SU676159A3 - Способ получени пирокатехина и гидрохинона - Google Patents
Способ получени пирокатехина и гидрохинонаInfo
- Publication number
- SU676159A3 SU676159A3 SU772556948A SU2556948A SU676159A3 SU 676159 A3 SU676159 A3 SU 676159A3 SU 772556948 A SU772556948 A SU 772556948A SU 2556948 A SU2556948 A SU 2556948A SU 676159 A3 SU676159 A3 SU 676159A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- phenol
- reaction
- solution
- hydroquinone
- Prior art date
Links
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 title claims description 20
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 29
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 claims description 17
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 8
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- -1 for example Chemical class 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 229940090181 propyl acetate Drugs 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XEPXTKKIWBPAEG-UHFFFAOYSA-N 1,1-dichloropropan-1-ol Chemical compound CCC(O)(Cl)Cl XEPXTKKIWBPAEG-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- MMCOUVMKNAHQOY-UHFFFAOYSA-N carbonoperoxoic acid Chemical compound OOC(O)=O MMCOUVMKNAHQOY-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical group CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2658943A DE2658943C3 (de) | 1976-12-24 | 1976-12-24 | Verfahren zur Herstellung von Brenzkatechin und Hydrochinon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU676159A3 true SU676159A3 (ru) | 1979-07-25 |
Family
ID=5996705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772556948A SU676159A3 (ru) | 1976-12-24 | 1977-12-21 | Способ получени пирокатехина и гидрохинона |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4182917A (enExample) |
| JP (1) | JPS585890B2 (enExample) |
| BE (1) | BE862236A (enExample) |
| CA (1) | CA1090827A (enExample) |
| CH (1) | CH630590A5 (enExample) |
| DE (1) | DE2658943C3 (enExample) |
| FR (1) | FR2375174A1 (enExample) |
| GB (1) | GB1569670A (enExample) |
| IL (1) | IL53664A (enExample) |
| IT (1) | IT1093074B (enExample) |
| NL (1) | NL7714193A (enExample) |
| SU (1) | SU676159A3 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3031736A1 (de) * | 1980-08-22 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von brenzkatechin und hydrochinon |
| DE3308769C2 (de) * | 1983-03-11 | 1985-01-24 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Dihydroxybenzolen |
| DE3308726C2 (de) * | 1983-03-11 | 1991-01-24 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Dihydroxybenzolen |
| DE3308763C2 (de) * | 1983-03-11 | 1985-01-24 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Dihydroxybenzolen |
| US4588845A (en) * | 1983-07-18 | 1986-05-13 | Fmc Corporation | Oxidation of unsaturated organic compounds with hydrogen peroxide |
| DE3632075A1 (de) * | 1986-09-20 | 1988-03-24 | Degussa | Verfahren zur herstellung von trihydroxy- bzw. alkoxyhydroxybenzolen |
| FR2700333B1 (fr) * | 1993-01-08 | 1995-03-10 | Rhone Poulenc Chimie | Procédé de préparation de composés aromatiques dihydroxyles. |
| DE102010008393A1 (de) | 2010-02-10 | 2011-10-06 | Technische Universität Dresden | Substrat zur Bodenverbesserung mit Wasser speichernder Eigenschaft, Verfahren zur Herstellung und dessen Verwendung |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL129007C (enExample) * | 1965-04-09 | 1900-01-01 | ||
| US3488395A (en) * | 1965-10-04 | 1970-01-06 | Ici Ltd | Oxidation process |
| FR1479354A (fr) * | 1966-03-15 | 1967-05-05 | Rhone Poulenc Sa | Procédé d'obtention de polyphénols |
| GB1167732A (en) * | 1966-07-25 | 1969-10-22 | Ici Ltd | Oxidation of Aromatic Hydrocarbons |
| FR2071464A5 (enExample) * | 1969-12-30 | 1971-09-17 | Rhone Poulenc Sa | |
| DE2150657C3 (de) * | 1971-07-17 | 1978-10-26 | Brichima S.P.A., Mailand (Italien) | Verfahren zur Herstellung einer Mischung aus Brenzcatechin und Hydrochinon |
| JPS5238023B2 (enExample) * | 1973-11-10 | 1977-09-27 | ||
| CA1024165A (en) * | 1972-12-25 | 1978-01-10 | Agency Of Industrial Science And Technology, Ministry Of International Trade And Industry | Method for manufacture of dihydric phenols |
| US3950437A (en) * | 1972-12-25 | 1976-04-13 | Oxirane Chemical Co. | Method for manufacture of dihydric phenols |
| JPS5833207B2 (ja) * | 1975-08-28 | 1983-07-18 | 工業技術院長 | ニカフエノ−ルノセイゾウホウホウ |
-
1976
- 1976-12-24 DE DE2658943A patent/DE2658943C3/de not_active Expired
-
1977
- 1977-12-05 US US05/857,622 patent/US4182917A/en not_active Expired - Lifetime
- 1977-12-19 GB GB52679/77A patent/GB1569670A/en not_active Expired
- 1977-12-20 CH CH1569777A patent/CH630590A5/de not_active IP Right Cessation
- 1977-12-20 IT IT52280/77A patent/IT1093074B/it active
- 1977-12-21 SU SU772556948A patent/SU676159A3/ru active
- 1977-12-21 NL NL7714193A patent/NL7714193A/xx not_active Application Discontinuation
- 1977-12-21 IL IL53664A patent/IL53664A/xx unknown
- 1977-12-21 JP JP52153066A patent/JPS585890B2/ja not_active Expired
- 1977-12-22 CA CA293,774A patent/CA1090827A/en not_active Expired
- 1977-12-23 BE BE2056546A patent/BE862236A/xx not_active IP Right Cessation
- 1977-12-23 FR FR7739101A patent/FR2375174A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IL53664A (en) | 1982-03-31 |
| CH630590A5 (de) | 1982-06-30 |
| CA1090827A (en) | 1980-12-02 |
| DE2658943C3 (de) | 1982-02-18 |
| US4182917A (en) | 1980-01-08 |
| NL7714193A (nl) | 1978-06-27 |
| FR2375174A1 (fr) | 1978-07-21 |
| GB1569670A (en) | 1980-06-18 |
| JPS585890B2 (ja) | 1983-02-02 |
| BE862236A (fr) | 1978-06-23 |
| IL53664A0 (en) | 1978-03-10 |
| FR2375174B1 (enExample) | 1983-12-02 |
| DE2658943A1 (de) | 1978-07-06 |
| DE2658943B2 (de) | 1979-03-15 |
| IT1093074B (it) | 1985-07-19 |
| JPS5379826A (en) | 1978-07-14 |
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