GB852972A - Production of xylylene diamines - Google Patents
Production of xylylene diaminesInfo
- Publication number
- GB852972A GB852972A GB1181/59A GB118159A GB852972A GB 852972 A GB852972 A GB 852972A GB 1181/59 A GB1181/59 A GB 1181/59A GB 118159 A GB118159 A GB 118159A GB 852972 A GB852972 A GB 852972A
- Authority
- GB
- United Kingdom
- Prior art keywords
- catalyst
- acid
- pyro
- phthalonitrile
- poly
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Xylylene diamines are prepared by catalytic hydrogenation under increased pressure of a phthalonitrile in dissolved form in the presence of a cobalt catalyst which contains, in addition to chromium and/or manganese, 0,05 to 5% based on the total weight of the catalyst, of a pyro or poly form of phosphoric, sulphuric or boric acid. The reduction is preferably carried out at 50-85 DEG C. and 100-500 atmospheres using a supported catalyst containing 10-20% Co, 0,03-5% Cr and/or 0,1-2% Mn and 0,3-1,5% of the pyro or poly acid. The solvent used may be ammonia or the corresponding xylylene diamine or preferably a mixture of both containing 55% ammonia which may be obtained as a discharge from the hydrogenation. In examples : (1) p-phthalonitrile in liquid ammonia is reduced in the presence of a Co, Cr and polyphosphoric acid on silica string catalyst, (2) and (4) m-phthalonitrile in liquid ammonia and m-xylylene diamine is reduced in the presence of a Co, Mn and polyphosphoric acid on silica string catalyst, and (3) m-phthalonitrile in liquid ammonia and m-xylylene diamine is reduced in the presence of a Co, Mn and polyphosphoric acid on Al2O3 catalyst.ALSO:A catalyst, used in hydrogenating phthalonitrile to xylylene diamine, comprises cobalt together with chromium and/or manganese and from 0.05 to 5%, based on the total weight of the catalyst, of a pyro or poly form of phosphoric, sulphuric or boric acid. The catalyst preferably contains 10-20% wt. of cobalt, 0.03 to 5% wt. chromium and/or 0.1 to 2% wt. manganese and 0.3 to 1.5% wt. of the pyro or poly acid, and may be unsupported or supported, e.g. on Fuller's earth, silica strings, silica gel, aluminium oxide or mangesium silicate. The catalyst may be prepared from water-soluble salts of the metal and the acid added and converted to the pyro or poly form by heating; alternatively the metal salts may be heated alone, the mass cooled, the acid then added and the mass reheated to convert the acid to the pyro or poly form.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE852972X | 1958-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB852972A true GB852972A (en) | 1960-11-02 |
Family
ID=6786423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1181/59A Expired GB852972A (en) | 1958-04-02 | 1959-04-02 | Production of xylylene diamines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB852972A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4482741A (en) * | 1984-01-09 | 1984-11-13 | Uop Inc. | Preparation of xylylenediamine |
| US6960691B2 (en) | 2001-06-18 | 2005-11-01 | Showa Denko K.K. | Production process for halogenated aromatic methylamine |
| JP2007505068A (en) * | 2003-09-10 | 2007-03-08 | ビーエーエスエフ アクチェンゲゼルシャフト | Method for producing xylylenediamine (XDA) |
| EP1762561A1 (en) | 2005-09-09 | 2007-03-14 | Mitsubishi Gas Chemical Company, Inc. | Process and catalysts for the preparation of amino compounds containing an aromatic ring |
| JP2007533616A (en) * | 2003-09-10 | 2007-11-22 | ビーエーエスエフ アクチェンゲゼルシャフト | Process for the production of xylylenediamine by continuous hydrogenation of liquid phthalodinitrile |
| EP1873137A1 (en) * | 2006-06-29 | 2008-01-02 | Mitsubishi Gas Chemical Company, Inc. | Production of Xylenediamines |
| CN100361959C (en) * | 2003-09-10 | 2008-01-16 | 巴斯福股份公司 | Method for the production of diaminoxylene by continuous hydrogenation of liquid phthalonitrile |
| JP2008031155A (en) * | 2006-06-29 | 2008-02-14 | Mitsubishi Gas Chem Co Inc | Method for producing xylylenediamine |
| US7728174B2 (en) | 2005-08-02 | 2010-06-01 | Basf Se | Continuous hydrogenation processes for the preparation of xylylenediamines |
-
1959
- 1959-04-02 GB GB1181/59A patent/GB852972A/en not_active Expired
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4482741A (en) * | 1984-01-09 | 1984-11-13 | Uop Inc. | Preparation of xylylenediamine |
| US6960691B2 (en) | 2001-06-18 | 2005-11-01 | Showa Denko K.K. | Production process for halogenated aromatic methylamine |
| JP2007505068A (en) * | 2003-09-10 | 2007-03-08 | ビーエーエスエフ アクチェンゲゼルシャフト | Method for producing xylylenediamine (XDA) |
| JP2007533616A (en) * | 2003-09-10 | 2007-11-22 | ビーエーエスエフ アクチェンゲゼルシャフト | Process for the production of xylylenediamine by continuous hydrogenation of liquid phthalodinitrile |
| CN100361959C (en) * | 2003-09-10 | 2008-01-16 | 巴斯福股份公司 | Method for the production of diaminoxylene by continuous hydrogenation of liquid phthalonitrile |
| US7323597B2 (en) | 2003-09-10 | 2008-01-29 | Basf Aktiengesellschaft | Method for the production of diaminoxylene by continuous hydrogenation of liquid phthalonitrile |
| US7339080B2 (en) | 2003-09-10 | 2008-03-04 | Basf Aktiengesellschaft | Method for the production of diaminoxylene by continuous hydrogenation of liquid phthalonitrile |
| US7368610B2 (en) | 2003-09-10 | 2008-05-06 | Basf Aktiengesellschaft | Preparation of xylylenediamine (XDA) |
| US7728174B2 (en) | 2005-08-02 | 2010-06-01 | Basf Se | Continuous hydrogenation processes for the preparation of xylylenediamines |
| US7449604B2 (en) | 2005-09-09 | 2008-11-11 | Mitsubishi Gas Chemical Company, Inc. | Production of aromatic ring-containing amino compounds and catalysts |
| EP1762561A1 (en) | 2005-09-09 | 2007-03-14 | Mitsubishi Gas Chemical Company, Inc. | Process and catalysts for the preparation of amino compounds containing an aromatic ring |
| JP2008031155A (en) * | 2006-06-29 | 2008-02-14 | Mitsubishi Gas Chem Co Inc | Method for producing xylylenediamine |
| US7626057B2 (en) | 2006-06-29 | 2009-12-01 | Mitsubishi Gas Chemical Company, Inc. | Production of xylylenediamines |
| EP1873137A1 (en) * | 2006-06-29 | 2008-01-02 | Mitsubishi Gas Chemical Company, Inc. | Production of Xylenediamines |
| CN101096343B (en) * | 2006-06-29 | 2012-07-11 | 三菱瓦斯化学株式会社 | Production of xylenediamines |
| TWI394739B (en) * | 2006-06-29 | 2013-05-01 | Mitsubishi Gas Chemical Co | Production of xylylenediamines |
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