IP Library Patent Application 16043657
Patent Application
App. No. 16/043,657

PD-CATALYZED DECOMPOSITION OF FORMIC ACID

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Patent No.
US None
App. No.
16/043,657
Abstract

Process for Pd-catalyzed decomposition of formic acid

Claims (51)

1 . Process comprising the process steps of:

a) presence of formic acid;

b) addition of a compound comprising Pd, wherein the Pd is capable of forming a complex;

c) addition of a compound of general formula (I):

wherein R 1 , R 2 , R 3 , R 4 are each independently selected from: —H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, —(C 4 -C 14 )-aryl, —O—(C 4 -C 14 )-aryl, cycloalkyl, —(C 1 -C 12 )-heteroalkyl, —O—(C 1 -C 12 )-heteroalkyl, —(C 3 -C 14 )-heteroaryl, —O—(C 3 -C 14 )-heteroaryl, —COO-alkyl, —COO-aryl, —C—O-alkyl, —C—O-aryl, NH 2 , halogen and the residues are also capable of forming a larger condensed ring;

wherein the recited alkyl groups, aryl groups, cycloalkyl, heteroalkyl groups, heteroaryl groups may be substituted as follows:

—(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, halogen;

and at least one of the radicals R 1 , R 2 , R 3 , R 4 does not represent phenyl;

d) addition of MeOH;

e) heating of the reaction mixture to decompose the formic acid.

2 . Process according to claim 1 ,

wherein the compound in process step b) is selected from:

Pd(acac) 2 , PdCl 2 , Pd(dba) 3 *CH 3 Cl (dba=dibenzylideneacetone), Pd(OAc) 2 , Pd(TFA) 2 , Pd(CH 3 CN)Cl 2 .

3 . Process according to claim 1 ,

wherein the compound in process step b) is Pd(OAc) 2 .

4 . Process according to claim 1 ,

wherein the process comprises additional process step f):

f) addition of an acid.

5 . Process according to claim 4 ,

wherein the acid in process step f) is selected from: H 2 SO 4 , CH 3 SO 3 H, CF 3 SO 3 H, PTSA.

6 . Process according to claim 4 ,

wherein the acid in process step f) is PTSA.

7 . Process according to claim 1 ,

wherein R 1 , R 2 , R 3 , R 4 are each independently selected from: —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, —(C 4 -C 14 )-aryl, —O—(C 4 -C 14 )-aryl, cycloalkyl, —(C 1 -C 12 )-heteroalkyl, —O—(C 1 -C 12 )-heteroalkyl, —(C 3 -C 14 )-heteroaryl, —O—(C 3 -C 14 )-heteroaryl, —COO-alkyl, —COO-aryl, —C—O-alkyl, —C—O-aryl, NH 2 , halogen and the residues are also capable of forming a larger condensed ring;

wherein the recited alkyl groups, aryl groups, cycloalkyl, heteroalkyl groups, heteroaryl groups may be substituted as follows:

—(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, halogen;

and at least one of the radicals R 1 , R 2 , R 3 , R 4 does not represent phenyl.

8 . Process according to claim 1 ,

wherein R 1 , R 2 , R 3 , R 4 are each independently selected from: —(C 1 -C 12 )-alkyl, —(C 4 -C 14 )-aryl, cycloalkyl, —(C 1 -C 12 )-heteroalkyl, —(C 3 -C 14 )-heteroaryl, halogen and the residues are also capable of forming a larger condensed ring;

wherein the recited alkyl groups, aryl groups, cycloalkyl, heteroalkyl groups, heteroaryl groups may be substituted as follows:

—(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, halogen;

and at least one of the radicals R 1 , R 2 , R 3 , R 4 does not represent phenyl.

9 . Process according to claim 1 ,

wherein R 1 , R 2 , R 3 , R 4 are each independently selected from: —(C 1 -C 12 )-alkyl, cycloalkyl, —(C 3 -C 14 )-heteroaryl and the residues are also capable of forming a larger condensed ring;

wherein the recited alkyl groups, cycloalkyl, heteroaryl groups may be substituted as follows:

—(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, halogen,

and at least one of the radicals R 1 , R 2 , R 3 , R 4 does not represent phenyl.

10 . Process according to claim 1 ,

wherein R 1 , R 4 are each independently selected from: —(C 1 -C 12 )-alkyl, cycloalkyl and the residues are also capable of forming a larger condensed ring;

wherein the recited alkyl groups, cycloalkyl may be substituted as follows:

—(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, halogen.

11 . Process according to claim 1 ,

wherein R 2 , R 3 each independently represent —(C 3 -C 14 )-heteroaryl,

wherein the recited heteroaryl groups may be substituted as follows:

—(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, halogen.

12 . Process according to claim 1 ,

wherein the compound of general formula (I) is selected from the structures (1) to (3):

13 . Process according to claim 1 ,

wherein the compound of general formula (I) has the structure (2):

14 . Process according to claim 1 ,

wherein the compound of general formula (I) has the structure (3):

Assignments (2)
CHANGE OF NAME Recorded Mar 29, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 052254/0052 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 8, 2019
From: SANG, RUI; LIU, JIE; DONG, KAIWU; JACKSTELL, RALF; BELLER, MATTHIAS; FRANKE, ROBERT
To: EVONIK DEGUSSA GMBH
Reel/Frame 049118/0827 →