JP5786268B2 - 固体塩基触媒 - Google Patents
固体塩基触媒 Download PDFInfo
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- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
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- B01J37/02—Impregnation, coating or precipitation
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- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
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- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
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- C07C209/38—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitroso groups
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- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
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- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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Description
固体塩基性触媒の製造
攪拌器と凝縮器が設置されている1000mlの四つ口フラスコに200gのD201樹脂と400gの25wt%TMAH水溶液を入れる。混合物を攪拌しながら加熱し、約75℃の温度で還流を維持する。還流反応は6時間持続する。反応混合物が室温まで冷却した後、フラスコに移動させて待機させる。濾過、水洗を経た後、水酸化テトラメチルアンモニウムを含有する樹脂が生成される。攪拌器と凝縮器が設置されている500mlの三つ口フラスコに200gの水酸化テトラメチルアンモニウムを含有する樹脂と200mlの50wt%水酸化カリウム水溶液を入れる。該混合物を攪拌しながら加熱し、約50〜100℃の温度で還流を2時間維持する。その後、該混合物を冷却させる。濾過を経た後、湿っている固相触媒をオーブンで(50℃より低い、0.098MPA) 乾燥するまでゆっくり加熱する。乾燥している固体塩基触媒を乾燥器に保存させる。
固体塩基性触媒の製造
攪拌器と凝縮器が設置されている1000mlの四つ口フラスコに300gの活性酸化アルミニウム(粒子直径2〜3mm、中国萍郷市天力化工填料有限公司で生産)と400gの25wt%TMAH水溶液を入れる。混合物を攪拌しながら加熱し、約75℃の温度で還流を維持する。還流反応は6時間持続する。反応混合物が室温まで冷却した後、フラスコに移動させて待機させる。200gを攪拌器と凝縮器が設置されている500mlの三つ口フラスコに入れ、また200mlの50wt%水酸化カリウム水溶液を入れる。該混合物を攪拌しながら加熱し、約50〜100℃の温度で還流を2時間維持する。その後、該混合物を冷却させる。濾過を経た後、湿っている固相触媒をオーブンで(50℃より低い、0.098MPA) 乾燥するまでゆっくり加熱する。
触媒を利用して4-ADPAを合成する
攪拌器と凝縮器が設置されている500mlの三つ口フラスコに50gの実施例1で製造した固体塩基触媒と150mlのアニリンを入れる。混合物を75℃まで加熱し、圧力を約0.095MPaに維持する。温度が70〜75℃間に制御された時、50mlのニトロベンゼンを入れ、縮合反応を行う。混合物から反応過程で生成した水を分離し出す。10時間反応後、ニトロベンゼンの残留量に対して持続的に分析を行う。残留したニトロベンゼンが1%より少ない時、反応を停止させる。
固定触媒を利用して4-ADPAを合成する 60メッシュの網状物で50gの実施例2で製造した固相触媒を包み、実施例3と同様な反応条件を利用して4-ADPAを合成する。反応が完了された後、固相触媒を回収せず、反応装置に保留する。
実施例1で製造した触媒を実施例3の方法により重複して15回利用し、第15回目に縮合反応を触媒する時のニトロベンゼン転換率は依然として98.5%である。
実施例2で製造した触媒を実施例3の方法により重複して15回利用し、第15回目に縮合反応を触媒する時のニトロベンゼン転換率は68%である。
Claims (9)
- (a)有機塩基と、
(b)無機塩基と、及び
(c)酸化アルミニウム、シリカゲル、珪藻土、分子篩、マクロポーラス吸着樹脂、及びこれらの混合物からなる群より選択される担体と、を含むことを特徴とするアニリンとニトロベンゼンの縮合を触媒して4−アミノジフェニルアミンを製造する固体塩基触媒。 - 前記有機塩基は、メチルアミン、エチルアミン、シクロヘキシルアミン、アニリン、フェニルジアミン、ドデシルトリメチルアンモニウムクロリド、トリメチルベンジルアンモニウムクロライド、塩化テトラメチルアンモニウム、臭化テトラメチルアンモニウム、水酸化テトラメチルアンモニウム、水酸化テトラエチルアンモニウム、水酸化テトラプロピルアンモニウム、水酸化テトラブチルアンモニウム、水酸化ベンジルトリメチルアンモニウム、水酸化ベンジルトリエチルアンモニウム、4−ジメチルアミノピリジン、クラウンエーテル、及びこれらの混合物からなる群より選択されることを特徴とする請求項1に記載の固体塩基触媒。
- 前記無機塩基は、水酸化カリウム、水酸化ナトリウム、水酸化カルシウム、水酸化セシウム、水酸化アルミニウム、ナトリウムメトキシド、ナトリウムエトキシド、カリウムメトキシド、カリウムエトキシド、及びこれらの混合物からなる群より選択されることを特徴とする請求項1に記載の固体塩基触媒。
- 前記有機塩基は、水酸化テトラメチルアンモニウム又は水酸化テトラエチルアンモニウムであり、前記無機塩基は、水酸化カリウム又は水酸化ナトリウムであることを特徴とする請求項2に記載の固体塩基触媒。
- 前記マクロポーラス吸着樹脂は、スチリル強塩基性陰イオン交換樹脂であることを特徴とする請求項1に記載の固体塩基触媒。
- 前記担体は、D201樹脂であることを特徴とする請求項5に記載の固体塩基触媒。
- 前記有機塩基と前記担体を重合させて、有機塩基を含有する担体を生成するステップと、及び
前記有機塩基を含有する担体と無機塩基の水溶液を反応させて、前記固体塩基触媒を生成するステップと、を含むことを特徴とする請求項1乃至6の中のいずれか一項に記載の固体塩基触媒を製造する方法。 - (a)請求項1乃至6の中のいずれか一項に記載の固体塩基触媒が存在する状況で、アニリンとニトロベンゼンを縮合させ、4−ニトロソジフェニルアミンと4−ニトロジフェニルアミンを生成するステップと、及び
(b)4−ニトロソジフェニルアミンと4−ニトロジフェニルアミンを水素化させ、4−アミノジフェニルアミンを生成するステップと、を含み、
前記固体塩基触媒の有機塩基は、メチルアミン、エチルアミン、シクロヘキシルアミン、アニリン、フェニルジアミン、ドデシルトリメチルアンモニウムクロリド、トリメチルベンジルアンモニウムクロライド、塩化テトラメチルアンモニウム、臭化テトラメチルアンモニウム、水酸化テトラメチルアンモニウム、水酸化テトラエチルアンモニウム、水酸化テトラプロピルアンモニウム、水酸化テトラブチルアンモニウム、水酸化ベンジルトリメチルアンモニウム、水酸化ベンジルトリエチルアンモニウム、4−ジメチルアミノピリジン、クラウンエーテル、及びこれらの混合物からなる群より選択されたものであり、
前記固体塩基触媒の無機塩基は、水酸化カリウム、水酸化ナトリウム、水酸化カルシウム、水酸化セシウム、水酸化アルミニウム、ナトリウムメトキシド、ナトリウムエトキシド、カリウムメトキシド、カリウムエトキシド、及びこれらの混合物からなる群より選択されたものであることを特徴とする4−アミノジフェニルアミンを製造する方法。 - 前記固体塩基触媒は、直接に循環利用されることを特徴とする請求項8に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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CN201010187702.7A CN102259029B (zh) | 2010-05-24 | 2010-05-24 | 固体碱催化剂 |
CN201010187702.7 | 2010-05-24 | ||
PCT/CN2011/074599 WO2011147308A1 (zh) | 2010-05-24 | 2011-05-24 | 固体碱催化剂 |
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JP2013532055A JP2013532055A (ja) | 2013-08-15 |
JP5786268B2 true JP5786268B2 (ja) | 2015-09-30 |
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US (1) | US9302259B2 (ja) |
EP (1) | EP2578313B1 (ja) |
JP (1) | JP5786268B2 (ja) |
KR (1) | KR101478716B1 (ja) |
CN (1) | CN102259029B (ja) |
BR (1) | BR112012029495B1 (ja) |
CA (1) | CA2800376C (ja) |
EA (1) | EA025024B1 (ja) |
ES (1) | ES2745117T3 (ja) |
MX (1) | MX360443B (ja) |
MY (1) | MY161105A (ja) |
PL (1) | PL2578313T3 (ja) |
PT (1) | PT2578313T (ja) |
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CN106366221A (zh) * | 2016-08-07 | 2017-02-01 | 刘天泽 | 一种大比表面、氨基功能化的大孔苯乙烯类树脂的制备方法 |
CN106311207A (zh) * | 2016-08-25 | 2017-01-11 | 铜仁学院 | 一种硅胶基固体碱的制备方法 |
CN108558675A (zh) * | 2018-04-25 | 2018-09-21 | 南通理工学院 | 一种4-氨基二苯胺的合成方法 |
CN110627660A (zh) * | 2018-06-25 | 2019-12-31 | 中国石油化工股份有限公司 | 一种固体碱法rt培司制备方法 |
CN110624602A (zh) * | 2018-06-25 | 2019-12-31 | 中国石油化工股份有限公司 | 一种固体碱催化剂制备方法及应用 |
CN111097542A (zh) * | 2018-10-29 | 2020-05-05 | 中国石油化工股份有限公司 | 一种固体碱及其制备方法 |
CN110330029B (zh) * | 2019-07-05 | 2021-06-01 | 中国石油大学(北京) | 一种多级孔zsm-5沸石及其制备方法与应用 |
CN112439454B (zh) * | 2019-09-05 | 2023-04-07 | 中国石油化工股份有限公司 | 一种rt培司缩合催化剂及其制备方法 |
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EP2578313A4 (en) | 2017-03-15 |
EP2578313B1 (en) | 2019-07-31 |
PL2578313T3 (pl) | 2020-03-31 |
CN102259029A (zh) | 2011-11-30 |
US20130079560A1 (en) | 2013-03-28 |
BR112012029495A2 (pt) | 2017-02-21 |
JP2013532055A (ja) | 2013-08-15 |
MX2012013321A (es) | 2013-02-01 |
KR20130028124A (ko) | 2013-03-18 |
MY161105A (en) | 2017-04-14 |
WO2011147308A1 (zh) | 2011-12-01 |
US9302259B2 (en) | 2016-04-05 |
EA025024B1 (ru) | 2016-11-30 |
KR101478716B1 (ko) | 2015-01-02 |
BR112012029495B1 (pt) | 2019-04-02 |
ES2745117T3 (es) | 2020-02-27 |
CA2800376C (en) | 2016-07-19 |
RS59456B1 (sr) | 2019-11-29 |
PT2578313T (pt) | 2019-09-16 |
MX360443B (es) | 2018-11-01 |
CN102259029B (zh) | 2014-12-10 |
EA201201581A1 (ru) | 2013-05-30 |
CA2800376A1 (en) | 2011-12-01 |
EP2578313A1 (en) | 2013-04-10 |
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