CH363032A - Verfahren zur kontinuierlichen Herstellung von Hexamethylendiamin aus Adipinsäuredinitril - Google Patents

Verfahren zur kontinuierlichen Herstellung von Hexamethylendiamin aus Adipinsäuredinitril

Info

Publication number: CH363032A
Authority: CH; Switzerland
Prior art keywords: dinitrile; hexamethylenediamine; adipic; hydrogenation; adipic acid
Prior art date: 1956-12-17

Application number

CH5325157A

Other languages

German (de)

English (en)

Inventor

Heinz Dr Indest

Gerhard Dr Meyer

Original Assignee

Glanzstoff 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.)

1956-12-17

Filing date

1957-11-30

Publication date

1962-07-15

1957-11-30 Application filed by Glanzstoff Ag filed Critical Glanzstoff Ag

1962-07-15 Publication of CH363032A publication Critical patent/CH363032A/de

Links

NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 title claims description 40
BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 title claims description 27
238000000034 method Methods 0.000 title claims description 16
238000010924 continuous production Methods 0.000 title claims description 4
238000005984 hydrogenation reaction Methods 0.000 claims description 15
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
150000001768 cations Chemical class 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
150000001450 anions Chemical class 0.000 claims description 9
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 6
229910052759 nickel Inorganic materials 0.000 claims description 6
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
229910000838 Al alloy Inorganic materials 0.000 claims description 3
229910001854 alkali hydroxide Inorganic materials 0.000 claims description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
239000006227 byproduct Substances 0.000 description 12
239000003054 catalyst Substances 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000004821 distillation Methods 0.000 description 6
150000002500 ions Chemical class 0.000 description 6
150000003335 secondary amines Chemical class 0.000 description 6
239000002253 acid Substances 0.000 description 5
239000003513 alkali Substances 0.000 description 5
238000000746 purification Methods 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
FHKPTEOFUHYQFY-UHFFFAOYSA-N 2-aminohexanenitrile Chemical compound CCCCC(N)C#N FHKPTEOFUHYQFY-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000004508 fractional distillation Methods 0.000 description 4
239000012535 impurity Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
ICIIBNHVHRSUJD-UHFFFAOYSA-N 6-n-hexylhexane-1,1,6-triamine Chemical compound CCCCCCNCCCCCC(N)N ICIIBNHVHRSUJD-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 3
230000007423 decrease Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
239000002904 solvent Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
229960002684 aminocaproic acid Drugs 0.000 description 2
-1 aminocaproic acid nitride Chemical class 0.000 description 2
238000005349 anion exchange Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000004140 cleaning Methods 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
238000005530 etching Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000002574 poison Substances 0.000 description 2
231100000614 poison Toxicity 0.000 description 2
238000003825 pressing Methods 0.000 description 2
230000007420 reactivation Effects 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
238000004383 yellowing Methods 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000004913 activation Effects 0.000 description 1
150000001279 adipic acids Chemical class 0.000 description 1
229910045601 alloy Inorganic materials 0.000 description 1
239000000956 alloy Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000005341 cation exchange Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000002542 deteriorative effect Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- 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)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH5325157A 1956-12-17 1957-11-30 Verfahren zur kontinuierlichen Herstellung von Hexamethylendiamin aus Adipinsäuredinitril CH363032A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEV11668A DE1027202B (de)	1956-12-17	1956-12-17	Verfahren zur kontinuierlichen Herstellung von Hexamethylendiamin durch Reduktion von Adipinsaeuredinitril

Publications (1)

Publication Number	Publication Date
CH363032A true CH363032A (de)	1962-07-15

Family

ID=7573558

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH5325157A CH363032A (de)	1956-12-17	1957-11-30	Verfahren zur kontinuierlichen Herstellung von Hexamethylendiamin aus Adipinsäuredinitril

Country Status (3)

Country	Link
CH (1)	CH363032A (es)
DE (1)	DE1027202B (es)
ES (1)	ES238780A1 (es)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE758296A (fr) *	1969-11-07	1971-04-01	Rhodiatoce	Procede de fabrication d'hexamethylenediamine

1956
- 1956-12-17 DE DEV11668A patent/DE1027202B/de active Pending
1957
- 1957-11-26 ES ES0238780A patent/ES238780A1/es not_active Expired
- 1957-11-30 CH CH5325157A patent/CH363032A/de unknown

Also Published As

Publication number	Publication date
DE1027202B (de)	1958-04-03
ES238780A1 (es)	1958-05-16

Publication	Publication Date	Title
DE60124482T2 (de)	2007-03-01	Verfahren zur Herstellung von Xylylendiamin
DE3125662A1 (de)	1983-01-13	Verfahren und katalysator zur herstellung von cyclischen iminen
DE2053799B2 (de)	1974-06-20	Verfahren zur Herstellung von Hexamethylendiamin durch katalytische Hydrierung von Adipinsäuredinitril in flüssiger Phase
DE69909619T2 (de)	2004-06-09	Verfahren zur herstellung eines aminonitrils und eines diamins
AT399149B (de)	1995-03-27	Verfahren zur herstellung primärer amine aus aldehyden
DE1518345B2 (de)	1974-12-05	Verfahren zur Herstellung von Trimethylhexamethylendiaminen
DE954416C (de)	1956-12-20	Verfahren zur Herstellung von Aminonitrilen und Diaminen
AT202556B (de)	1959-03-10	Verfahren zur kontinuierlichen Herstellung von Hexamethylendiamin aus Adipinsäuredinitril
DE2436651A1 (de)	1975-02-20	Verfahren zur herstellung von betaaminopropionitril
DE60015544T2 (de)	2005-10-27	Selektive trennung von eisen mit einem diphosphonsäuregruppen enthaltenden ionenaustauscherharz
DE3003731C2 (es)	1990-06-07
CH363032A (de)	1962-07-15	Verfahren zur kontinuierlichen Herstellung von Hexamethylendiamin aus Adipinsäuredinitril
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DE1518118B2 (de)	1973-12-20	Verfahren zur Hydrierung von Nitrilen
DE1119285B (de)	1961-12-14	Verfahren zur Herstellung von Xylylendiaminen
DE1116646B (de)	1961-11-09	Verfahren zur Reinigung von aliphatischen Dinitrilen
DE3123037C2 (es)	1987-10-29
EP0142070B1 (de)	1986-07-09	Verfahren zur Herstellung von N-Methylhomoveratrylamin
EP0153680A2 (de)	1985-09-04	Verfahren zur Herstellung von Tetrahydrofuran
EP0021073B1 (de)	1983-02-09	Kobaltkatalysator, seine Herstellung und Verwendung, insbesondere zur Herstellung von Aminen
DE2923686A1 (de)	1980-12-18	Verfahren zur herstellung gesaettigter sekundaerer alkylamine
DE2320061C3 (de)	1976-02-19	Verfahren zur Herstellung einer acrylnitrilhaltigen, konzentrierten, wäßrigen Acrylamidlösung durch katalytische Wasseranlagerung an Acrylnitril
DE1201262B (de)	1965-09-16	Verfahren zur praktisch voelligen Entfernung von in Wasser geloestem Sauerstoff
DE948784C (de)	1956-09-06	Verfahren zur Herstellung von Toluylendiamin
DE2734368C2 (de)	1986-07-03	Verfahren zur Herstellung von 3,5-Dichloranilin