DE283449C - - Google Patents
Info
- Publication number
- DE283449C DE283449C DENDAT283449D DE283449DA DE283449C DE 283449 C DE283449 C DE 283449C DE NDAT283449 D DENDAT283449 D DE NDAT283449D DE 283449D A DE283449D A DE 283449DA DE 283449 C DE283449 C DE 283449C
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- copper
- reduction
- salts
- parts
- 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.)
- Active
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 238000006722 reduction reaction Methods 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 150000001879 copper Chemical class 0.000 claims description 4
- 229910001385 heavy metal Inorganic materials 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 1
- 230000000875 corresponding Effects 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- QPLDLSVMHZLSFG-UHFFFAOYSA-N copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000005751 Copper oxide Substances 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N Sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229940116318 copper carbonate Drugs 0.000 description 2
- 229910000431 copper oxide Inorganic materials 0.000 description 2
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 239000008262 pumice Substances 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 0.000 description 2
- 239000004575 stone Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N al2o3 Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- -1 aromatic nitro compounds Chemical class 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- LILHXQCLSOZSRO-UHFFFAOYSA-J dizinc;oxozinc;dicarbonate;tetrahydrate Chemical compound O.O.O.O.[Zn+2].[Zn+2].[Zn]=O.[Zn]=O.[Zn]=O.[O-]C([O-])=O.[O-]C([O-])=O LILHXQCLSOZSRO-UHFFFAOYSA-J 0.000 description 1
- RAQDACVRFCEPDA-UHFFFAOYSA-L ferrous carbonate Chemical compound [Fe+2].[O-]C([O-])=O RAQDACVRFCEPDA-UHFFFAOYSA-L 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 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
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVi 283449 -" KLASSE 12 #. GRUPPE- JVi 283449 - "CLASS 12 #. GROUP
Zusatz zum Patent 282568.Addendum to patent 282568.
Patentiert im Deutschen Reiche vom 6. März 1914 ab. Längste Dauer: 6. November 1928.Patented in the German Empire on March 6, 1914. Longest duration: November 6, 1928.
Durch Patent 282568 ist ein Verfahren zur Darstellung aromatischer Amine aus den betreffenden Nitrokörpern durch katalytische Reduktion mit Wasserstoff in Gegenwart von Kupfer geschützt, welches darin besteht, daß man Kupfer verwendet, welches pyrogenetisch aus seinen Salzen, wenn nötig unter Zuleitung von reduzierend wirkenden Gasen, wie Kohlenoxyd oder Wasserstoff, hergestellt ist und bei Gegenwart von Aktivatoren arbeitet.By patent 282568 is a method for the preparation of aromatic amines from the subject Nitro bodies by catalytic reduction with hydrogen in the presence of Protected copper, which consists in using copper, which is pyrogenetic from its salts, if necessary with the addition of reducing gases such as carbon monoxide or hydrogen, is produced and operates in the presence of activators.
Es wurde nun weiter gefunden, daß die Kontaktmassen eine besondere Reaktionsfähigkeit und Haltbarkeit zeigen, wenn sie als Aktivatoren andere Schwermetalle oder deren Verbindungen enthalten. Man erhält derartige Kontaktmassen zweckmäßig in der Weise, daß man den Kupfersalzen oder dem durch Zersetzung bzw. Reduktion daraus erhaltenen Kupferoxyd oder feinverteilten Kupfer Oxyde oder Salze anderer Schwermetalle, z. B. von Eisen, Silber oder Zink, beimischt. Außer derartigen Metallen können noch sonstige Aktivatoren, wie Alkaliverbindungen, Magnesiumoxyd oder Aluminiumoxyd, oder Träger oder andere Zusätze zugegen sein.It has now also been found that the contact masses have a particular reactivity and show durability when used as activators other heavy metals or their Connections included. Such contact materials are expediently obtained in such a way that the copper salts or the copper oxide or finely divided copper oxides obtained therefrom by decomposition or reduction or salts of other heavy metals, e.g. B. of iron, silver or zinc, admixed. Except Such metals can also contain other activators, such as alkali compounds, magnesium oxide or aluminum oxide, or carriers or other additives.
130 Teile Bimsstein werden mit einer Mischung von 20 Teilen etwa 4oprozentiger Natriumsilicatlösung, 24,3 Teilen Kupfercarbonat, 2,7 Teilen Zinkcarbonat und etwas Wasser angeteigt. Man bringt die Masse in den Ofen und reduziert mit Wasserstoff bei 180 bis 220°.130 parts of pumice stone are mixed with 20 parts of about 4% sodium silicate solution, 24.3 parts of copper carbonate, 2.7 parts of zinc carbonate and a little water are made into a paste. You put the mass in the oven and reduced with hydrogen at 180 to 220 °.
Nach beendeter Reduktion leitet man über den Katalysator ein Gemisch von Nitrobenzol mit überschüssigem Wasserstoff bei einer Innentemperatur von etwa 200 °. Die den Ofen verlassenden Gase werden abgekühlt; man erhält ein Gemisch von Anilin und Wasser, aus dem das Anilin in üblicher Weise abgetrennt wird. Die Reduktion verläuft quantitativ; das erhaltene Anilin ist vollkommen farblos und wasserhell, und der Katalysator bleibt lange Zeit wirksam.When the reduction is complete, a mixture of nitrobenzene is passed over the catalyst with excess hydrogen at an internal temperature of about 200 °. The furnace leaving gases are cooled; a mixture of aniline and water is obtained from which the aniline is separated in the usual way. The reduction is quantitative; the aniline obtained is completely colorless and water-white, and the catalyst remains effective for a long time.
. .. .
130 Teile Bimsstein werden mit einer Mischung von 20 Teilen etwa 4oprozentiger Natriumsilicatlösung, 27 Teilen Kupfercarbonat, 3 Teilen Eisencarbonat und etwas Wasser angeteigt. Die Masse wird im Ofen bei 200 bis 2io° mit Wasserstoff reduziert. Der so erhaltene Katalysator wird in der in Beispiel 1 angegebenen Weise zur Reduktion von Nitrobenzol verwandt. ■130 parts of pumice stone are mixed with a mixture of 20 parts of about 4 percent strength sodium silicate solution, 27 parts of copper carbonate, 3 parts of iron carbonate and a little water are made into a paste. The mass is in the oven at 200 to 2io ° reduced with hydrogen. The catalyst obtained in this way is used in the in Example 1 indicated manner used for the reduction of nitrobenzene. ■
Analog verfährt man bei Verwendung von Mischungen aus Kupfersalzen oder daraus hergestelltem Kupferoxyd bzw. Kupfer und anderen Metallverbindungen sowie von anderen Aktivatoren oder Zμsätzen und von anderen aromatischen Nitroverbindungen.The procedure is analogous when using mixtures of copper salts or those made from them Copper oxide or copper and other metal compounds as well as other activators or additives and others aromatic nitro compounds.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE283449C true DE283449C (en) |
Family
ID=539012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT283449D Active DE283449C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE283449C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2320658A1 (en) * | 1972-04-22 | 1973-10-25 | Sumitomo Chemical Co | METHOD FOR PRODUCING ANILINE |
-
0
- DE DENDAT283449D patent/DE283449C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2320658A1 (en) * | 1972-04-22 | 1973-10-25 | Sumitomo Chemical Co | METHOD FOR PRODUCING ANILINE |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1163790B (en) | Process for the production of propionic acid | |
| DE2129423B2 (en) | Process for the production of acrylamide | |
| DE283449C (en) | ||
| DE1259899B (en) | Process for the production of amines | |
| DE3425629A1 (en) | METHOD FOR PRODUCING CYCLIC PRIMARY AMINES SUBSTITUTED ON THE RING | |
| EP0119421A1 (en) | Process for the isomerisation and transalkylation of alkylated phenols and/or phenol derivatives | |
| DE282568C (en) | ||
| DE282782C (en) | ||
| AT71168B (en) | Process for the preparation of aromatic amines. | |
| DE590232C (en) | ||
| DE510302C (en) | Process for the production of oxygen-containing organic compounds | |
| DE920963C (en) | Process for the preparation of hydroxylammonium salts | |
| DE215339C (en) | ||
| DE741683C (en) | Process for the preparation of primary amines | |
| DE838599C (en) | Carrying out catalytic reactions | |
| DE331303C (en) | Process for the preparation of aromatic amines | |
| DE848195C (en) | Process for the preparation of hexamethylenediamine from cyclohexanone oxime | |
| DE578826C (en) | Process for the catalytic production of hydrogen cyanide and cyano compounds | |
| DE254437C (en) | ||
| DE261507C (en) | ||
| DE238137C (en) | ||
| AT116601B (en) | Process for the preparation of methanol and other oxygen-containing organic compounds. | |
| DE263396C (en) | ||
| AT111844B (en) | Process for the production of hydrogen cyanide. | |
| DE229126C (en) |