NO134948B - - Google Patents
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- Publication number
- NO134948B NO134948B NO722111A NO211172A NO134948B NO 134948 B NO134948 B NO 134948B NO 722111 A NO722111 A NO 722111A NO 211172 A NO211172 A NO 211172A NO 134948 B NO134948 B NO 134948B
- Authority
- NO
- Norway
- Prior art keywords
- water
- hydroperoxide
- reaction mixture
- pressure
- sulfuric acid
- Prior art date
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 50
- 239000011541 reaction mixture Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 150000002432 hydroperoxides Chemical class 0.000 claims description 2
- 150000001451 organic peroxides Chemical class 0.000 claims description 2
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 67
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 28
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 19
- 239000008096 xylene Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 10
- 239000003513 alkali Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 9
- 239000012535 impurity Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 150000002978 peroxides Chemical class 0.000 description 7
- -1 saturated aliphatic hydroperoxides Chemical class 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- OPUAWDUYWRUIIL-UHFFFAOYSA-N methanedisulfonic acid Chemical compound OS(=O)(=O)CS(O)(=O)=O OPUAWDUYWRUIIL-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 3
- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 description 2
- YWBMNCRJFZGXJY-UHFFFAOYSA-N 1-hydroperoxy-1,2,3,4-tetrahydronaphthalene Chemical compound C1=CC=C2C(OO)CCCC2=C1 YWBMNCRJFZGXJY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- XIBAZLLABMNRRJ-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene hydrogen peroxide Chemical compound OO.CC(C)C1=CC=C(C(C)C)C=C1 XIBAZLLABMNRRJ-UHFFFAOYSA-N 0.000 description 1
- GULLRFZPBAYTRP-UHFFFAOYSA-N 1-(2-phenylpropan-2-ylperoxy)-1,2,3,4-tetrahydronaphthalene Chemical compound C(C)(C)(C1=CC=CC=C1)OOC1CCCC2=CC=CC=C12 GULLRFZPBAYTRP-UHFFFAOYSA-N 0.000 description 1
- FGGUTDUGUGZLRR-UHFFFAOYSA-N 1-[4-methyl-2-[4-methyl-4-phenyl-2-(4-propan-2-ylphenyl)pentan-2-yl]peroxy-4-phenylpentan-2-yl]-4-propan-2-ylbenzene Chemical compound C1=CC(C(C)C)=CC=C1C(C)(OOC(C)(CC(C)(C)C=1C=CC=CC=1)C=1C=CC(=CC=1)C(C)C)CC(C)(C)C1=CC=CC=C1 FGGUTDUGUGZLRR-UHFFFAOYSA-N 0.000 description 1
- PWUXJMROLBIZHH-UHFFFAOYSA-N 1-[[diphenyl-[2-(2-phenylpropan-2-yl)phenyl]methyl]peroxy-diphenylmethyl]-2-(2-phenylpropan-2-yl)benzene Chemical compound C(C)(C)(C1=CC=CC=C1)C1=C(C=CC=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)OOC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=C(C=CC=C1)C(C)(C)C1=CC=CC=C1 PWUXJMROLBIZHH-UHFFFAOYSA-N 0.000 description 1
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical compound CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 1
- OVBAHQVEJDOPKX-UHFFFAOYSA-N 1-tert-butyl-2-[[(2-tert-butylphenyl)-diphenylmethyl]peroxy-diphenylmethyl]benzene Chemical compound CC(C)(C)C1=CC=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)OOC(C=1C(=CC=CC=1)C(C)(C)C)(C=1C=CC=CC=1)C1=CC=CC=C1 OVBAHQVEJDOPKX-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 description 1
- HKLZOALUTLRUOI-UHFFFAOYSA-N 8a-hydroperoxy-2,3,4,4a,5,6,7,8-octahydro-1h-naphthalene Chemical compound C1CCCC2CCCCC21OO HKLZOALUTLRUOI-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- OFGOFFRAWCXEFM-UHFFFAOYSA-N [2,5,7,7-tetramethyl-3-(2,5,7,7-tetramethyl-2-phenyloctan-3-yl)peroxyoctan-2-yl]benzene Chemical compound C(C)(C)(C1=CC=CC=C1)C(CC(CC(C)(C)C)C)OOC(CC(CC(C)(C)C)C)C(C)(C)C1=CC=CC=C1 OFGOFFRAWCXEFM-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000012969 di-tertiary-butyl peroxide Substances 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004557 technical material Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2129524A DE2129524C3 (de) | 1971-06-15 | 1971-06-15 | Fungizide Mittel auf Basis von Phenylhydrazono-imid azolenin-Derivaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134948B true NO134948B (it) | 1976-10-04 |
| NO134948C NO134948C (it) | 1977-01-12 |
Family
ID=5810771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO722111A NO134948C (it) | 1971-06-15 | 1972-06-14 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3925551A (it) |
| JP (1) | JPS5544722B1 (it) |
| AT (1) | AT316925B (it) |
| AU (1) | AU456953B2 (it) |
| BE (1) | BE784855A (it) |
| BR (1) | BR7203828D0 (it) |
| CA (1) | CA983040A (it) |
| CH (1) | CH532895A (it) |
| CS (1) | CS170189B2 (it) |
| DD (1) | DD109980A5 (it) |
| DE (1) | DE2129524C3 (it) |
| DK (1) | DK131080B (it) |
| ES (1) | ES403903A1 (it) |
| FR (1) | FR2141980B1 (it) |
| GB (1) | GB1339378A (it) |
| HU (1) | HU165004B (it) |
| IL (1) | IL39670A (it) |
| IT (1) | IT960687B (it) |
| NL (1) | NL7207996A (it) |
| NO (1) | NO134948C (it) |
| PL (1) | PL82651B1 (it) |
| RO (1) | RO62439A (it) |
| TR (1) | TR17671A (it) |
| ZA (1) | ZA724108B (it) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2864075B2 (ja) * | 1991-12-04 | 1999-03-03 | 富士写真フイルム株式会社 | イミダゾールアゾ色素およびそれを含有する熱転写色素供与材料 |
-
1971
- 1971-06-15 DE DE2129524A patent/DE2129524C3/de not_active Expired
-
1972
- 1972-06-01 CS CS3798A patent/CS170189B2/cs unknown
- 1972-06-07 AU AU43190/72A patent/AU456953B2/en not_active Expired
- 1972-06-08 RO RO197271192A patent/RO62439A/ro unknown
- 1972-06-12 NL NL7207996A patent/NL7207996A/xx not_active Application Discontinuation
- 1972-06-12 US US261828A patent/US3925551A/en not_active Expired - Lifetime
- 1972-06-12 IL IL7239670A patent/IL39670A/xx unknown
- 1972-06-13 DD DD163663A patent/DD109980A5/xx unknown
- 1972-06-13 AT AT507072A patent/AT316925B/de not_active IP Right Cessation
- 1972-06-13 TR TR17671A patent/TR17671A/xx unknown
- 1972-06-13 IT IT25627/72A patent/IT960687B/it active
- 1972-06-14 HU HUBA2757A patent/HU165004B/hu unknown
- 1972-06-14 BR BR3828/72A patent/BR7203828D0/pt unknown
- 1972-06-14 BE BE784855A patent/BE784855A/xx unknown
- 1972-06-14 DK DK295772AA patent/DK131080B/da unknown
- 1972-06-14 CA CA144,662A patent/CA983040A/en not_active Expired
- 1972-06-14 GB GB2781772A patent/GB1339378A/en not_active Expired
- 1972-06-14 CH CH885072A patent/CH532895A/de not_active IP Right Cessation
- 1972-06-14 ZA ZA724108A patent/ZA724108B/xx unknown
- 1972-06-14 NO NO722111A patent/NO134948C/no unknown
- 1972-06-14 PL PL1972156014A patent/PL82651B1/pl unknown
- 1972-06-15 JP JP7259094A patent/JPS5544722B1/ja active Pending
- 1972-06-15 FR FR727221653A patent/FR2141980B1/fr not_active Expired
- 1972-06-15 ES ES403903A patent/ES403903A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT960687B (it) | 1973-11-30 |
| BR7203828D0 (pt) | 1973-07-05 |
| BE784855A (it) | 1972-12-14 |
| FR2141980A1 (it) | 1973-01-26 |
| TR17671A (tr) | 1975-07-23 |
| ZA724108B (en) | 1973-04-25 |
| DK131080B (da) | 1975-05-26 |
| CA983040A (en) | 1976-02-03 |
| DE2129524A1 (de) | 1973-01-25 |
| AU4319072A (en) | 1973-12-13 |
| NL7207996A (it) | 1972-12-19 |
| NO134948C (it) | 1977-01-12 |
| CH532895A (de) | 1973-01-31 |
| AT316925B (de) | 1974-08-12 |
| JPS5544722B1 (it) | 1980-11-13 |
| AU456953B2 (en) | 1974-12-18 |
| ES403903A1 (es) | 1975-05-16 |
| DD109980A5 (it) | 1974-12-05 |
| IL39670A0 (en) | 1972-08-30 |
| IL39670A (en) | 1975-07-28 |
| US3925551A (en) | 1975-12-09 |
| PL82651B1 (it) | 1975-10-31 |
| RO62439A (fr) | 1978-02-15 |
| CS170189B2 (it) | 1976-08-27 |
| FR2141980B1 (it) | 1974-02-15 |
| DE2129524C3 (de) | 1981-07-23 |
| DK131080C (it) | 1975-10-27 |
| HU165004B (it) | 1974-06-28 |
| USB261828I5 (it) | 1975-01-28 |
| GB1339378A (en) | 1973-12-05 |
| DE2129524B2 (de) | 1980-10-09 |
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