JP2006022098A - 第一級アミンの断熱的ホスゲン化によるポリイソシアネートの製造方法 - Google Patents
第一級アミンの断熱的ホスゲン化によるポリイソシアネートの製造方法 Download PDFInfo
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- JP2006022098A JP2006022098A JP2005195361A JP2005195361A JP2006022098A JP 2006022098 A JP2006022098 A JP 2006022098A JP 2005195361 A JP2005195361 A JP 2005195361A JP 2005195361 A JP2005195361 A JP 2005195361A JP 2006022098 A JP2006022098 A JP 2006022098A
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- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- 229920001228 polyisocyanate Polymers 0.000 title abstract description 10
- 239000005056 polyisocyanate Substances 0.000 title abstract description 10
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 23
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 31
- 150000001412 amines Chemical class 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 13
- 239000012948 isocyanate Substances 0.000 claims description 8
- 150000002513 isocyanates Chemical class 0.000 claims description 8
- 150000003141 primary amines Chemical class 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 239000002244 precipitate Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 10
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 5
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- 230000002411 adverse Effects 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000012619 stoichiometric conversion Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
【解決手段】第一級アミンのホスゲン化による単純なポリイソシアネートの製造方法を、少なくとも2段階で実施し、かつ該方法の第1段階の間で反応温度及び反応圧を調節して、温度を100〜220℃の温度に保持することによって解決される。
【選択図】なし
Description
a)第1段階において、アミンとホスゲンとを断熱的に行われる反応で反応させるにあたり、反応器中の絶対圧を減圧により8〜50バールの値に能動的に調整することによって反応温度を100〜220℃の値に制限し、かつホスゲンの化学量論的変換率が少なくとも80%に達するまでその温度を100〜220℃の値に保持し、
b)第2段階において、a)からの反応混合物を1〜15バールの絶対圧に減圧し、そして該反応混合物を更に90〜240℃、有利には90〜200℃の温度で、場合により熱を導入することで反応させる方法を提供している。
以下の組成による、ジフェニルメタンジアミン及びポリフェニレン−ポリメチレンポリアミン、いわゆるPMDAの混合物をホスゲン化のために使用した:
二核MDAの濃度:58.4%
多核PMDAの濃度:>39.2%
PMDAをクロロベンゼン(MCB)中に溶かした約50℃の温度を有する30質量%濃度の溶液27.6kg/h及びホスゲンをMCB中に溶かした約50℃の温度を有する45質量%濃度の溶液36.3kg/hを動的ミキサー(ピンミキサー)中で連続的に混合した。該ミキサー中の圧力は7バール(絶対)であった。そのミキサーからの排出口で、反応混合物は108℃の温度を有していた。ミキサー中で起き始める発熱反応によってミキサー中の温度の上昇が生じた。
イソシアネート基の濃度:38.1質量%
25℃での粘度:81mPas
7バールで作業された第1の管形反応器についての試験の完了後に行われた検査により、管の内表面上に明らかな固形物の粘結が見られた。
実施例1で使用したのと同じ組成を有するPMDAを使用した。
イソシアネート基の濃度:32.0質量%
25℃での粘度:73mPas
22バールで作業された第1の管形反応器についての試験の完了後に行われた検査により、管の内表面に固形物の粘結の徴候が全くないことが判明した。
Claims (1)
- 第一級アミンとホスゲンとを反応させることにより有機イソシアネートを製造するための2段階法において、
a)第1段階において、アミンとホスゲンとを温度制御される反応器中で断熱的に反応させるにあたり、反応器中の絶対圧を減圧により8〜50バールの値に能動的に調整することによって少なくとも80%のホスゲンが変換されるまで反応温度を100〜220℃の値に保持する、
b)第2段階において、a)からの反応混合物を1〜15バールの絶対圧に減圧し、そして更に減圧された反応混合物を90〜240℃の温度で、熱を導入するか又は導入せずに反応させる
ことを含む方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004032871A DE102004032871A1 (de) | 2004-07-07 | 2004-07-07 | Verfahren zur Herstellung von Polyisocyanaten durch adiabate Phosgenierung von primären Aminen |
DE102004032871.4 | 2004-07-07 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2006022098A true JP2006022098A (ja) | 2006-01-26 |
JP2006022098A5 JP2006022098A5 (ja) | 2008-08-07 |
JP5054291B2 JP5054291B2 (ja) | 2012-10-24 |
Family
ID=35262229
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2005195361A Expired - Fee Related JP5054291B2 (ja) | 2004-07-07 | 2005-07-04 | 第一級アミンの断熱的ホスゲン化によるポリイソシアネートの製造方法 |
Country Status (12)
Country | Link |
---|---|
US (1) | US8097751B2 (ja) |
EP (1) | EP1616857B2 (ja) |
JP (1) | JP5054291B2 (ja) |
KR (1) | KR101183756B1 (ja) |
CN (1) | CN100569742C (ja) |
AT (1) | ATE384040T1 (ja) |
BR (1) | BRPI0502604B1 (ja) |
DE (2) | DE102004032871A1 (ja) |
ES (1) | ES2299921T5 (ja) |
PT (1) | PT1616857E (ja) |
SG (1) | SG119294A1 (ja) |
TW (1) | TW200617049A (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008174549A (ja) * | 2006-12-13 | 2008-07-31 | Bayer Materialscience Ag | 気相中でのイソシアネートの製造方法 |
JP2009126865A (ja) * | 2007-11-22 | 2009-06-11 | Bayer Materialscience Ag | 気相中での芳香族ジイソシアネートの製造方法 |
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DE102004032871A1 (de) | 2004-07-07 | 2006-02-09 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyisocyanaten durch adiabate Phosgenierung von primären Aminen |
US7504533B2 (en) * | 2006-04-24 | 2009-03-17 | Bayer Materialscience Llc | Process for the production of isocyanates |
US7547801B2 (en) * | 2006-06-26 | 2009-06-16 | Bayer Materialscience Llc | Process for the continuous preparation of isocyanates |
EP2014641A3 (en) * | 2007-06-06 | 2009-03-18 | Huntsman International Llc | Process for preparing mixtures of diphenylmethane diisocyanates and polyphenyl polymethylene polyisocyanates |
DE102007061688A1 (de) | 2007-12-19 | 2009-06-25 | Bayer Materialscience Ag | Verfahren und Mischaggregat zur Herstellung von Isocyanaten durch Phosgenierung primärer Amine |
FR2940283B1 (fr) | 2008-12-18 | 2011-03-11 | Perstorp Tolonates France | Utilisation d'un reacteur de type piston pour la mise en oeuvre d'un procede de phosgenation. |
KR20120000078A (ko) | 2009-03-20 | 2012-01-03 | 바스프 에스이 | 이소시아네이트를 제조하기 위한 방법 및 장치 |
CN102396008B (zh) | 2009-04-15 | 2014-12-31 | 丰田自动车株式会社 | 警报输出控制装置 |
US8835673B2 (en) | 2009-12-04 | 2014-09-16 | Basf Se | Process for preparing isocyanates |
JP5931898B2 (ja) | 2010-11-17 | 2016-06-08 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | メチレンジ(フェニルイソシアネート)の製造方法 |
US8907124B2 (en) | 2010-11-17 | 2014-12-09 | Basf Se | Process for preparing methylenedi(phenyl isocyanate) |
BR112013029665A2 (pt) | 2011-05-24 | 2019-09-24 | Basf Se | "processo para a preparação de poliisocianatos, e, composição de poliisicianato" |
US8933262B2 (en) | 2011-05-24 | 2015-01-13 | Basf Se | Process for preparing polyisocyanates from biomass |
US9266824B2 (en) | 2014-01-13 | 2016-02-23 | Warsaw Orthopedic, Inc. | Methods and compositions for making an amino acid triisocyanate |
CN106458862B (zh) | 2014-03-27 | 2020-03-31 | 科思创德国股份有限公司 | 制备异氰酸酯的方法 |
HUE060286T2 (hu) | 2014-06-24 | 2023-02-28 | Covestro Intellectual Property Gmbh & Co Kg | Eljárás kémiai termékek elõállítására az eljárás megszakítása mellett |
PT3313565T (pt) | 2015-06-29 | 2019-10-30 | Covestro Deutschland Ag | Método de produção de poli-isocianatos |
US10815193B2 (en) | 2015-06-29 | 2020-10-27 | Covestro Deutschland Ag | Process for providing hydrogen chloride for chemical reactions |
WO2017050776A1 (de) | 2015-09-24 | 2017-03-30 | Covestro Deutschland Ag | Verfahren zur herstellung von isocyanaten |
HUE060897T2 (hu) | 2015-09-30 | 2023-04-28 | Covestro Intellectual Property Gmbh & Co Kg | Eljárás izocianátok elõállítására |
HUE061332T2 (hu) | 2015-11-20 | 2023-06-28 | Covestro Intellectual Property Gmbh & Co Kg | Eljárás aminobenzoesav vagy aminobenzoesav-származék elõállítására |
EP3478653B1 (de) | 2016-06-29 | 2020-02-19 | Covestro Deutschland AG | Verfahren zur herstellung von anilin oder eines anilinfolgeprodukts |
PT3500553T (pt) | 2016-08-17 | 2021-07-29 | Covestro Deutschland Ag | Processo para a produção de isocianato e pelo menos um outro produto químico num sistema de produção integrada |
HUE053496T2 (hu) | 2016-09-01 | 2021-07-28 | Covestro Intellectual Property Gmbh & Co Kg | Eljárás izocianátok elõállítására |
EP3558931B1 (de) | 2016-12-20 | 2022-04-20 | Covestro Intellectual Property GmbH & Co. KG | Verfahren zur herstellung von aminobenzoesäure oder eines aminobenzoesäurefolgeprodukts |
WO2019007834A1 (de) | 2017-07-03 | 2019-01-10 | Covestro Deutschland Ag | Produktionsanlage zur herstellung eines chemischen produkts durch umsetzung h-funktioneller reaktanten mit phosgen und verfahren zum betreiben derselben |
EP3735405B1 (de) | 2018-01-05 | 2021-11-24 | Covestro Intellectual Property GmbH & Co. KG | Verfahren zur herstellung von methylen-diphenylen-diisocyanaten und polymethylen-polyphenylen-polyisocyanaten |
CN112534057A (zh) | 2018-06-07 | 2021-03-19 | 科思创知识产权两合公司 | 制备氨基苯甲酸或氨基苯甲酸反应产物的方法 |
HUE060351T2 (hu) | 2018-07-27 | 2023-02-28 | Covestro Intellectual Property Gmbh & Co Kg | Eljárás anilin vagy anilin-származék elõállítására |
US10851048B2 (en) | 2018-11-13 | 2020-12-01 | Covestro Deutschland Ag | Process for preparing an isocyanate by partly adiabatically operated phosgenation of the corresponding amine |
US10875827B2 (en) | 2018-11-13 | 2020-12-29 | Covestro Deutschland Ag | Process for preparing an isocyanate by partly adiabatic phosgenation of the corresponding amine |
CN114787125A (zh) | 2019-12-18 | 2022-07-22 | 科思创德国股份有限公司 | 用于制备二苯基甲烷系列的二-和多异氰酸酯的方法 |
WO2021228977A1 (de) | 2020-05-15 | 2021-11-18 | Covestro Deutschland Ag | Verfahren zum betreiben einer anlage zur kontinuierlichen herstellung eines isocyanats |
WO2022253890A1 (de) | 2021-06-02 | 2022-12-08 | Covestro Deutschland Ag | Verfahren zur herstellung von anilin oder eines anilinfolgeproduktes |
CN117642446A (zh) | 2021-07-02 | 2024-03-01 | 赢创运营有限公司 | 从pu解聚过程中回收二异氰酸酯和/或多异氰酸酯 |
WO2023194110A1 (de) | 2022-04-06 | 2023-10-12 | Covestro Deutschland Ag | Verfahren zur herstellung von anilin oder eines anilinfolgeproduktes |
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-
2004
- 2004-07-07 DE DE102004032871A patent/DE102004032871A1/de not_active Withdrawn
-
2005
- 2005-06-24 ES ES05013631T patent/ES2299921T5/es active Active
- 2005-06-24 AT AT05013631T patent/ATE384040T1/de not_active IP Right Cessation
- 2005-06-24 EP EP05013631A patent/EP1616857B2/de active Active
- 2005-06-24 PT PT05013631T patent/PT1616857E/pt unknown
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Patent Citations (3)
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JPS4849721A (ja) * | 1971-10-25 | 1973-07-13 | ||
US4581174A (en) * | 1984-01-31 | 1986-04-08 | Basf Aktiengesellschaft | Process for the continuous preparation of organic mono-and/or polyisocyanates |
WO2004056756A1 (de) * | 2002-12-19 | 2004-07-08 | Basf Aktiengesellschaft | Verfahren zur kontinuierlichen herstellung von isocyanaten |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008174549A (ja) * | 2006-12-13 | 2008-07-31 | Bayer Materialscience Ag | 気相中でのイソシアネートの製造方法 |
KR101433379B1 (ko) * | 2006-12-13 | 2014-08-26 | 바이엘 머티리얼사이언스 아게 | 이소시아네이트의 기상 제조 방법 |
JP2009126865A (ja) * | 2007-11-22 | 2009-06-11 | Bayer Materialscience Ag | 気相中での芳香族ジイソシアネートの製造方法 |
Also Published As
Publication number | Publication date |
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CN1718570A (zh) | 2006-01-11 |
DE102004032871A1 (de) | 2006-02-09 |
US8097751B2 (en) | 2012-01-17 |
TW200617049A (en) | 2006-06-01 |
ES2299921T5 (es) | 2013-02-12 |
ATE384040T1 (de) | 2008-02-15 |
KR101183756B1 (ko) | 2012-09-17 |
PT1616857E (pt) | 2008-04-10 |
SG119294A1 (en) | 2006-02-28 |
KR20060049885A (ko) | 2006-05-19 |
BRPI0502604B1 (pt) | 2015-03-24 |
EP1616857A1 (de) | 2006-01-18 |
BRPI0502604A (pt) | 2006-02-21 |
EP1616857B2 (de) | 2012-09-26 |
CN100569742C (zh) | 2009-12-16 |
EP1616857B1 (de) | 2008-01-16 |
DE502005002540D1 (de) | 2008-03-06 |
US20060025556A1 (en) | 2006-02-02 |
ES2299921T3 (es) | 2008-06-01 |
JP5054291B2 (ja) | 2012-10-24 |
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