JP7050695B2 - ニトリルの合成方法 - Google Patents
ニトリルの合成方法 Download PDFInfo
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- JP7050695B2 JP7050695B2 JP2018555931A JP2018555931A JP7050695B2 JP 7050695 B2 JP7050695 B2 JP 7050695B2 JP 2018555931 A JP2018555931 A JP 2018555931A JP 2018555931 A JP2018555931 A JP 2018555931A JP 7050695 B2 JP7050695 B2 JP 7050695B2
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- 150000002825 nitriles Chemical class 0.000 title claims description 13
- 238000001308 synthesis method Methods 0.000 title 1
- 238000010438 heat treatment Methods 0.000 claims description 40
- 230000006698 induction Effects 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 29
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 25
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 18
- 230000005291 magnetic effect Effects 0.000 claims description 13
- 229930195733 hydrocarbon Natural products 0.000 claims description 12
- 150000002430 hydrocarbons Chemical class 0.000 claims description 12
- 229910021529 ammonia Inorganic materials 0.000 claims description 11
- 230000005294 ferromagnetic effect Effects 0.000 claims description 11
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 10
- 229910045601 alloy Inorganic materials 0.000 claims description 8
- 239000000956 alloy Substances 0.000 claims description 8
- 229910017060 Fe Cr Inorganic materials 0.000 claims description 7
- 229910002544 Fe-Cr Inorganic materials 0.000 claims description 7
- 230000003197 catalytic effect Effects 0.000 claims description 7
- UPHIPHFJVNKLMR-UHFFFAOYSA-N chromium iron Chemical compound [Cr].[Fe] UPHIPHFJVNKLMR-UHFFFAOYSA-N 0.000 claims description 7
- 229910017709 Ni Co Inorganic materials 0.000 claims description 6
- 229910003267 Ni-Co Inorganic materials 0.000 claims description 6
- 229910003262 Ni‐Co Inorganic materials 0.000 claims description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 6
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 5
- 230000002194 synthesizing effect Effects 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 3
- 229910002060 Fe-Cr-Al alloy Inorganic materials 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 3
- 229910000953 kanthal Inorganic materials 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 239000001282 iso-butane Substances 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 description 10
- 239000007789 gas Substances 0.000 description 8
- 239000003302 ferromagnetic material Substances 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000004020 conductor Substances 0.000 description 5
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000000576 coating method Methods 0.000 description 3
- 230000001939 inductive effect Effects 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000000696 magnetic material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- -1 platinum group metals Chemical class 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 229910001006 Constantan 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910000575 Ir alloy Inorganic materials 0.000 description 1
- 229910000914 Mn alloy Inorganic materials 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- 229910001260 Pt alloy Inorganic materials 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000005290 antiferromagnetic effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
- 229940099364 dichlorofluoromethane Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000005389 magnetism Effects 0.000 description 1
- 230000028161 membrane depolarization Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- HWLDNSXPUQTBOD-UHFFFAOYSA-N platinum-iridium alloy Chemical class [Ir].[Pt] HWLDNSXPUQTBOD-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/18—Preparation of carboxylic acid nitriles by reaction of ammonia or amines with compounds containing carbon-to-carbon multiple bonds other than in six-membered aromatic rings
-
- 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
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
- B01J8/0285—Heating or cooling the reactor
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/14—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of germanium, tin or lead
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/75—Cobalt
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/33—Electric or magnetic properties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B6/00—Heating by electric, magnetic or electromagnetic fields
- H05B6/02—Induction heating
- H05B6/10—Induction heating apparatus, other than furnaces, for specific applications
- H05B6/105—Induction heating apparatus, other than furnaces, for specific applications using a susceptor
- H05B6/108—Induction heating apparatus, other than furnaces, for specific applications using a susceptor for heating a fluid
-
- 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
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/00433—Controlling the temperature using electromagnetic heating
-
- 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
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/00433—Controlling the temperature using electromagnetic heating
- B01J2208/00469—Radiofrequency
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/02—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C255/03—Mononitriles
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
CH4 + NH3 <-> HCN(シアン化水素) + 3H2
C2H6 + NH3 <-> CH3CN(アセトニトリル) + 3H2
C3H8 + NH3 <-> C2H3CN(アクリロニトリル) + 4H2
C3H8 + NH3 <-> C2H5CN(プロピオニトリル) + 3H2
イソ-C4H10 + NH3 <-> イソ-C3H5CN(メタクリロニトリル) + 4H2
なお、本願は、特許請求の範囲に記載の発明に関するものであるが、他の態様として以下も包含し得る。
1.金属コイルに交流電流を通すことによって得られる加熱を用いて、アンモニアと炭化水素との触媒反応によるニトリルの合成方法であって、アンモニアと炭化水素との間の吸熱反応が、反応ゾーンにおいて直接誘導加熱による反応器内で行われる、上記の方法。
2.前記コイルが、合成の反応器内に取り付けられており、かつ、触媒はコイルの内側に配置されている、上記1に記載の方法。
3.前記コイルが、カンタル型(Fe-Cr-Al合金)ワイヤからなる、上記1または2に記載の方法。
4.誘導加熱が、適切なコーティングを備えた強磁性金属構造体である誘導加熱器を用いて行われ、そして、該加熱が、磁気ヒステリシス損失によって発生する、上記1または2に記載の方法。
5.前記誘導加熱器が、高い電気的保磁力を有する強磁性触媒からなる、上記4に記載の方法。
6.前記触媒が、磁性材料で希釈されている、上記5に記載の方法。
7.前記金属構造体が、Fe-CrおよびAl-Ni-Co合金から選択される金属である、上記1~4のいずれか一つに記載の方法。
8.前記金属構造体が、触媒相が含浸された多孔質酸化物表面で被覆されている、上記7に記載の方法。
9.前記触媒相が、CoまたはSnをベースとする触媒を含有している、上記8に記載の方法。
10.前記炭化水素が、メタン、エタン、プロパン、イソブタンおよびオレフィンである、上記1~9のいずれか一つに記載の方法。
Claims (5)
- 金属コイルに交流電流を通すことによって得られる加熱を用いて、アンモニアと炭化水素との触媒反応によるニトリルの合成方法であって、アンモニアと炭化水素との間の吸熱反応が、反応ゾーンにおいて直接誘導加熱による反応器内で行われ、
誘導加熱が、触媒相が含浸された多孔質酸化物表面でコーティングされている強磁性金属構造体である誘導加熱器を用いて行われ、そして、該加熱が、磁気ヒステリシス損失によって発生し、
前記ニトリルが、シアン化水素、アセトニトリル、アクリロニトリル、プロピオニトリルおよびメタクリロニトリルからなる群から選択される、
上記の方法。 - 前記コイルが、カンタル型(Fe-Cr-Al合金)ワイヤからなる、請求項1に記載の方法。
- 前記金属構造体が、Fe-CrおよびAl-Ni-Co合金から選択される金属である、請求項1または2に記載の方法。
- 前記触媒相が、CoまたはSnをベースとする触媒を含有している、請求項1~3のいずれか一つに記載の方法。
- 前記炭化水素が、メタン、エタン、プロパン、イソブタンおよびオレフィンである、請求項1~4のいずれか一つに記載の方法。
Applications Claiming Priority (3)
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DKPA201600246 | 2016-04-26 | ||
DKPA201600246 | 2016-04-26 | ||
PCT/EP2017/059598 WO2017186615A1 (en) | 2016-04-26 | 2017-04-24 | A process for the synthesis of nitriles |
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JP2019514901A JP2019514901A (ja) | 2019-06-06 |
JP7050695B2 true JP7050695B2 (ja) | 2022-04-08 |
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US (1) | US11319284B2 (ja) |
EP (1) | EP3448833A1 (ja) |
JP (1) | JP7050695B2 (ja) |
CN (1) | CN109071375A (ja) |
WO (1) | WO2017186615A1 (ja) |
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EP3574991A1 (en) | 2018-05-31 | 2019-12-04 | Haldor Topsøe A/S | Steam reforming heated by resistance heating |
FR3100990B1 (fr) * | 2019-09-19 | 2022-01-07 | Institut Nat Des Sciences Appliquees De Toulouse | Ensemble catalytique comprenant un matériau ferromagnétique micrométrique et utilisation dudit ensemble pour des réactions de catalyse hétérogène |
FR3100988B1 (fr) * | 2019-09-19 | 2023-03-10 | Institut Nat Des Sciences Appliquees De Toulouse | Procédé de catalyse hétérogène mettant en œuvre un matériau ferromagnétique chauffé par induction magnétique et support de catalyseur utilisé pour ledit procédé |
AU2020360751A1 (en) * | 2019-10-01 | 2022-03-03 | Haldor Topsøe A/S | Cyanide on demand |
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JP2005519832A (ja) | 2002-03-14 | 2005-07-07 | インヴィスタ テクノロジーズ エス.アー.アール.エル | 気相触媒反応用の誘導加熱反応器 |
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JP2019514825A (ja) | 2016-04-26 | 2019-06-06 | ハルドール・トプサー・アクチエゼルスカベット | メタノール分解による水素または合成ガスの製造方法 |
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US6315972B1 (en) * | 1994-02-01 | 2001-11-13 | E.I. Du Pont De Nemours And Company | Gas phase catalyzed reactions |
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US20120141345A1 (en) | 2007-05-14 | 2012-06-07 | Slaten Colin S | High Efficiency reactor and process |
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Also Published As
Publication number | Publication date |
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WO2017186615A1 (en) | 2017-11-02 |
EP3448833A1 (en) | 2019-03-06 |
US11319284B2 (en) | 2022-05-03 |
WO2017186615A9 (en) | 2018-12-13 |
JP2019514901A (ja) | 2019-06-06 |
CN109071375A (zh) | 2018-12-21 |
US20190144376A1 (en) | 2019-05-16 |
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