NL8204476A - Werkwijze voor de bereiding van parachinon- of orthochinonverbindingen, eventueel gealkoxyleerd of gearyloxyleerd, uitgaande van de overeenkomstige hydrochinon- respectievelijk pyrocatecholverbindingen. - Google Patents
Werkwijze voor de bereiding van parachinon- of orthochinonverbindingen, eventueel gealkoxyleerd of gearyloxyleerd, uitgaande van de overeenkomstige hydrochinon- respectievelijk pyrocatecholverbindingen. Download PDFInfo
- Publication number
- NL8204476A NL8204476A NL8204476A NL8204476A NL8204476A NL 8204476 A NL8204476 A NL 8204476A NL 8204476 A NL8204476 A NL 8204476A NL 8204476 A NL8204476 A NL 8204476A NL 8204476 A NL8204476 A NL 8204476A
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- NL
- Netherlands
- Prior art keywords
- formula
- group
- compound
- same meaning
- compounds
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Links
- -1 respectively Chemical class 0.000 title claims description 36
- 238000000034 method Methods 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title claims description 11
- WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical class O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 title claims description 4
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 title description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 title 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical class O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 23
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 229910001882 dioxygen Chemical class 0.000 claims description 18
- 238000007254 oxidation reaction Methods 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims description 16
- 229930195733 hydrocarbon Natural products 0.000 claims description 16
- 150000002430 hydrocarbons Chemical class 0.000 claims description 16
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 15
- YCIMNLLNPGFGHC-UHFFFAOYSA-N o-dihydroxy-benzene Natural products OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 14
- 230000003647 oxidation Effects 0.000 claims description 14
- 150000001879 copper Chemical class 0.000 claims description 12
- 239000012298 atmosphere Substances 0.000 claims description 11
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 9
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 9
- 229940045803 cuprous chloride Drugs 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000002274 desiccant Substances 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 101100440696 Caenorhabditis elegans cor-1 gene Proteins 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000005394 methallyl group Chemical group 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 16
- 239000001301 oxygen Substances 0.000 description 16
- 229910052760 oxygen Inorganic materials 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000010949 copper Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- WLDWSGZHNBANIO-UHFFFAOYSA-N 2',5'-Dihydroxyacetophenone Chemical compound CC(=O)C1=CC(O)=CC=C1O WLDWSGZHNBANIO-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000004699 copper complex Chemical class 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 150000004053 quinones Chemical class 0.000 description 3
- CLFRCXCBWIQVRN-UHFFFAOYSA-N 2,5-dihydroxybenzaldehyde Chemical compound OC1=CC=C(O)C(C=O)=C1 CLFRCXCBWIQVRN-UHFFFAOYSA-N 0.000 description 2
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
- VBYTYYWSXROOEY-UHFFFAOYSA-N 3,4-ditert-butylcyclohexa-3,5-diene-1,2-dione Chemical compound CC(C)(C)C1=C(C(C)(C)C)C(=O)C(=O)C=C1 VBYTYYWSXROOEY-UHFFFAOYSA-N 0.000 description 2
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 235000011132 calcium sulphate Nutrition 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- LPYUENQFPVNPHY-UHFFFAOYSA-N methoxycatechol Natural products COC1=CC=CC(O)=C1O LPYUENQFPVNPHY-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical class C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- CKLPUCARSNJTSJ-UHFFFAOYSA-N 1-(1,4-dihydroxynaphthalen-2-yl)ethanone Chemical compound C1=CC=CC2=C(O)C(C(=O)C)=CC(O)=C21 CKLPUCARSNJTSJ-UHFFFAOYSA-N 0.000 description 1
- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 1
- WXOYSNLFYSJUDB-UHFFFAOYSA-N 2-acetyl-3-methoxy-hydroquinone Natural products COC1=C(O)C=CC(O)=C1C(C)=O WXOYSNLFYSJUDB-UHFFFAOYSA-N 0.000 description 1
- PHMPPSWCMSVWGP-UHFFFAOYSA-N 2-acetyl-3-phenylmethoxycyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C(=O)C)=C1OCC1=CC=CC=C1 PHMPPSWCMSVWGP-UHFFFAOYSA-N 0.000 description 1
- PJZLSMMERMMQBJ-UHFFFAOYSA-N 3,5-ditert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC(O)=C(O)C(C(C)(C)C)=C1 PJZLSMMERMMQBJ-UHFFFAOYSA-N 0.000 description 1
- AQHGCOHCPFVVAP-UHFFFAOYSA-N 3-methoxy-5-[(4-nitrophenyl)methoxy]cyclohexa-3,5-diene-1,2-dione Chemical compound O=C1C(=O)C(OC)=CC(OCC=2C=CC(=CC=2)[N+]([O-])=O)=C1 AQHGCOHCPFVVAP-UHFFFAOYSA-N 0.000 description 1
- KZIFYYHSKBBEAR-UHFFFAOYSA-N 4-methyl-5-(4-nitrophenoxy)cyclohexa-3,5-diene-1,2-dione Chemical compound CC1=CC(=O)C(=O)C=C1OC1=CC=C([N+]([O-])=O)C=C1 KZIFYYHSKBBEAR-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- PWUBONDMIMDOQY-UHFFFAOYSA-N acetonitrile;hydrochloride Chemical compound Cl.CC#N PWUBONDMIMDOQY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000892 gravimetry Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- LSFYMYHEOPWITI-UHFFFAOYSA-N methyl 3,6-dioxocyclohexa-1,4-diene-1-carboxylate Chemical compound COC(=O)C1=CC(=O)C=CC1=O LSFYMYHEOPWITI-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/10—Polyhydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- 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
- C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring
-
- 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
- C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring
- C07C46/08—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring with molecular oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/02—Quinones with monocyclic quinoid structure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/38—Quinones containing —CHO or non—quinoid keto groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/122—Halides of copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Compounds Of Unknown Constitution (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8121606 | 1981-11-18 | ||
| FR8121606A FR2516505B1 (fr) | 1981-11-18 | 1981-11-18 | Nouveau systeme oxydant selectif a base de chlorure cuivreux et son application a l'oxydation des derives phenoliques en vue de l'obtention des derives quinoniques correspondants |
| FR8218607A FR2535713A1 (en) | 1982-11-05 | 1982-11-05 | Process for the preparation of alkoxylated or aryloxylated para- (or ortho-) quinones respectively from the corresponding hydroquinones or pyrocatechols. |
| FR8218607 | 1982-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8204476A true NL8204476A (nl) | 1983-06-16 |
Family
ID=26222628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8204476A NL8204476A (nl) | 1981-11-18 | 1982-11-18 | Werkwijze voor de bereiding van parachinon- of orthochinonverbindingen, eventueel gealkoxyleerd of gearyloxyleerd, uitgaande van de overeenkomstige hydrochinon- respectievelijk pyrocatecholverbindingen. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4486349A (it) |
| KR (1) | KR840002339A (it) |
| AU (1) | AU9066082A (it) |
| DE (1) | DE3242432A1 (it) |
| DK (1) | DK509982A (it) |
| ES (1) | ES517435A0 (it) |
| FI (1) | FI823921L (it) |
| GB (1) | GB2111981A (it) |
| GR (1) | GR78368B (it) |
| IL (1) | IL67293A0 (it) |
| IT (1) | IT1155373B (it) |
| LU (1) | LU84474A1 (it) |
| NL (1) | NL8204476A (it) |
| NO (1) | NO823749L (it) |
| SE (1) | SE8206479L (it) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5287555A (en) * | 1991-07-22 | 1994-02-15 | Motorola, Inc. | Power control circuitry for a TDMA radio frequency transmitter |
| US5502214A (en) * | 1993-07-19 | 1996-03-26 | Dana Farber Cancer Institute | 1,2-benzoquinones and methods for making and using same |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3213114A (en) * | 1962-06-19 | 1965-10-19 | Ethyl Corp | Preparation of quinones and hydroquinones |
| US3870731A (en) * | 1973-09-28 | 1975-03-11 | Goodyear Tire & Rubber | Oxidation of phenols and alkyl substituted phenols to their corresponding para-benzoquinone |
| US3987068A (en) * | 1975-07-28 | 1976-10-19 | E. I. Du Pont De Nemours And Company | Oxidation of monohydroxy aryl compounds to 1,4-quinones |
| DE2655826C2 (de) * | 1976-12-09 | 1983-09-01 | Haarmann & Reimer Gmbh, 3450 Holzminden | Verfahren zur Herstellung von Alkylaryläthern |
| FR2408570A1 (fr) * | 1977-06-27 | 1979-06-08 | Rhone Poulenc Ind | Procede de preparation de para-benzoquinone |
| DE2802863A1 (de) * | 1978-01-24 | 1979-07-26 | Hoechst Ag | Verfahren zur abtrennung von p-benzochinon aus den reaktionsprodukten der phenoloxydation |
| US4257968A (en) * | 1979-10-04 | 1981-03-24 | E. I. Du Pont De Nemours And Company | Oxidation of phenol to p-benzoquinone in acetonitrile/methanol cosolvent |
-
1982
- 1982-04-13 GR GR69791A patent/GR78368B/el unknown
- 1982-11-10 NO NO823749A patent/NO823749L/no unknown
- 1982-11-12 US US06/441,273 patent/US4486349A/en not_active Expired - Fee Related
- 1982-11-15 SE SE8206479A patent/SE8206479L/xx not_active Application Discontinuation
- 1982-11-15 GB GB08232571A patent/GB2111981A/en not_active Withdrawn
- 1982-11-16 FI FI823921A patent/FI823921L/fi not_active Application Discontinuation
- 1982-11-16 DK DK509982A patent/DK509982A/da not_active Application Discontinuation
- 1982-11-16 DE DE19823242432 patent/DE3242432A1/de not_active Withdrawn
- 1982-11-17 LU LU84474A patent/LU84474A1/fr unknown
- 1982-11-17 ES ES517435A patent/ES517435A0/es active Granted
- 1982-11-17 IL IL67293A patent/IL67293A0/xx unknown
- 1982-11-17 AU AU90660/82A patent/AU9066082A/en not_active Abandoned
- 1982-11-17 IT IT24300/82A patent/IT1155373B/it active
- 1982-11-18 NL NL8204476A patent/NL8204476A/nl not_active Application Discontinuation
- 1982-11-18 KR KR1019820005207A patent/KR840002339A/ko unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE8206479L (sv) | 1983-05-19 |
| IT1155373B (it) | 1987-01-28 |
| GB2111981A (en) | 1983-07-13 |
| IL67293A0 (en) | 1983-03-31 |
| ES8307699A1 (es) | 1983-08-16 |
| KR840002339A (ko) | 1984-06-25 |
| LU84474A1 (fr) | 1984-06-13 |
| ES517435A0 (es) | 1983-08-16 |
| FI823921A0 (fi) | 1982-11-16 |
| SE8206479D0 (sv) | 1982-11-15 |
| DK509982A (da) | 1983-05-19 |
| NO823749L (no) | 1983-05-19 |
| GR78368B (it) | 1984-09-26 |
| DE3242432A1 (de) | 1983-05-26 |
| IT8224300A1 (it) | 1984-05-17 |
| FI823921L (fi) | 1983-05-19 |
| AU9066082A (en) | 1983-05-26 |
| IT8224300A0 (it) | 1982-11-17 |
| US4486349A (en) | 1984-12-04 |
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