NO126468B - - Google Patents
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- Publication number
- NO126468B NO126468B NO2385/69A NO238569A NO126468B NO 126468 B NO126468 B NO 126468B NO 2385/69 A NO2385/69 A NO 2385/69A NO 238569 A NO238569 A NO 238569A NO 126468 B NO126468 B NO 126468B
- Authority
- NO
- Norway
- Prior art keywords
- quinone
- quinol
- solution
- solvent
- hydrogen
- Prior art date
Links
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 77
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 62
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 50
- 239000000243 solution Substances 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 32
- 239000003054 catalyst Substances 0.000 claims description 24
- 239000007787 solid Substances 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 230000003647 oxidation Effects 0.000 claims description 14
- 238000007254 oxidation reaction Methods 0.000 claims description 14
- 239000000725 suspension Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 230000036571 hydration Effects 0.000 claims description 9
- 238000006703 hydration reaction Methods 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 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 description 7
- 150000004056 anthraquinones Chemical class 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims description 4
- 150000002978 peroxides Chemical class 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 3
- 125000004151 quinonyl group Chemical group 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 238000009825 accumulation Methods 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 239000011872 intimate mixture Substances 0.000 claims 1
- 239000003863 metallic catalyst Substances 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000003799 water insoluble solvent Substances 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 238000006722 reduction reaction Methods 0.000 description 8
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical group C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 150000004053 quinones Chemical class 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- VIDOPANCAUPXNH-UHFFFAOYSA-N 1,2,3-triethylbenzene Chemical compound CCC1=CC=CC(CC)=C1CC VIDOPANCAUPXNH-UHFFFAOYSA-N 0.000 description 2
- GNRPVZNNVOGXHD-UHFFFAOYSA-N 1,2-dimethylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(C)C(C)=CC=C3C(=O)C2=C1 GNRPVZNNVOGXHD-UHFFFAOYSA-N 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
- 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 description 2
- PXLXSNXYTNRKFR-UHFFFAOYSA-N 6-ethyl-1,2,3,4-tetrahydroanthracene-9,10-dione Chemical compound O=C1C2=CC(CC)=CC=C2C(=O)C2=C1CCCC2 PXLXSNXYTNRKFR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BDJXVNRFAQSMAA-UHFFFAOYSA-N quinhydrone Chemical compound OC1=CC=C(O)C=C1.O=C1C=CC(=O)C=C1 BDJXVNRFAQSMAA-UHFFFAOYSA-N 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 239000008096 xylene Substances 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
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ADHYTCPJVXOAJX-UHFFFAOYSA-N 1,3-dimethylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3C(=O)C2=C1 ADHYTCPJVXOAJX-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical group ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 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 description 1
- RATJDSXPVPAWJJ-UHFFFAOYSA-N 2,7-dimethylanthracene-9,10-dione Chemical compound C1=C(C)C=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 RATJDSXPVPAWJJ-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- MCYPCBFOVKMNDW-UHFFFAOYSA-N 2-butan-2-ylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)CC)=CC=C3C(=O)C2=C1 MCYPCBFOVKMNDW-UHFFFAOYSA-N 0.000 description 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 description 1
- WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-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
- BQUNPXRABCSKJZ-UHFFFAOYSA-N 2-propan-2-ylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3C(=O)C2=C1 BQUNPXRABCSKJZ-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- CPIVYSAVIPTCCX-UHFFFAOYSA-N 4-methylpentan-2-yl acetate Chemical compound CC(C)CC(C)OC(C)=O CPIVYSAVIPTCCX-UHFFFAOYSA-N 0.000 description 1
- HXQPUEQDBSPXTE-UHFFFAOYSA-N Diisobutylcarbinol Chemical compound CC(C)CC(O)CC(C)C HXQPUEQDBSPXTE-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- IMXBRVLCKXGWSS-UHFFFAOYSA-N methyl 2-cyclohexylacetate Chemical compound COC(=O)CC1CCCCC1 IMXBRVLCKXGWSS-UHFFFAOYSA-N 0.000 description 1
- RXTNIJMLAQNTEG-UHFFFAOYSA-N methylamyl acetate Natural products CCCCC(C)OC(C)=O RXTNIJMLAQNTEG-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940052881 quinhydrone Drugs 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B63—SHIPS OR OTHER WATERBORNE VESSELS; RELATED EQUIPMENT
- B63B—SHIPS OR OTHER WATERBORNE VESSELS; EQUIPMENT FOR SHIPPING
- B63B35/00—Vessels or similar floating structures specially adapted for specific purposes and not otherwise provided for
- B63B35/66—Tugs
- B63B35/70—Tugs for pushing
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B63—SHIPS OR OTHER WATERBORNE VESSELS; RELATED EQUIPMENT
- B63B—SHIPS OR OTHER WATERBORNE VESSELS; EQUIPMENT FOR SHIPPING
- B63B35/00—Vessels or similar floating structures specially adapted for specific purposes and not otherwise provided for
- B63B35/66—Tugs
- B63B35/665—Floating propeller units, i.e. a motor and propeller unit mounted in a floating box
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Combustion & Propulsion (AREA)
- Mechanical Engineering (AREA)
- Ocean & Marine Engineering (AREA)
- Cleaning Or Clearing Of The Surface Of Open Water (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Measurement Of Unknown Time Intervals (AREA)
- Road Paving Structures (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75988368A | 1968-09-16 | 1968-09-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO126468B true NO126468B (de) | 1973-02-12 |
Family
ID=25057314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2385/69A NO126468B (de) | 1968-09-16 | 1969-06-09 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3486476A (de) |
| JP (1) | JPS4824199B1 (de) |
| DE (1) | DE1929398B2 (de) |
| GB (1) | GB1218508A (de) |
| IE (1) | IE33151B1 (de) |
| NL (1) | NL6909004A (de) |
| NO (1) | NO126468B (de) |
| SE (1) | SE347482B (de) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3613628A (en) * | 1969-12-18 | 1971-10-19 | Emilio C Garcia | Apparatus and method of joining tug and barge in ocean push-towing |
| US3663046A (en) * | 1971-03-22 | 1972-05-16 | William S Pine Inc | Load distribution and anti-rotation mechanism |
| US3735722A (en) * | 1971-12-09 | 1973-05-29 | Interstate Oil Transport Co | Rigid disconnectable coupling for waterborne vessels |
| US4013032A (en) * | 1971-12-16 | 1977-03-22 | Bludworth Robert A | Ocean going push-towing combination |
| GB1418920A (en) * | 1971-12-16 | 1975-12-24 | Bludworth R A | Marine push transportation combination |
| US3815539A (en) * | 1972-10-16 | 1974-06-11 | Catug Corp | Single hull tug and barge construction |
| PL94484B1 (pl) * | 1974-10-19 | 1977-08-31 | Urzadzenie laczace jednostki plywajace w zestaw pchany przystosowany do eksploatacji po morskich drogach wodnych | |
| JPS5483290A (en) * | 1977-12-15 | 1979-07-03 | Aoishin Kensetsu Kk | Cargoohandling boat |
| US4341174A (en) * | 1980-04-22 | 1982-07-27 | The United States Of America As Represented By The Secretary Of The Navy | Bow dock |
| US4356784A (en) * | 1980-12-22 | 1982-11-02 | Marine Industrie Limitee | Integrated tug-barge vessel |
| JPH045179Y2 (de) * | 1988-03-07 | 1992-02-14 | ||
| US5746150A (en) * | 1995-02-17 | 1998-05-05 | Beaulac; Daniel E. | Boat for use with a personal watercraft |
| US6053790A (en) * | 1998-03-31 | 2000-04-25 | Langford; Frederick | Train coupleable flotation tube for waterslides |
| CA2997714C (en) | 2017-03-17 | 2024-05-21 | David A. Arias | Infant float |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3345970A (en) * | 1966-03-28 | 1967-10-10 | Long Louis H De | Boat and barge combination |
| US3362372A (en) * | 1966-08-01 | 1968-01-09 | Earl A. Peterson | Integrated barge and tugboat |
-
1968
- 1968-09-16 US US759883A patent/US3486476A/en not_active Expired - Lifetime
-
1969
- 1969-06-09 NO NO2385/69A patent/NO126468B/no unknown
- 1969-06-09 GB GB29069/69D patent/GB1218508A/en not_active Expired
- 1969-06-09 IE IE788/69A patent/IE33151B1/xx unknown
- 1969-06-10 DE DE19691929398 patent/DE1929398B2/de active Pending
- 1969-06-11 SE SE08319/69A patent/SE347482B/xx unknown
- 1969-06-12 NL NL6909004A patent/NL6909004A/xx unknown
- 1969-06-16 JP JP44046914A patent/JPS4824199B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IE33151L (en) | 1970-03-16 |
| DE1929398A1 (de) | 1970-04-23 |
| IE33151B1 (en) | 1974-04-03 |
| US3486476A (en) | 1969-12-30 |
| GB1218508A (en) | 1971-01-06 |
| JPS4824199B1 (de) | 1973-07-19 |
| SE347482B (de) | 1972-08-07 |
| DE1929398B2 (de) | 1972-04-06 |
| NL6909004A (de) | 1970-03-18 |
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