TWI707724B - Pd催化之甲酸分解方法 - Google Patents
Pd催化之甲酸分解方法 Download PDFInfo
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- PTCJSHIPVOSFHK-UHFFFAOYSA-N C(c1c(CP(C2(CC(C3)C4)CC4CC3C2)c2ncccc2)cccc1)P(C1(CC(C2)C3)CC3CC2C1)c1ccccn1 Chemical compound C(c1c(CP(C2(CC(C3)C4)CC4CC3C2)c2ncccc2)cccc1)P(C1(CC(C2)C3)CC3CC2C1)c1ccccn1 PTCJSHIPVOSFHK-UHFFFAOYSA-N 0.000 description 1
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Abstract
一種Pd催化之甲酸分解方法。
Description
本發明係關於一種Pd催化之甲酸(HCOOH)分解方法。
甲酸在化學反應中係用作例如酸或溶劑,但也可能以反應副產物的形式產生。由於其腐蝕性質或發散強烈氣味的性質,可能會想要移除該甲酸。
本發明針對其目的必須提供一種方法,其中甲酸係在催化方法的幫助下有效率地分解。
該目的係藉由如申請專利範圍第1項之方法達成。
一種方法,其包含下列方法步驟:
a)提供甲酸;
b)添加包含Pd之化合物,其中該Pd能形成錯合物;
c)添加通式(I)之化合物:
其中R1
、R2
、R3
、R4
各自獨立選自:-H、-(C1
-C12
)-烷基、-O-(C1
-C12
)-烷基、-(C4
-C14
)-芳基、-O-(C4
-C14
)-芳基、環烷基、-(C1
-C12
)-雜烷基、-O-(C1
-C12
)-雜烷基、
-(C3
-C14
)-雜芳基、-O-(C3
-C14
)-雜芳基、-COO-烷基、
-COO-芳基、-C-O-烷基、-C-O-芳基、NH2
、鹵素且該等殘基也能形成較大稠合環;
其中所列舉之烷基基團、芳基基團、環烷基、雜烷基基團、雜芳基基團可經如下者取代:
-(C1
-C12
)-烷基、-O-(C1
-C12
)-烷基、鹵素;
且該等基團R1
、R2
、R3
、R4
之至少一者不表示苯基;
d)添加MeOH;
e)加熱反應混合物以分解該甲酸。
在該方法之一變化型中,在方法步驟b)中之化合物係選自:Pd(acac)2
、PdCl2
、Pd(dba)3
*CH3
Cl(dba=二(苯亞甲基)丙酮)、Pd(OAc)2
、Pd(TFA)2
、Pd(CH3
CN)Cl2
。
在該方法之一變化型中,該方法步驟b)中之化合物是Pd(OAc)2
。
在該方法之一變化型中,該方法包含額外方法步驟f):
f)添加酸。
在該方法之一變化型中,在方法步驟f)中該酸係選自:H2
SO4
、CH3
SO3
H、CF3
SO3
H、PTSA。
在該方法之一變化型中,在方法步驟f)中該酸是PTSA。
在該方法之一變化型中,R1
、R2
、R3
、R4
各自獨立選自:-(C1
-C12
)-烷基、-O-(C1
-C12
)-烷基、-(C4
-C14
)-芳基、
-O-(C4
-C14
)-芳基、環烷基、-(C1
-C12
)-雜烷基、-O-(C1
-C12
)-雜烷基、-(C3
-C14
)-雜芳基、-O-(C3
-C14
)-雜芳基、
-COO-烷基、-COO-芳基、-C-O-烷基、-C-O-芳基、NH2
、鹵素且該等殘基也能形成較大稠合環;
其中所列舉之烷基基團、芳基基團、環烷基、雜烷基基團、雜芳基基團可經如下者取代:
-(C1
-C12
)-烷基、-O-(C1
-C12
)-烷基、鹵素;
且該等基團R1
、R2
、R3
、R4
之至少一者不表示苯基。
在該方法之一變化型中,R1
、R2
、R3
、R4
各自獨立選自:-(C1
-C12
)-烷基、-(C4
-C14
)-芳基、環烷基、-(C1
-C12
)-雜烷基、-(C3
-C14
)-雜芳基、鹵素且該等殘基也能形成較大稠合環;
其中所列舉之烷基基團、芳基基團、環烷基、雜烷基基團、雜芳基基團可經如下者取代:
-(C1
-C12
)-烷基、-O-(C1
-C12
)-烷基、鹵素;
且該等基團R1
、R2
、R3
、R4
之至少一者不表示苯基。
在該方法之一變化型中,R1
、R2
、R3
、R4
各自獨立選自:-(C1
-C12
)-烷基、環烷基、-(C3
-C14
)-雜芳基且該等殘基也能形成較大稠合環;
其中所列舉之烷基基團、環烷基、雜芳基基團可經如下者取代:
-(C1
-C12
)-烷基、-O-(C1
-C12
)-烷基、鹵素;
且該等基團R1
、R2
、R3
、R4
之至少一者不表示苯基。
在該方法之一變化型中,R1
、R4
各自獨立選自:-(C1
-C12
)-烷基、環烷基且該等殘基也能形成較大稠合環;
其中所列舉之烷基基團、環烷基可經如下者取代:
-(C1
-C12
)-烷基、-O-(C1
-C12
)-烷基、鹵素。
在該方法之一變化型中,R2
、R3
各自獨立表示:-(C3
-C14
)-雜芳基,
其中所列舉之雜芳基基團可經如下者取代:
-(C1
-C12
)-烷基、-O-(C1
-C12
)-烷基、鹵素。
在該方法之一變化型中,通式(I)之化合物係選自結構(1)至(3): 。
在該方法之一變化型中,通式(I)之化合物具有該結構(2):。
在該方法之一變化型中,通式(I)之化合物具有該結構(3):
本發明藉由實例在下文中詳細闡明。
Pd催化之甲酸分解的調查
在氬氣氛下,將[Pd(OAc)2
](4.48 mg, 0.02 mmol, 0.05 mol%)、配位基L(0.08 mmol, 0.2 mol%)、PTSA·H2
O(76 mg, 0.4 mmol, 1.0 mol%)導入壓熱器中(在個別實驗中照著下表避開個別成分之添加。)隨後,利用注射器注射MeOH(6.5 ml)和HCOOH(40 mmol, 1.50 ml)。然後該壓熱器以氮(5巴)沖洗三次。將反應混合物加熱至100℃且維持在此溫度下18小時。在此時間後,將該壓熱器冷卻至室溫。
壓力係藉由電子式壓熱器壓力紀錄感測器測量。
CO、H2
和CO2
之選擇率係藉由氣體GC分析測定。
結果摘錄於下表中:
如上述實驗顯示的,該目的係藉由根據本發明之方法達成。
Claims (8)
- 如申請專利範圍第1項之方法,其中在方法步驟b)中之化合物係選自:Pd(acac)2、PdCl2、Pd(dba)3*CH3Cl(dba=二(苯亞甲基)丙酮)、Pd(OAc)2、Pd(TFA)2、Pd(CH3CN)Cl2。
- 如申請專利範圍第1或2項之方法, 其中該方法步驟b)中之化合物是Pd(OAc)2。
- 如申請專利範圍第1項之方法,其中該方法包含額外方法步驟f):f)添加酸。
- 如申請專利範圍第4項之方法,其中在方法步驟f)中該酸係選自:H2SO4、CH3SO3H、CF3SO3H、PTSA。
- 如申請專利範圍第4和5項中任一項之方法,其中在方法步驟f)中該酸是PTSA。
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??17185340.1 | 2017-08-08 | ||
EP17185340.1A EP3441137B1 (de) | 2017-08-08 | 2017-08-08 | Pd-katalysierten zersetzung von ameisensäure |
EP17185340.1 | 2017-08-08 |
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EP (1) | EP3441137B1 (zh) |
JP (1) | JP6987713B2 (zh) |
KR (1) | KR102132641B1 (zh) |
CN (1) | CN109381833B (zh) |
SG (1) | SG10201806668XA (zh) |
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CN102625731A (zh) * | 2009-09-03 | 2012-08-01 | 丹麦科技大学 | 包含两性离子和/或酸功能化的离子液体的钯催化剂体系 |
CN103635421A (zh) * | 2011-04-19 | 2014-03-12 | 拜尔技术服务有限责任公司 | 通过甲酸的催化分解获取氢气的方法 |
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GB1176654A (en) * | 1966-04-04 | 1970-01-07 | Ici Ltd | Decomposition of Formic Acid. |
JPS595341B2 (ja) * | 1975-06-17 | 1984-02-03 | 住友化学工業株式会社 | ギサンノブンカイホウホウ |
US6331502B1 (en) * | 1998-12-09 | 2001-12-18 | Council Of Scientific And Industrial Research | Catalyst system containing a semilabile anionic ligand and a use of such catalyst system to produce α, β, -unsaturated carboxylic acids and their esters |
EP1918247A1 (en) * | 2006-10-18 | 2008-05-07 | Ecole Polytechnique Fédérale de Lausanne (EPFL) | Hydrogen production from formic acid |
DE102011089008B4 (de) * | 2011-12-19 | 2017-08-24 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Estern aus Formiaten und olefinisch ungesättigten Verbindungen |
JP2016539793A (ja) * | 2013-12-02 | 2016-12-22 | キング アブドゥーラ ユニバーシティ オブ サイエンス アンド テクノロジー | ギ酸からの効率的な水素生成のためのn−hアーム脱プロトン化/ピリジン脱芳香族化を介した金属−配位子協奏触媒作用 |
US10052621B2 (en) * | 2015-07-14 | 2018-08-21 | University Of Southern California | Dehydrogenation of neat formic acid |
US9725398B2 (en) * | 2015-07-23 | 2017-08-08 | Evonik Degussa Gmbh | Benzene-based diphosphine ligands for alkoxycarbonylation |
CN105833914B (zh) * | 2016-04-13 | 2018-02-16 | 大连理工大学 | 一类双核配合物催化剂、制备方法及其应用于催化甲酸分解制氢 |
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CN103635421A (zh) * | 2011-04-19 | 2014-03-12 | 拜尔技术服务有限责任公司 | 通过甲酸的催化分解获取氢气的方法 |
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