GB821404A - Preparation of meta-and para-xylylenediamines - Google Patents

Preparation of meta-and para-xylylenediamines

Info

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
Application number
GB5931/58A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
California Research LLC
Original Assignee
California Research LLC
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by California Research LLC filed Critical California Research LLC
Publication of GB821404A publication Critical patent/GB821404A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/44Preparation 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
    • C07C209/48Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00Preparation of carboxylic acid nitriles
    • C07C253/22Preparation 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.
GB5931/58A 1957-03-22 1958-02-24 Preparation of meta-and para-xylylenediamines Expired GB821404A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (5)

* Cited by examiner, † Cited by third party
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

Similar Documents

Publication Publication Date Title
US4356124A (en) Process for the production of pyrrolidones
US2428590A (en) Production of allyl type compounds
US4352755A (en) Production of maleic anhydride
US4017494A (en) Catalyst for the manufacture of triethylenediamine
GB821404A (en) Preparation of meta-and para-xylylenediamines
US4263175A (en) Catalyst for the production of pyrrolidone
SE435925B (en) PROCEDURE FOR CATALYTIC CONVERSION OF ISOSMORIC ACID OR METHYLISOBUTYRATE
GB948687A (en) Process for producing acrylic acid and acrylic acid methyl ester
US3845094A (en) Process for vapor phase ammoxidation
US2884308A (en) Preparation of cyanogen
GB763339A (en) Improvements in recovery of maleic and phthalic acid anhydrides
US2874191A (en) Process for the manufacture of acetone
US3609197A (en) Preparation of a terpene alcohol
US3654354A (en) Process for the oxidation of unsaturated hydrocarbons
US3317563A (en) Preparation of epsilon-caprolactone
IE33593B1 (en) Improved process for the manufacture of adiponitrile
GB1044266A (en)
US2857416A (en) Preparation of isophthalonitrile and terephthalonitrile
US3206498A (en) Hydrodimerization of acrylonitriles
US2500256A (en) Production of nitriles
US3086017A (en) Catalytic process for producing nitrogen containing compounds
US3857796A (en) Oxidation catalyst
US3020282A (en) Process of preparing quinoline
ES434949A1 (en) Process for producing ethylphenols
US4442307A (en) Conversion of dimethyl ether to formaldehyde using Bi-Mo-Fe catalyst