KR830004194A - 사이클로헥산으로부터 사이클로헥산올 및 사이클로헥사논 함유 혼합물을 제조하는 방법 - Google Patents

사이클로헥산으로부터 사이클로헥산올 및 사이클로헥사논 함유 혼합물을 제조하는 방법 Download PDF

Info

Publication number
KR830004194A
KR830004194A KR1019800003900A KR800003900A KR830004194A KR 830004194 A KR830004194 A KR 830004194A KR 1019800003900 A KR1019800003900 A KR 1019800003900A KR 800003900 A KR800003900 A KR 800003900A KR 830004194 A KR830004194 A KR 830004194A
Authority
KR
South Korea
Prior art keywords
cyclohexane
benzene ring
cyclohexanone
ligand
cyclohexanol
Prior art date
Application number
KR1019800003900A
Other languages
English (en)
Other versions
KR850000379B1 (ko
Inventor
더그라스 드룰리너 죠
데일 일텔 스티븐
죠세프 크루시크 파울
알마 톨만 채드윅
Original Assignee
에이. 엔. 리에디
이. 아이. 듀퐁 드 네모아 앤드 캄파니
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 에이. 엔. 리에디, 이. 아이. 듀퐁 드 네모아 앤드 캄파니 filed Critical 에이. 엔. 리에디
Publication of KR830004194A publication Critical patent/KR830004194A/ko
Application granted granted Critical
Publication of KR850000379B1 publication Critical patent/KR850000379B1/ko

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C409/00Peroxy compounds
    • C07C409/02Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
    • C07C409/14Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom belonging to a ring other than a six-membered aromatic ring
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1815Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1825Ligands comprising condensed ring systems, e.g. acridine, carbazole
    • B01J31/183Ligands comprising condensed ring systems, e.g. acridine, carbazole with more than one complexing nitrogen atom, e.g. phenanthroline
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/48Preparation 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
    • C07C29/50Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00Preparation of peroxy compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/33Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/53Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0238Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
    • B01J2531/0241Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
    • B01J2531/0244Pincer-type complexes, i.e. consisting of a tridentate skeleton bound to a metal, e.g. by one to three metal-carbon sigma-bonds
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/70Complexes comprising metals of Group VII (VIIB) as the central metal
    • B01J2531/72Manganese
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84Metals of the iron group
    • B01J2531/842Iron
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84Metals of the iron group
    • B01J2531/845Cobalt
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated

Landscapes

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

Abstract

내용 없음

Description

사이클로헥산으로부터 사이클로헥산올 및 사이클로 헥사논함유 혼합물을 제조하는 방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
도면 1은 Co(BPI)2에 의한 CHHP 분해 반응시 발생되는 화학발광의 광강도(Ⅰ)를 시간의 함수로 도시한 것이고, 도면 3은 코발트 2-에틸헥사노에이트에 의한 CHHP 분해 반응시 발생되는 화학발광의 광강도(Ⅰ)를 시간의 함수로 도시한 것이고, 도면 5는 Co(BPI)2에 의한 CHHP분해 반응시 CHHP를 나누어 첨가하고 이때 발생되는 화학발광의 광강도(Ⅰ)를 시간의 함수로 도시한 것이고, 도면 7은 코발트 2-에틸 헥사노에이트에 의한 CHHP 분해 반응시 CHHP를 나누어 첨가하고 이때 발생되는 화학발광의 광강도(Ⅰ)를 시간의 함수로 도시한 것이고.

Claims (1)

  1. 사이클로헥산을 공기산화시켜 사이클로 헥실하이드로 퍼옥 사이드함유반응 혼합물을 제조하고 또 이 사이클로 헥실 하이드로퍼옥사이드를 출발물질 사이클로헥산 존재하에서 분해시켜 사이클로헥산올 및 사이클로헥사논 함유 혼합물을 제조하는 방법중,
    (1) 산화단계를 다음 구조식을 갖는 적어도 1개의 전이금속착화합물로 주로 구성되는 촉매물질이 촉매량만큼 존재하는 상태에서 사이클로헥산을 약 120 내지 160℃ 온도의 공기와 접촉시켜 진행하게 하고, 또/또는
    (2) 분해단계를 약 0.1 내지 약 10중량%의 사이클로헥실 하이드로퍼옥사이드와 사이클로헥산 함유 반응혼합물을 약 80°내지 160℃ 온도에서 촉매량 만큼의 촉매물질과 접촉시키며, 경우에 따라서는 산소분자 존재하에서 진행시키는 것을 특징으로 하는 사이클로헥산올 및 사이클로헥사논 함유 혼합물의 제조방법
    상기 구조식에서
    1차 리간드는 괄호 내 물질이고,
    M은 Co, Mn 또는 Fe이며,
    R1, R2, R3, R4, R5및 R6는 각각 수소, 저급알킬, 저급알콕시알킬, 페닐, 벤질 또는 펜에틸이거나 또는 R1내지 R6까지의 임의의 2개인접구성원은 피리딘 고리로 융해된 벤젠고리의 4개 CH구성체와 결합하고 있고, R7, R8, R9및 R10이 각각 수소, 저급알킬 또는 저급알콕시 알킬 또는 R7내지 R10까지의 임의의 2개 인접 구성원은 이소인돌린 모체의 벤젠고리로 융해된 벤젠고리의 4개 CH 구성체와 결합하고 있으며,
    X는 보조음이온 리간드이고,
    n는 1 또는 2이며,
    P는 0,1 또는 2이고, 또 n+P는 2 또는 3이다. 단 2개의 1차리간드가 있는 경우는 R1내지 R10의 값은 각개 리간드에 대해 다를 수 있으며, 또 2개의 보조음이온 리간드가 있는 경우는 X의 값이 다를 수 있다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019800003900A 1979-10-11 1980-10-11 사이클로헥산올 및 사이클로헥사논 함유 혼합물의 제조방법 KR850000379B1 (ko)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US8364479A 1979-10-11 1979-10-11
US083644 1979-10-11
US184635 1980-09-16
US06/184,635 US4326084A (en) 1979-10-11 1980-09-16 Process for producing a mixture containing cyclohexanol and cyclohexanone from cyclohexane

Publications (2)

Publication Number Publication Date
KR830004194A true KR830004194A (ko) 1983-07-06
KR850000379B1 KR850000379B1 (ko) 1985-03-23

Family

ID=26769541

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019800003900A KR850000379B1 (ko) 1979-10-11 1980-10-11 사이클로헥산올 및 사이클로헥사논 함유 혼합물의 제조방법

Country Status (8)

Country Link
US (1) US4326084A (ko)
EP (1) EP0027937B1 (ko)
JP (1) JPS56115729A (ko)
KR (1) KR850000379B1 (ko)
BR (1) BR8006498A (ko)
CA (1) CA1137511A (ko)
DE (1) DE3062638D1 (ko)
MX (1) MX155320A (ko)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4459427A (en) * 1981-10-31 1984-07-10 The British Petroleum Company P.L.C. Process for the conversion of an alkane to a mixture of an alcohol and a ketone
DE3222143A1 (de) * 1982-06-11 1983-12-15 Basf Ag, 6700 Ludwigshafen Kobalt enthaltende traegerkatalysatoren, deren herstellung und verwendung
US4499305A (en) * 1983-04-11 1985-02-12 E. I. Du Pont De Nemours And Company Process for preparation of cyclohexyl hydroperoxide decomposition catalysts
US4465861A (en) * 1983-04-11 1984-08-14 E. I. Du Pont De Nemours And Company Process for producing a mixture containing cyclohexanol and cyclohexanone
US4482746A (en) * 1983-04-11 1984-11-13 E. I. Du Pont De Nemours & Company Staged catalyst process for cyclohexyl hydroperoxide decomposition
US4503257A (en) * 1983-05-18 1985-03-05 E. I. Du Pont De Nemours And Company Cyclohexyl hydroperoxide decomposition process
FR2558826B1 (fr) * 1984-01-31 1986-11-28 Inst Francais Du Petrole Synthese d'alcool tertio-butylique par oxydation catalytique, en phase liquide de l'isobutane par l'oxygene
EP0157657B1 (fr) * 1984-01-31 1988-09-14 Institut Français du Pétrole Complexes peroxydiques de métaux, leur préparation et leur utilisation dans les réactions d'oxydations d'hydrocarbures en alcools et/ou cetone
DE3471093D1 (en) * 1984-06-12 1988-06-16 Sumitomo Chemical Co Method for producing a mixture containing cycloalkanones and cycloalkanols
US4568769A (en) * 1984-06-20 1986-02-04 Sumitomo Chemical Company Method for producing a mixture containing cycloalkanones and cycloalkanols
US4652647A (en) * 1984-12-26 1987-03-24 Exxon Research And Engineering Company Aromatic-metal chelate compositions
US4836912A (en) * 1985-09-04 1989-06-06 Exxon Research And Engineering Company Hydroconversion process using aromatic metal chelate compositions
FR2604998B1 (fr) * 1986-10-10 1989-06-09 Rhone Poulenc Chimie Procede de preparation d'un melange renfermant du cyclohexanol et de la cyclohexanone a partir du cyclohexane
FR2607805B1 (fr) * 1986-12-05 1989-03-24 Rhone Poulenc Chimie Procede de preparation d'un melange renfermant du cyclohexanol et de la cyclohexanone a partir du cyclohexane
NL8802592A (nl) * 1988-10-21 1990-05-16 Stamicarbon Werkwijze voor de bereiding van een k/a-mengsel.
FR2741340B1 (fr) * 1995-11-16 1997-12-26 Elf Aquitaine Procede d'oxydation de substrats organiques en presence de complexes metalliques de ligands tetra-, penta- et hexacoordinants et catalyseurs d'oxydation les contenant
CN1093109C (zh) 1996-09-03 2002-10-23 纳幕尔杜邦公司 分解氢过氧化物的方法
EP1012130B9 (en) 1997-02-11 2003-05-02 E.I. Du Pont De Nemours And Company Hydroperoxide decomposition process
US6160183A (en) * 1998-02-10 2000-12-12 E. I. Du Pont De Nemours And Company Direct oxidation of cycloalkanes
US6693154B2 (en) 2001-09-06 2004-02-17 Equistar Chemicals, Lp Transition metal catalysts for olefin polymerization
WO2003042131A1 (en) * 2001-11-15 2003-05-22 Stichting Voor De Technische Wetenschappen Hydrogenation catalyst and catalysed hydrogenation process
TW591009B (en) * 2003-02-19 2004-06-11 China Petrochemical Dev Corp Liquid phase oxidation of cycloalkane compound
CN1317074C (zh) * 2003-03-14 2007-05-23 中国科学院大连化学物理研究所 一种锆基复合氧化物催化剂及制备方法和应用
US6982040B2 (en) * 2003-04-16 2006-01-03 Zodiac Pool Care, Inc. Method and apparatus for purifying water
CN101462926B (zh) * 2007-12-19 2011-09-07 中国科学院大连化学物理研究所 一种络合催化分解环己基过氧化氢的方法
FR2952055B1 (fr) * 2009-11-05 2011-11-11 Rhodia Operations Procede de preparation de composes hydroperoxyde d'alkyle

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2851496A (en) * 1954-07-27 1958-09-09 Du Pont Preparation of oxidation products of cyclohexane
US3530185A (en) * 1966-08-08 1970-09-22 Du Pont Oxidation process
FR1547427A (fr) * 1967-05-26 1968-11-29 Rhone Poulenc Sa Perfectionnement à la préparation de mélanges cycloalcanols/cycloalcanones
US3927105A (en) * 1968-04-08 1975-12-16 Rhone Poulenc Sa Process for the preparation of mixtures of cycloalkanols and cycloalkanones
FR2087365A5 (ko) * 1970-05-15 1971-12-31 Rhone Poulenc Sa
GB1347913A (en) * 1970-06-09 1974-02-27 Basf Ag Production of cycloalkanols and cycloalkanones
US3957876A (en) * 1970-07-31 1976-05-18 E. I. Du Pont De Nemours And Company Process for the oxidation of cyclohexane
US3816548A (en) * 1971-04-27 1974-06-11 Mobil Oil Corp Catalytic oxidation process for isoparaffin hydrocarbons
DE2127520A1 (de) * 1971-06-03 1972-12-14 Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen Verfahren zur Herstellung von Cycloalkanol- und Cycloalkanon-Gemischen
US3987100A (en) * 1974-04-11 1976-10-19 E. I. Du Pont De Nemours And Company Cyclohexane oxidation in the presence of binary catalysts
US4034047A (en) * 1974-11-18 1977-07-05 Suntech, Inc. Process for catalytic oxidation of olefins to form hydroperoxides
US4243551A (en) * 1978-12-04 1981-01-06 Ashland Oil, Inc. Catalyst for oxidizing mercaptans and mercaptide compounds and method for preparing

Also Published As

Publication number Publication date
EP0027937B1 (en) 1983-04-06
DE3062638D1 (en) 1983-05-11
KR850000379B1 (ko) 1985-03-23
MX155320A (es) 1988-02-18
BR8006498A (pt) 1981-04-14
JPS56115729A (en) 1981-09-11
CA1137511A (en) 1982-12-14
US4326084A (en) 1982-04-20
JPS6411010B2 (ko) 1989-02-23
EP0027937A1 (en) 1981-05-06

Similar Documents

Publication Publication Date Title
KR830004194A (ko) 사이클로헥산으로부터 사이클로헥산올 및 사이클로헥사논 함유 혼합물을 제조하는 방법
Hughey IV et al. Flash photolysis evidence for metal-metal bond cleavage and loss of carbon monoxide in the photochemistry of bis [(. eta. 5-cyclopentadienyl) tricarbonylmolybdenum]
Hiatt et al. Homolytic decompositions of hydroperoxides. III. Radical-induced decompositions of primary and secondary hydroperoxides
Carrell et al. Oxidative catalysis by Mn4O46+ cubane complexes
KR900006268A (ko) 사이클로알카논 및/또는 사이클로알카놀의 제조방법
GB942435A (en) Process for the hydrogenation of organic compounds
Kochi Oxidation of allylic radicals by electron transfer: effect of complex copper salts
Herron et al. Reversible dioxygen binding by a totally synthetic nonporphyrin macrobicyclic iron (II) complex containing a persistent void
ES484183A1 (es) Procedimiento de obtencion de complejos metalicos para la sorcion de gases
KR830005900A (ko) 메타크롤레인 산화촉매
KR840001941A (ko) 에틸렌 글리콜의 제조방법
ATE110357T1 (de) Verfahren zur herstellung von o-hydroxy- benzaldehyden.
Di Furia et al. Metal catalysis in oxidation by peroxides. Part 5. On the mechanism of vanadium (V) catalysed oxidation by hydrogen peroxide
Sun et al. Rapid aerobic oxidation of alcohols to carbonyl compounds with dioxygen using metallodeuteroporphyrin dimethyl esters as catalysts in the presence of isobutylaldehyde
Barton et al. Metal dependence in gif-type reactions. The Cu (II)-catalyzed olefination of saturated hydrocarbons by tert-butyl hydroperoxide.
DE4331671A1 (de) Verfahren zur selektiven katalytischen Oxidation organischer Verbindungen
Majima et al. Redox-photosensitized chain monomerization of cis-syn-dimer of dimethylthymine; unusual effect of molecular oxygen
KR920005711A (ko) 사이클로 알카논 및/또는 사이클로알카놀의 제조방법
US1762688A (en) Oxidizing paraffins, waxes, and the like
US3891711A (en) Production of ketones
GB1249218A (en) Oxidation of secondary and tertiary alkyl aromatic hydrocarbons
KR850007055A (ko) 초산의 합성법
DE69314054D1 (de) Verfahren zur kontinuierlichen herstellung von gemischen aus einem cycloalkanon, einem cycloalkanol und einem cycloalkylhydroperoxid
DE168807T1 (de) Verfahren zur herstellung von maleinsaeureanhydrid.
US3836589A (en) Method for the oxidation of hydrocarbons