DE408811C - Process for the catalytic hydrogenation and dehydrogenation of organic compounds - Google Patents
Process for the catalytic hydrogenation and dehydrogenation of organic compoundsInfo
- Publication number
- DE408811C DE408811C DEB109165D DEB0109165D DE408811C DE 408811 C DE408811 C DE 408811C DE B109165 D DEB109165 D DE B109165D DE B0109165 D DEB0109165 D DE B0109165D DE 408811 C DE408811 C DE 408811C
- Authority
- DE
- Germany
- Prior art keywords
- dehydrogenation
- organic compounds
- catalytic hydrogenation
- alloys
- contact
- 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 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title claims description 3
- 238000006356 dehydrogenation reaction Methods 0.000 title claims description 3
- 150000002894 organic compounds Chemical class 0.000 title claims description 3
- 229910045601 alloy Inorganic materials 0.000 claims description 12
- 239000000956 alloy Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- OWXLRKWPEIAGAT-UHFFFAOYSA-N [Mg].[Cu] Chemical compound [Mg].[Cu] OWXLRKWPEIAGAT-UHFFFAOYSA-N 0.000 description 4
- 239000008262 pumice Substances 0.000 description 4
- 239000004575 stone Substances 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- ATTFYOXEMHAYAX-UHFFFAOYSA-N magnesium nickel Chemical compound [Mg].[Ni] ATTFYOXEMHAYAX-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 235000019353 potassium silicate Nutrition 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- 229910000978 Pb alloy Inorganic materials 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NACUKFIFISCLOQ-UHFFFAOYSA-N [Mg].[Cr] Chemical compound [Mg].[Cr] NACUKFIFISCLOQ-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
- 229940116229 borneol Drugs 0.000 description 1
- HAUBPZADNMBYMB-UHFFFAOYSA-N calcium copper Chemical compound [Ca].[Cu] HAUBPZADNMBYMB-UHFFFAOYSA-N 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- -1 copper aluminum zinc Chemical compound 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- HEPLMSKRHVKCAQ-UHFFFAOYSA-N lead nickel Chemical compound [Ni].[Pb] HEPLMSKRHVKCAQ-UHFFFAOYSA-N 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 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
- WACRXVBKMRXTCA-UHFFFAOYSA-N platinum sodium Chemical compound [Na].[Pt] WACRXVBKMRXTCA-UHFFFAOYSA-N 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/19—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings
- C07C29/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings in a non-condensed rings substituted with hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
- C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
- C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
- C07C29/153—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used
- C07C29/154—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing copper, silver, gold, or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
- C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
- C07C29/153—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used
- C07C29/156—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing iron group metals, platinum group metals or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/002—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur katalytischen Hydrierung und Dehydrierung organischer Verbindungen. Es hat sich gezeigt, daß man organische Verbindungen besonders leicht katalytisch hydrieren bzw. dehydrieren kann, wenn man Katalysatoren verwendet, die aus solchen Legierungen entstehen, die bei der Darstellung des Kontakts oder seiner Verwendung zerfallen. Unter Umständen kann während der Verwendung des Kontakts die Legierung intermediär zurückgebildet werden.Process for the catalytic hydrogenation and dehydrogenation of organic Links. It has been shown that organic compounds are particularly easy to use can catalytically hydrogenate or dehydrogenate when using catalysts that arise from such alloys that are used in the representation of the contact or his Use disintegrate. Under certain circumstances, while using the contact, the Alloy can be regressed intermediately.
Als Beispiele solcher besonders wirksamer Legierungen seien genannt die Legierungen von Alkali- :oder Erdalkalimetallen mit den katalytisch wirksamen Elementen Nickel, Kupfer usw. Trägt man z. B. gepulvertes Nickelmagnesium auf feuchten Bimsstein auf, so zerfällt die Legierung durch den Feuchtig. keitsgehalt des Kontaktträgers unter Bildung von Magnesiumoxyd oder -hydroxyd und einem außerordentlich fein verteilten, hochaktiven Nickel. Analog erhält man aus Kupfermagnesium einen sehr wirksamen Kupferkatalysator.Examples of such particularly effective alloys may be mentioned the alloys of alkali: or alkaline earth metals with the catalytically active ones Elements nickel, copper, etc. If you wear z. B. powdered nickel magnesium on damp Pumice stone, the alloy disintegrates due to the moisture. ity content of the contact carrier with the formation of magnesium oxide or hydroxide and an extraordinarily finely divided, highly active nickel. Similarly, a very effective copper catalyst is obtained from copper magnesium.
Auch andere Legierungen, die durch W asser zerfallen, wie Kupfercalcium, Platinnatrium, Kupferaluminiumzink, Chrommagnesium usw. sind verwendbar. Der katalytisch wirksame Anteil wird hierbei durchweg in außerordentlich fein verteilter und entsprechend wirksamer Form erhalten.Other alloys that disintegrate with water, such as copper calcium, Platinum sodium, copper aluminum zinc, chromium magnesium, etc. are usable. The catalytic effective portion is consistently distributed in an extraordinarily fine way and accordingly more effective form.
Auch solche Legierungen lassen sich verwenden, von denen ein Teil 'Wasserstoff in größeren Mengen aufnimmt, der andere nicht, wie z. B. Nichelbleilegierungen in fein verteilter Form. Hier zerfällt während der Verwendung die Legierung bzw. Mischung offenbar durch Voiumänderung eines der Bestandteile. Auch lassen sich Legierungen verwenden, die durch andere Mittel, wie z. B. Hitze, zerfallen, z. B. Amalgame. Die Zahl der die Legierung zusammensetzenden Metalle ist nicht beschränkt. Man kann bei der Darstellung der Kontaktmasse auch Aktivatoren verwenden.Such alloys can also be used, some of which 'Absorbs hydrogen in larger quantities, the other does not, such as. B. Nickel lead alloys in finely divided form. Here, the alloy or Mixing evidently by changing the volume of one of the components. Alloys can also be used use made by other means, such as B. heat, disintegrate, e.g. B. Amalgams. The number of metals composing the alloy is not limited. One can Also use activators when representing the contact mass.
Beispiel i.Example i.
Auf i3oo Volumteile bohnengroße Bimssteinstücke werden ioo Gewichtsteile fein gepulverte Kupfermagnesiumlegierung aufgetragen und durch Aufstäuben einer verdünnten Wasserglaslösung festgeklebt. Die Kontaktmasse wird ,48 Stunden bei 300° im Wasserstoffstrom erhitzt; sie ist alsdann gebrauchsfähig und gestattet schon bei 9o bis i oo° Ketone wie Aceton glatt zu hydrieren, während im allgemeinen Ketone durch gewöhnliche Kupferkontaktmassen nicht oder nur schlecht zu hydrieren sind. Beispiel z,. Auf erbsengroße Bimssteinstücke wird fein gepulvertes Kupfermagnesium aufgetragen und mit einer Lösung kolloidaler Kieselsäure festgeklebt. Der Katalysator wird bei 2oo° im Wasserstoffstrom 24. Stunden lang erhitzt; er gestattet, Borneol bei 2oo° in bekannter Weise durch Dehydrierung in Gasform glatt in Kampfer überzuführen.Pieces of pumice stone the size of beans for every 300 parts by volume become 100 parts by weight finely powdered copper magnesium alloy applied and by dusting a diluted water glass solution. The contact mass is 48 hours at 300 ° heated in a stream of hydrogen; it is then usable and already permits at 9o to 10o ° ketones such as acetone can be hydrogenated smoothly, while in general ketones cannot be hydrogenated or can only be hydrogenated with difficulty by ordinary copper contact masses. Example z ,. Finely powdered copper magnesium is placed on pea-sized pieces of pumice stone applied and with a solution of colloidal silica glued in place. The catalyst is heated at 2oo ° in a stream of hydrogen for 24 hours; he allows Borneol at 2oo ° in a known manner by dehydration in gaseous form into camphor convict.
Beispiel 3. ' Fein gepulvertes Kupfermagnesium wird mit Wasser zersetzt und alsdann auf Asbest aufgetragen. Der bei 200° im Wasserstoffstrom getrocknete Kontakt gestattet, bei 23o° und roo Atmosphären Kohlenoxyd glatt zu Methylalkohol zu reduzieren. Beispiel q..Example 3. Finely powdered copper magnesium is decomposed with water and then applied to asbestos. The one dried at 200 ° in a stream of hydrogen Contact allowed, at 23o ° and roo atmospheres, carbon monoxide to methyl alcohol to reduce. Example q ..
Auf bohnengroße Bimssteinstücke wird eine fein gepulverte Legierung von Nickelmagnesium aufgetragen und mit einer verdünnten, Wasserglaslösung festgeklebt. Der Kontakt cvird 72 Stunden bei 300' im Wasserstoffstrom erhitzt. Er ist sehr wirksam und reduziert Phenol bei Gegenwart von überschüssigem Wasserstoff bei 16o bis i 8o' glatt zu Cyclohexanol.A finely powdered alloy of nickel magnesium is applied to bean-sized pieces of pumice stone and glued in place with a dilute, water-glass solution. The contact is heated in a stream of hydrogen at 300 ° for 72 hours. It is very effective and, in the presence of excess hydrogen, smoothly reduces phenol to cyclohexanol at 16o to 18o '.
Analog verfährt man bei Verwendung anderer Legierungen.The same procedure is used when using other alloys.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB109165D DE408811C (en) | 1923-04-04 | 1923-04-04 | Process for the catalytic hydrogenation and dehydrogenation of organic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB109165D DE408811C (en) | 1923-04-04 | 1923-04-04 | Process for the catalytic hydrogenation and dehydrogenation of organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE408811C true DE408811C (en) | 1925-01-24 |
Family
ID=6992392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB109165D Expired DE408811C (en) | 1923-04-04 | 1923-04-04 | Process for the catalytic hydrogenation and dehydrogenation of organic compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE408811C (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2421416A (en) * | 1944-08-30 | 1947-06-03 | Hoffmann La Roche | Catalytic hydrogenation of sugars |
| US2475718A (en) * | 1946-08-12 | 1949-07-12 | Schering Corp | Process for the hydrogenation of naphthalene compounds |
| DE974067C (en) * | 1949-11-06 | 1960-09-01 | Ici Ltd | Process for the production of phenols |
| US2964577A (en) * | 1959-02-05 | 1960-12-13 | Socony Mobil Oil Co Inc | Activation of metals for hydrocarbon dehydrogenation |
| FR2471963A1 (en) * | 1979-12-17 | 1981-06-26 | Unisearch Ltd | PROCESS FOR PRODUCING CATALYST COMPOSITION FOR LOW TEMPERATURE METHANOL SYNTHESIS, CATALYST FOR USE, AND METHOD FOR PRODUCTION OF METHANOL |
-
1923
- 1923-04-04 DE DEB109165D patent/DE408811C/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2421416A (en) * | 1944-08-30 | 1947-06-03 | Hoffmann La Roche | Catalytic hydrogenation of sugars |
| US2475718A (en) * | 1946-08-12 | 1949-07-12 | Schering Corp | Process for the hydrogenation of naphthalene compounds |
| DE974067C (en) * | 1949-11-06 | 1960-09-01 | Ici Ltd | Process for the production of phenols |
| US2964577A (en) * | 1959-02-05 | 1960-12-13 | Socony Mobil Oil Co Inc | Activation of metals for hydrocarbon dehydrogenation |
| FR2471963A1 (en) * | 1979-12-17 | 1981-06-26 | Unisearch Ltd | PROCESS FOR PRODUCING CATALYST COMPOSITION FOR LOW TEMPERATURE METHANOL SYNTHESIS, CATALYST FOR USE, AND METHOD FOR PRODUCTION OF METHANOL |
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