PL182675B1 - Sposób katalitycznego utleniania węglowodorów izoalkiloaromatycznych - Google Patents
Sposób katalitycznego utleniania węglowodorów izoalkiloaromatycznychInfo
- Publication number
- PL182675B1 PL182675B1 PL96313418A PL31341896A PL182675B1 PL 182675 B1 PL182675 B1 PL 182675B1 PL 96313418 A PL96313418 A PL 96313418A PL 31341896 A PL31341896 A PL 31341896A PL 182675 B1 PL182675 B1 PL 182675B1
- Authority
- PL
- Poland
- Prior art keywords
- aromatic hydrocarbons
- oxidising
- isoalkyl
- salt
- tbab
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 150000002576 ketones Chemical class 0.000 claims abstract description 6
- 150000001298 alcohols Chemical class 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 150000002978 peroxides Chemical class 0.000 claims abstract description 5
- 125000005210 alkyl ammonium group Chemical group 0.000 claims abstract description 4
- 239000010949 copper Substances 0.000 claims abstract description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052802 copper Inorganic materials 0.000 claims abstract description 3
- 239000007791 liquid phase Substances 0.000 claims abstract description 3
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 150000001868 cobalt Chemical class 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- -1 alkyl phosphonium salt Chemical class 0.000 abstract description 5
- 239000002184 metal Substances 0.000 abstract description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 150000002696 manganese Chemical class 0.000 abstract 1
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 16
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 10
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- 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 5
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 description 4
- TVYVQNHYIHAJTD-UHFFFAOYSA-N 2-propan-2-ylnaphthalene Chemical compound C1=CC=CC2=CC(C(C)C)=CC=C21 TVYVQNHYIHAJTD-UHFFFAOYSA-N 0.000 description 4
- GWLLTEXUIOFAFE-UHFFFAOYSA-N 2,6-diisopropylnaphthalene Chemical compound C1=C(C(C)C)C=CC2=CC(C(C)C)=CC=C21 GWLLTEXUIOFAFE-UHFFFAOYSA-N 0.000 description 3
- 101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 description 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
- 150000001451 organic peroxides Chemical class 0.000 description 3
- XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical compound C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 2
- QLPNXSSDHYYKBS-UHFFFAOYSA-N p-t-butylisopropylbenzene Natural products CC(C)C1=CC=C(C(C)(C)C)C=C1 QLPNXSSDHYYKBS-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 1
- DSCHOXDNLZEJKS-UHFFFAOYSA-L decanoate;iron(2+) Chemical compound [Fe+2].CCCCCCCCCC([O-])=O.CCCCCCCCCC([O-])=O DSCHOXDNLZEJKS-UHFFFAOYSA-L 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/16—Peroxy compounds the —O—O— group being bound between two carbon atoms not further substituted by oxygen atoms, i.e. peroxides
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0239—Quaternary ammonium compounds
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0255—Phosphorus containing compounds
- B01J31/0267—Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen
- B01J31/0268—Phosphonium compounds, i.e. phosphine with an additional hydrogen or carbon atom bonded to phosphorous so as to result in a formal positive charge on phosphorous
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/36—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in compounds containing six-membered aromatic rings
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Sposób katalitycznego utleniania weglowodorów izoalkiloaromatycznych tlenem w fazie cieklej do nadtlenków, ketonów i alkoholi, znamienny tym, ze stosuje sie katalizator zlozony z soli miedzi lub kobaltu, korzystnie chlorku lub stearynianu i czwartorzedowej soli oniowej, korzystnie alkiloamoniowej lub alkilofosfoniowej i proces prowadzi sie w temperaturze 60-120°C przez 2-20 godzin. PL
Description
Przedmiotem wynalazku jest sposób katalitycznego utleniania węglowodorów izoalkiloaromatycznych, zwłaszcza takich jak kumen, p-tert-butylo-kumen (TBK), 2-izopropylonaftalen (2IPN) i 2,6-diizopropylonaftalen (2,6-DIPN) do nadtlenków organicznych oraz ketonów i alkoholi.
Utlenianie węglowodorów izoalkiloaromatycznych do nadtlenków organicznych jest procesem o dużym znaczeniu przemysłowym i stosowane jest głównie do wytwarzania wodoronadtlenków izoalkiloaromatycznych, których rozkład prowadzi do wytworzenia odpowiednich związków hydroksyaromatycznych.
Z polskiego opisu patentowego nr 156 813 znany jest sposób otrzymywania nadtlenku dikumylowego w wyniku reakcji kumenu z wodoronadtlenkiem kumylowym oraz z japońskiego opisu patentowego nr 6 049 191 sposób otrzymywania nadtlenku dikumylowego w reakcji kondensacji wodoronadtlenku kumylowego z 2-fenylo-2-propanolem.
Znany jest również z patentu czeskiego nr 198 676 sposób otrzymywania nadtlenku dikumylowego, 2-fenylo-2-propanolu i acetofenonu przez bezpośrednie utlenianie kumenu powietrzem wobec kaprynianu żelaza w temperaturze 94°C. Proces ten przebiega jednak z małą szybkością. Po 65 h otrzymano produkt zawierający 21,7% nadtlenku dikumylowego, 12,5% acetofenonu i 22,2% 2-fenylo-2-propanolu.
Ponadto znany jest sposób otrzymywania nadtlenku di(2-izopropylonaftylowego), alkoholu 2-izopropylonaftalenu tlenem, wobec azotanu miedzi (II) oraz azodiizobutyronitrylu w temperaturze 95°C. Po 68 h otrzymuje się produkt zawierający 34,1 % mol. nadtlenku di(2-izopropylonaftylowego), 9,4% mol. alkoholu 2-izopropylonaftylowego oraz 12,2% mol. 2-acetylonaftalenu (Neftekhimiya, tom 11,1971, str. 862-866).
Wszystkie te znane sposoby charakteryzują się bardzo długimi czasami reakcji (powyżej 10 godzin) i niezadowalającą konwersją wyjściowego węglowodoru, nie przekraczającą zazwyczaj 60%. W związku z tym ich praktyczna stosowalność jest ograniczona.
Sposób katalitycznego utleniania węglowodorów izoalkiloaromatycznych tlenem w fazie ciekłej do nadtlenków, ketonów i alkoholi, według wynalazku polega na tym, że jako katalizator utleniania stosuje się katalizator złożony z soli miedzi lub kobaltu, korzystnie chlorku lub stearynianu i czwartorzędowej soli oniowej, korzystnie alkiloamoniowej lub alkilofosfoniowej. Proces prowadzi się w temperaturze 60-120°C przez 2-20 godzin.
W sposobie tym można, dobierając odpowiednio warunki utleniania, wytwarzać nadtlenki organiczne - zawartość w produkcie około 30% i/lub odpowiednie alkohole i ketony - zawartości w produkcie ponad 45% przy krótkich czasach reakcji.
Przykładl
Do reaktora szklanego o pojemności 40 cm3, zaopatrzonego w mieszadło, chłodnicę zwrotną, barbotkę, termometr oraz płaszcz grzejny wprowadza się 0,28 mola kumenu, 2,56 · 104 mola dwuwodnego chlorku miedzi (II) i 5,36 · 106 mola bromku tetrabutyloamoniowego (TBAB) a na182 675 stępnie ogrzewa się do temperatury 110°C i poddaje działaniu tlenu cząsteczkowego, przepuszczanego z szybkością 15 dm3/h, przez 12 godzin. Wytworzony produkt zawiera 32,5% nadtlenku dikumylowego, 18,6% 2-fenylo-2-propanolu i 23,6% acetofenonu.
Przykłady II-XII
Postępując tak jak w przykładzie I uzyskuje się z różnych surowców produkty o składzie podanym w tabeli.
182 675
| Skłdd produktu | alkohol [% wag.] | 37,0 | 21,6 | 39,0 | 37,0 | 39,0 | 38,4 | © r- CO | 35,0 | 31,2 | 32,4 | nie oznaczano |
| keton % wag.] | 41,0 | 18,2 | 16,4 | © 4 | 23,4 | 28,6 | l 35,0 | 29,0 | UD~ CO | 28,7 | nee oznaczano | |
| nadtlenek [% wag.] | 15,0 | 22,6 | 10,7 | 15,0 | r- | 11,0 | Tt 2 | 19,0 | 00 kO | 4 C~ | 20,5 (suma nadtlenków) | |
| Ukted katalityczny | Sól oniowa |moM05] | 5,32 TBAB | 3 e CO UD | 53,20 TBAB | 5,32 TBAB | 5,32 TBAB | 5,32 TBAB | Tt 0 tzi K < 1 ♦ 2 CO ud | O i£ £ * * 2 co ud | 5,32 TBAB | 5,32 TBAB | 5,32 TBAB |
| Sól metalu przejść, [mol-103] | O CM 2 CM H U 3 U ko UD 2 | 0 CM £ 2 CM U □ u kO 2 © | O CM £ 2 CM U 3 U © ri | O CM 2 CM O 3 U ko UD ri | CM U 0 u 0 υγ ri | 2,156 stearyrnan Cu(II) | 0 CM £ 2 CM U 3 O kO UD 2 | 0 CM 2 CM U □ 0 kO UD^ 2 | O CM W 2 CM U 3 U 0 UD 2 | O CM £ 2 CM U 3 U 0 υγ 2 | O CM £ 2 CM U 3 U Ό UD ri | |
| Czas [h] | 8,5 | 8,5 | <3 ci | © UD | 5,0 | © kO | UD | 2,5 | © | |||
| Przepływ tlenu [dm3/h] | UD | 2 | UD | UD | UD | UD | UD | UD | UD | UD | UD | |
| Tempe- ratura [°C] | © | © | 70 | © | © | 2 | © | © | © | © | © T—4 | |
| Surowiec | kumen | kumen | kumen | kumen | kumen | kumen | kumen | kumen | 2IPN | TBK | 2,6-DIPN | |
| Przykład | > | > | > | ΠΛ | > | IX | IX | ΠΧ |
* TBAHSO4 - wodorosirccznn tetrabutyloamoniowy **TBPhCl - chlorek tetrabutylofosfoniowy
Departament Wydawnictw UP RP. Nakład 50 egz. Cena 2,00 zł.
Claims (1)
- Zastrzeżenie patentoweSposób katalitycznego utleniania węglowodorów izoalkiloaromatycznych tlenem w fazie ciekłej do nadtlenków, ketonów i alkoholi, znamienny tym, że stosuje się katalizator złożony z soli miedzi lub kobaltu, korzystnie chlorku lub stearynianu i czwartorzędowej soli oniowej, korzystnie alkiloamoniowej lub alkilofosfoniowej i proces prowadzi się w temperaturze 60-120°C przez 2-20 godzin.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL96313418A PL182675B1 (pl) | 1996-03-20 | 1996-03-20 | Sposób katalitycznego utleniania węglowodorów izoalkiloaromatycznych |
| EP97104444A EP0796835B1 (de) | 1996-03-20 | 1997-03-15 | Verfahren zur Oxidation isoalkyl-aromatischer Kohlenwasserstoffe und Katalysator zur Durchführung des Verfahrens |
| DE59701685T DE59701685D1 (de) | 1996-03-20 | 1997-03-15 | Verfahren zur Oxidation isoalkyl-aromatischer Kohlenwasserstoffe und Katalysator zur Durchführung des Verfahrens |
| JP9105076A JPH1059883A (ja) | 1996-03-20 | 1997-03-19 | イソアルキル芳香族炭化水素を酸化する方法及びその方法を実施するための触媒 |
| US08/821,019 US5990357A (en) | 1996-03-20 | 1997-03-19 | Process for the oxidation of isoalkylaromatic hydrocarbons, and catalyst for the execution of the process |
| CZ1997832A CZ293692B6 (cs) | 1996-03-20 | 1997-03-19 | Způsob katalytické oxidace izoalkylaromatických uhlovodíků a katalyzátor pro provádění tohoto způsobu |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL96313418A PL182675B1 (pl) | 1996-03-20 | 1996-03-20 | Sposób katalitycznego utleniania węglowodorów izoalkiloaromatycznych |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL313418A1 PL313418A1 (en) | 1997-09-29 |
| PL182675B1 true PL182675B1 (pl) | 2002-02-28 |
Family
ID=20067135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL96313418A PL182675B1 (pl) | 1996-03-20 | 1996-03-20 | Sposób katalitycznego utleniania węglowodorów izoalkiloaromatycznych |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5990357A (pl) |
| EP (1) | EP0796835B1 (pl) |
| JP (1) | JPH1059883A (pl) |
| CZ (1) | CZ293692B6 (pl) |
| DE (1) | DE59701685D1 (pl) |
| PL (1) | PL182675B1 (pl) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7423187B1 (en) | 2003-03-10 | 2008-09-09 | Gradient Technology | Recovery of TNT and RDX from bulk composition B explosives |
| DE10326917A1 (de) * | 2003-06-16 | 2005-02-10 | Bayer Chemicals Ag | Herstellung von fluorhaltigen Acetophenonen |
| DE102004010744A1 (de) * | 2004-03-05 | 2005-09-22 | Rütgers Chemicals AG | Verfahren zur Herstellung von aromatischen Alkoxyketonen |
| RU2680599C1 (ru) * | 2017-12-06 | 2019-02-25 | Общество с ограниченной ответственностью "Ярославские Химические Технологии" (ООО "ЯрХимТех") | Способ получения пара-трет-бутилфенола и ацетона |
| CN119874589B (zh) * | 2025-03-27 | 2025-05-30 | 山东博远化工有限公司 | 过氧化二异丙苯及其制备方法与应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB309005A (en) * | 1927-12-31 | 1929-04-02 | Ig Farbenindustrie Ag | Process for the manufacture of oxygenated organic compounds |
| US3898288A (en) * | 1969-12-11 | 1975-08-05 | Labofina Sa | Oxidation of alkyl aromatics |
| US4362821A (en) * | 1981-10-29 | 1982-12-07 | Texaco Inc. | Process for preparing alkanols from synthesis gas |
| US4448892A (en) * | 1982-04-01 | 1984-05-15 | Phillips Petroleum Company | Olefin oxidation catalyst |
| US4879266A (en) * | 1984-09-20 | 1989-11-07 | Texaco Inc. | Catalyst for preparation of dimethyl carbonate |
| JPS63119430A (ja) * | 1986-11-07 | 1988-05-24 | Kureha Chem Ind Co Ltd | 芳香族化合物の酸化方法 |
| PL156813B1 (pl) * | 1988-12-12 | 1992-04-30 | Konstantin Makedonsky | Sposób wytwarzania III rzędowych nadtlenków alkiloaromatycznych |
| JPH07196573A (ja) * | 1993-12-09 | 1995-08-01 | Shell Internatl Res Maatschappij Bv | アセトフェノンの製造法 |
| AU5892694A (en) * | 1994-01-27 | 1995-08-15 | Dsm N.V. | Process for the manufacture of benzaldehyde |
-
1996
- 1996-03-20 PL PL96313418A patent/PL182675B1/pl not_active IP Right Cessation
-
1997
- 1997-03-15 EP EP97104444A patent/EP0796835B1/de not_active Expired - Lifetime
- 1997-03-15 DE DE59701685T patent/DE59701685D1/de not_active Expired - Fee Related
- 1997-03-19 JP JP9105076A patent/JPH1059883A/ja active Pending
- 1997-03-19 US US08/821,019 patent/US5990357A/en not_active Expired - Fee Related
- 1997-03-19 CZ CZ1997832A patent/CZ293692B6/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CZ293692B6 (cs) | 2004-07-14 |
| EP0796835A1 (de) | 1997-09-24 |
| DE59701685D1 (de) | 2000-06-21 |
| PL313418A1 (en) | 1997-09-29 |
| US5990357A (en) | 1999-11-23 |
| CZ83297A3 (cs) | 1998-03-18 |
| EP0796835B1 (de) | 2000-05-17 |
| JPH1059883A (ja) | 1998-03-03 |
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Legal Events
| Date | Code | Title | Description |
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| LAPS | Decisions on the lapse of the protection rights |
Effective date: 20060320 |