GB894959A - Manufacture of cyclopentadienyl manganese carbonyl compounds - Google Patents
Manufacture of cyclopentadienyl manganese carbonyl compoundsInfo
- Publication number
- GB894959A GB894959A GB23843/58A GB2384358A GB894959A GB 894959 A GB894959 A GB 894959A GB 23843/58 A GB23843/58 A GB 23843/58A GB 2384358 A GB2384358 A GB 2384358A GB 894959 A GB894959 A GB 894959A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclopentadienyl
- compound
- ethers
- ether
- manganese
- 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
- -1 cyclopentadienyl manganese carbonyl compounds Chemical class 0.000 title abstract 8
- 238000004519 manufacturing process Methods 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 6
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 3
- DEIHRWXJCZMTHF-UHFFFAOYSA-N [Mn].[CH]1C=CC=C1 Chemical compound [Mn].[CH]1C=CC=C1 DEIHRWXJCZMTHF-UHFFFAOYSA-N 0.000 abstract 3
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- LCGVCXIFXLGLHG-UHFFFAOYSA-N cyclopenta-1,3-diene;manganese(2+) Chemical compound [Mn+2].C1C=CC=[C-]1.C1C=CC=[C-]1 LCGVCXIFXLGLHG-UHFFFAOYSA-N 0.000 abstract 3
- 150000002170 ethers Chemical class 0.000 abstract 3
- 229930195733 hydrocarbon Natural products 0.000 abstract 3
- 229910021380 Manganese Chloride Inorganic materials 0.000 abstract 2
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 abstract 2
- 238000005810 carbonylation reaction Methods 0.000 abstract 2
- 238000004821 distillation Methods 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 235000002867 manganese chloride Nutrition 0.000 abstract 2
- 239000011565 manganese chloride Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- ANHQLUBMNSSPBV-UHFFFAOYSA-N 4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical group C1=CN=C2NC(=O)COC2=C1 ANHQLUBMNSSPBV-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052748 manganese Inorganic materials 0.000 abstract 1
- 239000011572 manganese Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract 1
- 230000000737 periodic effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000007858 starting material 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
- C07F17/00—Metallocenes
-
- 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
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Cyclopentadienyl manganese tricarbonyl compounds (e.g. methyl cyclopentadienyl manganese tricarbonyl) is added to gasoline to increase the octane rating.ALSO:Cyclopentadienyl manganese tricarbonyl compounds are prepared by reacting a bis(cyclopentadienyl) manganese compound with carbon monoxide, the bis(cyclopentadienyl)manganese compound being prepared by reacting a cyclopentadienyl alkali metal compound with manganous chloride at a temperature above 100 DEG C. in a glycol dialkyl ether solvent which is present in a concentration of not greater than 1 mole per mole of manganous chloride. The carbonylation reaction may be carried out at a temperature from 50 DEG C. to 300 DEG C. using carbon monoxide or a compound which liberates carbon monoxide such as a carbonyl of a metal of Group 1 (b), V (b), VI (b) and VIII of the Periodic Table (Deming). Ethers specified include ethylene glycol-dimethyl, -methylethyl, -diethyl, -methylbutyl and -butyllauryl ethers, and diethylene glycol-dimethyl, ethylmethyl, -diethyl, -ethylbutyl, -dibutyl, and -butyllauryl ethers, and dimethyl and diethyl triethylene glycol ethers. The same solvent as is used in later stages may be used for the preparation of the alkali metal cyclopentadienyl compound to be used as starting material for this bis(cyclopentadienyl)manganese compound. The product of the carbonylation reaction may be isolated by distilling the reaction product mixture to remove the major quantity (above about 90%) of the ether and cyclopentadienyl hydrocarbon are removed leaving a concentrated stream containing the cyclopentadienyl manganese tricarbonyl and only minor (less than 5%) of the ether and/or hydrocarbon, and then subjecting this concentrated stream to a second distillation to form a second vapour stream containing the residual quantities of ether and/or hydrocarbon and a portion of the cyclopentadienyl manganese tricarbonyl. This second vapour stream is recycled back to the first distillation for treatment with fresh impure mixture. The purified stream may then be fractionated.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US894959XA | 1957-09-18 | 1957-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB894959A true GB894959A (en) | 1962-04-26 |
Family
ID=22217964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23843/58A Expired GB894959A (en) | 1957-09-18 | 1958-07-24 | Manufacture of cyclopentadienyl manganese carbonyl compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB894959A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111518138A (en) * | 2020-05-21 | 2020-08-11 | 开封泓盈化工发展有限公司 | Process for separating and extracting methylcyclopentadienyl manganese tricarbonyl by reduced pressure distillation method |
| CN111620895A (en) * | 2020-05-27 | 2020-09-04 | 开封泓盈化工发展有限公司 | Process for producing cyclopentadienyl sodium or methyl cyclopentadienyl sodium |
-
1958
- 1958-07-24 GB GB23843/58A patent/GB894959A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111518138A (en) * | 2020-05-21 | 2020-08-11 | 开封泓盈化工发展有限公司 | Process for separating and extracting methylcyclopentadienyl manganese tricarbonyl by reduced pressure distillation method |
| CN111620895A (en) * | 2020-05-27 | 2020-09-04 | 开封泓盈化工发展有限公司 | Process for producing cyclopentadienyl sodium or methyl cyclopentadienyl sodium |
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