JPH0512281B2 - - Google Patents
Info
- Publication number
- JPH0512281B2 JPH0512281B2 JP63329528A JP32952888A JPH0512281B2 JP H0512281 B2 JPH0512281 B2 JP H0512281B2 JP 63329528 A JP63329528 A JP 63329528A JP 32952888 A JP32952888 A JP 32952888A JP H0512281 B2 JPH0512281 B2 JP H0512281B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- aqueous solvent
- carbon dioxide
- solvent
- operating
- 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
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 43
- 239000001569 carbon dioxide Substances 0.000 claims description 30
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 30
- 239000012530 fluid Substances 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 28
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 16
- 239000003125 aqueous solvent Substances 0.000 claims description 12
- 239000000356 contaminant Substances 0.000 claims description 10
- 150000004056 anthraquinones Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- -1 carboxylate esters Chemical class 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000003209 petroleum derivative Substances 0.000 claims description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 20
- 239000007788 liquid Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 7
- 238000011084 recovery Methods 0.000 description 6
- 238000000746 purification Methods 0.000 description 5
- 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 4
- 238000010586 diagram Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 230000001172 regenerating effect Effects 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- HXQPUEQDBSPXTE-UHFFFAOYSA-N Diisobutylcarbinol Chemical compound CC(C)CC(O)CC(C)C HXQPUEQDBSPXTE-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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- GOOYDFBDQNFLQJ-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,9a,10a-decahydroanthracene-9,10-dione Chemical compound O=C1C2=CCCCC2C(=O)C2C1CCCC2 GOOYDFBDQNFLQJ-UHFFFAOYSA-N 0.000 description 1
- OTBHDFWQZHPNPU-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1CCCC2 OTBHDFWQZHPNPU-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- UMWZLYTVXQBTTE-UHFFFAOYSA-N 2-pentylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(CCCCC)=CC=C3C(=O)C2=C1 UMWZLYTVXQBTTE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- DCZFGQYXRKMVFG-UHFFFAOYSA-N cyclohexane-1,4-dione Chemical class O=C1CCC(=O)CC1 DCZFGQYXRKMVFG-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052914 metal silicate Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000002277 temperature effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US141387 | 1988-01-07 | ||
| US07/141,387 US4824609A (en) | 1988-01-07 | 1988-01-07 | Process for purifying a working compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01215704A JPH01215704A (ja) | 1989-08-29 |
| JPH0512281B2 true JPH0512281B2 (enExample) | 1993-02-17 |
Family
ID=22495477
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63329528A Granted JPH01215704A (ja) | 1988-01-07 | 1988-12-28 | 操作化合物精製方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4824609A (enExample) |
| EP (1) | EP0325135A1 (enExample) |
| JP (1) | JPH01215704A (enExample) |
| BR (1) | BR8900055A (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI96678C (fi) * | 1994-09-21 | 1996-08-12 | Kemira Chemicals Oy | Menetelmä vetyperoksidin puhdistamiseksi |
| US6342196B2 (en) * | 1998-06-29 | 2002-01-29 | University Of Pittsburgh | Synthesis of hydrogen peroxide |
| US6180804B1 (en) | 1998-09-10 | 2001-01-30 | Fmc Corporation | Reversion of expoxide in the production of Hydrogen peroxide |
| US6656446B1 (en) * | 1999-04-29 | 2003-12-02 | University Of Pittsburgh | Synthesis of hydrogen peroxide |
| US7238335B2 (en) * | 2003-08-11 | 2007-07-03 | Degussa Ag | Process for the preparation of hydrogen peroxide by the anthraquinone cyclic process |
| RU2458856C2 (ru) * | 2006-06-27 | 2012-08-20 | Акцо Нобель Н.В. | Способ получения пероксида водорода |
| US7645438B2 (en) * | 2006-06-27 | 2010-01-12 | Akzo Nobel N.V. | Process for the production of hydrogen peroxide |
| US8217191B2 (en) * | 2008-11-05 | 2012-07-10 | Aiken John E | Process for integrated co-production of hydrogen peroxide and epoxidized esters |
| CN102395527A (zh) * | 2009-03-27 | 2012-03-28 | 索尔维公司 | 生产过氧化氢的方法 |
| CN108264455B (zh) * | 2016-12-30 | 2021-11-12 | 中国石油化工股份有限公司 | 一种制备四氢-2-戊基蒽醌的方法和一种过氧化氢的生产方法 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA608824A (en) * | 1960-11-15 | E.I. Du Pont De Nemours And Company | Regeneration of degraded working solutions for producing hydrogen peroxide | |
| BE621220A (enExample) * | ||||
| US2739875A (en) * | 1951-12-06 | 1956-03-27 | Du Pont | Regeneration of degraded alkylanthraquinone solutions for the production of hydrogen peroxide |
| US2940987A (en) * | 1957-05-24 | 1960-06-14 | Du Pont | Regeneration of degraded anthraquinone working solutions used for producing hydrogen peroxide |
| CH408879A (fr) * | 1961-02-14 | 1966-03-15 | Solvay | Procédé de régénération et d'épuration de la solution navette utilisée pour la fabrication d'eau oxygénée par l'intermédiaire des alkylanthraquinones |
| NL123981C (enExample) * | 1961-02-27 | 1900-01-01 | ||
| US3073680A (en) * | 1961-03-20 | 1963-01-15 | Fmc Corp | Production of hydrogen peroxide |
| US3330625A (en) * | 1963-10-22 | 1967-07-11 | Pittsburgh Plate Glass Co | Hydrogen peroxide manufacture |
| GB1141299A (en) * | 1965-06-21 | 1969-01-29 | Laporte Chemical | Process for or relating to the production of hydrogen peroxide |
| US3432267A (en) * | 1967-05-26 | 1969-03-11 | Fmc Corp | Regeneration of anthraquinone working solution used in the production of hydrogen peroxide |
| US3965251A (en) * | 1970-08-18 | 1976-06-22 | Mitsubishi Gas Chemical Company, Inc. | Method of regenerating a degraded working solution for the production of hydrogen peroxide |
| US3767779A (en) * | 1971-07-06 | 1973-10-23 | Oxysynthese | Process for manufacturing hydrogen peroxide |
| ZA728652B (en) * | 1971-12-20 | 1973-08-29 | Laporte Industries Ltd | Improvements in a cyclic process for hydrogen peroxide production |
| DE2263247C3 (de) * | 1972-12-23 | 1981-08-27 | Bayer Ag, 5090 Leverkusen | Verfahren zur Reinigung von Anthrachinon |
| US4308200A (en) * | 1980-07-10 | 1981-12-29 | Champion International Corporation | Extraction of coniferous woods with fluid carbon dioxide and other supercritical fluids |
| US4566998A (en) * | 1981-09-28 | 1986-01-28 | Foret S.A. | Production of hydrogen peroxide |
| US4547292A (en) * | 1983-10-31 | 1985-10-15 | General Electric Company | Supercritical fluid extraction and enhancement for liquid liquid extraction processes |
| US4584140A (en) * | 1984-12-17 | 1986-04-22 | National Distillers And Chemical Corporation | Process for separating fatty materials from supported nickel catalysts |
| JPS62237A (ja) * | 1985-06-26 | 1987-01-06 | 日清製粉株式会社 | パン生地の製造法 |
| US4568447A (en) * | 1985-07-29 | 1986-02-04 | Uop Inc. | Process for the removal of trace quantities of hydrocarbonaceous compounds from an aqueous stream |
| US4668436A (en) * | 1985-12-13 | 1987-05-26 | Fmc Corporation | Process for purifying a working solution |
-
1988
- 1988-01-07 US US07/141,387 patent/US4824609A/en not_active Expired - Fee Related
- 1988-12-28 JP JP63329528A patent/JPH01215704A/ja active Granted
-
1989
- 1989-01-06 BR BR898900055A patent/BR8900055A/pt unknown
- 1989-01-09 EP EP89100277A patent/EP0325135A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| BR8900055A (pt) | 1989-09-05 |
| EP0325135A1 (en) | 1989-07-26 |
| JPH01215704A (ja) | 1989-08-29 |
| US4824609A (en) | 1989-04-25 |
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