GB867679A - Improved process for the preparation of hydrogen peroxide - Google Patents
Improved process for the preparation of hydrogen peroxideInfo
- Publication number
- GB867679A GB867679A GB29850/59A GB2985059A GB867679A GB 867679 A GB867679 A GB 867679A GB 29850/59 A GB29850/59 A GB 29850/59A GB 2985059 A GB2985059 A GB 2985059A GB 867679 A GB867679 A GB 867679A
- Authority
- GB
- United Kingdom
- Prior art keywords
- line
- solution
- oxidation
- added
- working solution
- 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
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title abstract 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 6
- 230000003647 oxidation Effects 0.000 abstract 6
- 238000007254 oxidation reaction Methods 0.000 abstract 6
- 239000012224 working solution Substances 0.000 abstract 6
- 239000000243 solution Substances 0.000 abstract 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 238000005984 hydrogenation reaction Methods 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 229910052763 palladium Inorganic materials 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 239000000908 ammonium hydroxide Substances 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 abstract 2
- 239000007789 gas Substances 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 2
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 239000008096 xylene Substances 0.000 abstract 2
- 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 abstract 1
- 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 abstract 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 abstract 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- -1 air Chemical compound 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 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 abstract 1
- 150000004056 anthraquinones Chemical class 0.000 abstract 1
- 239000011324 bead Substances 0.000 abstract 1
- 239000000920 calcium hydroxide Substances 0.000 abstract 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000003610 charcoal Substances 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- 239000012153 distilled water Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 abstract 1
- 239000000347 magnesium hydroxide Substances 0.000 abstract 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- ZWRUINPWMLAQRD-UHFFFAOYSA-N n-Nonyl alcohol Natural products CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 abstract 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 abstract 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 230000002195 synergetic effect Effects 0.000 abstract 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)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
<PICT:0867679/III/1> In the production of hydrogen peroxide by the successive hydrogenation and oxidation of a 9:10-anthraquinone or 5:6:7:8-tetrahydro-9:10-anthraquinone alkylated in only the 1-, 2-, 3- or 4-position (or mixtures thereof) dissolved in an inert water-immiscible solvent followed by extraction of the hydrogen peroxide formed with water, oxidation with elemental oxygen is effected in the presence of between 0.002 and 0.25% by weight of the working solution of a water-soluble inorganic alkaline substance, whereby the oxidation of the corresponding tetrahydroanthrahydroquinone present is accelerated. The alkyl group may be a methyl, ethyl, propyl or isobutyl group, and the alkaline substance may be sodium carbonate or ammonium, sodium, potassium, calcium or magnesium hydroxide. The solvent may contain a component dissolving the quinone, e.g. benzene, toluene or xylene, a component dissolving the hydroquinone, e.g. cyclohexanol, methyl cyclohexanol, or amyl, octyl, nonyl or decyl alcohol, and a synergistic solvent such as acetophenone. The initial working solution may contain a mixture of anthraquinone and tetrahydroanthraquinone only. As shown, the working solution is introduced through line 1 into reduction chamber 2 maintained at 20-50 DEG C. under a pressure of 1-5 p.s.i.g. The hydrogenation catalyst, e.g. palladium or platinum on a solid support, preferably 5% by weight of palladium on a charcoal or alumina carrier, is also added through line 1. Hydrogen is forced by pump 3 through line 4 into the bottom of chamber 2, and is released from the top through line 5 to the suction side of pump 3. Additional hydrogen is added via line 6. The hydrogenated solution is discharged from chamber 2 through line 7 into a centrifuge 8 wherein the catalyst is separated and returned via line 9 to chamber 2, while the solution flows through line 11 into after-cooler 12 and then through line 13 into oxidation tower 14 filled with Berl saddles or glass beads. The oxidation catalyst, preferably ammonium or sodium hydroxide, may be added through line 10 or introduced directly into tower 14. Gas containing free oxygen, e.g. air, is introduced into tower 14 by compressor 15 and line 16, while exhausted gas is released through line 17 and valve 18. Acid, such as sulphuric or phosphoric acid, to suppress emulsion-forming tendency is added through line 21 to the solution withdrawn through line 19. The solution passes to centrifugal extractor 22 to which distilled water is fed via line 23, and the hydrogen peroxide solution is withdrawn via line 24, the remaining working solution passing back to chamber 2 via lines 25, 26, loss being replaced through line 27. In Example 1, the working solution comprises (by weight) 34.1 parts acetophenone, 27.1 parts capryl alcohol, and 23.7 parts xylene, and contains 15.1% of a mixture of 2-ethyltetrahydroanthraquinone (61%) and 2-ethylanthraquinone (39%). 0.5% of a hydrogenation catalyst consisting of 5% by weight of palladium on a carbon carrier is used, while 0.03 parts by weight of sodium hydroxide is added to the working solution prior to oxidation. 0.05% of sulphuric acid is added to the oxidized solution. Examples 2 to 6 are similar, Examples 3 and 4 using ammonia and Examples 5 and 6 using sodium carbonate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US867679XA | 1958-10-06 | 1958-10-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB867679A true GB867679A (en) | 1961-05-10 |
Family
ID=22200770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB29850/59A Expired GB867679A (en) | 1958-10-06 | 1959-09-01 | Improved process for the preparation of hydrogen peroxide |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB867679A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2432791A1 (en) * | 1978-04-13 | 1980-02-29 | Sodeco Compteurs De Geneve | SMALL ELECTRIC MOTOR |
| EP0750037A2 (en) | 1989-08-16 | 1996-12-27 | Cetus Oncology Corporation | TNF-convertase and method measuring inhibition of TNF convertase |
| CN109678121A (en) * | 2017-10-19 | 2019-04-26 | 中国石油化工股份有限公司 | A kind of efficient hydrogenation process and system of hydrogen dioxide solution production by anthraquinone process |
| CN111115584A (en) * | 2020-01-02 | 2020-05-08 | 黎明化工研究设计院有限责任公司 | Oxidation tower for preparing hydrogen peroxide by anthraquinone process |
| CN111732083A (en) * | 2020-05-26 | 2020-10-02 | 湖北三里枫香科技有限公司 | Fluidized bed hydrogen peroxide process |
| CN111977615A (en) * | 2020-07-13 | 2020-11-24 | 中国空分工程有限公司 | Efficient hydrogen peroxide solution production hydrogenation system |
-
1959
- 1959-09-01 GB GB29850/59A patent/GB867679A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2432791A1 (en) * | 1978-04-13 | 1980-02-29 | Sodeco Compteurs De Geneve | SMALL ELECTRIC MOTOR |
| EP0750037A2 (en) | 1989-08-16 | 1996-12-27 | Cetus Oncology Corporation | TNF-convertase and method measuring inhibition of TNF convertase |
| CN109678121A (en) * | 2017-10-19 | 2019-04-26 | 中国石油化工股份有限公司 | A kind of efficient hydrogenation process and system of hydrogen dioxide solution production by anthraquinone process |
| CN111115584A (en) * | 2020-01-02 | 2020-05-08 | 黎明化工研究设计院有限责任公司 | Oxidation tower for preparing hydrogen peroxide by anthraquinone process |
| CN111115584B (en) * | 2020-01-02 | 2024-04-05 | 黎明化工研究设计院有限责任公司 | Oxidation tower for preparing hydrogen peroxide by anthraquinone process |
| CN111732083A (en) * | 2020-05-26 | 2020-10-02 | 湖北三里枫香科技有限公司 | Fluidized bed hydrogen peroxide process |
| CN111977615A (en) * | 2020-07-13 | 2020-11-24 | 中国空分工程有限公司 | Efficient hydrogen peroxide solution production hydrogenation system |
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