CA2111027C - Process for producing hydrogen peroxide - Google Patents
Process for producing hydrogen peroxide Download PDFInfo
- Publication number
- CA2111027C CA2111027C CA002111027A CA2111027A CA2111027C CA 2111027 C CA2111027 C CA 2111027C CA 002111027 A CA002111027 A CA 002111027A CA 2111027 A CA2111027 A CA 2111027A CA 2111027 C CA2111027 C CA 2111027C
- Authority
- CA
- Canada
- Prior art keywords
- working solution
- alkyl
- substituted
- set forth
- anthraquinone
- 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 - Lifetime
Links
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title claims abstract description 85
- 238000000034 method Methods 0.000 title claims abstract description 46
- 239000012224 working solution Substances 0.000 claims abstract description 92
- 150000004056 anthraquinones Chemical class 0.000 claims abstract description 58
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 47
- 230000003647 oxidation Effects 0.000 claims abstract description 45
- 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 claims abstract description 44
- 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 claims abstract description 40
- 230000009467 reduction Effects 0.000 claims abstract description 36
- PCFMUWBCZZUMRX-UHFFFAOYSA-N 9,10-Dihydroxyanthracene Chemical class C1=CC=C2C(O)=C(C=CC=C3)C3=C(O)C2=C1 PCFMUWBCZZUMRX-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 239000012429 reaction media Substances 0.000 claims abstract description 19
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 claims description 14
- INPHIYULSHLAHR-UHFFFAOYSA-N 1-pentylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CCCCC INPHIYULSHLAHR-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 10
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- HXQPUEQDBSPXTE-UHFFFAOYSA-N Diisobutylcarbinol Chemical compound CC(C)CC(O)CC(C)C HXQPUEQDBSPXTE-UHFFFAOYSA-N 0.000 claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 150000003672 ureas Chemical class 0.000 claims description 2
- HSKPJQYAHCKJQC-UHFFFAOYSA-N 1-ethylanthracene-9,10-dione Chemical group O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CC HSKPJQYAHCKJQC-UHFFFAOYSA-N 0.000 claims 1
- BGJQNPIOBWKQAW-UHFFFAOYSA-N 1-tert-butylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)(C)C BGJQNPIOBWKQAW-UHFFFAOYSA-N 0.000 claims 1
- -1 amyl-substituted anthraquinone Chemical group 0.000 claims 1
- 229960002163 hydrogen peroxide Drugs 0.000 description 39
- 238000006722 reduction reaction Methods 0.000 description 29
- 238000005984 hydrogenation reaction Methods 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 239000012046 mixed solvent Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- LZNGSHFBWBKBFH-UHFFFAOYSA-N 1-pentyl-1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(CCCCC)CCC2 LZNGSHFBWBKBFH-UHFFFAOYSA-N 0.000 description 8
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 238000006701 autoxidation reaction Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WMXSYGRDANLILV-UHFFFAOYSA-N 1-(2-methylbutan-2-yl)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)(C)CC WMXSYGRDANLILV-UHFFFAOYSA-N 0.000 description 1
- NWRDELZDTLTIOU-UHFFFAOYSA-N 1-pentan-2-ylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)CCC NWRDELZDTLTIOU-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 230000000332 continued effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 239000002912 waste gas Substances 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)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP346,209/92 | 1992-12-25 | ||
| JP34620992A JP3617532B2 (ja) | 1992-12-25 | 1992-12-25 | 過酸化水素の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2111027A1 CA2111027A1 (en) | 1994-06-26 |
| CA2111027C true CA2111027C (en) | 2003-10-14 |
Family
ID=18381850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002111027A Expired - Lifetime CA2111027C (en) | 1992-12-25 | 1993-12-09 | Process for producing hydrogen peroxide |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5399333A (en:Method) |
| EP (1) | EP0603624B1 (en:Method) |
| JP (1) | JP3617532B2 (en:Method) |
| KR (1) | KR0185425B1 (en:Method) |
| CN (1) | CN1034008C (en:Method) |
| AU (1) | AU659040B2 (en:Method) |
| CA (1) | CA2111027C (en:Method) |
| DE (1) | DE69314445T2 (en:Method) |
| FI (1) | FI112860B (en:Method) |
| TW (1) | TW285660B (en:Method) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5853693A (en) * | 1996-04-03 | 1998-12-29 | Mitsubishi Gas Chemical Company, Inc. | Hydrogenation catalyst for production of hydrogen peroxide, and method for preparation of same |
| USH1787H (en) * | 1996-04-12 | 1999-02-02 | Ogasawara; Kazuharu | Regeneration method of working solution |
| US6300378B1 (en) | 1996-09-27 | 2001-10-09 | University Of New Mexico | Tropodegradable bromine-containing halocarbon additives to decrease flammability of refrigerants foam blowing agents solvents aerosol propellants and sterilants |
| DE19816297A1 (de) * | 1998-04-11 | 1999-10-21 | Degussa | Verfahren zur Herstellung von Wasserstoffperoxid und Reaktionsträger zu seiner Durchführung |
| ATE314309T1 (de) * | 1999-11-22 | 2006-01-15 | Akzo Nobel Nv | Verfahren und zusammensetzung zur herstellung von wasserstoffperoxid |
| WO2005071828A1 (en) | 2004-01-22 | 2005-08-04 | The Regents Of The University Of Michigan | Demodulatr, chip and method for digitally demodulating an fsk signal |
| CN100362002C (zh) * | 2004-03-25 | 2008-01-16 | 浙江新安化工集团股份有限公司 | 一种双甘膦氧化制备草甘膦的方法 |
| ES2380231T3 (es) * | 2005-08-31 | 2012-05-09 | Fmc Corporation | Producción por autooxidación de peróxido de hidrógeno mediante oxidación de un microreactor |
| 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 |
| CN105021684B (zh) * | 2014-04-29 | 2018-12-25 | 中国石油化工股份有限公司 | 蒽醌法生产双氧水过程中氢化效率、氧化效率和萃余浓度的测定方法 |
| CN115924853B (zh) * | 2022-11-15 | 2024-01-05 | 黎明化工研究设计院有限责任公司 | 一种蒽醌法生产过氧化氢的高产能工作液体系 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE892747C (de) * | 1949-11-05 | 1953-10-08 | Du Pont | Verfahren zur Herstellung von Wasserstoffperoxyd |
| US2739042A (en) * | 1954-01-12 | 1956-03-20 | Allied Chem & Dye Corp | Process for the production of hydrogen peroxide |
| GB856420A (en) * | 1956-06-19 | 1960-12-14 | Columbia Southern Chem Corp | Method of making hydrogen peroxide |
| US2901490A (en) * | 1957-01-29 | 1959-08-25 | Du Pont | Regeneration of degraded anthraquinone working solutions for the production of hydrogen peroxide |
| US3073680A (en) * | 1961-03-20 | 1963-01-15 | Fmc Corp | Production of hydrogen peroxide |
| US3323868A (en) * | 1961-12-14 | 1967-06-06 | Laporte Chemical | Manufacture of hydrogen peroxide |
| US3408163A (en) * | 1964-10-06 | 1968-10-29 | Franchuk Valentin Iosifovich | Anthraquinone process for the production of hydrogen peroxide |
| GB1132693A (en) * | 1964-11-17 | 1968-11-06 | Laporte Chemical | Improvements in or relating to hydrogen peroxide |
| DE2003268C3 (de) * | 1970-01-26 | 1974-01-31 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Vorrichtung zur Durchführung der Oxydation im Anthrachinonverfahren zur Herstellung von Wasserstoffperoxid |
| US3767779A (en) * | 1971-07-06 | 1973-10-23 | Oxysynthese | Process for manufacturing hydrogen peroxide |
| BE769675A (fr) * | 1971-07-08 | 1972-01-10 | Solvay | Procede cyclique de fabrication de peroxyde d'hydrogene. |
| US4539196A (en) * | 1984-04-19 | 1985-09-03 | Fmc Corporation | Process for hydrogenating an alkylated anthraquinone |
| 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 |
-
1992
- 1992-12-25 JP JP34620992A patent/JP3617532B2/ja not_active Expired - Fee Related
-
1993
- 1993-12-04 TW TW082110323A patent/TW285660B/zh not_active IP Right Cessation
- 1993-12-06 AU AU52168/93A patent/AU659040B2/en not_active Expired
- 1993-12-06 US US08/162,305 patent/US5399333A/en not_active Expired - Lifetime
- 1993-12-06 EP EP93119636A patent/EP0603624B1/en not_active Expired - Lifetime
- 1993-12-06 DE DE69314445T patent/DE69314445T2/de not_active Expired - Lifetime
- 1993-12-09 CA CA002111027A patent/CA2111027C/en not_active Expired - Lifetime
- 1993-12-23 KR KR1019930029336A patent/KR0185425B1/ko not_active Expired - Lifetime
- 1993-12-23 FI FI935831A patent/FI112860B/fi not_active IP Right Cessation
- 1993-12-24 CN CN93121085A patent/CN1034008C/zh not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2111027A1 (en) | 1994-06-26 |
| DE69314445T2 (de) | 1998-02-05 |
| FI935831A0 (fi) | 1993-12-23 |
| EP0603624B1 (en) | 1997-10-08 |
| TW285660B (en:Method) | 1996-09-11 |
| CN1034008C (zh) | 1997-02-12 |
| FI112860B (fi) | 2004-01-30 |
| JPH06191803A (ja) | 1994-07-12 |
| KR0185425B1 (ko) | 1999-04-15 |
| KR940014142A (ko) | 1994-07-16 |
| US5399333A (en) | 1995-03-21 |
| FI935831L (fi) | 1994-06-26 |
| AU5216893A (en) | 1994-07-07 |
| EP0603624A1 (en) | 1994-06-29 |
| JP3617532B2 (ja) | 2005-02-09 |
| DE69314445D1 (de) | 1997-11-13 |
| AU659040B2 (en) | 1995-05-04 |
| CN1088885A (zh) | 1994-07-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20131209 |