TW531525B - Method of producing hydrogen peroxide and reaction carriers therefor - Google Patents
Method of producing hydrogen peroxide and reaction carriers therefor Download PDFInfo
- Publication number
- TW531525B TW531525B TW088105454A TW88105454A TW531525B TW 531525 B TW531525 B TW 531525B TW 088105454 A TW088105454 A TW 088105454A TW 88105454 A TW88105454 A TW 88105454A TW 531525 B TW531525 B TW 531525B
- Authority
- TW
- Taiwan
- Prior art keywords
- reaction
- anthraquinone
- item
- hydrogen peroxide
- iheaq
- Prior art date
Links
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title claims abstract description 111
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 87
- 238000000034 method Methods 0.000 title claims abstract description 53
- 239000000969 carrier Substances 0.000 title claims abstract description 16
- NQVBCGTZRWHVSY-UHFFFAOYSA-N 2-(4-Methyl-3-pentenyl)anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CCC=C(C)C)=CC=C3C(=O)C2=C1 NQVBCGTZRWHVSY-UHFFFAOYSA-N 0.000 claims abstract description 55
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 51
- -1 cyclic anthraquinone Chemical class 0.000 claims abstract description 28
- 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 26
- 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 abstract description 23
- JWXBQHIMYKKGJT-UHFFFAOYSA-N 2-(4-methylpentyl)anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(CCCC(C)C)=CC=C3C(=O)C2=C1 JWXBQHIMYKKGJT-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000012224 working solution Substances 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 49
- 238000004519 manufacturing process Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 24
- 238000011049 filling Methods 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 20
- 150000004056 anthraquinones Chemical class 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 230000002079 cooperative effect Effects 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 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 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 7
- 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 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 6
- 239000010970 precious metal Substances 0.000 claims description 6
- 239000007868 Raney catalyst Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 4
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 241000920033 Eugenes Species 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 150000004905 tetrazines Chemical class 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 22
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 7
- GTVWRXDRKAHEAD-UHFFFAOYSA-N Tris(2-ethylhexyl) phosphate Chemical compound CCCCC(CC)COP(=O)(OCC(CC)CCCC)OCC(CC)CCCC GTVWRXDRKAHEAD-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 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 5
- 230000000875 corresponding effect Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- SNDGLCYYBKJSOT-UHFFFAOYSA-N 1,1,3,3-tetrabutylurea Chemical compound CCCCN(CCCC)C(=O)N(CCCC)CCCC SNDGLCYYBKJSOT-UHFFFAOYSA-N 0.000 description 4
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 4
- YOUHDCYXXDRNLO-UHFFFAOYSA-N 2-(4-methylpent-1-enyl)anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C=CCC(C)C)=CC=C3C(=O)C2=C1 YOUHDCYXXDRNLO-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 230000008929 regeneration Effects 0.000 description 4
- 238000011069 regeneration method Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052762 osmium Inorganic materials 0.000 description 3
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZTORCDJTFKLKCU-UHFFFAOYSA-N 1-(4-methylpentyl)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CCCC(C)C ZTORCDJTFKLKCU-UHFFFAOYSA-N 0.000 description 2
- BVEIKFLZWBDLJG-UHFFFAOYSA-N 1-butylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CCCC BVEIKFLZWBDLJG-UHFFFAOYSA-N 0.000 description 2
- PIABOMSCKRXHJL-UHFFFAOYSA-N 2-(4-methylpent-3-enyl)-1,4-dihydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1CC(CCC=C(C)C)=CC2 PIABOMSCKRXHJL-UHFFFAOYSA-N 0.000 description 2
- BMKLLNJUULWIIV-UHFFFAOYSA-N 2-(4-methylpentyl)-1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1CC(CCCC(C)C)CC2 BMKLLNJUULWIIV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005698 Diels-Alder reaction Methods 0.000 description 2
- HXQPUEQDBSPXTE-UHFFFAOYSA-N Diisobutylcarbinol Chemical compound CC(C)CC(O)CC(C)C HXQPUEQDBSPXTE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000374 eutectic mixture Substances 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 201000006747 infectious mononucleosis Diseases 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene Chemical class C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- HMXQIFUGFZEJEO-UHFFFAOYSA-N 1,2-dihydropyrrol-3-one Chemical compound O=C1CNC=C1 HMXQIFUGFZEJEO-UHFFFAOYSA-N 0.000 description 1
- JDQRYRLJZGMNIB-UHFFFAOYSA-N 1-hexylazepan-2-one Chemical compound CCCCCCN1CCCCCC1=O JDQRYRLJZGMNIB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HFAOGQINQCONCU-UHFFFAOYSA-N 2-(2,2-dimethylpropyl)anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(CC(C)(C)C)=CC=C3C(=O)C2=C1 HFAOGQINQCONCU-UHFFFAOYSA-N 0.000 description 1
- LJKDOMVGKKPJBH-UHFFFAOYSA-N 2-ethylhexyl dihydrogen phosphate Chemical compound CCCCC(CC)COP(O)(O)=O LJKDOMVGKKPJBH-UHFFFAOYSA-N 0.000 description 1
- IFHQWLHVCATXGU-UHFFFAOYSA-N 2-pentan-2-ylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)CCC)=CC=C3C(=O)C2=C1 IFHQWLHVCATXGU-UHFFFAOYSA-N 0.000 description 1
- WYBPLXLPOLAWTE-UHFFFAOYSA-N 2-pentylanthracene Chemical compound C1=CC=CC2=CC3=CC(CCCCC)=CC=C3C=C21 WYBPLXLPOLAWTE-UHFFFAOYSA-N 0.000 description 1
- JEGXLJDYOKKUNM-UHFFFAOYSA-N 3-(2-phenylethenyl)cyclohexa-3,5-diene-1,2-dione Chemical compound O=C1C(=O)C=CC=C1C=CC1=CC=CC=C1 JEGXLJDYOKKUNM-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical compound OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 description 1
- YWPRFYWNCPEOAL-UHFFFAOYSA-N 6-hexan-2-yl-1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC(C(C)CCCC)=CC=C2C(=O)C2=C1CCCC2 YWPRFYWNCPEOAL-UHFFFAOYSA-N 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- LSOTZYUVGZKSHR-UHFFFAOYSA-N anthracene-1,4-dione Chemical compound C1=CC=C2C=C3C(=O)C=CC(=O)C3=CC2=C1 LSOTZYUVGZKSHR-UHFFFAOYSA-N 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Inorganic materials [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 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
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229940060367 inert ingredients Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- IMXBRVLCKXGWSS-UHFFFAOYSA-N methyl 2-cyclohexylacetate Chemical compound COC(=O)CC1CCCCC1 IMXBRVLCKXGWSS-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- OVYTZAASVAZITK-UHFFFAOYSA-M sodium;ethanol;hydroxide Chemical compound [OH-].[Na+].CCO OVYTZAASVAZITK-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010457 zeolite 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/16—Quinones the quinoid structure being part of a condensed ring system containing three rings
- C07C50/20—Quinones the quinoid structure being part of a condensed ring system containing three rings with unsaturation outside the ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19816297A DE19816297A1 (de) | 1998-04-11 | 1998-04-11 | Verfahren zur Herstellung von Wasserstoffperoxid und Reaktionsträger zu seiner Durchführung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW531525B true TW531525B (en) | 2003-05-11 |
Family
ID=7864353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW088105454A TW531525B (en) | 1998-04-11 | 1999-04-06 | Method of producing hydrogen peroxide and reaction carriers therefor |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US6153169A (enExample) |
| EP (1) | EP1073607B1 (enExample) |
| JP (1) | JP4416321B2 (enExample) |
| KR (1) | KR100601009B1 (enExample) |
| CN (1) | CN1259232C (enExample) |
| AR (1) | AR014842A1 (enExample) |
| AT (1) | ATE326426T1 (enExample) |
| AU (1) | AU752501B2 (enExample) |
| BR (1) | BR9909563B1 (enExample) |
| CA (1) | CA2328106C (enExample) |
| DE (2) | DE19816297A1 (enExample) |
| ES (1) | ES2260909T3 (enExample) |
| ID (1) | ID29264A (enExample) |
| IL (1) | IL138211A (enExample) |
| NZ (1) | NZ506967A (enExample) |
| PL (1) | PL194883B1 (enExample) |
| RU (1) | RU2220903C2 (enExample) |
| TR (1) | TR200002856T2 (enExample) |
| TW (1) | TW531525B (enExample) |
| WO (1) | WO1999052819A1 (enExample) |
| ZA (1) | ZA200005562B (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE10038101A1 (de) * | 2000-08-04 | 2002-02-14 | Degussa | Verfahren zur Herstellung von 2-(4-Methyl-3-pentenyl)-anthrachinon |
| CN1317253C (zh) * | 2004-04-29 | 2007-05-23 | 中国石油化工股份有限公司 | 一种磁稳定床烷基蒽醌加氢方法 |
| US7547430B2 (en) * | 2005-08-31 | 2009-06-16 | Fmc Corporation | Auto-oxidation production of hydrogen peroxide via hydrogenation in a 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 |
| EP2589570A1 (en) | 2011-11-07 | 2013-05-08 | Solvay Sa | Process for the manufacture of hydrogen peroxide |
| KR102381010B1 (ko) * | 2014-05-30 | 2022-04-01 | 바스프 에스이 | 2,6- 및 2,7-이치환 안트라퀴논 유도체의 제조 |
| WO2015181283A1 (en) * | 2014-05-30 | 2015-12-03 | Basf Se | Preparation of 2,6- and 2,7-disubstituted anthraquinone derivates |
| CN104085859B (zh) * | 2014-07-31 | 2016-04-06 | 湖南兴鹏化工科技有限公司 | 用于蒽醌法过氧化氢生产工艺的工作液溶剂体系 |
| CN107539955B (zh) * | 2016-06-23 | 2020-12-08 | 中国石油化工股份有限公司 | 蒽醌法生产双氧水的溶剂体系、双向工作液及应用 |
| EP3543208A1 (en) * | 2018-03-19 | 2019-09-25 | Solvay Sa | Process for manufacturing an aqueous hydrogen peroxide solution |
| CL2021001192A1 (es) | 2020-05-28 | 2021-11-19 | Evonik Operations Gmbh | Dispositivo y proceso para producir peróxido de hidrógeno mediante un proceso de antraquinona |
| HUE061154T2 (hu) | 2020-10-21 | 2023-05-28 | Evonik Operations Gmbh | Eljárás 1,2-propándiol elõállítása propánból |
| CN116003235A (zh) * | 2021-10-21 | 2023-04-25 | 潍坊门捷化工有限公司 | 一种2-（4-甲基-3-戊烯基）蒽醌的合成方法 |
| CN116062700A (zh) * | 2021-10-29 | 2023-05-05 | 中国石油化工股份有限公司 | 一种过氧化氢生产方法和一种烷基蒽醌工作液 |
| CN116062702A (zh) * | 2021-10-29 | 2023-05-05 | 中国石油化工股份有限公司 | 一种多烷基蒽醌工作液及其应用 |
| CN117945351A (zh) * | 2022-10-31 | 2024-04-30 | 中国石油化工股份有限公司 | 一种用于蒽醌法生产双氧水的工作液 |
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| US2966397A (en) * | 1956-10-24 | 1960-12-27 | Fmc Corp | Production of hydrogen peroxide |
| DE1195279B (de) * | 1956-10-31 | 1965-06-24 | Edogawa Kagaku Kogyo Kabushiki | Verfahren zur Herstellung von Wasserstoff-peroxyd im Kreislauf |
| DE1112051B (de) * | 1957-10-12 | 1961-08-03 | Edogawa Kagaku Kogyo Kabushiki | Kreislaufverfahren zur Herstellung von Wasserstoffperoxyd |
| DE1106737B (de) * | 1958-12-19 | 1961-05-18 | Edogawa Kagaku Kogyo Kabushiki | Verfahren zur Herstellung von Wasserstoffperoxyd im Kreislauf |
| GB1252822A (enExample) * | 1969-06-24 | 1971-11-10 | ||
| AT304483B (de) * | 1970-05-13 | 1973-01-10 | Sandoz Ag | Verfahren zur Herstellung von Alkylphthalsäuren |
| CA973179A (en) * | 1970-10-09 | 1975-08-19 | E. I. Du Pont De Nemours And Company | Certain 1-alkyl-9,10-anthraquinones and their 5,6,7,8-tetrahydro derivatives and the use of the latter in the production of hydrogen peroxide |
| US4110353A (en) * | 1973-11-21 | 1978-08-29 | E. I. Du Pont De Nemours And Company | Process for the production of tetrahydroanthraquinones |
| US3998937A (en) * | 1974-03-14 | 1976-12-21 | E. I. Du Pont De Nemours And Company | 1-Alkyl-substituted-1,2,3,4-tetrahydroanthraquinones |
| US4374820A (en) * | 1981-07-29 | 1983-02-22 | E. I. Du Pont De Nemours And Company | Manufacture of H2 O2 |
| JPS58180452A (ja) * | 1982-04-14 | 1983-10-21 | Kawasaki Kasei Chem Ltd | アントラキノン誘導体 |
| JPS5951235A (ja) * | 1982-09-17 | 1984-03-24 | Kawasaki Kasei Chem Ltd | ２―（４―メチル―ペンチル）―アントラキノンの製造法 |
| SE459919C (sv) * | 1987-03-27 | 1991-03-25 | Eka Nobel Ab | Foerfarande foer framstaellning av vaeteperoxid genom reduktion och oxidation av en antrakinon |
| DE4013090A1 (de) * | 1990-04-25 | 1991-10-31 | Peroxid Chemie Gmbh | Verfahren zur herstellung von alkyltetrahydroanthrahydrochinon und diese enthaltende arbeitsloesungen fuer die wasserstoffperoxid-herstellung nach dem anthrachinonverfahren |
| 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 |
| SE9504327D0 (sv) * | 1995-12-04 | 1995-12-04 | Eka Nobel Ab | Method of treating a catalyst |
| DE19816297A1 (de) * | 1998-04-11 | 1999-10-21 | Degussa | Verfahren zur Herstellung von Wasserstoffperoxid und Reaktionsträger zu seiner Durchführung |
-
1998
- 1998-04-11 DE DE19816297A patent/DE19816297A1/de not_active Withdrawn
- 1998-10-20 US US09/175,729 patent/US6153169A/en not_active Expired - Lifetime
-
1999
- 1999-03-20 ES ES99917845T patent/ES2260909T3/es not_active Expired - Lifetime
- 1999-03-20 TR TR2000/02856T patent/TR200002856T2/xx unknown
- 1999-03-20 RU RU2000128028/15A patent/RU2220903C2/ru not_active IP Right Cessation
- 1999-03-20 IL IL13821199A patent/IL138211A/en not_active IP Right Cessation
- 1999-03-20 WO PCT/EP1999/001972 patent/WO1999052819A1/de not_active Ceased
- 1999-03-20 KR KR1020007011280A patent/KR100601009B1/ko not_active Expired - Fee Related
- 1999-03-20 CN CNB99804976XA patent/CN1259232C/zh not_active Expired - Lifetime
- 1999-03-20 EP EP99917845A patent/EP1073607B1/de not_active Expired - Lifetime
- 1999-03-20 DE DE59912359T patent/DE59912359D1/de not_active Expired - Lifetime
- 1999-03-20 CA CA2328106A patent/CA2328106C/en not_active Expired - Lifetime
- 1999-03-20 PL PL343456A patent/PL194883B1/pl not_active IP Right Cessation
- 1999-03-20 BR BRPI9909563-7A patent/BR9909563B1/pt not_active IP Right Cessation
- 1999-03-20 NZ NZ506967A patent/NZ506967A/xx unknown
- 1999-03-20 AT AT99917845T patent/ATE326426T1/de active
- 1999-03-20 JP JP2000543387A patent/JP4416321B2/ja not_active Expired - Fee Related
- 1999-03-20 AU AU35984/99A patent/AU752501B2/en not_active Ceased
- 1999-03-20 ID IDW20002314A patent/ID29264A/id unknown
- 1999-04-06 TW TW088105454A patent/TW531525B/zh not_active IP Right Cessation
- 1999-04-09 AR ARP990101653A patent/AR014842A1/es not_active Application Discontinuation
-
2000
- 2000-07-27 US US09/627,412 patent/US6355815B1/en not_active Expired - Lifetime
- 2000-10-10 ZA ZA200005562A patent/ZA200005562B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2220903C2 (ru) | 2004-01-10 |
| CA2328106A1 (en) | 1999-10-21 |
| US6355815B1 (en) | 2002-03-12 |
| PL343456A1 (en) | 2001-08-13 |
| KR20010042604A (ko) | 2001-05-25 |
| IL138211A0 (en) | 2001-10-31 |
| TR200002856T2 (tr) | 2001-02-21 |
| NZ506967A (en) | 2003-04-29 |
| WO1999052819A1 (de) | 1999-10-21 |
| CA2328106C (en) | 2010-05-18 |
| AU752501B2 (en) | 2002-09-19 |
| IL138211A (en) | 2004-06-01 |
| BR9909563A (pt) | 2000-12-19 |
| EP1073607B1 (de) | 2006-05-17 |
| JP4416321B2 (ja) | 2010-02-17 |
| AR014842A1 (es) | 2001-03-28 |
| DE59912359D1 (de) | 2007-06-28 |
| US6153169A (en) | 2000-11-28 |
| BR9909563B1 (pt) | 2009-01-13 |
| DE19816297A1 (de) | 1999-10-21 |
| PL194883B1 (pl) | 2007-07-31 |
| JP2002511377A (ja) | 2002-04-16 |
| CN1296461A (zh) | 2001-05-23 |
| ATE326426T1 (de) | 2006-06-15 |
| ES2260909T3 (es) | 2006-11-01 |
| ID29264A (id) | 2001-08-16 |
| AU3598499A (en) | 1999-11-01 |
| ZA200005562B (en) | 2002-06-26 |
| KR100601009B1 (ko) | 2006-07-19 |
| CN1259232C (zh) | 2006-06-14 |
| EP1073607A1 (de) | 2001-02-07 |
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