NO116368B - - Google Patents
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- Publication number
- NO116368B NO116368B NO160413A NO16041365A NO116368B NO 116368 B NO116368 B NO 116368B NO 160413 A NO160413 A NO 160413A NO 16041365 A NO16041365 A NO 16041365A NO 116368 B NO116368 B NO 116368B
- Authority
- NO
- Norway
- Prior art keywords
- percent
- hydrogenation
- working solution
- stated
- grams
- Prior art date
Links
- 238000005984 hydrogenation reaction Methods 0.000 claims description 68
- 238000000034 method Methods 0.000 claims description 53
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 42
- 239000012224 working solution Substances 0.000 claims description 34
- 238000004519 manufacturing process Methods 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 19
- 150000004053 quinones Chemical class 0.000 claims description 18
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 14
- 230000003647 oxidation Effects 0.000 claims description 12
- 238000007254 oxidation reaction Methods 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- JORLUGVBYJSSAW-UHFFFAOYSA-N 2-ethyl-1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1CC(CC)CC2 JORLUGVBYJSSAW-UHFFFAOYSA-N 0.000 claims description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
- 238000004064 recycling Methods 0.000 claims description 7
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 239000011877 solvent mixture Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- VVDZWMOQABVVHC-UHFFFAOYSA-N (1-methylcyclohexyl) acetate Chemical compound CC(=O)OC1(C)CCCCC1 VVDZWMOQABVVHC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- 239000011343 solid material Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 description 23
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 5
- 150000004056 anthraquinones Chemical class 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 230000008929 regeneration Effects 0.000 description 4
- 238000011069 regeneration method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- HSKPJQYAHCKJQC-UHFFFAOYSA-N 1-ethylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CC HSKPJQYAHCKJQC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- -1 ester compound Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- OTBHDFWQZHPNPU-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1CCCC2 OTBHDFWQZHPNPU-UHFFFAOYSA-N 0.000 description 1
- RKMPHYRYSONWOL-UHFFFAOYSA-N 1-ethyl-1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(CC)CCC2 RKMPHYRYSONWOL-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HPXRVTGHNJAIIH-PTQBSOBMSA-N cyclohexanol Chemical class O[13CH]1CCCCC1 HPXRVTGHNJAIIH-PTQBSOBMSA-N 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 238000003969 polarography Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B15/00—Peroxides; Peroxyhydrates; Peroxyacids or salts thereof; Superoxides; Ozonides
- C01B15/01—Hydrogen peroxide
- C01B15/022—Preparation from organic compounds
- C01B15/023—Preparation from organic compounds by the alkyl-anthraquinone process
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB46786/64A GB1132693A (en) | 1964-11-17 | 1964-11-17 | Improvements in or relating to hydrogen peroxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO116368B true NO116368B (da) | 1969-03-17 |
Family
ID=10442594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO160413A NO116368B (da) | 1964-11-17 | 1965-11-09 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3540847A (da) |
| JP (1) | JPS494635B1 (da) |
| BE (1) | BE672419A (da) |
| BR (1) | BR6574751D0 (da) |
| DE (1) | DE1567640C3 (da) |
| DK (1) | DK116503B (da) |
| FI (1) | FI46148C (da) |
| FR (1) | FR1458818A (da) |
| GB (1) | GB1132693A (da) |
| NL (1) | NL6514971A (da) |
| NO (1) | NO116368B (da) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5297739A (en) * | 1977-02-10 | 1977-08-16 | Ricoh Co Ltd | Deodorizing treating means for dry type diazo copying machine |
| FR2503124A1 (fr) * | 1981-04-07 | 1982-10-08 | Ugine Kuhlmann | Amelioration au procede de fabrication cyclique du peroxyde d'hydrogene |
| US4394369A (en) * | 1982-05-24 | 1983-07-19 | Fmc Corporation | Hydrogen peroxide process |
| US4514376A (en) * | 1984-04-19 | 1985-04-30 | Fmc Corporation | Pregeneration of tetrahydroanthraquinones in a make-up solution to be added to a hydrogen peroxide working solution |
| US4539196A (en) * | 1984-04-19 | 1985-09-03 | Fmc Corporation | Process for hydrogenating an alkylated anthraquinone |
| JP3617532B2 (ja) * | 1992-12-25 | 2005-02-09 | 三菱瓦斯化学株式会社 | 過酸化水素の製造方法 |
| JP4973041B2 (ja) * | 2006-07-14 | 2012-07-11 | 三菱瓦斯化学株式会社 | 過酸化水素の製造方法 |
| KR100998082B1 (ko) * | 2008-07-22 | 2010-12-03 | 오씨아이 주식회사 | 생산성을 향상시킨 과산화수소 제조 방법 및 이를 위한조성물 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA561674A (en) * | 1958-08-12 | Columbia-Southern Chemical Corporation | Process for removing colour from hydrogen peroxide solution | |
| US2927002A (en) * | 1951-02-23 | 1960-03-01 | Porte Chemicals Ltd | Process for the manufacture of hydrogen peroxide |
| US2860036A (en) * | 1953-05-04 | 1958-11-11 | Laporte Chemical | Purification of anthraquinone solutions |
-
1964
- 1964-11-17 GB GB46786/64A patent/GB1132693A/en not_active Expired
-
1965
- 1965-11-09 NO NO160413A patent/NO116368B/no unknown
- 1965-11-11 BR BR174751/65A patent/BR6574751D0/pt unknown
- 1965-11-15 DE DE1567640A patent/DE1567640C3/de not_active Expired
- 1965-11-15 FI FI652728A patent/FI46148C/fi active
- 1965-11-17 DK DK591465AA patent/DK116503B/da unknown
- 1965-11-17 NL NL6514971A patent/NL6514971A/xx unknown
- 1965-11-17 JP JP40070316A patent/JPS494635B1/ja active Pending
- 1965-11-17 FR FR38770A patent/FR1458818A/fr not_active Expired
- 1965-11-17 BE BE672419D patent/BE672419A/xx unknown
-
1968
- 1968-06-11 US US739898A patent/US3540847A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE1567640A1 (de) | 1969-07-10 |
| NL6514971A (da) | 1966-05-18 |
| US3540847A (en) | 1970-11-17 |
| DK116503B (da) | 1970-01-19 |
| DE1567640B2 (de) | 1975-05-07 |
| FI46148C (fi) | 1973-01-10 |
| FI46148B (da) | 1972-10-02 |
| FR1458818A (fr) | 1966-11-10 |
| GB1132693A (en) | 1968-11-06 |
| BR6574751D0 (pt) | 1973-09-11 |
| DE1567640C3 (de) | 1975-12-11 |
| BE672419A (da) | 1966-05-17 |
| JPS494635B1 (da) | 1974-02-01 |
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