % to about 0.5 GC area %.
- Aspect 16 is the composition of any of Aspects 1-15, wherein the at least one inorganic impurity is present in total in an amount from about 0.01 wt. % to about 1.5 wt. % of the composition.
- Aspect 17 is the composition of any of Aspects 1-15, wherein the at least one inorganic impurity is present in total in an amount from about 0.01 wt. % to about 0.5 wt. % of the composition.
- Aspect 18 is the composition of any of Aspects 1-17, wherein the at least one inorganic impurity comprises iodine in amount from about 0.001 wt. % to about 0.5 wt. % of the composition.
- Aspect 19 is the composition of any of Aspects 1-18, wherein the at least one inorganic impurity comprises hydrogen iodide in amount from about 0.0001 wt. % to about 0.5 wt. % of the composition.
- Aspect 20 is the composition of any of Aspects 1-18, wherein the at least one inorganic impurity comprises hydrogen triiodide in amount from about 0.0001 wt. % to about 0.5 wt. % of the composition.
- Aspect 21 is composition of any of claims 1 - 19 , wherein the at least one organic impurity is present, in GC area % of total organic compounds, in an amount from about 0.05 GC area % to about 5.0 GC area %, and the at least one inorganic impurity is present in an amount from about 0.01 wt. % to about 0.5 wt. % of the composition.
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US17/495,506 US20220112226A1 (en) | 2020-10-14 | 2021-10-06 | Trifluoroacetyl iodide compositions useful for making trifluoroiodomethane |
PCT/US2021/071841 WO2022082181A1 (en) | 2020-10-14 | 2021-10-13 | Trifluoroacetyl iodide compositions useful for making trifluoroiodomethane |
MX2023003909A MX2023003909A (es) | 2020-10-14 | 2021-10-13 | Composiciones de yoduro de trifluoroacetilo utiles para fabricar trifluoroyodometano. |
EP21881308.7A EP4229023A1 (en) | 2020-10-14 | 2021-10-13 | Trifluoroacetyl iodide compositions useful for making trifluoroiodomethane |
CN202180066344.0A CN116234788A (zh) | 2020-10-14 | 2021-10-13 | 可用于制备三氟碘甲烷的三氟乙酰碘组合物 |
KR1020237011647A KR20230087462A (ko) | 2020-10-14 | 2021-10-13 | 트리플루오로요오도메탄을 제조하는데 유용한 트리플루오로아세틸 요오드 조성물 |
JP2023519486A JP2023545387A (ja) | 2020-10-14 | 2021-10-13 | トリフルオロヨードメタンの製造に有用なトリフルオロアセチルヨージド組成物 |
US18/400,050 US20240166677A1 (en) | 2020-10-14 | 2023-12-29 | Trifluoroacetyl iodide compositions useful for making trifluoroiodomethane |
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US20240166677A1 (en) | 2024-05-23 |
JP2023545387A (ja) | 2023-10-30 |
KR20230087462A (ko) | 2023-06-16 |
CN116234788A (zh) | 2023-06-06 |
MX2023003909A (es) | 2023-04-24 |
EP4229023A1 (en) | 2023-08-23 |
WO2022082181A1 (en) | 2022-04-21 |
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