NO119791B - - Google Patents
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- NO119791B NO119791B NO19868A NO19868A NO119791B NO 119791 B NO119791 B NO 119791B NO 19868 A NO19868 A NO 19868A NO 19868 A NO19868 A NO 19868A NO 119791 B NO119791 B NO 119791B
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- Norway
- Prior art keywords
- hydrogen peroxide
- isoamyl
- mixture
- hydrogenated
- anthraquinone
- Prior art date
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 22
- 238000005984 hydrogenation reaction Methods 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- OFFBXWKJONNRTH-UHFFFAOYSA-N 2-(3-methylbutyl)-1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound C(CC(C)C)C1CC=2C(C3=CC=CC=C3C(C2CC1)=O)=O OFFBXWKJONNRTH-UHFFFAOYSA-N 0.000 claims description 8
- CQYMOXYSVSNADQ-UHFFFAOYSA-N 2-(3-methylbutyl)anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(CCC(C)C)=CC=C3C(=O)C2=C1 CQYMOXYSVSNADQ-UHFFFAOYSA-N 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000012224 working solution Substances 0.000 description 18
- 230000003647 oxidation Effects 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 238000000605 extraction Methods 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- AXHVNJGQOJFMHT-UHFFFAOYSA-N 1-tert-butyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C(C)(C)C AXHVNJGQOJFMHT-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- GSSDZVRLQDXOPL-UHFFFAOYSA-N 2,2-dimethylhexan-1-ol Chemical compound CCCCC(C)(C)CO GSSDZVRLQDXOPL-UHFFFAOYSA-N 0.000 description 4
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical class CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 4
- QVSQHZWVVIRGDW-UHFFFAOYSA-N C(CC(C)C)C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O Chemical class C(CC(C)C)C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O QVSQHZWVVIRGDW-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000007669 thermal treatment Methods 0.000 description 2
- -1 alicyclic alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Fremgangsmåte til fremstilling av hydrogenperoksyd. Process for the production of hydrogen peroxide.
Foreliggende oppfinnelse vedrorer en fremgangsmåte til The present invention relates to another method
fremstilling av hydrogenperoksyd. production of hydrogen peroxide.
Ved en kjent fremgangsmåte til fremstilling av hydrogenperoksyd hydrogeneres en blanding av 2-isoamyl-antrakinon og tetra-hydro-2-isoamyl-antrakinon i et organisk opplosningsmiddel i nærvær av en nikkelkatalysator, slik som beskrevet i fransk patent nr. 1 410 2'/6, fulgt av oksydasjon av hydrogeneringsproduktene og isoler-ing av det frembragte hydrogenperoksyd i reaksjonen. In a known method for the production of hydrogen peroxide, a mixture of 2-isoamyl-anthraquinone and tetra-hydro-2-isoamyl-anthraquinone is hydrogenated in an organic solvent in the presence of a nickel catalyst, as described in French patent no. 1 410 2'/ 6, followed by oxidation of the hydrogenation products and isolation of the hydrogen peroxide produced in the reaction.
Ulempen med denne metode ligger i den lille mengde hydrogenperoksyd som oppnåes per volumdel av den oksyderte opprinnelige opp-løsning (13-17 g/l) når tilgjengelige organiske opplosningsmidler (alkylbenzener, alifatiske og alicykliske alkoholer osv.) anvendes i The disadvantage of this method lies in the small amount of hydrogen peroxide that is obtained per volume part of the oxidized original solution (13-17 g/l) when available organic solvents (alkylbenzenes, aliphatic and alicyclic alcohols, etc.) are used in
prosessen. the process.
For å oke utbyttet av hydrogenperoksyd (27 g/l) i den kjente metode, anvendes den vanskelig oppnåelige forbindelse 2,o,8-trimetyl-4-nonanon, som opplosningsmiddel. In order to increase the yield of hydrogen peroxide (27 g/l) in the known method, the difficult-to-obtain compound 2,o,8-trimethyl-4-nonanone is used as solvent.
I nevnte metode overskrider ikke hydrogeneringsgraden av karbonylgriippene i isoamylantrakinonene, som anvendes som utgangs-materiale, ^ 0%. In the aforementioned method, the degree of hydrogenation of the carbonyl groups in the isoamyl anthraquinones, which are used as starting material, does not exceed ^ 0%.
Formålet med foreliggende oppfinnelse er å eliminere de ovenfor omtalte ulemper. The purpose of the present invention is to eliminate the disadvantages mentioned above.
Spesielt er formålet med oppfinnelsen å tilveiebringe en fremgangsmåte til fremstilling av hydrogenperoksyd hvor utbyttet av hydrogenperoksyd blir betraktelig hoyere under anvendelse av de van-lige benyttede tilgjengelige opplosningsmidler for denne prosess. In particular, the purpose of the invention is to provide a method for the production of hydrogen peroxide in which the yield of hydrogen peroxide is considerably higher using the commonly used solvents available for this process.
Ifolge foreliggende oppfinnelse er det således tilveiebragt en fremgangsmåte til fremstilling av hydrogenperoksyd hvor en blanding sv 2-isoamylantrakinon og tetrahydro-2-isoamylantrakinon i et organisk opplosningsmiddel hydrogeneres i nærvær av en nikkelkatalysator som for bruk behandles termisk i et alkalisk medium ved en temperatur på fra 120° til l60°C, hvoretter hydrogeneringsproduktene oksyderes og det dannede hydrogenperoksyd separeres, kjennetegnet ved at tetrahydro-2-isoamylantrakinoninnholdet i blandingen som hydrogeneres er mellom l60 og 300 g/l. According to the present invention, a method for the production of hydrogen peroxide has thus been provided in which a mixture of sv 2-isoamyl anthraquinone and tetrahydro-2-isoamyl anthraquinone in an organic solvent is hydrogenated in the presence of a nickel catalyst which for use is thermally treated in an alkaline medium at a temperature of from 120° to 160°C, after which the hydrogenation products are oxidized and the hydrogen peroxide formed is separated, characterized in that the tetrahydro-2-isoamylanthraquinone content in the mixture being hydrogenated is between 160 and 300 g/l.
Foreliggende fremgangsmåte utfores på folgende måte. The present method is carried out in the following way.
F,n blanding av 2-isoamylantrakinon og tetrahydro-2-isoamyl-antrakinon opplost i et organisk opplosningsmiddel, hydrogeneres i nærvær av en nikkelkatalysator, hvoretter de dannede antrakinoner oksyderes og det frembragte hydrogenperoksyd isoleres ved hjelp av ekstraksjon. A mixture of 2-isoamyl anthraquinone and tetrahydro-2-isoamyl anthraquinone dissolved in an organic solvent is hydrogenated in the presence of a nickel catalyst, after which the anthraquinones formed are oxidized and the hydrogen peroxide produced is isolated by means of extraction.
Hydrogeneringsprosessen anvender en nikkelkatalysator som for bruk er utsatt for en termisk behandling i et alkalisk medium ved 120°-l60°C. Kn slik behandling gir nikkelkatalysatoren selektive egenskaper,s hvilket muliggjor at den kan anvendes i reaksjonsbland-ingen bestående av isoamylantrakinoner med et hoyere innhold av tetrahydro-2-isoamylantrakinon. The hydrogenation process uses a nickel catalyst which before use is subjected to a thermal treatment in an alkaline medium at 120°-160°C. Such treatment gives the nickel catalyst selective properties, which enables it to be used in the reaction mixture consisting of isoamyl anthraquinones with a higher content of tetrahydro-2-isoamyl anthraquinone.
Ved foreliggende fremgangsmåte når hydrogeneringsgraden av karbonylgruppene i isoamylantrakinonene 55~60$, idet utbyttet av hydrogenperoksyd er 36-44 g/l av arbeidsopplosningen. In the present method, the degree of hydrogenation of the carbonyl groups in the isoamyl anthraquinones reaches 55~60$, the yield of hydrogen peroxide being 36-44 g/l of the working solution.
For bedre forståelse av oppfinnelsen gis folgende illustrer-ende eksempler. For a better understanding of the invention, the following illustrative examples are given.
Eksempel 1 Example 1
2-isoamylantrakinon og tetrahydro-2-isoamylantrakinon i mengder på 100 g/l og 250 r/l respektivt, ble opplost i en blanding av tert-butyltoluen og hydrogenert terpineol i et volumforhold på 1:1. Hen resulterende blanding ble hydrogenert ved 60°-65°C i nærvær av en nikkelkatalysator, som for bruk var utsatt for en termisk behandling i et alkalisk medium ved 120°-lb0°C. Hydrogeneringen ble utfort inntil 20.46 1 hydrogen per liter av arbeidsopplosningen var forbrukt. 2-isoamyl anthraquinone and tetrahydro-2-isoamyl anthraquinone in amounts of 100 g/l and 250 r/l respectively were dissolved in a mixture of tert-butyltoluene and hydrogenated terpineol in a volume ratio of 1:1. The resulting mixture was hydrogenated at 60°-65°C in the presence of a nickel catalyst, which for use was subjected to a thermal treatment in an alkaline medium at 120°-lb0°C. The hydrogenation was continued until 20.46 1 hydrogen per liter of the working solution had been consumed.
K-tter hydrogenering ble arbeidsopplosningen, etter sepa-rering av katalysatoren, utsatt for oksydasjon med oksygen eller en oksygenholdig gass. Ved slutten av reaksjonen ble det dannede hydrogenperoksyd ekstrahert med f.eks. vann. Konsentrasjonen av hydrogenperoksyd i ekstraktet var 3L07 g/l av arbeidsopplosningen. After hydrogenation, the working solution, after separation of the catalyst, was subjected to oxidation with oxygen or an oxygen-containing gas. At the end of the reaction, the hydrogen peroxide formed was extracted with e.g. water. The concentration of hydrogen peroxide in the extract was 3L07 g/l of the working solution.
Eksempel 2 Example 2
I en blanding av tert-butyltoluen og hydrogenert terpineol i et volumforhold på 1:1, ble 2-isoamylantrakinon (200 g/l) og tetra-hydro-2-isoamylantrakinon (250 g/l) opplost og den resulterende blanding ble hydrogenert inntil 22.92 1 hydrogen var forbrukt per liter av arbeidsopplosningen. In a mixture of tert-butyltoluene and hydrogenated terpineol in a 1:1 volume ratio, 2-isoamylthraquinone (200 g/l) and tetrahydro-2-isoamylthraquinone (250 g/l) were dissolved and the resulting mixture was hydrogenated until 22.92 1 hydrogen was consumed per liter of the working solution.
Hydrogenering, oksydasjon og ekstraksjon ble utfort på samme måte som beskrevet i eksempel 1. Hydrogenation, oxidation and extraction were carried out in the same way as described in example 1.
Konsentrasjonen av hydrogenperoksyd i ekstraktet var 34«8 g/l av arbeidsopplosningen. The concentration of hydrogen peroxide in the extract was 34-8 g/l of the working solution.
Eksempel 3 Example 3
I en blanding av benzen og hydrogenert terpineol i et volumforhold på 1:1 ble 2-isoamylantrakinon i en mengde på 250 g/l og tetrahydro-2-isoamylantrakinon i en mengde på 200 g/l, opplost, ^en resulterende blanding ble hydrogenert inntil 24.9 1 hydrogen var forbrukt per liter av arbeidsopplosningen. In a mixture of benzene and hydrogenated terpineol in a volume ratio of 1:1, 2-isoamyl anthraquinone in an amount of 250 g/l and tetrahydro-2-isoamyl anthraquinone in an amount of 200 g/l were dissolved, ^a resulting mixture was hydrogenated up to 24.9 1 hydrogen was consumed per liter of the working solution.
Hydrogenering, oksydasjon og ekstraksjon ble utfort på samme måte som beskrevet i eksempel 1. Hydrogenation, oxidation and extraction were carried out in the same way as described in example 1.
Konsentrasjonen av hydrogenperoksyd i ekstraktet var 37«9 g/l av arbeidsopplosningen. The concentration of hydrogen peroxide in the extract was 37-9 g/l of the working solution.
Eksempel 4 Example 4
2-isoamylantrakinon (250 g/l) og tetrahydro-2-isoamylantrakinon (250 g/l) ble opplost i en blanding av tert-butyltoluen og oktanol-2- i et volumforhold på 1:1. nen resulterende blanding ble hydrogenert inntil 25.4 1 hydrogen var forbrukt per liter av arbeidsopplosningen. 2-isoamylthraquinone (250 g/l) and tetrahydro-2-isoamylthraquinone (250 g/l) were dissolved in a mixture of tert-butyltoluene and octanol-2- in a volume ratio of 1:1. The resulting mixture was hydrogenated until 25.4 liters of hydrogen were consumed per liter of the working solution.
Hydrogenering, oksydasjon og ekstraksjon ble utfort på samme måte som beskrevet i eksempel 1. Hydrogenation, oxidation and extraction were carried out in the same way as described in example 1.
Konsentrasjonen av hydrogenperoksyd i ekstraktet var 38.6 g/l av arbeidsopplosningen. The concentration of hydrogen peroxide in the extract was 38.6 g/l of the working solution.
Eksempel 5 Example 5
2-isoamylantrakinon (250 g/l) og tetrahydro-2-isoamylantrakinon (300 g/l) ble opplost i en blanding av tert-butyltoluen og oktanol-2 i et volumforhold på 1:1. rien resulterende blanding ble hydrogenert inntil 26.25 1 hydrogen var forbrukt per liter av arbeidsopplosningen . 2-isoamylthraquinone (250 g/l) and tetrahydro-2-isoamylthraquinone (300 g/l) were dissolved in a mixture of tert-butyltoluene and octanol-2 in a volume ratio of 1:1. The resulting mixture was hydrogenated until 26.25 liters of hydrogen were consumed per liter of the working solution.
Hydrogenering, oksydasjon og ekstraksjon ble utfort på samme måte som beskrevet i eksempel 1. Hydrogenation, oxidation and extraction were carried out in the same way as described in example 1.
Konsentrasjonen av hydrogenperoksyd i ekstraktet var 39-9 g/l av arbeidsopplosningen. The concentration of hydrogen peroxide in the extract was 39-9 g/l of the working solution.
Eksempel 6 Example 6
2-isoamylantrakinon (250 g/l) og tetrahydro-2-isoamylantrakinon (250 g/l) ble opplost i en blanding av benzen og hydrogenert terpineol i et volumforhold på 1:1. r>en resulterende blanding ble hydrogenert inntil 26.6 1 hydrogen var forbrukt per liter av arbeidsopplosningen. 2-isoamylthraquinone (250 g/l) and tetrahydro-2-isoamylthraquinone (250 g/l) were dissolved in a mixture of benzene and hydrogenated terpineol in a volume ratio of 1:1. The resulting mixture was hydrogenated until 26.6 liters of hydrogen were consumed per liter of the working solution.
Hydrogenering, oksydasjon og ekstraksjon ble utfort på samme måte som beskrevet i eksempel 1. Hydrogenation, oxidation and extraction were carried out in the same way as described in example 1.
Konsentrasjonen av hydrogenperoksyd i ekstraktet var 40-4 g/l av arbeidsopplosningen. The concentration of hydrogen peroxide in the extract was 40-4 g/l of the working solution.
Eksempel Example
2-isoamylantrakinon (350 g/l) og tetrahydro-2-isoamylantrakinon (200 g/l) ble opplost i en blanding av tert-butyltoluen og oktanol-2 i et volumforhold på 1:1. Hen resulterende blanding ble hydrogenert inntil 27-11 1 hydrogen var forbrukt per liter av arbeidsopplosningen . 2-isoamyl anthraquinone (350 g/l) and tetrahydro-2-isoamyl anthraquinone (200 g/l) were dissolved in a mixture of tert-butyltoluene and octanol-2 in a volume ratio of 1:1. The resulting mixture was hydrogenated until 27-11 1 hydrogen was consumed per liter of the working solution.
Hydrogenering, oksydasjon og ekstraksjon ble utfort på samme måte som beskrevet i eksempel 1. Hydrogenation, oxidation and extraction were carried out in the same way as described in example 1.
Konsentrasjonen av hydrogenperoksyd i ekstraktet var 42.4 g/l av arbeidsopplosningen. The concentration of hydrogen peroxide in the extract was 42.4 g/l of the working solution.
Eksempel 8 Example 8
2-isoamylantrakinon (350 g/l) og tetrahydro-2-isoamylantrakinon (220 g/l) ble opplost i en blanding av tert-butyltoluen og oktanol-2 i et volumforhold på 1:1. T) en resulterende blanding ble hydrogenert inntil 29-54 1 hydrogen var forbrukt per liter av arbeidsopplosningen . 2-isoamylthraquinone (350 g/l) and tetrahydro-2-isoamylthraquinone (220 g/l) were dissolved in a mixture of tert-butyltoluene and octanol-2 in a volume ratio of 1:1. T) a resulting mixture was hydrogenated until 29-54 l of hydrogen were consumed per liter of the working solution.
Hydrogenering, oksydasjon og ekstraksjon ble utfort på samme måte som beskrevet i eksempel 1. Hydrogenation, oxidation and extraction were carried out in the same way as described in example 1.
Konsentrasjonen av hydrogenperoksyd i ekstraktet var 44'8 g/l av arbeidsopplosningen. The concentration of hydrogen peroxide in the extract was 44.8 g/l of the working solution.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO19868A NO119791B (en) | 1968-01-17 | 1968-01-17 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO19868A NO119791B (en) | 1968-01-17 | 1968-01-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO119791B true NO119791B (en) | 1970-07-06 |
Family
ID=19877438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19868A NO119791B (en) | 1968-01-17 | 1968-01-17 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO119791B (en) |
-
1968
- 1968-01-17 NO NO19868A patent/NO119791B/no unknown
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