WO2018182463A1 - Silica-supported palladium-based catalysts for an industrial process of alcohol amination using nitroarenes and aniline - Google Patents
Silica-supported palladium-based catalysts for an industrial process of alcohol amination using nitroarenes and aniline Download PDFInfo
- Publication number
- WO2018182463A1 WO2018182463A1 PCT/SA2018/000008 SA2018000008W WO2018182463A1 WO 2018182463 A1 WO2018182463 A1 WO 2018182463A1 SA 2018000008 W SA2018000008 W SA 2018000008W WO 2018182463 A1 WO2018182463 A1 WO 2018182463A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- nitroarenes
- silica
- supported palladium
- aniline
- amines
- Prior art date
Links
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title abstract 3
- 239000003054 catalyst Substances 0.000 title abstract 3
- 229910052763 palladium Inorganic materials 0.000 title abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title 2
- 238000005576 amination reaction Methods 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 abstract 5
- 150000001412 amines Chemical class 0.000 abstract 3
- 239000003814 drug Substances 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 1
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
Classifications
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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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- B01J35/393—
-
- 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
- B01J37/0201—Impregnation
- B01J37/0203—Impregnation the impregnation liquid 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
- B01J37/0201—Impregnation
- B01J37/0205—Impregnation in several steps
-
- 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
- B01J37/16—Reducing
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
This invention has two important disclosures. The first is a method for preparing a highly active silica-supported palladium catalyst. The second is the possibility of applying this method to synthesise different high-value amines using alcohol, nitroarenes and amines. The method is used in the preparation of particles of the present drugs/pharmaceuticals (benzylaniline). This catalyst is useful in a process for producing primary amines from alcohol and amines, which is considered a very difficult process.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SA117380521A SA117380521B1 (en) | 2017-03-26 | 2017-03-26 | Process for Preparing Palladium Nanoparticles Supported on Silica and using it to Produce N-benzylanilines |
SA117380521 | 2017-03-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2018182463A1 true WO2018182463A1 (en) | 2018-10-04 |
Family
ID=62784212
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/SA2018/000008 WO2018182463A1 (en) | 2017-03-26 | 2018-03-08 | Silica-supported palladium-based catalysts for an industrial process of alcohol amination using nitroarenes and aniline |
Country Status (2)
Country | Link |
---|---|
SA (1) | SA117380521B1 (en) |
WO (1) | WO2018182463A1 (en) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006121553A2 (en) * | 2005-05-10 | 2006-11-16 | Headwaters Technology Innovation Llc | Methods for manufacturing supported nanocatalysts and methods for using supported nanocatalysts |
US20080108497A1 (en) * | 2006-11-08 | 2008-05-08 | Holland Brian T | Metal-rich siliceous compositions and methods of producing same |
WO2012121156A1 (en) * | 2011-03-09 | 2012-09-13 | 和光純薬工業株式会社 | Partial hydrogenation reaction of alkyne derivative |
-
2017
- 2017-03-26 SA SA117380521A patent/SA117380521B1/en unknown
-
2018
- 2018-03-08 WO PCT/SA2018/000008 patent/WO2018182463A1/en active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006121553A2 (en) * | 2005-05-10 | 2006-11-16 | Headwaters Technology Innovation Llc | Methods for manufacturing supported nanocatalysts and methods for using supported nanocatalysts |
US20080108497A1 (en) * | 2006-11-08 | 2008-05-08 | Holland Brian T | Metal-rich siliceous compositions and methods of producing same |
WO2012121156A1 (en) * | 2011-03-09 | 2012-09-13 | 和光純薬工業株式会社 | Partial hydrogenation reaction of alkyne derivative |
Non-Patent Citations (2)
Title |
---|
B. SREEDHAR ET AL: "Direct One-Pot Reductive Amination of Aldehydes with Nitroarenes in a Domino Fashion: Catalysis by Gum-Acacia-Stabilized Palladium Nanoparticles", JOURNAL OF ORGANIC CHEMISTRY, vol. 74, no. 22, 20 October 2009 (2009-10-20), US, pages 8806 - 8809, XP055248790, ISSN: 0022-3263, DOI: 10.1021/jo901787t * |
M. OUSMANE ET AL: "Highly selective direct amination of primary alcohols over a Pd/K-OMS-2 catalyst", JOURNAL OF CATALYSIS., vol. 309, 28 November 2013 (2013-11-28), US, pages 439 - 452, XP055480686, ISSN: 0021-9517, DOI: 10.1016/j.jcat.2013.10.003 * |
Also Published As
Publication number | Publication date |
---|---|
SA117380521B1 (en) | 2022-02-06 |
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