JP2012506397A - ニトリル官能基を有する化合物を製造するための方法 - Google Patents
ニトリル官能基を有する化合物を製造するための方法 Download PDFInfo
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- IIOOIYHUTINYQO-UHFFFAOYSA-N C[Si](C)(c1ccccc1)[Si](C)(C)c1ccccc1 Chemical compound C[Si](C)(c1ccccc1)[Si](C)(C)c1ccccc1 IIOOIYHUTINYQO-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
[(R)a−(X)y−]nM−M1[−(X)z−(R1)a1]n1
式中:
M、M1は同一のものでも異なるものでもよく、次の元素:B、Si、Ge、Sn、Pb、Mo、Ni、Fe、W及びCrよりなる群から選択される元素を表し、
R、R1は同一のものでも異なるものでもよく、置換された又は置換されていない、かつ、架橋されていても架橋されていなくてもよい脂肪族基又は芳香族若しくは脂環式環を有する基、又はハロゲン化物基を表し、
Xは、酸素、窒素、硫黄又は珪素原子を表し、
y及びzは、同一でも同一でなくてもよい、0又は1の整数であり、
n及びn1は、M、M1元素の原子価を1で除したものに等しい整数であり、
a及びa1は、同一でも同一でなくてもよく、y及びzが1に等しい場合にはX元素の原子価を1で除したものに等しい整数であり、又はy及びzが0に等しい場合には1に等しい整数である。
・ビス(ネオペンチルグリコラト)ジボロン(RN CAS 201733−56−4)
・ビス(ヘキシレングリコラト)ジボロン(RN CAS 230299−21−5)
・ビス(ピナコラト)ジボロン(RN CAS 73183−34−3)
・テトラキス(ピロリニド)ジボロン(RN CAS 158752−98−8)
・ヘキサメチルジシラン(RN CAS 1450−14−2)
・テトラフェニルジメチルジシラン(RN CAS 1172−76−5)
・ジフェニルテトラメチルジシラン(RN CAS 1145−98−8)
・トリス(トリメチルシリル)シラン(RN CAS 1873−77−4)
・テトラキス(トリメチルシリル)シラン(RN CAS 4098−98−0)
・ヘキサフェニルジシラン(RN CAS 1450−23−3)
・ヘキサメチルジゲルマン(RN CAS 993−52−2)
・ヘキサエチルジゲルマン(RN CAS 993−62−4)
・ヘキサフェニルジゲルマン(RN CAS 2816−39−9)
・ヘキサメチルジスタンナン(RN CAS 661−69−8)
・ヘキサブチルジスタンナン(RN CAS 813−19−4)
・ヘキサフェニルジスタンナン(RN CAS 1064−10−4)
・トリフェニルスタンニルジメチルフェニルシラン(RN CAS 210362−76−8)
・トリフェニルゲルマニルトリフェニルスタンナン(RN CAS 13904−13−7)
・ヘキサフェニル二鉛(RN CAS 3124−01−4)
・シクロペンタジエニル鉄ジカルボニルダイマー(RN CAS 38117−54−3)
・シクロペンタジエニルクロムジカルボニルダイマー(RN CAS 37299−12−0)
・シクロペンタジエニルニッケルカルボニルダイマー(RN CAS 12170−92−2)
・シクロペンタジエニルタングステントリカルボニルダイマー(RN CAS 12566−66−4)
・メチルシクロペンタジエニルモリブデントリカルボニルダイマー(RN CAS 33056−03−0)
の群から選択される。
Cod:シクロオクタジエン
3PN:3−ペンテンニトリル
AdN:アジポニトリル
ESN:エチルスクシノニトリル
MGN:メチルグルタロニトリル
TTP:亜リン酸トリ−p−トリル
DPPX:ビス(ジフェニルホスフィノメチル)−1,2−ベンゼン
DC(Y):転化されたYのモル数対初期Yモル数の比に相当する、水素化される生成物Yの転化率
線状性(L):形成されたAdNのモル数対形成されたジニトリルのモル数(AdN、ESN及びMGNのモルの合計)の比。
使用した一般的な手順は次のとおりである:
次のものをアルゴン雰囲気下で隔壁ストッパーを備えたショット型の60mLガラス管に連続的に装填する:
配位子[配位子がTTPやトリチエニルホスフィンなどの単座の場合にはNi1原子当たり5モル当量の配位子、又は配位子がDPPXなどの二座の場合にはNi1原子当たり2.5モル当量]、
1.21g(15mmol、30当量)の無水3PN、
138mg(0.5mmol、1当量)のNi(Cod)2、
ルイス酸(性質及び量については以下の表1の表示を参照)。
Claims (7)
- ゼロの酸化状態を有するニッケルと有機ホスフィット、有機ホスホナイト、有機ホスフィナイト及び有機ホスフィンよりなる群から選択される少なくとも1個の有機リン配位子との錯体と、共触媒とを含む触媒系の存在下で、少なくとも1個の非共役不飽和を有し2〜20個の炭素原子を含む有機化合物をシアン化水素との反応により水素化することによって少なくとも1個のニトリル官能基を有する化合物を製造する方法であって、該共触媒が次の一般式I:
[(R)a−(X)y−]nM−M1[−(X)z−(R1)a1]n1
(式中:
M、M1は同一のものでも異なるものでもよく、次の元素:B、Si、Ge、Sn、Pb、Mo、Ni、Fe、W及びCrよりなる群から選択される元素を表し、
R、R1は同一のものでも異なるものでもよく、置換された若しくは置換されていない、かつ、架橋されていても架橋されていなくてもよい脂肪族基若しくは芳香族若しくは脂環式環を有する基、又はハロゲン化物基を表し、
Xは、酸素、窒素、硫黄又は珪素原子を表し、
y及びzは、同一でも同一でなくてもよい、0又は1の整数であり、
n及びn1は、M、M1元素の原子価を1で除したものに等しい整数であり、
a及びa1は、同一でも同一でなくてもよく、y及びzが1に等しい場合にはX元素の原子価を1で除したものに等しい整数であり、又はy及びzが0に等しい場合には1に等しい整数である。)
に相当する有機金属化合物であることを特徴とする製造方法。 - R及びR1は同一のもの又は異なるものであってよく、置換若しくは非置換でかつ架橋されていても架橋されていなくてもよい芳香族、脂肪族若しくは脂環式基、又はハロゲン化物基を表すことを特徴とする、請求項1に記載の製造方法。
- 前記共触媒が、次の化合物:
・ビス(ネオペンチルグリコラト)ジボロン
・ビス(ヘキシレングリコラト)ジボロン
・ビス(ピナコラト)ジボロン
・テトラキス(ピロリニド)ジボロン
・ヘキサメチルジシラン
・テトラフェニルジメチルジシラン
・ジフェニルテトラメチルジシラン
・トリス(トリメチルシリル)シラン
・テトラキス(トリメチルシリル)シラン
・ヘキサフェニルジシラン
・ヘキサメチルジゲルマン
・ヘキサエチルジゲルマン
・ヘキサフェニルジゲルマン
・ヘキサメチルジスタンナン
・ヘキサブチルジスタンナン
・ヘキサフェニルジスタンナン
・トリフェニルスタンニルジメチルフェニルシラン
・トリフェニルゲルマニルトリフェニルスタンナン
・ヘキサフェニル二鉛
・シクロペンタジエニル鉄ジカルボニルダイマー
・シクロペンタジエニルクロムジカルボニルダイマー
・シクロペンタジエニルニッケルカルボニルダイマー
・シクロペンタジエニルタングステントリカルボニルダイマー
・メチルシクロペンタジエニルモリブデントリカルボニルダイマー
よりなる群から選択されることを特徴とする、請求項1又は2に記載の方法。 - 前記触媒系は、Niのモルに対する共触媒のモル比が0.1〜10であることを特徴とする、請求項1〜3のいずれかに記載の製造方法。
- 前記有機リン配位子が単座有機リン化合物及び二座有機リン化合物よりなる群から選択されることを特徴とする、請求項1〜4のいずれかに記載の製造方法。
- ジニトリル化合物に転化される有機化合物がペンテンニトリル化合物であることを特徴とする、請求項1〜5のいずれかに記載の製造方法。
- 前記少なくとも1個のニトリル官能基を有する化合物がアジポニトリル、メチルグルタロニトリル及びスクシノニトリルであることを特徴とする、請求項6に記載の製造方法。
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Application Number | Priority Date | Filing Date | Title |
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FR0805821 | 2008-10-21 | ||
FR0805821A FR2937321B1 (fr) | 2008-10-21 | 2008-10-21 | Procede de fabrication de composes comprenant des fonctions nitriles |
PCT/EP2009/062896 WO2010046226A1 (fr) | 2008-10-21 | 2009-10-05 | Procede de fabrication de composes comprenant des fonctions nitriles |
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JP2012516295A (ja) * | 2009-01-29 | 2012-07-19 | ロディア オペレーションズ | ニトリル官能基を有する化合物の製造方法 |
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FR2946649B1 (fr) | 2009-06-16 | 2012-04-13 | Rhodia Operations | Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique |
FR2980792B1 (fr) | 2011-09-30 | 2013-09-06 | Rhodia Operations | Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique |
CN109304192A (zh) * | 2018-10-30 | 2019-02-05 | 重庆中平紫光科技发展有限公司 | 一种利用蒙脱土固载路易斯酸合成己二腈的方法 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3496217A (en) * | 1967-05-23 | 1970-02-17 | Du Pont | Hydrocyanation of olefins |
US3864380A (en) * | 1974-01-17 | 1975-02-04 | Du Pont | Hydrocyanation of Olefins |
JPH026451A (ja) * | 1988-03-31 | 1990-01-10 | E I Du Pont De Nemours & Co | アジポニトリルの製造方法 |
US6127567A (en) * | 1997-07-29 | 2000-10-03 | E. I. Du Pont De Nemours And Company | Hydrocyanation processes and multidentate phosphite ligand and nickel catalyst compositions therefor |
WO2001060780A1 (fr) * | 2000-02-15 | 2001-08-23 | Showa Denko K.K. | Procede de production d'ester fumarique |
JP2001513528A (ja) * | 1997-08-04 | 2001-09-04 | ビーエーエスエフ アクチェンゲゼルシャフト | モノオレフィン性c5モノニトリルの混合物を、少なくとも1個のメタロセン−燐(iii)−ニッケル(0)錯体を含有する触媒の存在下に、接触的ヒドロシアン化により製造する方法 |
JP2003507451A (ja) * | 1999-08-26 | 2003-02-25 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | モノオレフィン類のニッケル触媒ヒドロシアノ化のための不溶性ルイス酸促進剤 |
WO2007062370A2 (en) * | 2005-11-22 | 2007-05-31 | Smithkline Beecham Corporation | Calcilytic compounds |
Family Cites Families (52)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR800381A (fr) | 1935-01-11 | 1936-07-03 | Pignon de roue libre pour bicyclettes | |
US3496215A (en) | 1965-11-23 | 1970-02-17 | Du Pont | Hydrocyanation of olefins using selected nickel phosphite catalysts |
GB1112539A (en) | 1965-11-26 | 1968-05-08 | Du Pont | Preparation of organic nitriles |
FR1529134A (fr) | 1966-06-24 | 1968-06-14 | Du Pont | Procédé d'addition de l'acide cyanhydrique aux oléfines et produits obtenus par ce procédé |
US3694485A (en) | 1967-11-06 | 1972-09-26 | Du Pont | Hydrocyanation of olefins |
US3655723A (en) | 1969-10-31 | 1972-04-11 | Du Pont | Hydrocyanation of olefins |
BE757731A (fr) | 1969-11-13 | 1971-04-01 | Du Pont | Procede de cyanuration des olefines |
US3631191A (en) | 1970-04-08 | 1971-12-28 | Du Pont | Synthesis of zero valent nickel-tetrakis triaryl phosphite complexes |
US3766231A (en) | 1971-08-02 | 1973-10-16 | Du Pont | Compounds of zero valent nickel containing n bonded nitriles |
US3766237A (en) | 1972-01-25 | 1973-10-16 | Du Pont | Hydrocyanation of olefins |
US3773809A (en) | 1972-06-28 | 1973-11-20 | Du Pont | Separation of organic phosphorus compounds and their metal complexes from organic nitriles in the hydrocyanation of olefins |
US4082811A (en) | 1977-02-23 | 1978-04-04 | E. I. Du Pont De Nemours And Company | Recovery of metal and triarylborane catalyst components from olefin hydrocyanation residue |
US4339395A (en) | 1981-04-15 | 1982-07-13 | E. I. Du Pont De Nemours And Company | Treatment of olefin hydrocyanation products |
US4416825A (en) | 1982-02-23 | 1983-11-22 | E. I. Du Pont De Nemours & Co. | Preparation of zerovalent nickel complexes |
US4774353A (en) * | 1986-06-05 | 1988-09-27 | E. I. Du Pont De Nemours And Company | Triorganotin catalyst promoters for hydrocyanation |
US4874884A (en) | 1988-03-31 | 1989-10-17 | E. I. Du Pont De Nemours And Company | Promoter synergism in pentenenitrile hydrocyanation |
FR2711987B1 (fr) * | 1993-11-03 | 1995-12-15 | Rhone Poulenc Chimie | Procédé d'hydrocyanation de nitriles insaturés en dinitriles. |
WO1996001182A1 (en) | 1994-07-06 | 1996-01-18 | Cartolit A/S | Method and apparatus for use in connection with mounting of carton liners in freezing frames |
US5512696A (en) * | 1995-07-21 | 1996-04-30 | E. I. Du Pont De Nemours And Company | Hydrocyanation process and multidentate phosphite and nickel catalyst composition therefor |
IN187044B (ja) | 1995-01-27 | 2002-01-05 | Du Pont | |
US5693843A (en) | 1995-12-22 | 1997-12-02 | E. I. Du Pont De Nemours And Company | Process for hydrocyanation of diolefins and isomerization of nonconjugated 2 alkyl-3-monoalkenenitriles |
IT1286497B1 (it) | 1996-11-20 | 1998-07-15 | Italfarmaco Sud Spa | Difosfine di tipo misto eteroariliche-ariliche come leganti chirali, relativi complessi con metalli di transizione e impiego di detti |
ZA986374B (en) | 1997-07-29 | 2000-01-17 | Du Pont | Hydrocyanation of diolefins and isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles. |
US5847191A (en) | 1997-07-29 | 1998-12-08 | E. I. Du Pont De Nemours And Company | Process for the hydrocyanation of monoolefins using bidentate phosphite ligands and zero-valent nickel |
US5959135A (en) | 1997-07-29 | 1999-09-28 | E. I. Du Pont De Nemours And Company | Hydrocyanation processes and multidentate phosphite ligand and nickel catalyst compositions thereof |
ZA986369B (en) | 1997-07-29 | 2000-01-17 | Du Pont | Hydrocyanation of diolefins and isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles. |
ATE269158T1 (de) | 1998-04-16 | 2004-07-15 | Du Pont | Hydrocyanierung von olefinen und isomerisierung von nichtkonjugierten 2-alkyl-3-monoalken- nitrilen |
US6229052B1 (en) | 1998-05-29 | 2001-05-08 | E. I. Du Pont De Nemours And Company | Hydroformylation of olefins using supported bis(phosphorus) ligands |
DE19825212A1 (de) | 1998-06-05 | 1999-12-09 | Basf Ag | Katalysator, umfassend einen Komplex eines Metalls der VIII. Nebengruppe auf Basis eines zweizähnigen Phosphonitliganden und Verfahren zur Herstellung von Nitrilen |
AU4253799A (en) | 1998-06-12 | 2000-01-05 | Micrologix Biotech, Inc. | Cancer therapy with cationic peptides |
DE19953058A1 (de) | 1999-11-03 | 2001-05-10 | Basf Ag | Phosphite |
DE10038037A1 (de) | 2000-08-02 | 2002-04-18 | Basf Ag | Zur Herstellung von Nitrilen geeigneter Katalysator und Verfahren zur Herstellung von Nitrilen |
FR2815344B1 (fr) | 2000-10-13 | 2004-01-30 | Rhodia Polyamide Intermediates | Procede d'hydrocyanation de composes organiques a insaturation ethylenique |
FR2819250B1 (fr) | 2001-01-05 | 2004-12-03 | Rhodia Polyamide Intermediates | Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique |
DE10100708A1 (de) | 2001-01-10 | 2002-07-11 | Oxeno Olefinchemie Gmbh | Neue N-Phenylpyrrolbisphosphanverbindungen und deren Metallkomplexe |
DE10136488A1 (de) | 2001-07-27 | 2003-02-06 | Basf Ag | Ni(O) enthaltendes Katalysatorsystem |
FR2830530B1 (fr) | 2001-10-08 | 2004-07-02 | Rhodia Polyamide Intermediates | Procede de transformation, d'une part, de composes a insaturation ethylenique en nitriles et, d'autre part, de nitriles branches en nitriles lineaires |
FR2835833B1 (fr) | 2002-02-13 | 2004-03-19 | Rhodia Polyamide Intermediates | Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique |
FR2842196B1 (fr) | 2002-07-15 | 2006-01-13 | Rhodia Polyamide Intermediates | Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique |
FR2842197A1 (fr) | 2002-07-15 | 2004-01-16 | Rhodia Polyamide Intermediates | Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique |
US6599398B1 (en) | 2002-07-17 | 2003-07-29 | E. I. Du Pont De Nemours And Company | Recovery of adiponitrile from a mixture of adiponitrile, aminocapronitrile and hexamethylenediamine |
FR2845379B1 (fr) | 2002-10-04 | 2004-12-03 | Rhodia Polyamide Intermediates | Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique |
FR2847898A1 (fr) | 2002-12-02 | 2004-06-04 | Rhodia Polyamide Intermediates | Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique |
FR2849027B1 (fr) | 2002-12-23 | 2005-01-21 | Rhodia Polyamide Intermediates | Procede de synthese de composes comprenant des fonctions nitriles a partir de composes a insaturations ethyleniques |
DE10314761A1 (de) | 2003-03-31 | 2004-10-14 | Basf Ag | Als Katalysator für die Hydrocyanierung von olefinisch ungesättigten Verbindungen geeignetes System |
FR2854892B1 (fr) | 2003-05-12 | 2005-06-24 | Rhodia Polyamide Intermediates | Procede de fabrication de dinitriles |
PL1626651T3 (pl) | 2003-05-28 | 2007-01-31 | Michel Lata S A | Podłoże warstwowe z wzorem utajnionym |
DE102004052040A1 (de) | 2004-10-26 | 2006-04-27 | Basf Ag | Liganden zur asymmetrischen Hydroformylierung |
FR2926816B1 (fr) | 2008-01-25 | 2010-05-14 | Rhodia Operations | Procede de fabrication de composes comprenant des fonctions nitriles |
FR2932476B1 (fr) | 2008-06-17 | 2010-07-30 | Rhodia Operations | Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique |
FR2932477B1 (fr) | 2008-06-17 | 2013-01-18 | Rhodia Operations | Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique |
FR2941455B1 (fr) | 2009-01-29 | 2011-02-11 | Rhodia Operations | Procede de fabrication de composes comprenant des fonctions nitriles |
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2008
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- 2009-10-05 JP JP2011532571A patent/JP5470397B2/ja not_active Expired - Fee Related
- 2009-10-05 UA UAA201106360A patent/UA107333C2/uk unknown
- 2009-10-05 WO PCT/EP2009/062896 patent/WO2010046226A1/fr active Application Filing
- 2009-10-05 KR KR1020117008971A patent/KR101280092B1/ko not_active IP Right Cessation
- 2009-10-05 US US13/123,721 patent/US9174207B2/en not_active Expired - Fee Related
- 2009-10-05 CN CN200980141787.0A patent/CN102186810B/zh active Active
- 2009-10-05 SG SG2014004386A patent/SG196844A1/en unknown
- 2009-10-05 EP EP09783737.1A patent/EP2346815B1/fr not_active Not-in-force
- 2009-10-05 RU RU2011120460/04A patent/RU2472776C1/ru not_active IP Right Cessation
-
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Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3496217A (en) * | 1967-05-23 | 1970-02-17 | Du Pont | Hydrocyanation of olefins |
US3864380A (en) * | 1974-01-17 | 1975-02-04 | Du Pont | Hydrocyanation of Olefins |
JPH026451A (ja) * | 1988-03-31 | 1990-01-10 | E I Du Pont De Nemours & Co | アジポニトリルの製造方法 |
US6127567A (en) * | 1997-07-29 | 2000-10-03 | E. I. Du Pont De Nemours And Company | Hydrocyanation processes and multidentate phosphite ligand and nickel catalyst compositions therefor |
JP2001513528A (ja) * | 1997-08-04 | 2001-09-04 | ビーエーエスエフ アクチェンゲゼルシャフト | モノオレフィン性c5モノニトリルの混合物を、少なくとも1個のメタロセン−燐(iii)−ニッケル(0)錯体を含有する触媒の存在下に、接触的ヒドロシアン化により製造する方法 |
JP2003507451A (ja) * | 1999-08-26 | 2003-02-25 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | モノオレフィン類のニッケル触媒ヒドロシアノ化のための不溶性ルイス酸促進剤 |
WO2001060780A1 (fr) * | 2000-02-15 | 2001-08-23 | Showa Denko K.K. | Procede de production d'ester fumarique |
WO2007062370A2 (en) * | 2005-11-22 | 2007-05-31 | Smithkline Beecham Corporation | Calcilytic compounds |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012516295A (ja) * | 2009-01-29 | 2012-07-19 | ロディア オペレーションズ | ニトリル官能基を有する化合物の製造方法 |
Also Published As
Publication number | Publication date |
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RU2011120460A (ru) | 2012-11-27 |
EP2346815A1 (fr) | 2011-07-27 |
CN102186810B (zh) | 2014-10-22 |
WO2010046226A1 (fr) | 2010-04-29 |
FR2937321A1 (fr) | 2010-04-23 |
US20120004440A1 (en) | 2012-01-05 |
UA107333C2 (uk) | 2014-12-25 |
JP5470397B2 (ja) | 2014-04-16 |
KR20110058891A (ko) | 2011-06-01 |
RU2472776C1 (ru) | 2013-01-20 |
US20160009638A1 (en) | 2016-01-14 |
US9174207B2 (en) | 2015-11-03 |
CN102186810A (zh) | 2011-09-14 |
EP2346815B1 (fr) | 2016-04-20 |
SG196844A1 (en) | 2014-02-13 |
KR101280092B1 (ko) | 2013-06-28 |
FR2937321B1 (fr) | 2010-10-22 |
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