GB2314517A - Catalyst and its use in epoxidation - Google Patents

Catalyst and its use in epoxidation Download PDF

Info

Publication number
GB2314517A
GB2314517A GB9613687A GB9613687A GB2314517A GB 2314517 A GB2314517 A GB 2314517A GB 9613687 A GB9613687 A GB 9613687A GB 9613687 A GB9613687 A GB 9613687A GB 2314517 A GB2314517 A GB 2314517A
Authority
GB
United Kingdom
Prior art keywords
catalyst
support
transition metal
metal compound
epoxidation
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Withdrawn
Application number
GB9613687A
Other versions
GB9613687D0 (en
Inventor
James Hanley Clark
Andrew Butterworth
Tony William Bastock
Simon John Barlow
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
CONTRACT CHEMICALS Ltd
Original Assignee
CONTRACT CHEMICALS Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by CONTRACT CHEMICALS Ltd filed Critical CONTRACT CHEMICALS Ltd
Priority to GB9613687A priority Critical patent/GB2314517A/en
Publication of GB9613687D0 publication Critical patent/GB9613687D0/en
Publication of GB2314517A publication Critical patent/GB2314517A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/74—Iron group metals
    • B01J23/75—Cobalt
    • 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
    • B01J31/0237—Amines
    • 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
    • B01J31/0272—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255
    • B01J31/0274—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255 containing silicon
    • 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
    • B01J31/0272—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255
    • B01J31/0275—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing elements other than those covered by B01J31/0201 - B01J31/0255 also containing elements or functional groups covered by B01J31/0201 - B01J31/0269
    • 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
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0201—Impregnation
    • B01J37/0203—Impregnation the impregnation liquid containing organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
    • C07D301/06—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the liquid phase
    • 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
    • B01J2231/72—Epoxidation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

There is disclosed a catalyst comprising a transition metal compound bound to a derivatised inert support. There is also disclosed a method of manufacturing the catalyst and a process for the epoxidation of an organic compound using the catalyst.

Description

DESCRIPTION CATALYST AND ITS USE IN EPOXIDATION The present invention relates to a catalyst and to the use of a catalyst in epoxidation.
Many processes are known for the epoxidation of organic compounds. However, there are many disadvantages associated with such processes. Careful control of conditions, unstable, potentially vigorous or explosive reagents, expensive catalysts, long reaction times and many other factors, all which can result in poor yields and conversions and lead to unacceptable environmental effects. Other problems can be associated with recycling or disposing of expensive, possibly toxic or harmful, catalyst wastes.
There are four main types of reagent used for epoxidation reactions, peracids, hydrogen peroxide, alkyl peroxides or molecular oxygen. Use of peracids, hydrogen peroxide and alkyl peroxides for epoxidation, with and without catalyst, co-reagents etc. has been studied extensively and several reviews on the method are available in Trahanovsky, "Oxidation in Organic Chemistry1,, pt. C, pp211-252, Academic Press, New York, 1978; Swern in Swern "Organic Peroxides" vol 2, pp355533, Interscience, New York, 1971; House, "Modern Synthetic Reactions", 2d. ed., pp292-321, W.A.
Benjamin, New York, 1972. Equally, use of molecular oxygen in such processes, is well documented and has been reviewed by Filippova and Blyumberg, Russ. Chem.
Rev.. 51. 582-591 (1982) and also by Budnik and Kochi, J.Ora. Chem.. 41, 1384 (1976). One of the main disadvantages with all these methods is that the reaction often does not stop at the epoxide but continues through to give the dihydroxy or even cleavage products.
Recent developments as outlined in several publications such as Iqbal et at., Tetrahedron Lett., 35 (18), 2959-2960, 1995 and ibid., 36(1) 159-162, have seen the use of molecular oxygen with sacrificial aldehydes with various catalysts to achieve both oxidation and epoxidation.
The types of catalysts involved in such processes prove to be wide ranging and diverse, but what is important on environmental grounds is that the catalyst ideally should act heterogeneously. Such materials can be based on inorganic supports such as described in Baiker et al., J. Chem. Soc. Chem. Commun.. 163, 1995; Rachdi et al. ibid., 539, 1995; and Kurusu, Reactive Polvmers, 25. 63-68, 1995. These then can act catalytically in the epoxidation of particularly olefinic materials.
According to the present invention there is provided a catalyst, particularly an epoxidation catalyst, which comprises a transition metal compound bound to a derivatised inert support.
The transition metal compound is preferably in the form of a salt, particularly an acetate of a first row transition metal such as cobalt or copper or vanadium.
Although acetates are preferred, many other ligands can be considered, for example, acetylacetates.
The essential feature of the invention relates to the attachment of the metal to the surface of the support. This is achieved by derivatisation of the surface by known methods which then allows for strong bonding of the transition metal species to the support giving heterogeneous catalyst not prone to leaching.
One method of derivatising the catalyst comprises firstly activating the support by acid hydrolysis, then mixing this activated material with a functionalised silane reagent, for example 2-cyanoethyltriethylsilane, in an anhydrous medium. The quantity of silane reagent preferred is in the range of 0.01 to 100mmol per gram of support. The mixture is then heated to reflux to yield the functionalised silane coupled to the surface of the inert support. Further processing for example acid hydrolysis, produces the surface activated material containing groups for example of carboxylic acids with the ability to strongly bond with the transition metal compounds.
Other methods for derivatisation of the support and making of the catalyst maybe employed.
One method of preparing the epoxidation catalyst then involves dissolution of the transition metal compound in a suitable solvent and mixing this with the functionalised support. The loading of transition metal compound is typically in the range 0.01 to 10mmol per gram of the support. The solvent is then removed, under vacuum in the temperature range 0 to 1500C to yield the catalyst as a finely divided powder.
The supported catalyst may be used as so prepared or may be further manipulated prior to use in epoxidation reactions. Such further treatment may involve, for example, washing or thermal drying. In any of the examples of catalyst preparation given it is intended to achieve a dispersion of the transition metal ion across the modified surface of the support where it is tightly bound.
According to another embodiment of the present invention there is provided a process for the epoxidation of an organic compound which comprises reacting an organic substrate with a gas containing molecular oxygen in the presence of an aldehyde and in the presence of a catalyst which comprises a transition metal compound bound to the modified surface of an inorganic support.
Suitable organic substrates which may be used in the process of the present invention include those compounds having the general formulae:
Wherein R1 to R4 may independently each be H, D (deuterium), halogen, alkyl (preferably Cm20), substituted or unsubstituted aryl (preferably 1 to 10 rings) substituted or unsubstituted cycloalkyl (preferably 1 to 10 rings), substituted or unsubstituted heteroaryl (preferably 1 to 10 rings), CHO,COR,COOR,COH, CN, CS,CRRR,NO,NO2,NRR,SO,SO2,OH,OR.
The various R groups each independently represent a group having a value as defined for R1 to R4 which may optionally be substituted by any combination of the conventional substituents. Substituents may be, or may contain rings, or a combination of substituents may form rings.
Other organic substrates which may be used in the process of the present invention include: (1) Condensed aromatic compounds such as, for example, naphthalene, anthracene or phenanthrene; (2) Sulphur containing compounds; and (3) Heterocyclic compounds.
The substrate to be epoxidised may, for example, by mixed with an appropriate amount of catalyst and aldehyde, in a suitable solvent and the stirred mixture contacted with an oxygen containing gas at a desired temperature.
Alternatively, air under a suitable pressure may be used in a closed system.
The reaction is continued for an appropriate time and the catalyst is then separated by filtration, centrifugation, decantation or a similar technique. In contrast with many known processes the catalyst may be reused.
The product of the epoxidation can then be isolated and purified by standard, known techniques.
The present invention will now be further described with reference to, but is in no manner limited to, the following Examples.
Example 1 A catalyst was prepared by treating an acid activated silica (log) with 2-cyanoethyltriethoxysilane (6.519g, 30mmol) dissolved in toluene (200ml) which was then ref fluxed under a nitrogen atmosphere for 24h. The intermediate derivatised silica was isolated by filtration, washed with diethylether and vacuum dried at 800C. The nitrile groups were subsequently hydrolysed by ref fluxing the silica (2.65g) in 50% sulphuric acid (140g) for several hours and again isolating the now carboxylic acid dirvatised silica by filtration and washing with water before drying in vacuo at 800C overnight. Cobalt acetate (0.247g, 1.0 mmol) was dissolved in water and the carboxylic acid derivatised silica (1.00g) added. The water was slowly removed by evaporation and the resultant purple solid further dried in vacuo at 800C overnight.
Example 2 The catalyst (0.60g, cobalt acetate on carboxy derivatised silica) was slurried in dichloromethane (120ml) and cyclohexene (1.64g, 20mmol) and propionaldehyde (3.48g, 60mmol) added. The system was then placed under an oxygen atmosphere (1 atm.) and stirred at room temperature. Analysis of the reaction mixture by GC showed 78% conversion of the cyclohexene to cyclohexene oxide after 7h.
Example 3 The catalyst (0.60g, cobalt acetate on carboxy derivatised silica) was slurried in dichloromethane (120ml) and 1-octene (2.24g, 20mmol) and isobutyraldehyde (4.33g, 60mmol) added. The system was then placed under an oxygen atmosphere (1 atm.) and stirred at room temperature. Analysis of the reaction mixture by GC showed 45% conversion of the cyclohexene to cyclohexene oxide after 5h.
Example 4 A catalyst was prepared by treating an acid activated silica (lOg) with 3 aminopropyltriethoxysilane (6.3g, 30mmol) dissolved in toluene (200ml) and then refluxed under a nitrogen atmosphere for 24h. The intermediate amine derivatised silica was isolated by filtration, washed with diethyl ether and vacuum dried at 800C. The amine groups were subsequently reacted by treating the silica (5.0g) with salicyladehyde (1.8g, 15mmol) in ethanol. The now salen derivatised silica was then isolated by filtration and washed with ethanol before being vacuum dried at 800C overnight. Cobalt acetate (0.22g, 0.9mmol) was dissolved in water and the salen derivatised silica (3.00g) added. The water was slowly removed by evaporation and the resultant red/brown solid further dried in vacuo at 800C overnight.
Example 5 The catalyst (0.60g, cosalen on silica) was slurried in dichloromethane (120ml) and 2,2,4trimethylpent-2-ene (2.24g, 20mmol) and isobutyraldeheyde (4.33g, 60mmol) added. The system was then placed under an oxygen atmosphere (1 atm.) and stirred at room temperature. Analysis of the reaction mixture by GC showed > 98% conversion of the 2,2,4trimethylpent-2-ene to 2,2,4-trimethylpent-2-ene oxide after 5h.
Example 6 The catalyst (0.60g, cosalen on silica) was slurried in dichloromethane (120ml) and cyclohexene (1.64g, 20mmol) and isobutyraldeheyde (4.33g, 60mmol) added. The system was then placed under an oxygen atmosphere (1 atm.) and stirred at room temperature.
Analysis of the reaction mixture by GC showed 73 conversion of the cyclohexene to cyclohexene oxide after 5h.

Claims (15)

1. A catalyst comprising a transition metal compound bound to a derivatised inert support.
2. A catalyst as claimed in claim 1, in which the transition metal compound is in the form of a salt.
3. A catalyst as claimed in claim 2, wherein the salt is an acetate of a first row transition metal.
4. A catalyst as claimed in any one of the preceding claims, in which the loading of the transition metal compound is from 0.01 to 10mmol per gram of support.
5. A method of manufacturing a catalyst as claimed in any one of the preceding claims, which comprises attaching a transition metal compound to a derivatised inert support.
6. A method as claimed in claim 5, in which the support is derivatised by firstly activating the support by acid hydrolysis, then mixing this activated material with a functionalised silane reagent, heatingto reflux to yield the functionalised silane coupled to the surface of the inert support, and subjecting the support to further processing by acid hydrolysis.
7. A method as claimed in claim 6, in which the quantity of silane reagent is in the range of 0.01 to 100mmol per gram of support.
8. A method of preparing a catalyst as claimed in any one of claims 1 to 4, which comprises dissolving the transition metal compound in a suitable solvent and mixing this with the functionalised support, and removing the solvent under vacuum in the temperature range 0 to 1500C.
9. A method as claimed in any one of claims 5 to 8, in which the catalyst is further manipulated prior to use.
10. A method as claimed in claim 9, in which said further manipulation comprises washing or thermal drying.
11. A process for the epoxidation of an organic compound which comprises reacting an organic substrate with a gas containing molecular oxygen in the presence of an aldehyde and in the presence of a catalyst as claimed in any one of claims 1 to 4.
12. A process as claimed in claim 11, which is carried out in a suitable solvent and the mixture contacted with an oxygen containing gas at a desired temperature.
13. A catalyst substantially as hereinbefore described in any one of the foregoing examples.
14. A method of manufacturing a catalyst substantially as hereinbefore described in any one of the foregoing examples.
15. A process for the epoxidation of an organic compound substantially as hereinbefore described in any one of the foregoing examples.
GB9613687A 1996-06-28 1996-06-28 Catalyst and its use in epoxidation Withdrawn GB2314517A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB9613687A GB2314517A (en) 1996-06-28 1996-06-28 Catalyst and its use in epoxidation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB9613687A GB2314517A (en) 1996-06-28 1996-06-28 Catalyst and its use in epoxidation

Publications (2)

Publication Number Publication Date
GB9613687D0 GB9613687D0 (en) 1996-08-28
GB2314517A true GB2314517A (en) 1998-01-07

Family

ID=10796099

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9613687A Withdrawn GB2314517A (en) 1996-06-28 1996-06-28 Catalyst and its use in epoxidation

Country Status (1)

Country Link
GB (1) GB2314517A (en)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4053534A (en) * 1974-02-19 1977-10-11 Mobil Oil Corporation Organic compound conversion
EP0138624A2 (en) * 1983-10-18 1985-04-24 BP Chemicals Limited Organo metallic complexes and the use thereof in epoxidation of olefins
US4657884A (en) * 1984-11-07 1987-04-14 Hoechst Aktiengesellschaft Carrier-supported catalyst for making monocarboxylic anhydrides
EP0287347A2 (en) * 1987-04-16 1988-10-19 MITSUI TOATSU CHEMICALS, Inc. Method for preparing epichlorohydrins
WO1992016487A1 (en) * 1991-03-25 1992-10-01 Dsm N.V. Process for preparing an alkanone and/or alkanol
US5162279A (en) * 1990-07-10 1992-11-10 Director-General Of Agency Of Industrial Science And Technology Immobilized metal complexes
WO1994004268A1 (en) * 1992-08-20 1994-03-03 Dsm N.V. Epoxidation catalyst

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4053534A (en) * 1974-02-19 1977-10-11 Mobil Oil Corporation Organic compound conversion
EP0138624A2 (en) * 1983-10-18 1985-04-24 BP Chemicals Limited Organo metallic complexes and the use thereof in epoxidation of olefins
US4657884A (en) * 1984-11-07 1987-04-14 Hoechst Aktiengesellschaft Carrier-supported catalyst for making monocarboxylic anhydrides
EP0287347A2 (en) * 1987-04-16 1988-10-19 MITSUI TOATSU CHEMICALS, Inc. Method for preparing epichlorohydrins
US5162279A (en) * 1990-07-10 1992-11-10 Director-General Of Agency Of Industrial Science And Technology Immobilized metal complexes
WO1992016487A1 (en) * 1991-03-25 1992-10-01 Dsm N.V. Process for preparing an alkanone and/or alkanol
WO1994004268A1 (en) * 1992-08-20 1994-03-03 Dsm N.V. Epoxidation catalyst

Also Published As

Publication number Publication date
GB9613687D0 (en) 1996-08-28

Similar Documents

Publication Publication Date Title
Clark et al. Preparation of a novel silica-supported palladium catalyst and its use in the Heck reaction
Ho et al. Ruthenium nanoparticles supported on hydroxyapatite as an efficient and recyclable catalyst for cis-dihydroxylation and oxidative cleavage of alkenes
Baig et al. Organic synthesis via magnetic attraction: benign and sustainable protocols using magnetic nanoferrites
González‐Arellano et al. Pd (II)‐Schiff base complexes heterogenised on MCM‐41 and delaminated zeolites as efficient and recyclable catalysts for the Heck reaction
Han et al. Immobilised photosensitisers for continuous flow reactions of singlet oxygen in supercritical carbon dioxide
US6028025A (en) Metalloporphyrin oxidation catalyst covalently coupled to an inorganic surface and method making same
GEP19971024B (en) Method of producing acrolein
WO1998017389A9 (en) Metalloporphyrin oxidation catalyst indirectly covalenty coupled to an inorganic surface and methods of making same
Hajipour et al. Proline-functionalized chitosan–palladium (ii) complex, a novel nanocatalyst for C–C bond formation in water
Chisem et al. Catalytic oxidation of alkyl aromatics using a novel silica supported Schiff base complex
Miller et al. Alkene epoxidations catalysed by molybdenum (VI) supported on imidazole-containing polymers. Part 3. Epoxidation of oct-1-ene and propene
EP0367326B1 (en) Process for preparing a cycloalkanone and/or cycloalkanol
Diamond et al. Cobalt nitro complexes as oxygen transfer agents. 4. Epoxidation of olefins
Chisem et al. Liquid phase oxidations using novel surface functionalised silica supported metal catalysts
Verma et al. Nanocrystalline starch grafted palladium (II) complex for the Mizoroki–Heck reaction
CN111229314A (en) Carboxyl aryl functionalized MXene material and preparation method and application thereof
Mao et al. Iron chloride supported on pyridine-modified mesoporous silica: an efficient and reusable catalyst for the allylic oxidation of olefins with molecular oxygen
Liu et al. Epoxidation of propylene with molecular oxygen in methanol over a peroxo-heteropoly compound immobilized on palladium exchanged HMS
GB2314517A (en) Catalyst and its use in epoxidation
Tangestaninejad et al. MoO 2 (acac) 2 supported on MCM-41: an efficient and reusable catalyst for alkene epoxidation with tert-BuOOH
CN113231103B (en) Cobalt Schiff base catalyst grafted by imine bond, preparation method and application thereof
Tangestaninejad et al. Polystyrene-bound manganese (III) porphyrin as a heterogeneous catalyst for alkene epoxidation
Shiney et al. Polystyrene‐bound dioxirane: a new class of recyclable oxidising reagent
Zhao et al. Preparation of encapsulated and anchored alanine–salicylaldehyde Schiff base Mn (III)(Sal–Ala–Mn) complexes by sol–gel method and their performance in aerobic epoxidation of cyclohexene
CN114787114A (en) Improved process for the photocatalytic hydrocarboxylation of methanol using CO2 to produce acetic acid

Legal Events

Date Code Title Description
WAP Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1)