JP5234726B2 - 3級アミンの製造法 - Google Patents
3級アミンの製造法 Download PDFInfo
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- JP5234726B2 JP5234726B2 JP2007243489A JP2007243489A JP5234726B2 JP 5234726 B2 JP5234726 B2 JP 5234726B2 JP 2007243489 A JP2007243489 A JP 2007243489A JP 2007243489 A JP2007243489 A JP 2007243489A JP 5234726 B2 JP5234726 B2 JP 5234726B2
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- tertiary amine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
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- 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
- B01J12/00—Chemical processes in general for reacting gaseous media with gaseous media; Apparatus specially adapted therefor
- B01J12/007—Chemical processes in general for reacting gaseous media with gaseous media; Apparatus specially adapted therefor in the presence of catalytically active bodies, e.g. porous plates
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- 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
- B01J23/72—Copper
-
- 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
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8926—Copper and noble metals
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/064—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof containing iron group metals, noble metals or copper
- B01J29/072—Iron group metals or copper
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0215—Coating
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0215—Coating
- B01J37/0219—Coating the coating containing organic compounds
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0215—Coating
- B01J37/0225—Coating of metal substrates
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00002—Chemical plants
- B01J2219/00027—Process aspects
- B01J2219/00038—Processes in parallel
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
- B01J2531/16—Copper
-
- 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
- B01J33/00—Protection of catalysts, e.g. by coating
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Description
本発明の製造法によれば、3級アミンを高収率で効率的に製造することができる。
容量1Lの容器に合成ゼオライトを仕込み、次いで硝酸銅と硝酸ニッケル及び塩化ルテニウムを各金属原子のモル比でCu:Ni:Ru=4:1:0.01となるように水に溶かしたものを入れ、撹拌しながら昇温した。90℃で10%炭酸ナトリウム水溶液をpH9〜10にコントロールしながら徐々に滴下した。1時間の熟成後、沈殿物を濾過・水洗後80℃で10時間乾燥し、600℃で3時間焼成して粉末状触媒を得た。得られた粉末状触媒(以下粉末状触媒aという)における金属酸化物の割合は50%、合成ゼオライトの割合は50%であった。
溶媒としてメチルイソブチルケトン(MIBK)、バインダーとしてフェノール樹脂(住友ベークライト製PR−9480)、上記粉末状触媒aの順に、250mlの広口ポリエチレン製ビンに入れた。粉末状触媒aが80部(65g)に対し、フェノール樹脂の不揮発分が20部となる配合比率とし、MIBKの配合量は、配合物の固形分が60%となる量とした。さらに分散メディアとして、直径1mmのガラスビーズ(見かけ容積65ml)を広口のポリエチレン製ビンに入れた。広口ポリエチレン製ビンをペイントシェーカーにセットし、調製時間として30分間混合分散処理を行い、塗料を得た。
溶媒としてMIBK、バインダーとしてフェノール樹脂(住友ベークライト製PR−9480)、上記粉末状触媒aの順に、250mlの広口ポリエチレン製ビンに入れた。粉末状触媒aが75部(65g)に対し、フェノール樹脂の不揮発分が25部となる配合比率とし、MIBKの配合量は、配合物の固形分が60%となる量とした。さらに分散メディアとして、直径1mmのガラスビーズ(見かけ容積65ml)を広口のポリエチレン製ビンに入れた。広口ポリエチレン製ビンをペイントシェーカーにセットし、調製時間として30分間混合分散処理を行い、塗料を得た。
溶媒としてMIBK、バインダーとしてフェノール樹脂(住友ベークライト製PR−9480)、上記粉末状触媒aの順に、250mlの広口ポリエチレン製ビンに入れた。粉末状触媒aが75部(65g)に対し、フェノール樹脂の不揮発分が25部となる配合比率とし、MIBKの配合量は、配合物の固形分が60%となる量とした。さらに分散メディアとして、直径1mmのガラスビーズ(見かけ容積65ml)を広口のポリエチレン製ビンに入れた。広口ポリエチレン製ビンをペイントシェーカーにセットし、調製時間として30分間混合分散処理を行い、塗料を得た。
図1に示す循環固定床型反応装置を用い、ラウリルアルコールとジメチルアミンとを原料として、以下に示す方法でN−ドデシル−N,N−ジメチルアミンを製造した。
比較例1
実施例1において、触媒の還元温度を200℃、還元時間を90分とした他は実施例1と同様にして触媒の還元を行った。
図2に示すバブリング槽型反応装置を用い、デシルアルコールとモノメチルアミンとを原料として、以下に示す方法でN,N−ジデシル−N−メチルアミンを製造した。
フィルム型触媒Bの代わりに製造例3で得たフィルム型触媒Cを用いる以外は、実施例2と同様にして触媒の還元を行った。
2 緩衝槽
3 外部循環用ポンプ
4 外部循環用導管
5 充填塔用導管
6 充填塔
7 反応槽
8 フィルム型触媒
9 濾過板
10 導管
11 導管
12 凝縮器
Claims (7)
- 熱硬化性樹脂と活性金属を含有するフィルム型触媒の存在下、アルコールと1級又は2級アミンとを反応させて3級アミンを製造する方法であって、反応前にアルコールの存在下110〜140℃の温度で触媒の還元を行う還元工程を有し、還元時間が30〜600分である3級アミンの製造法。
- 還元工程終了後に還元に用いたアルコールの全量を抜き出す、請求項1記載の3級アミンの製造法。
- フィルム型触媒が、80〜170℃の温度で硬化処理されたものである、請求項1又は2記載の3級アミンの製造法。
- 熱硬化性樹脂がフェノール樹脂である、請求項1〜3いずれかに記載の3級アミンの製造法。
- 活性金属が銅を含有するものである、請求項1〜4いずれかに記載の3級アミンの製造法。
- フィルム型触媒が、支持体表面に固定化されたものであり、硬化後の支持体を除く触媒の厚みが0.01〜500μmである、請求項1〜5いずれかに記載の3級アミンの製造法。
- アルコールが炭素数8〜36の飽和又は不飽和の脂肪族アルコールであり、1級又は2級アミンが脂肪族1級又は2級アミンである、請求項1〜6いずれかに記載の3級アミンの製造法。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007243489A JP5234726B2 (ja) | 2007-09-20 | 2007-09-20 | 3級アミンの製造法 |
PCT/JP2008/067366 WO2009038223A1 (ja) | 2007-09-20 | 2008-09-18 | 3級アミンの製造法 |
CN200880107697.5A CN101801908B (zh) | 2007-09-20 | 2008-09-18 | 叔胺的制造方法 |
DE112008002506T DE112008002506T5 (de) | 2007-09-20 | 2008-09-18 | Verfahren zur Erzeugung eines tertiären Amins |
US12/678,226 US8338647B2 (en) | 2007-09-20 | 2008-09-18 | Method for producing tertiary amine |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007243489A JP5234726B2 (ja) | 2007-09-20 | 2007-09-20 | 3級アミンの製造法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2009073754A JP2009073754A (ja) | 2009-04-09 |
JP5234726B2 true JP5234726B2 (ja) | 2013-07-10 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2007243489A Expired - Fee Related JP5234726B2 (ja) | 2007-09-20 | 2007-09-20 | 3級アミンの製造法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US8338647B2 (ja) |
JP (1) | JP5234726B2 (ja) |
CN (1) | CN101801908B (ja) |
DE (1) | DE112008002506T5 (ja) |
WO (1) | WO2009038223A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI732960B (zh) | 2016-10-17 | 2021-07-11 | 日商可樂麗可樂富麗世股份有限公司 | 片狀物收納容器 |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4354341B2 (ja) | 2004-06-11 | 2009-10-28 | 花王株式会社 | 反応装置 |
EP2072130A4 (en) * | 2006-10-06 | 2010-09-29 | Kao Corp | FILM CATALYST AND METHOD FOR PRODUCING THE SAME |
JP4938125B2 (ja) * | 2009-12-22 | 2012-05-23 | 花王株式会社 | 3級アミンの製造方法 |
WO2012086582A1 (ja) * | 2010-12-21 | 2012-06-28 | 花王株式会社 | 3級アミンの製造方法 |
JP5090567B2 (ja) * | 2010-12-21 | 2012-12-05 | 花王株式会社 | 3級アミンの製造方法 |
CA2848167A1 (en) * | 2011-09-06 | 2013-03-14 | Sumitomo Bakelite Co., Ltd. | Resin-supported catalyst and method for preparing resin-supported catalyst |
US9289741B2 (en) * | 2012-02-01 | 2016-03-22 | Battelle Memorial Institute | Suspended-slurry reactor |
CN110498746B (zh) * | 2019-09-17 | 2022-10-04 | 江苏万盛大伟化学有限公司 | 一种脂肪叔胺质量提升的方法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02234A (ja) * | 1987-10-16 | 1990-01-05 | Kao Corp | N−置換アミンの製造方法 |
DE4230554A1 (de) | 1992-09-12 | 1994-03-17 | Basf Ag | Verfahren zur Herstellung von tertiären Aminen |
JP2001151734A (ja) * | 1999-11-26 | 2001-06-05 | Kao Corp | 第3級アミンの製造法 |
CN100512964C (zh) * | 2003-10-08 | 2009-07-15 | 花王株式会社 | 叔胺制造用薄膜型催化剂以及使用该催化剂的叔胺的制造方法 |
JP4354341B2 (ja) * | 2004-06-11 | 2009-10-28 | 花王株式会社 | 反応装置 |
JP4549802B2 (ja) * | 2004-10-08 | 2010-09-22 | 花王株式会社 | フィルム状触媒およびフィルム状触媒の製造方法 |
JP2007197396A (ja) * | 2006-01-30 | 2007-08-09 | Kao Corp | 3級アミンの製造方法 |
-
2007
- 2007-09-20 JP JP2007243489A patent/JP5234726B2/ja not_active Expired - Fee Related
-
2008
- 2008-09-18 WO PCT/JP2008/067366 patent/WO2009038223A1/ja active Application Filing
- 2008-09-18 US US12/678,226 patent/US8338647B2/en not_active Expired - Fee Related
- 2008-09-18 DE DE112008002506T patent/DE112008002506T5/de not_active Ceased
- 2008-09-18 CN CN200880107697.5A patent/CN101801908B/zh not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI732960B (zh) | 2016-10-17 | 2021-07-11 | 日商可樂麗可樂富麗世股份有限公司 | 片狀物收納容器 |
Also Published As
Publication number | Publication date |
---|---|
CN101801908B (zh) | 2014-06-04 |
WO2009038223A1 (ja) | 2009-03-26 |
CN101801908A (zh) | 2010-08-11 |
JP2009073754A (ja) | 2009-04-09 |
US20100217044A1 (en) | 2010-08-26 |
US8338647B2 (en) | 2012-12-25 |
DE112008002506T5 (de) | 2010-10-21 |
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