GB821404A - Preparation of meta-and para-xylylenediamines - Google Patents
Preparation of meta-and para-xylylenediaminesInfo
- Publication number
- GB821404A GB821404A GB5931/58A GB593158A GB821404A GB 821404 A GB821404 A GB 821404A GB 5931/58 A GB5931/58 A GB 5931/58A GB 593158 A GB593158 A GB 593158A GB 821404 A GB821404 A GB 821404A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phthalonitrile
- acid
- zone
- hydrogenation
- solvent
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/22—Preparation of carboxylic acid nitriles by reaction of ammonia with carboxylic acids with replacement of carboxyl groups by cyano groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises a process for the preparation of m and p xylylenediamines by contacting solid iso or terephthalic acid with gaseous ammonia, under such conditions that a phthalonitrile containing vaporous mixture is produced, passing said mixture into a phthalonitrile recovery zone containing a solvent for the phthalonitrile, which is substantially unreactive under subsequent hydrogenating conditions, withdrawing an effluent comprising the phthalonitrile dissolved in said solvent, passing the effluent without purification directly into a hydrogenation zone, contacting the dissolved phthalonitrile with hydrogen in the presence of a hydrogenation catalyst, under hydrogenating conditions and separating the xylylenediamine so formed, from the effluent from the hydrogenation zone. The phthalonitrile is preferably produced in two stages. In a first non-catalytic stage ammonia and phthalic acid are contacted in a reaction incomplete enough to convert substantially all of the acid to phthalonitrile, a portion of the acid remaining uncoverted. In the second catalytic stage the reaction is completed. The first stage may be carried out by continuously charging solid iso and/or terephthalic acid into a volatilization zone above about 500 DEG C. and below the melting point of the acid, from about 0.1-20 atmospheres, continuously passing sufficient gaseous ammonia through the zone to form a molten and relatively volatile mass of unreacted and partially reacted portions of the acid, i.e. until to 70% of the carboxyl groups have reacted with ammonia, and also to serve as a carrier for the vapours of the said mass. The vapours are then passed into a dehydration zone at e.g. about 650-900 DEG F. containing a dehydration catalyst. Where water is removed, and unreacted and partially reacted acid is converted into phthalonitrile. Suitable specified dehydration catalysts are activated alumina, silica, and thoria, zirconium, beryllium, tungsten and vanadium oxides, basic aluminium phosphate, basic aluminium sulphate or phosphoric acid. The catalysts may be supported. The effluent is then passed into a recovery zone and into the desired solvent, above e.g. about 200 DEG F., and the resulting solvent-phthalonitrile passed to a hydrogenation zone containing a hydrogenating catalyst, the so formed xylylenediamines being recovered from the effluent. Specified hydrogenation catalysts are reduced cobalt oxide, or nickel, and suitable hydrogenation conditions are 1,500 to 10,000 p.s.i.g., 180-400 DEG F. a space rate of 0.05 to 8 grams of phthalonitrile per c.c. of catalyst per hour, and a make-up hydrogen rate, excluding recycle hydrogen, which may be used if desired, 4 to 20 moles. hydrogen per mole. of phthalonitrile. From 10 to 50% by weight of the total feed to the hydrogenation zone of ammonia may also be added at this stage. The effluent from the recovery zone should preferably contain from about 50-90% by weight of the solvent before undergoing hydrogenation. Specified solvents are xylene, isopropyl alcohol dioxane, benzene and methanol and their mixtures. The solubility parameter of the solvent or mixed solvent should not differ in either direction from that of the nitrile by more than about 2.5. Nitrogen may be passed into the vaporizer together with the solid acid in order to facilitate the passage of the acid to the vaporizer. Examples are given.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US821404XA | 1957-03-22 | 1957-03-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB821404A true GB821404A (en) | 1959-10-07 |
Family
ID=22169316
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB5931/58A Expired GB821404A (en) | 1957-03-22 | 1958-02-24 | Preparation of meta-and para-xylylenediamines |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB821404A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4671890A (en) * | 1985-06-17 | 1987-06-09 | Mitsui Toatsu Chemicals, Inc. | Aminobenzylamine composition |
EP1378504A3 (en) * | 2002-07-01 | 2004-09-29 | Mitsubishi Gas Chemical Company, Inc. | Process for production of xylylenediamine and/or cyanobenzylamine |
CN101869818A (en) * | 2010-06-13 | 2010-10-27 | 浙江逸盛石化有限公司 | Method and device for reducing internal pressure of terephthalic acid make-up tank |
-
1958
- 1958-02-24 GB GB5931/58A patent/GB821404A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4671890A (en) * | 1985-06-17 | 1987-06-09 | Mitsui Toatsu Chemicals, Inc. | Aminobenzylamine composition |
EP1378504A3 (en) * | 2002-07-01 | 2004-09-29 | Mitsubishi Gas Chemical Company, Inc. | Process for production of xylylenediamine and/or cyanobenzylamine |
US7119230B2 (en) | 2002-07-01 | 2006-10-10 | Mitsubishi Gas Chemical Co., Inc. | Process for production of xylylenediamine and/or cyanobenzylamine |
CN101869818A (en) * | 2010-06-13 | 2010-10-27 | 浙江逸盛石化有限公司 | Method and device for reducing internal pressure of terephthalic acid make-up tank |
CN101869818B (en) * | 2010-06-13 | 2012-08-22 | 浙江逸盛石化有限公司 | Method and device for reducing internal pressure of terephthalic acid make-up tank |
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