CH410896A - Verfahren zur Herstellung von Adipodinitril - Google Patents

Verfahren zur Herstellung von Adipodinitril

Info

Publication number: CH410896A
Authority: CH; Switzerland
Prior art keywords: adiponitrile; cleavage; hydrogen; treated; pressure
Prior art date: 1959-07-11

Application number

CH574960A

Other languages

German (de)

English (en)

Inventor

Kurt Dr Sennewald

Goetz Armin Dr Dipl-Chem

Kallrath Gottfried

Original Assignee

Knapsack Ag

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.)

1959-07-11

Filing date

1960-05-19

Publication date

1966-04-15

1960-05-19 Application filed by Knapsack Ag filed Critical Knapsack Ag

1966-04-15 Publication of CH410896A publication Critical patent/CH410896A/de

Links

BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 title claims description 20
238000000034 method Methods 0.000 title claims description 14
238000004519 manufacturing process Methods 0.000 title claims description 6
238000003776 cleavage reaction Methods 0.000 claims description 20
230000007017 scission Effects 0.000 claims description 18
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000003054 catalyst Substances 0.000 claims description 9
CZPLUOCTUPJSIZ-UHFFFAOYSA-N cyclobutane-1,2-dicarbonitrile Chemical compound N#CC1CCC1C#N CZPLUOCTUPJSIZ-UHFFFAOYSA-N 0.000 claims description 9
238000005984 hydrogenation reaction Methods 0.000 claims description 9
239000000243 solution Substances 0.000 claims description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 8
229910052759 nickel Inorganic materials 0.000 claims description 7
239000011541 reaction mixture Substances 0.000 claims description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
239000003495 polar organic solvent Substances 0.000 claims description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
229910017052 cobalt Inorganic materials 0.000 claims description 3
239000010941 cobalt Substances 0.000 claims description 3
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
239000011261 inert gas Substances 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
KKCBUQHMOMHUOY-UHFFFAOYSA-N Na2O Inorganic materials [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
238000001035 drying Methods 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
230000035484 reaction time Effects 0.000 claims description 2
229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
238000004140 cleaning Methods 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
239000002904 solvent Substances 0.000 description 5
PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 4
238000002360 preparation method Methods 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
-1 for example Chemical compound 0.000 description 2
239000000047 product Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000001273 butane Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
230000006837 decompression Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000000887 hydrating effect Effects 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 1
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
229910000008 nickel(II) carbonate Inorganic materials 0.000 description 1
ZULUUIKRFGGGTL-UHFFFAOYSA-L nickel(ii) carbonate Chemical compound [Ni+2].[O-]C([O-])=O ZULUUIKRFGGGTL-UHFFFAOYSA-L 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

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
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CH574960A 1959-07-11 1960-05-19 Verfahren zur Herstellung von Adipodinitril CH410896A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEK38187A DE1104936B (de)	1959-07-11	1959-07-11	Verfahren zur Herstellung von Adipinsaeuredinitril

Publications (1)

Publication Number	Publication Date
CH410896A true CH410896A (de)	1966-04-15

Family

ID=7221288

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH574960A CH410896A (de)	1959-07-11	1960-05-19	Verfahren zur Herstellung von Adipodinitril

Country Status (4)

Country	Link
BE (1)	BE592835A (fr)
CH (1)	CH410896A (fr)
DE (1)	DE1104936B (fr)
GB (1)	GB900357A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB943270A (en)	1959-10-19	1963-12-04	Du Pont	Preparation of dicarboxylic acid nitriles
CN112939784B (zh) *	2021-02-04	2022-12-02	山西铁峰化工有限公司	一种己二胺的工业制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2439308A (en) *	1946-07-18	1948-04-06	Du Pont	Process for simultaneous dimerization and reduction

1959
- 1959-07-11 DE DEK38187A patent/DE1104936B/de active Pending
1960
- 1960-05-19 CH CH574960A patent/CH410896A/de unknown
- 1960-06-10 GB GB2057560A patent/GB900357A/en not_active Expired
- 1960-07-11 BE BE592835A patent/BE592835A/fr unknown

Also Published As

Publication number	Publication date
DE1104936B (de)	1961-04-20
BE592835A (fr)	1960-10-31
GB900357A (en)	1962-07-04

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EP0066212B1 (fr)	1984-10-24	Procédé d'hydrogénation catalytique du di-(4-aminophényl)-méthane
DE2626676A1 (de)	1977-01-27	Verfahren zur herstellung von 2-pyrrolidon
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DE2626675A1 (de)	1977-01-20	Verfahren zur herstellung von 2-pyrrolidon
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DE1282018B (de)	1968-11-07	Verfahren zur Herstellung eines Isomerengemisches von Bis-(4-aminocyclohxyl)-methan mit Gleichgewichtsverteilung der Isomeren
DE855561C (de)	1952-11-13	Verfahren zur Herstellung cyclischer Imine bzw. ihrer Salze
DE539099C (de)	1931-11-20	Verfahren zur Herstellung von Butyraldehyd aus Crotonaldehyd
DE576388C (de)	1933-05-12	Verfahren zur Darstellung von Camphen
DE955497C (de)	1957-01-03	Verfahren zur Herstellung von N-monosubstituierten 1-Aminoindanen
DE960199C (de)	1957-03-21	Verfahren zur Herstellung von Cyclohexylhydroxylamin durch katalytische Hydrierung von Nitrocyclohexan
DE2125790A1 (en)	1972-12-07	Bis-(aminocyclohexyl) - methane prepn - using ruthenium oxide and basic oxide catalyst
DE909457C (de)	1954-04-22	Verfahren zur Herstellung von Diaminodicyclohexylmethanen oder ihren Derivaten
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DE858094C (de)	1952-12-04	Verfahren zur Herstellung von Butandiol-(1, 4) und seinen in 1- oder 1, 4-Stellung durch Kohlenwasserstoffreste oder heterocyclische Reste substituierten Abkoemmlingen
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