JP2021536440A - トリフルオロヨードメタンを生成するためのプロセス - Google Patents
トリフルオロヨードメタンを生成するためのプロセス Download PDFInfo
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- JP2021536440A JP2021536440A JP2021510221A JP2021510221A JP2021536440A JP 2021536440 A JP2021536440 A JP 2021536440A JP 2021510221 A JP2021510221 A JP 2021510221A JP 2021510221 A JP2021510221 A JP 2021510221A JP 2021536440 A JP2021536440 A JP 2021536440A
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- Prior art keywords
- trifluoroacetyl
- reaction
- trifluoroiodomethane
- less
- iodide
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- 238000000034 method Methods 0.000 title claims abstract description 126
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 title claims abstract description 100
- 238000006243 chemical reaction Methods 0.000 claims abstract description 116
- 239000003054 catalyst Substances 0.000 claims abstract description 80
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 68
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims abstract description 66
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000009826 distribution Methods 0.000 claims abstract description 32
- 239000007789 gas Substances 0.000 claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 claims abstract description 18
- DTJIBVSGNIAPCX-UHFFFAOYSA-N 2,2,2-trifluoroacetyl bromide Chemical compound FC(F)(F)C(Br)=O DTJIBVSGNIAPCX-UHFFFAOYSA-N 0.000 claims abstract description 12
- DCEPGADSNJKOJK-UHFFFAOYSA-N 2,2,2-trifluoroacetyl fluoride Chemical compound FC(=O)C(F)(F)F DCEPGADSNJKOJK-UHFFFAOYSA-N 0.000 claims abstract description 11
- -1 trifluoroacetyl halides Chemical class 0.000 claims description 79
- 150000002894 organic compounds Chemical class 0.000 claims description 47
- MTRCYRVBLMQHPZ-UHFFFAOYSA-N 2,2,2-trifluoroacetyl iodide Chemical compound FC(F)(F)C(I)=O MTRCYRVBLMQHPZ-UHFFFAOYSA-N 0.000 claims description 39
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 7
- 238000010924 continuous production Methods 0.000 claims description 3
- 238000003672 processing method Methods 0.000 claims 2
- 239000012530 fluid Substances 0.000 claims 1
- 238000010586 diagram Methods 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 45
- 238000004817 gas chromatography Methods 0.000 description 20
- 238000004821 distillation Methods 0.000 description 17
- 239000012071 phase Substances 0.000 description 17
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 13
- 229910002091 carbon monoxide Inorganic materials 0.000 description 13
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- 239000011630 iodine Substances 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 229910000039 hydrogen halide Inorganic materials 0.000 description 5
- 239000012433 hydrogen halide Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- PDJAZCSYYQODQF-UHFFFAOYSA-N iodine monofluoride Chemical group IF PDJAZCSYYQODQF-UHFFFAOYSA-N 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 229910001182 Mo alloy Inorganic materials 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine 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
- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- DDTIGTPWGISMKL-UHFFFAOYSA-N molybdenum nickel Chemical compound [Ni].[Mo] DDTIGTPWGISMKL-UHFFFAOYSA-N 0.000 description 1
- QPJSUIGXIBEQAC-UHFFFAOYSA-N n-(2,4-dichloro-5-propan-2-yloxyphenyl)acetamide Chemical compound CC(C)OC1=CC(NC(C)=O)=C(Cl)C=C1Cl QPJSUIGXIBEQAC-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000003507 refrigerant Substances 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
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Images
Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/087—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated halogenated hydrocarbons
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
-
- 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
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/42—Use of additives, e.g. for stabilisation
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
式1: HI+CF3COX → CF3I+CO+HX。
少なくとも1種のハロゲン化水素酸は、フッ化水素酸(HF)、塩酸(HCl)、及び臭化水素酸(HBr)からなる群から選択されてよい。
この実施例では、上記の式1による、ヨウ化水素及びトリフルオロアセチルクロリドからのトリフルオロヨードメタンの製造が実証される。等モル量のトリフルオロアセチルクロリド及び無水ヨウ化水素を予熱器に通し、一連の9回の実験で約100℃の温度に加熱した。次いで、加熱した反応物を、直径3/8インチ(9.5mm)、長さ6インチ(152mm)のステンレス管に通した。実験によっては、管を350℃〜380℃の範囲の温度に加熱し、各実験前に窒素で少なくとも1時間パージして、全ての水分を飛ばした。各実験では、管は、数種類の触媒のうちの1種を含有していた。接触時間は、12秒〜30秒と様々であった。GC分析及びGC−MS分析のために、各実験について排出された全ての蒸気を試料バッグに回収した。結果を表1、表2、及び表3に示す。
態様
Claims (10)
- トリフルオロヨードメタン(CF3I)を生成するための気相処理方法であって、
ヨウ化水素と、トリフルオロアセチルクロリド、トリフルオロアセチルフルオリド、トリフルオロアセチルブロミド、及びこれらの組み合わせからなる群から選択されるトリフルオロアセチルハライドと、を含む反応物流を提供することと、
前記反応物流を触媒の存在下で約200℃〜約600℃の反応温度で反応させて、前記トリフルオロヨードメタンを含む生成物流を生成することと、を含む、処理方法。 - 前記提供する工程において、前記反応物流が約500体積ppm未満の酸素を含み、前記ヨウ化水素が約500重量ppm未満の水を含む、請求項1に記載の処理方法。
- 前記反応させる工程において、前記触媒は、活性炭触媒及びメソカーボン触媒の群から選択される少なくとも1種の触媒を含む、請求項1に記載の処理方法。
- 前記反応させる工程において、前記反応温度は約350℃〜約400℃である、請求項1に記載の処理方法。
- 前記生成物流中の有機化合物が、全有機化合物のGC面積%で、約10%〜約99%のトリフルオロヨードメタン、約1%〜約60%の未反応トリフルオロアセチルハライド、約80%未満のトリフルオロアセチルヨージド、並びに約10%未満の、トリフルオロヨードメタン、トリフルオロアセチルハライド、及びトリフルオロアセチルヨージド以外の有機化合物からなる、請求項1に記載の処理方法。
- 前記未反応トリフルオロアセチルハライドを前記生成物流体から分離する追加工程と、
前記分離した未反応トリフルオロアセチルハライドを前記反応物流に戻す追加工程と、を更に含む、請求項5に記載の処理方法。 - 前記生成物流から前記トリフルオロアセチルヨージドを分離する追加工程を更に含む、請求項5に記載の処理方法。
- 前記生成物流から未反応ヨウ化水素を分離し、前記未反応ヨウ化水素を前記反応物流に戻す追加工程を更に含む、請求項1に記載の処理方法。
- 前記処理方法は連続プロセスである、請求項1に記載の処理方法。
- 請求項1に記載の処理方法によって製造される組成物であって、約99重量%を超えるトリフルオロヨードメタンの濃度を含む、組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201862722553P | 2018-08-24 | 2018-08-24 | |
US62/722,553 | 2018-08-24 | ||
PCT/US2019/047814 WO2020041653A1 (en) | 2018-08-24 | 2019-08-23 | Processes for producing trifluoroiodomethane |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2021536440A true JP2021536440A (ja) | 2021-12-27 |
JP7386233B2 JP7386233B2 (ja) | 2023-11-24 |
Family
ID=69584316
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2021510221A Active JP7386233B2 (ja) | 2018-08-24 | 2019-08-23 | トリフルオロヨードメタンを生成するためのプロセス |
Country Status (8)
Country | Link |
---|---|
US (1) | US10752565B2 (ja) |
EP (1) | EP3841082A4 (ja) |
JP (1) | JP7386233B2 (ja) |
KR (1) | KR20210036984A (ja) |
CN (1) | CN112739672A (ja) |
CA (1) | CA3110484A1 (ja) |
MX (1) | MX2021002101A (ja) |
WO (1) | WO2020041653A1 (ja) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20210036985A (ko) * | 2018-08-24 | 2021-04-05 | 허니웰 인터내셔날 인코포레이티드 | 트라이플루오로요오도메탄 및 트라이플루오로아세틸 요오다이드의 제조 방법 |
US11554956B2 (en) | 2019-04-16 | 2023-01-17 | Honeywell International Inc. | Integrated process and catalysts for manufacturing hydrogen iodide from hydrogen and iodine |
US11453631B2 (en) | 2020-10-14 | 2022-09-27 | Honeywell International Inc. | Methods for removal HI/I2/HI3 from trifluoroacetyl iodide (TFAI) feedstock and pyrolysis reactor effluent |
US11565992B2 (en) | 2020-11-13 | 2023-01-31 | Honeywell International Inc. | Methods for separation of azeotrope or azeotrope-like compositions of trifluoroiodomethane (CF3I) and trifluoroacetyl chloride (CF3COCI) |
CN115181004B (zh) * | 2022-09-09 | 2022-12-27 | 天津绿菱气体有限公司 | 一种三氟碘甲烷制备方法 |
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2019
- 2019-08-23 CN CN201980061211.7A patent/CN112739672A/zh active Pending
- 2019-08-23 CA CA3110484A patent/CA3110484A1/en active Pending
- 2019-08-23 JP JP2021510221A patent/JP7386233B2/ja active Active
- 2019-08-23 MX MX2021002101A patent/MX2021002101A/es unknown
- 2019-08-23 WO PCT/US2019/047814 patent/WO2020041653A1/en unknown
- 2019-08-23 KR KR1020217008198A patent/KR20210036984A/ko active Search and Examination
- 2019-08-23 US US16/549,389 patent/US10752565B2/en active Active
- 2019-08-23 EP EP19852362.3A patent/EP3841082A4/en active Pending
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