GB334193A - Improvements in the manufacture and production of valuable products from gaseous acetylene hydrocarbons or aldehydes - Google Patents
Improvements in the manufacture and production of valuable products from gaseous acetylene hydrocarbons or aldehydesInfo
- Publication number
- GB334193A GB334193A GB601829A GB601829A GB334193A GB 334193 A GB334193 A GB 334193A GB 601829 A GB601829 A GB 601829A GB 601829 A GB601829 A GB 601829A GB 334193 A GB334193 A GB 334193A
- Authority
- GB
- United Kingdom
- Prior art keywords
- over
- hydrogen
- acetylene
- silica gel
- mixture
- 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
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
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
Abstract
334,193. Johnson, J. Y., (I. G. Farbenindustrie Akt.-Ges.). Feb. 23, 1929. Amines; nitriles; heterocyclic nitrogen compounds.-Nitrogenous products are obtained by passing acetylene, or mixtures thereof with its homologues, together with ammonia and/or amines, and if desired with steam, over heated condensation catalysts, and then conducting the products, without isolation, together with hydrogen over metallic hydrogenating catalysts. Instead of acetylene, aliphtic aldehydes may be employed, or mixtures thereof with the acetylene hydrocarbons. The condensation and hydrogenation may be effected simultaneously by mixing the two catalysts and introducing the hydrogen at the beginning of the operation. The condensation catalysts comprise compounds of aluminium or of metals, except arsenic, having a specific gravity above 4.4 and belonging to the second to the seventh periodic groups; hydrogenating catalysts mentioned are metals of the iron group, copper and platinum. Industrial gas mixtures containing hydrogen and acetylenic hydrocarbons may be employed, e.g. coke-oven gas or gas mixtures obtained by passing coke-oven gas or a mixture of methane and hydrogen through a high tension electric arc. The condensation is effected at a temperature of 250‹- 500‹ C., whilst the hydrogenation preferably takes place at a lower temperature, e.g. 150- 250‹ C. When producing hydrogenated heterocyclic bases from mixtures of acetylene with ammonia and/or an amine in the presence of steam, the gas mixture is preferably passed over the catalyst at a speed of at least 10 litres of the hydrocarbon per hour per litre of the catalyst. According to the examples, (1) acetylene, ammonia and hydrogen are passed at 350‹ C. over a mixture of equal parts by weight of zinc oxide and thorium oxide precipitated on silica gel and then over finely-divided nickel on silica gel at 150‹ C. ; the condensate consists mainly of piperidine and monoethylamine; the addition of steam increases the proportion of the piperidine; (2) ammonia and acetaldehyde vapour mixed with hydrogen are led at 350‹ C. over zinc oxide mounted on silica gel incorporated with thorium oxide and then at 150‹ C. over nickel on silica gel; the product mainly comprises piperidine and a small quantity of amines; (3) ammonia, acetylene, hydrogen and the vapours of acetaldehyde and ethylamine are passed at 400‹ C. over a mixture of zinc oxide, thorium oxide and metallic cadmium on silica gel and then at 120‹ C. over nickel on silica gel; the condensate consists chiefly of ethylamine and piperidines, together with small quantities of acetonitrile, propionitrile, pyridine bases and pyrrol derivatives; (4) aniline vapour, acetylene and hydrogen are conducted at 300‹ C. over a mixture of chromic oxide, aluminium oxide and zinc oxide on silica gel and then at 200‹ C. over nickel on silica gel; the condensate mainly comprises hydrogenated quinolines, chiefly tetrahydroquinoline; (5) acety. lene, hydrogen, methane and nitrogen (obtained by treating a mixture of methane and hydrogen in the electric arc and containing a small amount of allylene and diacetylene) is mixed with ammonia and passed at 380‹ C. over a mixture of zinc and chromic oxides and then at 150‹ C. over activated nickel; on cooling, a product consisting of primary ethylamine and acetonitrile is obtained. Specifications 109,983, 265,960, 321,177 and 332,623 are referred to. The Provisional Specification describes the use of any acetylene hydrocarbon.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB601829A GB334193A (en) | 1929-02-23 | 1929-02-23 | Improvements in the manufacture and production of valuable products from gaseous acetylene hydrocarbons or aldehydes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB601829A GB334193A (en) | 1929-02-23 | 1929-02-23 | Improvements in the manufacture and production of valuable products from gaseous acetylene hydrocarbons or aldehydes |
Publications (1)
Publication Number | Publication Date |
---|---|
GB334193A true GB334193A (en) | 1930-08-25 |
Family
ID=9806931
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB601829A Expired GB334193A (en) | 1929-02-23 | 1929-02-23 | Improvements in the manufacture and production of valuable products from gaseous acetylene hydrocarbons or aldehydes |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB334193A (en) |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2443420A (en) * | 1946-02-21 | 1948-06-15 | Du Pont | Synthesis of nitriles |
US2452187A (en) * | 1946-02-21 | 1948-10-26 | Du Pont | Synthesis of nitriles |
US2468363A (en) * | 1942-02-19 | 1949-04-26 | Alais & Froges & Camarque Cie | Methods for preparing acetonitrile |
US2523580A (en) * | 1944-12-11 | 1950-09-26 | Phillips Petroleum Co | Production of alkyl pyridines |
US2525818A (en) * | 1946-06-24 | 1950-10-17 | Phillips Petroleum Co | Production of nitriles |
US2605264A (en) * | 1944-02-25 | 1952-07-29 | Shell Dev | Process for the production of pyridines |
US2762813A (en) * | 1952-04-03 | 1956-09-11 | Distillers Co Yeast Ltd | Process of producing piperidine compounds |
US2995558A (en) * | 1957-11-05 | 1961-08-08 | Phillips Petroleum Co | Production of pyridine homologs |
WO2014031226A1 (en) * | 2012-08-21 | 2014-02-27 | Uop Llc | The production of nitrogen compounds from a methane conversion process |
US8927769B2 (en) | 2012-08-21 | 2015-01-06 | Uop Llc | Production of acrylic acid from a methane conversion process |
US8933275B2 (en) | 2012-08-21 | 2015-01-13 | Uop Llc | Production of oxygenates from a methane conversion process |
US8937186B2 (en) | 2012-08-21 | 2015-01-20 | Uop Llc | Acids removal and methane conversion process using a supersonic flow reactor |
US9205398B2 (en) | 2012-08-21 | 2015-12-08 | Uop Llc | Production of butanediol from a methane conversion process |
US9308513B2 (en) | 2012-08-21 | 2016-04-12 | Uop Llc | Production of vinyl chloride from a methane conversion process |
US9327265B2 (en) | 2012-08-21 | 2016-05-03 | Uop Llc | Production of aromatics from a methane conversion process |
US9370757B2 (en) | 2012-08-21 | 2016-06-21 | Uop Llc | Pyrolytic reactor |
US9434663B2 (en) | 2012-08-21 | 2016-09-06 | Uop Llc | Glycols removal and methane conversion process using a supersonic flow reactor |
US9656229B2 (en) | 2012-08-21 | 2017-05-23 | Uop Llc | Methane conversion apparatus and process using a supersonic flow reactor |
US9689615B2 (en) | 2012-08-21 | 2017-06-27 | Uop Llc | Steady state high temperature reactor |
US9707530B2 (en) | 2012-08-21 | 2017-07-18 | Uop Llc | Methane conversion apparatus and process using a supersonic flow reactor |
-
1929
- 1929-02-23 GB GB601829A patent/GB334193A/en not_active Expired
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2468363A (en) * | 1942-02-19 | 1949-04-26 | Alais & Froges & Camarque Cie | Methods for preparing acetonitrile |
US2605264A (en) * | 1944-02-25 | 1952-07-29 | Shell Dev | Process for the production of pyridines |
US2523580A (en) * | 1944-12-11 | 1950-09-26 | Phillips Petroleum Co | Production of alkyl pyridines |
US2443420A (en) * | 1946-02-21 | 1948-06-15 | Du Pont | Synthesis of nitriles |
US2452187A (en) * | 1946-02-21 | 1948-10-26 | Du Pont | Synthesis of nitriles |
US2525818A (en) * | 1946-06-24 | 1950-10-17 | Phillips Petroleum Co | Production of nitriles |
US2762813A (en) * | 1952-04-03 | 1956-09-11 | Distillers Co Yeast Ltd | Process of producing piperidine compounds |
US2995558A (en) * | 1957-11-05 | 1961-08-08 | Phillips Petroleum Co | Production of pyridine homologs |
US8933275B2 (en) | 2012-08-21 | 2015-01-13 | Uop Llc | Production of oxygenates from a methane conversion process |
US8927769B2 (en) | 2012-08-21 | 2015-01-06 | Uop Llc | Production of acrylic acid from a methane conversion process |
WO2014031226A1 (en) * | 2012-08-21 | 2014-02-27 | Uop Llc | The production of nitrogen compounds from a methane conversion process |
US8937186B2 (en) | 2012-08-21 | 2015-01-20 | Uop Llc | Acids removal and methane conversion process using a supersonic flow reactor |
US9023255B2 (en) | 2012-08-21 | 2015-05-05 | Uop Llc | Production of nitrogen compounds from a methane conversion process |
US9205398B2 (en) | 2012-08-21 | 2015-12-08 | Uop Llc | Production of butanediol from a methane conversion process |
US9308513B2 (en) | 2012-08-21 | 2016-04-12 | Uop Llc | Production of vinyl chloride from a methane conversion process |
US9327265B2 (en) | 2012-08-21 | 2016-05-03 | Uop Llc | Production of aromatics from a methane conversion process |
US9370757B2 (en) | 2012-08-21 | 2016-06-21 | Uop Llc | Pyrolytic reactor |
US9434663B2 (en) | 2012-08-21 | 2016-09-06 | Uop Llc | Glycols removal and methane conversion process using a supersonic flow reactor |
US9656229B2 (en) | 2012-08-21 | 2017-05-23 | Uop Llc | Methane conversion apparatus and process using a supersonic flow reactor |
US9689615B2 (en) | 2012-08-21 | 2017-06-27 | Uop Llc | Steady state high temperature reactor |
US9707530B2 (en) | 2012-08-21 | 2017-07-18 | Uop Llc | Methane conversion apparatus and process using a supersonic flow reactor |
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