DE19811517A1 - Continuous selective oxidation of hydrocarbon, especially cyclohexane to cyclohexanone - Google Patents
Continuous selective oxidation of hydrocarbon, especially cyclohexane to cyclohexanoneInfo
- Publication number
- DE19811517A1 DE19811517A1 DE19811517A DE19811517A DE19811517A1 DE 19811517 A1 DE19811517 A1 DE 19811517A1 DE 19811517 A DE19811517 A DE 19811517A DE 19811517 A DE19811517 A DE 19811517A DE 19811517 A1 DE19811517 A1 DE 19811517A1
- Authority
- DE
- Germany
- Prior art keywords
- ozone
- hydrocarbon
- cyclohexanone
- cyclohexane
- oxidation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 230000003647 oxidation Effects 0.000 title claims abstract description 16
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 16
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 9
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 9
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims description 38
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims description 15
- 239000004215 Carbon black (E152) Substances 0.000 title claims 6
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000000463 material Substances 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 12
- 239000004809 Teflon Substances 0.000 claims description 4
- 229920006362 Teflon® Polymers 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 238000000066 reactive distillation Methods 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims 1
- 239000011521 glass Substances 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- 239000004033 plastic Substances 0.000 claims 1
- 239000010453 quartz Substances 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012159 carrier gas Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-PTQBSOBMSA-N cyclohexanol Chemical group O[13CH]1CCCCC1 HPXRVTGHNJAIIH-PTQBSOBMSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
Classifications
-
- 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
- C07C45/40—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with ozone; by ozonolysis
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Die vorliegende Erfindung betrifft ein neues katalysatorfreies Verfahren zur selektiven Oxidation von Kohlenwasserstoffen, Ozon in einem inerten Reaktor. Das Verfahren bezieht sich insbesondere auf die selektive Herstellung von Cyclohexanon durch die Oxidation von Cyclohexan mit Ozon in der Flüssig- und Gasphase in der Abwesenheit von Katalysatoren, Metallteilen und anderen Einbauten, die Ozon zersetzen.The present invention relates to a new catalyst-free process for selective oxidation of hydrocarbons, ozone in an inert reactor. The process relates in particular to the selective production of Cyclohexanone through the oxidation of cyclohexane with ozone in the liquid and Gas phase in the absence of catalysts, metal parts and others Internals that decompose ozone.
Cyclohexanol und Cyclohexanon dienen sowohl zur Herstellung des Massenprodukts Caprolactam als auch zur Herstellung des während der Oxidation anfallenden Folgeprodukts Adipinsäure. Diese wird durch Polykondensation mit Hexamethylendiamin zu Nylon-6,6 weiterverarbeitet. Die Oxidation von Cyclohexan mit Ozon ist bekannt. Von Nachteil ist die bisher immer simultan mit Cyclohexanon erfolgende Bildung von Cyclohexanol. In der Literatur und in dem Patentschrifttum werden verschiedene Verfahren zur Darstellung von Cyclohexanol und Cyclohexanon beschrieben, wobei beide Produkte simultan meist in vergleichbaren Größenordnungen anfallen (US Pat. 3,957,876; Ger. Offen. 2,154,656; US Pat. 3,404,185 und US Pat. 3,598,869; WO 94/17021 und WO 96/3145 (L.G. Galimova, V.D. Komissarov, E. T. Denisov, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Trans.) 295 (1973) und L.V. Ruban, S.K. Rakovski, S.D. Razumovskii, G.E. Zaikov, , Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Trans.) 1972 (1976)). Es auch wird beschrieben, daß mehr Cyclohexanol als Cyclohexanon entsteht (L.V. Ruban, S.K. Rakovski, A.A. Popov, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Trans.) 1834 (1976)) und es wird über Verhältnisse von Cyclohexanol zu Cyclohexanon von (2,5 ± 0,5): 1 berichtet ((V.D. Komissarov, L.G. Galimova, I.N. Komissarova, V.V. Shereshovets, E. T. Denisov, Dokl. Phys. Chem. (Engl. Trans.) 235 838 (1977). Ein Verfahren mit hoher Selektivität zur direkten Erzeugung von Cyclohexanon aus Cyclohexan ist bisher nicht bekannt. Cyclohexanol and cyclohexanone are both used to make the Bulk product Caprolactam as well as for the production of during the Oxidation resulting adipic acid. This is through Polycondensation with hexamethylenediamine processed to nylon-6,6. The Oxidation of cyclohexane with ozone is known. So far, this has been a disadvantage Cyclohexanol always forms simultaneously with cyclohexanone. In the Literature and in the patent literature are different methods for Representation of cyclohexanol and cyclohexanone described, both Products usually occur simultaneously in comparable orders of magnitude (US Pat. 3,957,876; Ger. Open. 2,154,656; U.S. Pat. 3,404,185 and U.S. Pat. 3,598,869; WO 94/17021 and WO 96/3145 (L.G. Galimova, V.D. Komissarov, E. T. Denisov, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Trans.) 295 (1973) and L.V. Ruban, S.K. Rakovski, S.D. Razumovskii, G.E. Zaikov,, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Trans.) 1972 (1976)). It also describes that more cyclohexanol than cyclohexanone is formed (L.V. Ruban, S.K. Rakovski, A.A. Popov, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Trans.) 1834 (1976)) and cyclohexanol to cyclohexanone ratios of (2.5 ± 0.5): 1 reported ((V.D. Komissarov, L.G. Galimova, I.N. Komissarova, V.V. Shereshovets, E. T. Denisov, Doc. Phys. Chem. (Engl. Trans.) 235 838 (1977). A process with high selectivity for the direct production of cyclohexanone from cyclohexane is not yet known.
Wir haben nun überraschenderweise gefunden, daß die unerwünschte Bildung von Cyclohexanol bei der Oxidation von Cyclohexan mit Ozon zu Cyclohexanon nahezu vollständig unterdrückt werden kann, wenn die Reaktion in einem inerten Reaktorraum, d. H. in Abwesenheit von Katalysatoren, Metallteilen und anderen Einbauten, die Ozon zersetzen, durchgeführt wird. Der wesentliche Vorteil der vorliegenden Erfindung ist, daß zur selektiven Darstellung von Cyclohexanon keine Katalysatoren benötigt werden, sondern Cyclohexanon durch die Oxidation von Cyclohexan mit Ozon selektiv in einem Schritt dargestellt werden kann.We have now surprisingly found that the undesirable formation of cyclohexanol in the oxidation of cyclohexane with ozone to cyclohexanone can be almost completely suppressed if the reaction occurs in one inert reactor space, d. H. in the absence of catalysts, metal parts and other installations that decompose ozone. The essential The advantage of the present invention is that for the selective display of Cyclohexanone no catalysts are required, but cyclohexanone by the oxidation of cyclohexane with ozone selectively in one step can be represented.
Die Oxidation von Cyclohexan mit Ozon kann in der Flüssig- und in der Gasphase bei Normaldruck in einem Temperaturbereich von 0-140°C erfolgen. Um bei der Oxidation entstehende Folgeprodukte, wie z. B. Adipinsäure, zu vermeiden, bietet sich die Reaktivdestillation als besonders geeignet an. Die Reaktivdestillation ist eine Methode der Reaktionsführung, in der Reaktion und Produktabtrennung simultan durchgeführt werden. Für die Herstellung von Cyclohexanon aus Cyclohexanol wird eine kontinuierliche Destillation so eingestellt, daß am Kolonnenkopf nahezu reines Cyclohexan vorliegt, während im Kolonnensumpf Cyclohexanon überwiegt. Im Kolonnenkopf kann nun Ozon und Cyclohexanon kontinuierlich zudosiert werden, während Cyclohexanon kontinuierlich aus dem Kolonnensumpf abgetrennt werden kann. Das Verfahren ist nicht nur zur selektiven Oxidation von gesättigten Kohlenwasserstoffen wie cyclischen und acyclischen verzweigten und unverzweigten Alkenen, sondern auch zur selektiven Oxidation von aromatischen Verbindungen und ungesättigten Verbindungen, wie Alkenen, geeignet. Es ist für das Verfahren unerheblich, ob das Ozon nun aus trockener Luft, synthetischer Luft, reinem Sauerstoff oder jeder anderen Mischung von Sauerstoff mit inerten Gasen wie Ar, Ne, Xe, He, N2, CO2 und anderen erzeugt wird und rein oder im Gemisch eingesetzt wird. The oxidation of cyclohexane with ozone can take place in the liquid and in the gas phase at normal pressure in a temperature range of 0-140 ° C. In order to result in the oxidation of secondary products such. B. to avoid adipic acid, reactive distillation is particularly suitable. Reactive distillation is a method of carrying out the reaction in which the reaction and product separation are carried out simultaneously. For the production of cyclohexanone from cyclohexanol, a continuous distillation is set so that almost pure cyclohexane is present at the top of the column, while cyclohexanone predominates in the bottom of the column. Ozone and cyclohexanone can now be metered in continuously at the top of the column, while cyclohexanone can be continuously separated from the bottom of the column. The process is not only suitable for the selective oxidation of saturated hydrocarbons such as cyclic and acyclic branched and unbranched alkenes, but also for the selective oxidation of aromatic compounds and unsaturated compounds such as alkenes. It is irrelevant to the process whether the ozone is generated from dry air, synthetic air, pure oxygen or any other mixture of oxygen with inert gases such as Ar, Ne, Xe, He, N 2 , CO 2 and others and pure or is used in a mixture.
Ozon wird durch stille elektrische Entladung aus einem Inertgas /Sauerstoffgemisch generiert. In einem Satzreaktor aus Teflon werden 10 ml (0,093 mol) Cyclohexan vorgelegt und ozonhaltiges Argon (Ozonkonzentration 36,0 g/Nm3) wird über einen Teflonschlauch mit einem Fluß von 38 ml/min direkt in das Cyclohexan geleitet und über einen Intensivkühler wieder aus dem Reaktor abgeführt. Die Reaktionsmischung wird bei Raumtemperatur mit einem Magnetrührer gerührt. Die Ozonkonzentration wird am jeweiligen Reaktorein- und -ausgang UV-spektrometrisch überwacht. Die Produkte werden in einer Kühlfalle ausgefroren. Die Produkte werden gaschromatographisch analysiert und die entstandene Menge an Kohlendioxid wird mit einem Kohlendioxidsensor gemessen. Nach einer Reaktionszeit von 17,5 h werden 5% Cyclohexanon mit einer Selektivität von < 98% gebildet.Ozone is generated by silent electrical discharge from an inert gas / oxygen mixture. 10 ml (0.093 mol) of cyclohexane are placed in a set reactor made of Teflon, and argon containing ozone (ozone concentration 36.0 g / Nm 3 ) is fed directly into the cyclohexane via a Teflon tube with a flow of 38 ml / min and then discharged again via an intensive cooler discharged to the reactor. The reaction mixture is stirred at room temperature with a magnetic stirrer. The ozone concentration is monitored by UV spectrometry at the respective reactor inlet and outlet. The products are frozen out in a cold trap. The products are analyzed by gas chromatography and the amount of carbon dioxide generated is measured with a carbon dioxide sensor. After a reaction time of 17.5 h, 5% cyclohexanone are formed with a selectivity of <98%.
Zur Oxidation von Cyclohexan in der Gasphase wird ozonhaltiges Trägergas mit einem Fluß von 76 ml/min durch einen Rohrreaktor geleitet. Die Ozonkonzentration beträgt am Reaktoreingang 36,0 g/Nm3 Trägergas. Cyclohexan wird kontinuierlich mit einer Dosiergeschwindigkeit von 6 mg/min zugegeben. Bei einer Temperatur von 100°C bilden sich Cyclohexanon und Cyclohexanol im Verhältnis 22 : 5.For the oxidation of cyclohexane in the gas phase, the carrier gas containing ozone is passed through a tube reactor at a flow of 76 ml / min. The ozone concentration at the reactor inlet is 36.0 g / Nm 3 carrier gas. Cyclohexane is added continuously at a rate of 6 mg / min. At a temperature of 100 ° C cyclohexanone and cyclohexanol form in a ratio of 22: 5.
In einen Satzreaktor mit 30 ml Cyclohexan wird Ozon-haltiges Trägergas über einen Teflonschlauch mit einem Fluß von 180 ml/min direkt in das Cyclohexan geleitet. Die Reaktionsmischung wird bei 30°C mit einem Begasungsrührer gerührt. Nach 4 h enthält das Produktgemisch 61% Cyclohexanon und 33% Cyclohexanol, die Ausbeute bezüglich des eingesetzten Ozons beträgt 73%.Carrier gas containing ozone is transferred into a batch reactor with 30 ml of cyclohexane a Teflon tube with a flow of 180 ml / min directly into the cyclohexane headed. The reaction mixture is at 30 ° C with a gassing touched. After 4 hours, the product mixture contains 61% cyclohexanone and 33% Cyclohexanol, the yield based on the ozone used is 73%.
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19811517A DE19811517A1 (en) | 1998-03-17 | 1998-03-17 | Continuous selective oxidation of hydrocarbon, especially cyclohexane to cyclohexanone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19811517A DE19811517A1 (en) | 1998-03-17 | 1998-03-17 | Continuous selective oxidation of hydrocarbon, especially cyclohexane to cyclohexanone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19811517A1 true DE19811517A1 (en) | 1999-09-23 |
Family
ID=7861170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19811517A Withdrawn DE19811517A1 (en) | 1998-03-17 | 1998-03-17 | Continuous selective oxidation of hydrocarbon, especially cyclohexane to cyclohexanone |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE19811517A1 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102382025A (en) * | 2010-08-31 | 2012-03-21 | 中国石油化工股份有限公司 | Method for oxidizing naphthenic hydrocarbon |
| CN102698403A (en) * | 2012-02-06 | 2012-10-03 | 西安费斯达自动化工程有限公司 | Method for treating cyclohexane with ozone |
| EP3009418A1 (en) * | 2014-10-13 | 2016-04-20 | National Tsing Hua University | Preparation method of carboxylic acids or ketones using ozone, singlet state-oxygen atom or hydroxyl free radical |
| WO2018031749A1 (en) * | 2016-08-11 | 2018-02-15 | University Of Kansas | Ozone-facilitated selective oxidation of alkanes in liquid carbon dioxide |
| CN115210217A (en) * | 2020-03-03 | 2022-10-18 | 沙特基础工业全球技术有限公司 | Process and system for oxidizing cumene and hydrocarbons |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3401672A1 (en) * | 1983-12-23 | 1985-09-26 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | METHOD FOR PRODUCING MONO OR BISCARBONYL COMPOUNDS |
-
1998
- 1998-03-17 DE DE19811517A patent/DE19811517A1/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3401672A1 (en) * | 1983-12-23 | 1985-09-26 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | METHOD FOR PRODUCING MONO OR BISCARBONYL COMPOUNDS |
Non-Patent Citations (10)
| Title |
|---|
| CAPLUS, Ref. 1998:436991 * |
| Chemical Abstracts: Vol. 92, 1980, Ref. 214610x * |
| DURLAND,John R., ADKINS,Homer: Oxidation of Methyne and Methylene Groups by Ozone. In: J. Am. Chem. Soc. 61, S.429-433 * |
| JAPIO, Ref. 82-064634 zu JP 57064634 A * |
| KURON,Dieter, GRÄFEN,Hubert: Spezielle Korrosionsschutz-Maßnahmen im Chemie- Apparatebau. In: Chem.-Ing.-Tech. 60, 1988, Nr.8, S.604-612 * |
| Vol. 70, 1969, Ref. 2949k * |
| Vol. 75, 1971, Ref. 91146q * |
| Vol. 79, 1973, Ref. 136586j * |
| Vol. 79, 1973, Ref. 4689k * |
| Vol. 90, 1979, Ref. 54214z * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102382025A (en) * | 2010-08-31 | 2012-03-21 | 中国石油化工股份有限公司 | Method for oxidizing naphthenic hydrocarbon |
| CN102382025B (en) * | 2010-08-31 | 2014-10-29 | 中国石油化工股份有限公司 | Method for oxidizing naphthenic hydrocarbon |
| CN102698403A (en) * | 2012-02-06 | 2012-10-03 | 西安费斯达自动化工程有限公司 | Method for treating cyclohexane with ozone |
| CN102698403B (en) * | 2012-02-06 | 2014-11-26 | 西安费斯达自动化工程有限公司 | Method for treating cyclohexane with ozone |
| EP3009418A1 (en) * | 2014-10-13 | 2016-04-20 | National Tsing Hua University | Preparation method of carboxylic acids or ketones using ozone, singlet state-oxygen atom or hydroxyl free radical |
| WO2018031749A1 (en) * | 2016-08-11 | 2018-02-15 | University Of Kansas | Ozone-facilitated selective oxidation of alkanes in liquid carbon dioxide |
| US10730814B2 (en) | 2016-08-11 | 2020-08-04 | University Of Kansas | Ozone-facilitated selective oxidation of alkanes in liquid carbon dioxide |
| CN115210217A (en) * | 2020-03-03 | 2022-10-18 | 沙特基础工业全球技术有限公司 | Process and system for oxidizing cumene and hydrocarbons |
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| 8139 | Disposal/non-payment of the annual fee |