GB853111A - Process for the manufacture of agents suitable for making organic acetylene compounds - Google Patents
Process for the manufacture of agents suitable for making organic acetylene compoundsInfo
- Publication number
- GB853111A GB853111A GB21029/59A GB2102959A GB853111A GB 853111 A GB853111 A GB 853111A GB 21029/59 A GB21029/59 A GB 21029/59A GB 2102959 A GB2102959 A GB 2102959A GB 853111 A GB853111 A GB 853111A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bromide
- solvent
- ammonia
- manufacture
- reacted
- 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
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 5
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 abstract 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 abstract 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 239000012345 acetylating agent Substances 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 150000001247 metal acetylides Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/325—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a metal atom
- C07C1/328—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a metal atom the hetero-atom being an alkali metal atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/22—Aliphatic unsaturated hydrocarbons containing carbon-to-carbon triple bonds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
An acetylating agent is prepared by dissolving an alkali metal in liquid ammonia, reacting with acetylene and replacing at least part of the ammonia with an inert, anydrous, organic solvent in which the monoalkali metal acetylide is at best partially soluble. The solvent is preferably dimethylformamide or other dialkylformamide. The agent may be reacted with aldehydes or ketones or more particularly alkyl halides. Halides containing less than 6 carbon atoms can be added with the solvent. After any remaining ammonia is expelled before or after adding the halide the mixture is stirred for 1/2 to 3 hours at 30-70 DEG C. In the examples sodium acetylide is reacted, in the presence of dimethylformamide with (1) n-octyl bromide to form n-decine-1, (2) n-decyl bromide to form a-dodecine-1, (3) n-dodecyl bromide to form n-tetradecine-1, (4) n-octedecyl bromide to form n-eicosine-1 and the preparation of n-pentadecine-1, n-hexadecine-1 and n-octadecine-1 is also referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH853111X | 1958-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB853111A true GB853111A (en) | 1960-11-02 |
Family
ID=4542452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21029/59A Expired GB853111A (en) | 1958-06-18 | 1959-06-18 | Process for the manufacture of agents suitable for making organic acetylene compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB853111A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3441621A (en) * | 1966-12-30 | 1969-04-29 | Air Reduction | Process for the preparation of alkali metal acetylides |
-
1959
- 1959-06-18 GB GB21029/59A patent/GB853111A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3441621A (en) * | 1966-12-30 | 1969-04-29 | Air Reduction | Process for the preparation of alkali metal acetylides |
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