CS253124B1 - Method of 1,2,3,4-tetrahydro-1-oxonaphtalene production - Google Patents
Method of 1,2,3,4-tetrahydro-1-oxonaphtalene production Download PDFInfo
- Publication number
- CS253124B1 CS253124B1 CS858252A CS825285A CS253124B1 CS 253124 B1 CS253124 B1 CS 253124B1 CS 858252 A CS858252 A CS 858252A CS 825285 A CS825285 A CS 825285A CS 253124 B1 CS253124 B1 CS 253124B1
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- CS
- Czechoslovakia
- Prior art keywords
- tetrahydro
- tetrahydronaphthalene
- oxonaphthalene
- solution
- oxidation
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000003647 oxidation Effects 0.000 claims abstract description 8
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 8
- 230000005855 radiation Effects 0.000 claims abstract description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 claims description 2
- SQZZGEUJERGRIN-UHFFFAOYSA-N manganese;pentane-2,4-dione Chemical compound [Mn].CC(=O)CC(C)=O SQZZGEUJERGRIN-UHFFFAOYSA-N 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JAAJQSRLGAYGKZ-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-ol Chemical compound C1=CC=C2C(O)CCCC2=C1 JAAJQSRLGAYGKZ-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Způsob výroby 1,2,3,4-tetrahydro-l-oxonaftalenu, založený na fotochemické oxidaci 1.2.3.4-tetrahydronaftalenu v organickém rozpouštědle účinkem záření o vlnové délce 254 až 436 rai. Vysoké selektivity vzniku 1.2.3.4-tetrahydro-l-oxonaftalenu se dosáhne provedením fotochemické oxidace za přítomnosti 1 až 5 % hmot. 2,4-pentandionátu železitého a/nebo manganitého, vztaženo na výchozí množství 1,2,3,4-tetrahydronaftalenu. Řešeni je použitelné při výrobě meziproduktu pro chemický průmysl.Process for preparing 1,2,3,4-tetrahydro-1-oxonaphthalene, based on photochemical oxidation 1,2,3,4-tetrahydronaphthalene in organic with the effect of radiation at wavelength 254 to 436 rai. High selectivity 1,2,3,4-tetrahydro-1-oxonaphthalene is obtained performing photochemical oxidation after % of the presence of 1 to 5 wt. 2,4-pentanedioate of ferric and / or manganese, based on to a starting amount of 1,2,3,4-tetrahydronaphthalene. The solution is applicable in production intermediate for the chemical industry.
Description
Vynález se týká způsobu výroby 1,2,3,4-tetrahydro-l-oxonaftalenu oxidací 1,2,3,4-tetrahydronaftalenu .The invention relates to a process for the preparation of 1,2,3,4-tetrahydro-1-oxonaphthalene by oxidation of 1,2,3,4-tetrahydronaphthalene.
1,2,3,4-tetrahydro-l-oxonaftalen je výchozí surovinou pro výrobu 1-naftolu. Při přípravě 1,2,3,4-tetrahydro-l-oxonaftalenu termickou oxidací 1,2,3,4-tetrahydronaftalenu dikyslíkem vzniká směs 1,2,3,4-tetrahydro-l-oxonaftalenu a 1,2,3,4-tetrahydro-l-naftolu (Mizukami F., Imanura J.: Bull. Chem. Soc. Japan 51 (5), 1 404 (1978)). Dělení této směsi rektifikací je značně obtížné v důsledku blízkých teplot varu obou produktů.1,2,3,4-tetrahydro-1-oxonaphthalene is the starting material for the production of 1-naphthol. In the preparation of 1,2,3,4-tetrahydro-1-oxonaphthalene by thermal oxidation of 1,2,3,4-tetrahydronaphthalene with oxygen, a mixture of 1,2,3,4-tetrahydro-1-oxonaphthalene and 1,2,3,4 Tetrahydro-1-naphthol (Mizukami F., Imanura J .: Bull. Chem. Soc. Japan 51 (5), 1440 (1978)). The separation of this mixture by rectification is quite difficult due to the near boiling points of both products.
Nevýhody uvedeného postupu do značné míry odstraňuje předložený vynález, jehož předmětem je způsob výroby 1,2,3,4-tetrahydro-l-oxonaftalenu oxidací 1,2,3,4-tetrahydronaftalenu.The disadvantages of this process are largely overcome by the present invention, which is directed to a process for the preparation of 1,2,3,4-tetrahydro-1-oxonaphthalene by oxidation of 1,2,3,4-tetrahydronaphthalene.
Podstata vynálezu spočívá v pracovním postupu, při němž se roztok 1,2,3,4-tetrahydronaftalenu v organickém rozpouštědle vystaví záření o vlnové délce 254-436 nm. Organickými rozpouštědly zvláště vhodnými pro daný účel jsou ethylmethylketon, 1,1,2-trichlor-l,2,2-trifluorethan a acetonítril. Vysoké selektivity vzniku 1,2,3,4-tetrahydro-l-oxonaftalenu se dosáhne, jestliže se fotochemická oxidace provede za přítomnosti 1 až 5 % hmot. 2,4-pentandionátu železitého a/nebo manganitého, vztaženo na výchozí množství 1,2,3,4-tetrahydronaftalenu.The present invention is based on a process in which a solution of 1,2,3,4-tetrahydronaphthalene in an organic solvent is exposed to radiation at a wavelength of 254-436 nm. Particularly suitable organic solvents are ethylmethylketone, 1,1,2-trichloro-1,2,2-trifluoroethane and acetonitrile. High selectivity of 1,2,3,4-tetrahydro-1-oxonaphthalene formation is achieved when the photochemical oxidation is carried out in the presence of 1 to 5 wt. Ferric and / or manganese-2,4-pentanedione, based on the starting amount of 1,2,3,4-tetrahydronaphthalene.
Výhodou uvedeného řešení je vysoká selektivita vzniku 1,2,3,4-tetrahydro-l-oxonaftalenu a malá energetická náročnost.The advantage of said solution is high selectivity of 1,2,3,4-tetrahydro-1-oxonaphthalene formation and low energy consumption.
Způsob výroby podle vynálezu je dále ilustrován příklady jeho praktického provedení.The production method according to the invention is further illustrated by the following examples.
Příklad 1Example 1
Do fotochemického reaktoru bylo předloženo 5,7 g 1,2,3,4-tetrahydronaftalenu rozpuštěného ve 100 ml ethylmethylketonu. K roztoku bylo přidáno 0,17 g 2,4-pentandionátu železitého. Roztok byl při 25 °C probubláván dikyslíkem a ozařován středotlakou rtutovou výbojkou RVL X 125 W (vlnová délka v rozsahu 254-436 nm). Po 4 h bylo oddestilováno rozpuštědlo a destilační zbytek byl rektifikován. Bylo získáno 1,1 g 1,2,3,4-tetrahydro-l-oxonaftalenu při 20» konverzi.5.7 g of 1,2,3,4-tetrahydronaphthalene dissolved in 100 ml of ethyl methyl ketone was charged to the photochemical reactor. 0.17 g of ferric 2,4-pentanedionate was added to the solution. Oxygen was bubbled through the solution at 25 ° C and irradiated with a RVL X 125 W medium pressure mercury lamp (wavelength range 254-436 nm). After 4 h, the solvent was distilled off and the distillation residue was rectified. 1.1 g of 1,2,3,4-tetrahydro-1-oxonaphthalene were obtained at 20? Conversion.
Příklad 2Example 2
Do fotochemického reaktoru bylo předloženo 6,2 g 1,2,3,4-tetrahydronaftalenu rozpuštěného va 100 ml ethylmethylketonu. K roztoku bylo přidáno 0,17 g 2,4-pentandionátu manganitého. Roztok byl probubláván dikyslíkem při 25 °C a ozařován středotlakou rtutovou výbojkou RVL X 125 W. Po 4 bylo oddestilováno rozpouštědlo a destilaění zbytek byl rektifikován. Bylo získáno 1,1 g 1,2,3,4-tetrahydro-l-oxonaftalenu při 32 % konverzi.6.2 g of 1,2,3,4-tetrahydronaphthalene dissolved in 100 ml of ethyl methyl ketone were charged to the photochemical reactor. 0.17 g of manganese 2,4-pentanedionate was added to the solution. The solution was bubbled with oxygen at 25 ° C and irradiated with a medium pressure mercury vapor lamp RVL X 125 W. After 4, the solvent was distilled off and the distillation residue was rectified. 1.1 g of 1,2,3,4-tetrahydro-1-oxonaphthalene were obtained at 32% conversion.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS858252A CS253124B1 (en) | 1985-11-16 | 1985-11-16 | Method of 1,2,3,4-tetrahydro-1-oxonaphtalene production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS858252A CS253124B1 (en) | 1985-11-16 | 1985-11-16 | Method of 1,2,3,4-tetrahydro-1-oxonaphtalene production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS825285A1 CS825285A1 (en) | 1987-03-12 |
| CS253124B1 true CS253124B1 (en) | 1987-10-15 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS858252A CS253124B1 (en) | 1985-11-16 | 1985-11-16 | Method of 1,2,3,4-tetrahydro-1-oxonaphtalene production |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS253124B1 (en) |
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1985
- 1985-11-16 CS CS858252A patent/CS253124B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS825285A1 (en) | 1987-03-12 |
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