JPS6214484B2 - - Google Patents
Info
- Publication number
- JPS6214484B2 JPS6214484B2 JP58014697A JP1469783A JPS6214484B2 JP S6214484 B2 JPS6214484 B2 JP S6214484B2 JP 58014697 A JP58014697 A JP 58014697A JP 1469783 A JP1469783 A JP 1469783A JP S6214484 B2 JPS6214484 B2 JP S6214484B2
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolidone
- alkyl
- substituted
- manufacturing
- solvent
- 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
Links
- 239000002904 solvent Substances 0.000 claims abstract description 39
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 28
- 150000004056 anthraquinones Chemical class 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 19
- 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 16
- -1 N-substituted-2-pyrrolidones Chemical class 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract 2
- 239000012224 working solution Substances 0.000 claims description 19
- 239000000243 solution Substances 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- GTVWRXDRKAHEAD-UHFFFAOYSA-N Tris(2-ethylhexyl) phosphate Chemical compound CCCCC(CC)COP(=O)(OCC(CC)CCCC)OCC(CC)CCCC GTVWRXDRKAHEAD-UHFFFAOYSA-N 0.000 claims description 5
- PZYDAVFRVJXFHS-UHFFFAOYSA-N n-cyclohexyl-2-pyrrolidone Chemical group O=C1CCCN1C1CCCCC1 PZYDAVFRVJXFHS-UHFFFAOYSA-N 0.000 claims description 5
- 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 4
- 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 4
- YTPSFXZMJKMUJE-UHFFFAOYSA-N 2-tert-butylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)(C)C)=CC=C3C(=O)C2=C1 YTPSFXZMJKMUJE-UHFFFAOYSA-N 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 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 claims description 3
- GKZJJXFFNOSPHJ-UHFFFAOYSA-N 1-(2-phenylethyl)pyrrolidin-2-one Chemical group O=C1CCCN1CCC1=CC=CC=C1 GKZJJXFFNOSPHJ-UHFFFAOYSA-N 0.000 claims description 2
- LVUQCTGSDJLWCE-UHFFFAOYSA-N 1-benzylpyrrolidin-2-one Chemical group O=C1CCCN1CC1=CC=CC=C1 LVUQCTGSDJLWCE-UHFFFAOYSA-N 0.000 claims description 2
- ZRECPFOSZXDFDT-UHFFFAOYSA-N 1-decylpyrrolidin-2-one Chemical group CCCCCCCCCCN1CCCC1=O ZRECPFOSZXDFDT-UHFFFAOYSA-N 0.000 claims description 2
- NJPQAIBZIHNJDO-UHFFFAOYSA-N 1-dodecylpyrrolidin-2-one Chemical group CCCCCCCCCCCCN1CCCC1=O NJPQAIBZIHNJDO-UHFFFAOYSA-N 0.000 claims description 2
- WPPOGHDFAVQKLN-UHFFFAOYSA-N N-Octyl-2-pyrrolidone Chemical group CCCCCCCCN1CCCC1=O WPPOGHDFAVQKLN-UHFFFAOYSA-N 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- PCFMUWBCZZUMRX-UHFFFAOYSA-N 9,10-Dihydroxyanthracene Chemical compound C1=CC=C2C(O)=C(C=CC=C3)C3=C(O)C2=C1 PCFMUWBCZZUMRX-UHFFFAOYSA-N 0.000 abstract description 11
- 238000006701 autoxidation reaction Methods 0.000 abstract 1
- 238000002474 experimental method Methods 0.000 description 12
- 239000003849 aromatic solvent Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 7
- 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 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 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 3
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 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
- 238000000605 extraction Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 150000004040 pyrrolidinones Chemical class 0.000 description 2
- 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
- PLQHRVKYQVNEEK-UHFFFAOYSA-N 1-(2-acetyl-3-benzoylphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1C(C)=O PLQHRVKYQVNEEK-UHFFFAOYSA-N 0.000 description 1
- LVQFKRXRTXCQCZ-UHFFFAOYSA-N 1-(2-acetylphenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1C(C)=O LVQFKRXRTXCQCZ-UHFFFAOYSA-N 0.000 description 1
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- JLEXUIVKURIPFI-UHFFFAOYSA-N tris phosphate Chemical compound OP(O)(O)=O.OCC(N)(CO)CO JLEXUIVKURIPFI-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003953 γ-lactams 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)
- Pyrrole Compounds (AREA)
- Oxygen, Ozone, And Oxides In General (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US381592 | 1982-05-24 | ||
| US06/381,592 US4394369A (en) | 1982-05-24 | 1982-05-24 | Hydrogen peroxide process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58204804A JPS58204804A (ja) | 1983-11-29 |
| JPS6214484B2 true JPS6214484B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-04-02 |
Family
ID=23505613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58014697A Granted JPS58204804A (ja) | 1982-05-24 | 1983-02-02 | 過酸化水素の製造法 |
Country Status (8)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE459919C (sv) * | 1987-03-27 | 1991-03-25 | Eka Nobel Ab | Foerfarande foer framstaellning av vaeteperoxid genom reduktion och oxidation av en antrakinon |
| FR2614015B1 (fr) * | 1987-04-16 | 1989-07-13 | Atochem | Procede de production cyclique de peroxyde d'hydrogene |
| US5658940A (en) * | 1995-10-06 | 1997-08-19 | Celgene Corporation | Succinimide and maleimide cytokine inhibitors |
| TWI480264B (zh) * | 2013-04-12 | 2015-04-11 | Daxin Materials Corp | 液晶配向劑、液晶配向膜、以及液晶顯示元件及其製造方法 |
| CN105565277A (zh) * | 2014-11-03 | 2016-05-11 | 中国石油化工股份有限公司 | 一种蒽醌法生产双氧水的工作液 |
| CN105600755A (zh) * | 2016-03-17 | 2016-05-25 | 中国天辰工程有限公司 | 一种蒽醌法生产过氧化氢用工作液 |
| EP3543208A1 (en) * | 2018-03-19 | 2019-09-25 | Solvay Sa | Process for manufacturing an aqueous hydrogen peroxide solution |
| US12150446B2 (en) | 2018-11-12 | 2024-11-26 | Diversey, Inc | C3-C6 N-alkyl-gamma-butyrolactam- and peroyxgen-containing antimicrobial compositions |
| FR3131292A1 (fr) | 2021-12-23 | 2023-06-30 | Arkema France | Procédé de production de peroxyde d’hydrogène |
| FR3141158B1 (fr) | 2022-10-25 | 2024-10-04 | Arkema France | Procédé de production de peroxyde d’hydrogène |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT360853A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1937-04-07 | |||
| US2668753A (en) * | 1949-11-05 | 1954-02-09 | Du Pont | Production of hydrogen peroxide |
| US2537516A (en) * | 1950-03-09 | 1951-01-09 | Buffalo Electro Chem Co | Process of producing hydrogen peroxide by the alternate reduction and oxidation of alkylated anthraquinones |
| US2537655A (en) * | 1950-03-09 | 1951-01-09 | Buffalo Electro Chem Co | Auto-oxidation of alkylated anthraquinones |
| US2927002A (en) * | 1951-02-23 | 1960-03-01 | Porte Chemicals Ltd | Process for the manufacture of hydrogen peroxide |
| IT496667A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1951-12-14 | |||
| US2768066A (en) * | 1952-02-01 | 1956-10-23 | Fmc Corp | Manufacture of hydrogen peroxide |
| US2919974A (en) * | 1952-05-05 | 1960-01-05 | Etat Francais Soc D Electrochi | Solvents for the manufacture of hydrogen peroxide by hydrogenation and oxidation of the alkylated anthraquinones |
| US2791491A (en) * | 1952-09-19 | 1957-05-07 | Laporte Chemical | Process for the manufacture of hydrogen peroxide |
| US3002817A (en) * | 1953-10-15 | 1961-10-03 | Electrochimie Electrometallurg | Process for the preparation of hydrogen peroxide |
| US2890105A (en) * | 1954-05-05 | 1959-06-09 | Allied Chem | Solvent medium for the anthraquinone process for the production of hydrogen peroxide |
| US2975033A (en) * | 1956-11-24 | 1961-03-14 | Fmc Corp | Process for preparation of hydrogen peroxide |
| US2990251A (en) * | 1956-11-24 | 1961-06-27 | Fmc Corp | Process for preparation of hydrogen peroxide |
| US3038786A (en) * | 1958-12-19 | 1962-06-12 | Hiratsuka Kizo | Process for the cyclic production of hydrogen peroxide |
| US3132001A (en) * | 1961-04-28 | 1964-05-05 | Solvay | Process for the generation of recycle solutions employed for the manufacture of hydrogen peroxide via intermediary alkylanthraquinones |
| DE1261838B (de) * | 1963-09-03 | 1968-02-29 | Degussa | Verfahren zur Herstellung von Wasserstoffperoxyd |
| FR1405861A (fr) * | 1964-04-16 | 1965-07-16 | Oxysynthese | Perfectionnement au procédé cyclique de production d'eau oxygénée |
| GB1132693A (en) * | 1964-11-17 | 1968-11-06 | Laporte Chemical | Improvements in or relating to hydrogen peroxide |
| US3441574A (en) * | 1966-01-12 | 1969-04-29 | United States Steel Corp | Process for making anthraquinone |
| FR2053457A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1969-07-04 | 1971-04-16 | Rhone Poulenc Sa | |
| NL170124C (nl) * | 1970-04-18 | 1982-10-01 | Degussa | Werkwijze ter bereiding van waterstofperoxyde volgens het antrachinonprocede; werkwijze voor het bereiden van een viervoudig gesubstitueerd ureum. |
| DE2039822B2 (de) * | 1970-08-11 | 1974-12-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 1-Nitroanthrachinon |
| NL171693C (nl) * | 1971-05-21 | 1983-05-02 | Degussa | Werkwijze voor het overbrengen van waterstofperoxyde uit een waterige oplossing in een dampvormig of vloeibaar mengsel met organische verbindingen. |
| DE2232446C3 (de) * | 1972-07-01 | 1979-05-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von reinem 1-Nitroanthrachinon |
| US4046868A (en) * | 1973-09-26 | 1977-09-06 | E. I. Du Pont De Nemours And Company | Production of hydrogen peroxide |
| US3923966A (en) * | 1973-11-21 | 1975-12-02 | Du Pont | Direct manufacture of hydrogen peroxide from hydrogen sulfide |
| US3994932A (en) * | 1974-04-02 | 1976-11-30 | Mitsui Toatsu Chemicals, Incorporated | Process for the preparation of 1-aminoanthraquinone |
| DE3027253C2 (de) * | 1980-07-18 | 1982-11-04 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Wasserstoffperoxid |
-
1982
- 1982-05-24 US US06/381,592 patent/US4394369A/en not_active Expired - Fee Related
-
1983
- 1983-01-11 CA CA000419201A patent/CA1176431A/en not_active Expired
- 1983-01-20 EP EP83300297A patent/EP0095822B1/en not_active Expired
- 1983-01-20 DE DE8383300297T patent/DE3360244D1/de not_active Expired
- 1983-01-20 AT AT83300297T patent/ATE13754T1/de not_active IP Right Cessation
- 1983-01-20 MX MX195972A patent/MX158175A/es unknown
- 1983-01-24 ES ES519226A patent/ES8500185A1/es not_active Expired
- 1983-02-02 JP JP58014697A patent/JPS58204804A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3360244D1 (en) | 1985-07-18 |
| ATE13754T1 (de) | 1985-06-15 |
| EP0095822B1 (en) | 1985-06-12 |
| US4394369A (en) | 1983-07-19 |
| ES519226A0 (es) | 1984-10-01 |
| ES8500185A1 (es) | 1984-10-01 |
| JPS58204804A (ja) | 1983-11-29 |
| EP0095822A1 (en) | 1983-12-07 |
| MX158175A (es) | 1989-01-13 |
| CA1176431A (en) | 1984-10-23 |
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