DE851188C - Process for the preparation of dicyclohexylamine - Google Patents
Process for the preparation of dicyclohexylamineInfo
- Publication number
- DE851188C DE851188C DEB6155D DEB0006155D DE851188C DE 851188 C DE851188 C DE 851188C DE B6155 D DEB6155 D DE B6155D DE B0006155 D DEB0006155 D DE B0006155D DE 851188 C DE851188 C DE 851188C
- Authority
- DE
- Germany
- Prior art keywords
- cyclohexylamine
- dicyclohexylamine
- preparation
- aniline
- hydrogenation catalysts
- 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
- 238000000034 method Methods 0.000 title claims description 5
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 title description 7
- 238000002360 preparation method Methods 0.000 title description 3
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 26
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- TXTHKGMZDDTZFD-UHFFFAOYSA-N n-cyclohexylaniline Chemical compound C1CCCCC1NC1=CC=CC=C1 TXTHKGMZDDTZFD-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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)
Description
Verfahren zur Herstellung von Dicyclohexylamin Bei der katalytischen Hydrierung von Anilin erhält man ein Gemisch etwa gleicher Mengen Cyclohexylamin und Dicyclohexylamin neben geringen Mengen Cyclohexylanilin. Andererseits ist bekannt, daß Cyclohexylamin beim Leiten seiner Dämpfe im Gemisch mit Wasserstoff über Hydrierungskatalysatoren Dicyclohexylamin liefert, wobei aber viel Cyclohexylamin unverändert bleibt und beträchtliche Mengen Anilin und Cyclohexylanilin entstehen.Process for the preparation of dicyclohexylamine In the catalytic Hydrogenation of aniline gives a mixture of approximately equal amounts of cyclohexylamine and dicyclohexylamine in addition to small amounts of cyclohexylaniline. On the other hand it is known that cyclohexylamine when passing its vapors in a mixture with hydrogen over hydrogenation catalysts Dicyclohexylamine delivers, but much of the cyclohexylamine remains unchanged and considerable amounts of aniline and cyclohexylaniline are produced.
Es wurde nun gefunden, daß man Dicyclohexylamin in sehr guter Ausbeute erhalten kann, wenn man Dämpfe von Cyclohexylamin im Wasserstoffkreislauf über Hydrierungskatalysatoren leitet und das Kreisgas nach der Kondensation der flüssigen Reaktionsprodukte durch Berieseln mit Wasser oder mit wäbrigen Salzlösungen vom entstandenen Ammoniak befreit, bevor man es erneut mit Cyclohexylamin belädt. Man erhält auf diese Weise ein Rohprodukt, das keine aromatischen Amine enthält und das sich durch Destillation in die einzelnen Bestandteile zerlegen läßt.It has now been found that dicyclohexylamine can be obtained in very good yield can be obtained when vapors of cyclohexylamine in the hydrogen cycle over hydrogenation catalysts and the cycle gas passes through after the condensation of the liquid reaction products Sprinkling with water or with aqueous salt solutions freed from the ammonia formed, before reloading it with cyclohexylamine. In this way a crude product is obtained which does not contain aromatic amines and which is broken down into the individual by distillation Components can be disassembled.
Als Katalysatoren eignen sich in erster Linie die Metalle der achten Gruppe des Periodischen Systems und metallisches Kupfer. Sie können als reine Metalle auf Trägern oder im Gemisch miteinander oder mit aktivierenden Zusätzen, wie Chrom- oder Muminiumoxyd, angewandt werden.The metals of the eighth are primarily suitable as catalysts Periodic Table Group and metallic copper. They can be considered pure metals on carriers or mixed with one another or with activating additives, such as chromium or aluminum oxide, can be used.
Die Umsetzung erfolgt bei Temperaturen zwischen i 5o und 27o°, insbesondere bei 180 bis 23o°. Gegenüber dem aus der amerikanischen Patentschrift 1 982 985 bekannten Verfahren zur Herstellung von Dicyclohexylamin durch Hydrieren eines Gemisches von Anilin und Phenol hat das vorliegende Verfahren den Vorteil, daß es von einem einzigen Ausgangsstoff, dem Anilin, ausgeht; da die dabei entstehenden Nebenprodukte Cyclohexylamin und Cyclohexanol der Umsetzung ebenfalls wieder zugeführt werden können, gestattet es eine praktisch vollständige Umwandlung von Anilin in Dicyclohexylamin. Beispiel Über 75- kg eines mit 60J0 Chromoxyd aktivierten, auf Bimsstein aufgetragenen Nickelkatalysators leitet man bei 18o bis 200° im Kreislauf stündlich Zoo mg Wasserstoff, dem 4o kg Cyclohexylamindampf beigemischt sind. Das den Ofen verlassende Gasgemisch wird abg;kühlt, wobei sich das RöliprodVkt kondensiert. Aus dem Kreislaufwasserstoff wird durch Berieseln mit Wasser jeweils das Ammoniak entfernt, bevor er mit Cyclohexylamindampf beladen wird. Das Rohprodukt ist frei von Anilin und Cyclohexylamin. 1's enthält 6o% Dicyciohexylamin und 2o% Cyclohexylamin, das erneut umgesetzt werden kann. Außerdem entstehen 20°l0 Cyclohexanol.The reaction takes place at temperatures between 15o and 27o °, in particular at 180 to 23o °. Compared to the process known from US Pat. No. 1,982,985 for the preparation of dicyclohexylamine by hydrogenating a mixture of aniline and phenol, the present process has the advantage that it starts from a single starting material, aniline; Since the byproducts cyclohexylamine and cyclohexanol can also be fed back into the reaction, it allows practically complete conversion of aniline into dicyclohexylamine. Example Over 75 kg of a nickel catalyst, activated with 60% chromium oxide and applied to pumice stone, zoo mg of hydrogen, to which 40 kg of cyclohexylamine vapor have been admixed, are circulated at 18o to 200 °. The gas mixture leaving the furnace is cooled, whereby the RöliprodVkt condenses. The ammonia is removed from the circulating hydrogen by sprinkling with water before it is loaded with cyclohexylamine vapor. The crude product is free from aniline and cyclohexylamine. 1's contains 6o% dicyciohexylamine and 2o% cyclohexylamine, which can be reacted again. In addition, 20 ° 10 cyclohexanol is formed.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB6155D DE851188C (en) | 1943-02-18 | 1943-02-18 | Process for the preparation of dicyclohexylamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB6155D DE851188C (en) | 1943-02-18 | 1943-02-18 | Process for the preparation of dicyclohexylamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE851188C true DE851188C (en) | 1952-10-02 |
Family
ID=6954416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB6155D Expired DE851188C (en) | 1943-02-18 | 1943-02-18 | Process for the preparation of dicyclohexylamine |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE851188C (en) |
-
1943
- 1943-02-18 DE DEB6155D patent/DE851188C/en not_active Expired
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