TW201919757A - Ｐｄ催化之甲酸分解方法 - Google Patents

Ｐｄ催化之甲酸分解方法 Download PDF

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TW201919757A
TW201919757A TW107127010A TW107127010A TW201919757A TW 201919757 A TW201919757 A TW 201919757A TW 107127010 A TW107127010 A TW 107127010A TW 107127010 A TW107127010 A TW 107127010A TW 201919757 A TW201919757 A TW 201919757A
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桑睿
劉劼
董開武
雷夫 傑克斯泰爾
馬席爾斯 貝勒
羅柏特 法蘭克
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德商贏創德固賽有限責任公司
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Abstract

一種Pd催化之甲酸分解方法。

Description

Ｐｄ催化之甲酸分解方法
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 (14)

  1. 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。
  2. 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 *CH3 Cl(dba=二(苯亞甲基)丙酮)、Pd(OAc)2 、Pd(TFA)2 、Pd(CH3 CN)Cl2 。
  3. 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 。
  4. 如申請專利範圍第1至3項中任一項之方法， 其中該方法包含額外方法步驟f)： f)添加酸。
  5. 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：H2 SO4 、CH3 SO3 H、CF3 SO3 H、PTSA。
  6. 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。
  7. 如申請專利範圍第1至6項中任一項之方法， 其中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。
  8. 如申請專利範圍第1至7項中任一項之方法， 其中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。
  9. 如申請專利範圍第1至8項中任一項之方法， 其中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。
  10. 如申請專利範圍第1至9項中任一項之方法， 其中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。
  11. 如申請專利範圍第1至10項中任一項之方法， 其中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。
  12. 如申請專利範圍第1至11項中任一項之方法，其中通式(I)之化合物係選自結構(1)至(3)：。
  13. 如申請專利範圍第1至12項中任一項之方法，其中通式(I)之化合物具有該結構(2)：。
  14. 如申請專利範圍第1至12項中任一項之方法，其中通式(I)之化合物具有該結構(3)：。
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