GB784638A - Improvements in or relating to catalysts - Google Patents
Improvements in or relating to catalystsInfo
- Publication number
- GB784638A GB784638A GB27318/54A GB2731854A GB784638A GB 784638 A GB784638 A GB 784638A GB 27318/54 A GB27318/54 A GB 27318/54A GB 2731854 A GB2731854 A GB 2731854A GB 784638 A GB784638 A GB 784638A
- Authority
- GB
- United Kingdom
- Prior art keywords
- copper
- acetylene
- solution
- silicate
- catalyst
- 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
- 239000003054 catalyst Substances 0.000 title abstract 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 10
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 8
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 8
- 239000000463 material Substances 0.000 abstract 6
- ZZBBCSFCMKWYQR-UHFFFAOYSA-N copper;dioxido(oxo)silane Chemical compound [Cu+2].[O-][Si]([O-])=O ZZBBCSFCMKWYQR-UHFFFAOYSA-N 0.000 abstract 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 3
- 150000001879 copper Chemical class 0.000 abstract 3
- 229910052802 copper Inorganic materials 0.000 abstract 3
- 239000010949 copper Substances 0.000 abstract 3
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 abstract 2
- 239000005995 Aluminium silicate Substances 0.000 abstract 2
- NPKGQBIUYHHPOT-UHFFFAOYSA-N [Cu+2].[C-]#[C-] Chemical compound [Cu+2].[C-]#[C-] NPKGQBIUYHHPOT-UHFFFAOYSA-N 0.000 abstract 2
- 229910052910 alkali metal silicate Inorganic materials 0.000 abstract 2
- 235000012211 aluminium silicate Nutrition 0.000 abstract 2
- 229910052797 bismuth Inorganic materials 0.000 abstract 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 abstract 2
- 239000003112 inhibitor Substances 0.000 abstract 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 abstract 2
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 abstract 1
- 239000008098 formaldehyde solution Substances 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 235000019353 potassium silicate Nutrition 0.000 abstract 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 abstract 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2286—Alkynes, e.g. acetylides
-
- 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
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
- B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
- B01J2231/342—Aldol type reactions, i.e. nucleophilic addition of C-H acidic compounds, their R3Si- or metal complex analogues, to aldehydes or ketones
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
- B01J2531/16—Copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A copper acetylide catalyst, for use in the reaction between acetylene and formaldehyde to form 2-butyne-1:4-diol, is prepared by mixing a solution of a copper salt and a solution of an alkali metal silicate to precipitate a copper silicate material containing 15-60 per cent by weight of copper and then treating this material with acetylene. Before treatment with acetylene the copper silicate may be washed and dried and broken into granules, or it may be extruded into rods or pelletted; to increase the copper content, the copper silicate may be impregnated with a solution of a copper salt and ignited. The copper silicate may be suspended in water and treated with acetylene, or it may be suspended in aqueous formaldehyde and treated with acetylene in situ in the reactor at above 60 DEG C. A "cuprene inhibitor" such as bismuth may be included in the catalyst; inert materials, such as kaolin, may also be added. In examples, catalysts are prepared starting from copper nitrate, water glass, and bismuth nitrate.ALSO:2 - Butyne - 1 : 4 - diol is prepared by reaction between acetylene and formaldehyde in the presence of a copper acetylide catalyst prepared by mixing a solution of a copper salt and a solution of an alkali metal silicate to precipitate a copper silicate material containing 15-60 per cent by weight of copper and then treating this material with acetylene (see Group III). The catalyst may also contain a "cuprene inhibitor" such as bismuth and an inert material such as kaolin. In an example, acetylene is admitted at 20 atmospheres pressure and 80 DEG or 100 DEG C. to an autoclave containing the catalyst and a formaldehyde solution. The product contains propargyl alcohol in addition to 2-butyne-1 : 4-diol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB27318/54A GB784638A (en) | 1954-09-21 | 1954-09-21 | Improvements in or relating to catalysts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB27318/54A GB784638A (en) | 1954-09-21 | 1954-09-21 | Improvements in or relating to catalysts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB784638A true GB784638A (en) | 1957-10-16 |
Family
ID=10257634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27318/54A Expired GB784638A (en) | 1954-09-21 | 1954-09-21 | Improvements in or relating to catalysts |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB784638A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3294849A (en) * | 1965-04-15 | 1966-12-27 | Gen Aniline & Film Corp | Production of alkynols and alkynediols using continuous phase silica gel carrier impregnated with 15 to 20 percent copper and 2 to 9 percent bismuth |
| DE1235295B (en) * | 1960-10-25 | 1967-03-02 | Gen Aniline & Film Corp | Process for the production of butynediol mixed with propynol |
| DE1238009B (en) * | 1960-10-25 | 1967-04-06 | Gen Aniline & Film Corp | Process for the production of butynediol mixed with propynol |
| DE1238008B (en) * | 1960-10-25 | 1967-04-06 | Gen Aniline & Film Corp | Process for the production of butynediol mixed with propynol |
| US7282614B2 (en) | 2003-07-24 | 2007-10-16 | Basf Aktiengesellschaft | Method for the production of propargyl alcohol |
-
1954
- 1954-09-21 GB GB27318/54A patent/GB784638A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1235295B (en) * | 1960-10-25 | 1967-03-02 | Gen Aniline & Film Corp | Process for the production of butynediol mixed with propynol |
| DE1238009B (en) * | 1960-10-25 | 1967-04-06 | Gen Aniline & Film Corp | Process for the production of butynediol mixed with propynol |
| DE1238008B (en) * | 1960-10-25 | 1967-04-06 | Gen Aniline & Film Corp | Process for the production of butynediol mixed with propynol |
| US3294849A (en) * | 1965-04-15 | 1966-12-27 | Gen Aniline & Film Corp | Production of alkynols and alkynediols using continuous phase silica gel carrier impregnated with 15 to 20 percent copper and 2 to 9 percent bismuth |
| US7282614B2 (en) | 2003-07-24 | 2007-10-16 | Basf Aktiengesellschaft | Method for the production of propargyl alcohol |
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