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4-Vinylcyclohexene dioxide (VCD) is a colorless liquid with a faint olefinic odor, known for its combustible properties. It is the diepoxide of 4-vinylcyclohexene and sets to glass at -67°F. VCD is primarily used as a chemical intermediate and in research studies to understand its mechanisms of toxicity and effects on ovarian follicles and epithelial differentiation.

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  • 106-87-6 Structure
  • Basic information

    1. Product Name: 4-VINYLCYCLOHEXENE DIOXIDE
    2. Synonyms: 1-EPOXYETHYL-3.4-EPOXYCYCLOHEXANE;4-VINYLCYCLOHEXENE DIOXIDE;4-VINYL-1-CYCLOHEXENE DIEPOXIDE;4-VINYL-1-CYCLOHEXENE DIOXIDE;3-EPOXYETHYL-7-OXABICYCLO [4.1.0] HEPTANE;ERL(R) 4206;ERL 4206;VINYL-4-CYCLOHEXENE DIOXIDE
    3. CAS NO:106-87-6
    4. Molecular Formula: C8H12O2
    5. Molecular Weight: 140.18
    6. EINECS: 203-437-7
    7. Product Categories: N/A
    8. Mol File: 106-87-6.mol
  • Chemical Properties

    1. Melting Point: -55°C
    2. Boiling Point: 230-232 °C(lit.)
    3. Flash Point: 225 °F
    4. Appearance: colourless liquid
    5. Density: 1.094 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.119mmHg at 25°C
    7. Refractive Index: n20/D 1.477(lit.)
    8. Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
    9. Solubility: N/A
    10. Water Solubility: 154.7g/L(20 oC)
    11. Stability: Stable. Combustible. Incompatible with strong oxidizing agents, alcohols, amines and other compounds containg an active hydrogen
    12. BRN: 106071
    13. CAS DataBase Reference: 4-VINYLCYCLOHEXENE DIOXIDE(CAS DataBase Reference)
    14. NIST Chemistry Reference: 4-VINYLCYCLOHEXENE DIOXIDE(106-87-6)
    15. EPA Substance Registry System: 4-VINYLCYCLOHEXENE DIOXIDE(106-87-6)
  • Safety Data

    1. Hazard Codes: T
    2. Statements: 23/24/25-68/20/21/22-68
    3. Safety Statements: 23-24-45
    4. RIDADR: UN 2810 6.1/PG 3
    5. WGK Germany: 1
    6. RTECS: RN8640000
    7. HazardClass: 6.1(b)
    8. PackingGroup: III
    9. Hazardous Substances Data: 106-87-6(Hazardous Substances Data)

106-87-6 Usage

Uses

Used in Chemical Synthesis:
4-Vinylcyclohexene dioxide is used as a chemical intermediate for the production of various compounds and materials.
Used in Epoxy Resins and Diepoxides:
4-Vinylcyclohexene dioxide is used as a reactive diluent for diepoxides and epoxy resins, enhancing their properties and performance.
Used in Toxicity Research:
4-Vinylcyclohexene dioxide is used as an ovotoxin in research studies to investigate its toxicity and mechanisms of action on ovarian follicles and epithelial differentiation. This helps in understanding the potential effects of VCD on reproductive health and developing possible countermeasures or treatments.

Production Methods

VCHD is manufactured by epoxidation of 4-vinylcyclohexene with peroxyacetic acid .

Air & Water Reactions

Water soluble. Hydrolyzes slowly in water.

Reactivity Profile

4-VINYLCYCLOHEXENE DIOXIDE reacts with active hydrogen compounds (such as alcohols and amines). . Epoxides are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.

Hazard

Toxic by ingestion and skin absorption, strong irritant to skin and tissue. Female and male reproductive damage. Possible carcinogen.

Health Hazard

Vinyl cyclohexene dioxide (VCD) is an irritant to the skin, eyes, and respiratory system. It is ovotoxic and carcinogenic in experimental animals.

Safety Profile

Confirmed carcinogen with experimental carcinogenic and tumorigenic data. Poison by unspecified route. Moderately toxic by ingestion and skin contact. Mildly toxic by inhalation. Experimental reproductive effects. Mutation data reported. A severe skin irritant.Combustible when exposed to heat or flame. To fight fire, use water, foam, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

This material is used as a monomer in the production of epoxy resins for coatings and adhesives; as a chemical intermediate and as a reactive diluent.

Carcinogenicity

4-Vinyl-1-cyclohexene diepoxide is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity fromstudies in experimental animals.

Shipping

UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Incompatibilities

When heated or in contact with catalysts, epoxides may cause violent polymerization. Epoxides are incompatible with reducing agents and oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. May react, possibly violently, with water in the presence of acid and other catalysts. Reacts with alcohols, amines and other active hydrogen compounds. Slowly hydrolyzes in water.

Waste Disposal

Concentrated waste containing no peroxides: discharge liquid at a controlled rate near a pilot flame. Concentrated waste containing peroxides: perforation of a container of the waste from a safe distance followed by open burning.

Check Digit Verification of cas no

The CAS Registry Mumber 106-87-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 6 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 106-87:
(5*1)+(4*0)+(3*6)+(2*8)+(1*7)=46
46 % 10 = 6
So 106-87-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H12O2/c1-2-6-7(10-6)3-5(1)8-4-9-8/h5-8H,1-4H2

106-87-6 Well-known Company Product Price

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  • Sigma

  • (94956)  Vinylcyclohexenedioxide  purum, for electron microscopy, mixture of isomers, ≥96.0% (GC)

  • 106-87-6

  • 94956-100ML

  • 4,278.69CNY

  • Detail
  • Sigma

  • (94956)  Vinylcyclohexenedioxide  purum, for electron microscopy, mixture of isomers, ≥96.0% (GC)

  • 106-87-6

  • 94956-250ML

  • 8,558.55CNY

  • Detail

106-87-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-vinylcyclohexene dioxide

1.2 Other means of identification

Product number -
Other names 4-vinylcyclohexene diepoxide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:106-87-6 SDS

106-87-6Synthetic route

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

Conditions
ConditionsYield
With 2,2,2-Trifluoroacetophenone; dihydrogen peroxide In acetonitrile; tert-butyl alcohol at 20℃; for 1h; Green chemistry;88%
With fluorosulfonyl fluoride; dihydrogen peroxide; potassium carbonate In 1,4-dioxane; water at 20℃; for 1h;81%
With hypochloric acid Behandeln des Reaktionsproduktes mit wss. Natronlauge.;
4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

A

4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

C8H12O

C8H12O

Conditions
ConditionsYield
With C20H26FeN4(2+)*2CF3O3S(1-); dihydrogen peroxide; acetic acid In acetonitrile at 0℃; for 0.166667h; regioselective reaction;A n/a
B 74%
1,1,3,3-tetrachloropropanone
632-21-3

1,1,3,3-tetrachloropropanone

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

A

4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

B

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

C

7,8-Epoxy-1-Cyclohexene
5116-65-4

7,8-Epoxy-1-Cyclohexene

D

tetrachloroacetone hydrate
78950-58-0

tetrachloroacetone hydrate

Conditions
ConditionsYield
With disodium hydrogenphosphate; dihydrogen peroxide In chloroform for 24h; Ambient temperature;A 2%
B 60%
C 2.5%
D n/a
With disodium hydrogenphosphate; dihydrogen peroxide In chloroform for 24h; Ambient temperature;A 2%
B 60%
C 1.5%
D n/a
4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

A

4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

B

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

C

7,8-Epoxy-1-Cyclohexene
5116-65-4

7,8-Epoxy-1-Cyclohexene

Conditions
ConditionsYield
With dimethylammonium tetrakis(diperoxotungsto)phosphate; dihydrogen peroxide In benzene at 60℃; for 1h;A 3 % Chromat.
B 83 % Chromat.
C 2 % Chromat.
With dihydrogen peroxide; cetylpyridinium bromide; H3PMo10W2O40 In acetonitrile at 60℃; for 3h; Product distribution; Further Variations:; Catalysts; Solvents; Temperatures;
4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

A

4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

B

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

Conditions
ConditionsYield
With tert.-butylhydroperoxide; silica gel; molybdenum trioxide In decane at 50℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With air; bis(hexafluoroacetylacetonato)cobalt; isobutyraldehyde In 1,2-dichloro-ethane at 20℃; under 7600 Torr; for 24h; Product distribution; Further Variations:; Reagents; Pressures;A 20 % Chromat.
B 80 % Chromat.
With air; bis(hexafluoroacetylacetonato)cobalt; isobutyraldehyde In 1,2-dichloro-ethane at 20℃; under 7600 Torr; for 24h;A 20 % Chromat.
B 80 % Chromat.
With [Mn(CF3SO3)2(H,MePyTACN)]; dihydrogen peroxide; acetic acid In acetonitrile at 0℃; for 1.5h; chemoselective reaction;
methanol
67-56-1

methanol

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

A

4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

B

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

C

7,8-Epoxy-1-Cyclohexene
5116-65-4

7,8-Epoxy-1-Cyclohexene

D

cyclohex-3-enyl acetaldehyde
24480-99-7

cyclohex-3-enyl acetaldehyde

F

2-Methoxy-5-vinyl-cyclohexanol

2-Methoxy-5-vinyl-cyclohexanol

G

C9H16O2
1243451-21-9

C9H16O2

Conditions
ConditionsYield
With dihydrogen peroxide In water at 64.84℃; for 2h; regioselective reaction;
4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

carbon dioxide
124-38-9

carbon dioxide

cis-5-(2-oxo-1,3-dioxolan-4-yl)hexahydrobenzo[d][1,3]dioxol-2-one

cis-5-(2-oxo-1,3-dioxolan-4-yl)hexahydrobenzo[d][1,3]dioxol-2-one

Conditions
ConditionsYield
With C20H13FeN2O5; tetrabutylammomium bromide at 100℃; under 3750.38 - 7500.75 Torr; for 12h; Sealed tube;99%
4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

carbon dioxide
124-38-9

carbon dioxide

C10H12O6

C10H12O6

Conditions
ConditionsYield
With tetrabutylammomium bromide In neat (no solvent) at 100℃; for 12h; chemoselective reaction;99%
4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

carbon dioxide
124-38-9

carbon dioxide

C10H12O6

C10H12O6

Conditions
ConditionsYield
With calcium iodide In neat (no solvent) at 90℃; under 37503.8 Torr; for 48h; diastereoselective reaction;93%
4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

carbon dioxide
124-38-9

carbon dioxide

4-(7-oxabicyclo[4.1.0]heptan-3-yl)-1,3-dioxolan-2-one

4-(7-oxabicyclo[4.1.0]heptan-3-yl)-1,3-dioxolan-2-one

Conditions
ConditionsYield
With 18-crown-6 ether; calcium iodide In neat (no solvent) at 23℃; under 760.051 Torr; for 24h;92%
4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

n-butyl magnesium bromide
693-03-8

n-butyl magnesium bromide

6-pentyl-7-oxabicyclo<3.2.1>octan-2-ol

6-pentyl-7-oxabicyclo<3.2.1>octan-2-ol

Conditions
ConditionsYield
With triphenylphosphine; copper(I) bromide 1.) THF, Et2O, 0 deg C, 30 min, 2.) THF, Et2O, 0 deg C, 2 h; Yield given; Multistep reaction;
4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

polymer, from photosensitized cationic polymerization; monomer(s): 4-vinylcyclohexene dioxide

polymer, from photosensitized cationic polymerization; monomer(s): 4-vinylcyclohexene dioxide

Conditions
ConditionsYield
With 10-(2-(vinyloxy)ethyl)-10H-phenothiazine; (4-n-decyloxyphenyl) phenyliodonium hexafluoroantimonate at 20℃; Product distribution; Further Variations:; Reagents; UV-irradiation;
4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

4-(1,2-dihydroxyethyl)cyclohexane-1,2-diol
5581-28-2

4-(1,2-dihydroxyethyl)cyclohexane-1,2-diol

Conditions
ConditionsYield
With sulfuric acid In water; acetone
4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

2,2,4-trimethyl-decahydro-quinoline
65125-45-3

2,2,4-trimethyl-decahydro-quinoline

1-[2'-hydroxy-2'-(3,4-epoxycyclohexyl)ethyl]-2,2,4-trimethyldecahydroquinoline
65825-48-1

1-[2'-hydroxy-2'-(3,4-epoxycyclohexyl)ethyl]-2,2,4-trimethyldecahydroquinoline

Conditions
ConditionsYield
With Hg In ethylene glycol

106-87-6Relevant articles and documents

Covalent heterogenization of a discrete Mn(II) Bis-Phen complex by a metal-template/metal-exchange method: An epoxidation catalyst with enhanced reactivity

Terry, Tracy J.,Daniel,Stack

, p. 4945 - 4953 (2008)

Considerable attention has been devoted to the immobilization of discrete epoxidation catalysts onto solid supports due to the possible benefits of site isolation such as increased catalyst stability, catalyst recycling, and product separation. A synthetic metal-template/metal-exchange method to imprint a covalently attached bis-1,10-phenanthroline coordination environment onto high-surface area, mesoporous SBA-15 silica is reported herein along with the epoxidation reactivity once reloaded with manganese. Comparisons of this imprinted material with material synthesized by random grafting of the ligand show that the template method creates more reproducible, solution-like bis-1,10-phenanthroline coordination at a variety of ligand loadings. Olefin epoxidation with peracetic acid shows the imprinted manganese catalysts have improved product selectivity for epoxides, greater substrate scope, more efficient use of oxidant, and higher reactivity than their homogeneous or grafted analogues independent of ligand loading. The randomly grafted manganese catalysts, however, show reactivity that varies with ligand loading while the homogeneous analogue degrades trisubstituted olefins and produces trans-epoxide products from cis-olefins. Efficient recycling behavior of the templated catalysts is also possible.

Simple iron catalyst for terminal alkene epoxidation

Dubois, Geraud,Murphy, Andrew,Daniel,Stack

, p. 2469 - 2472 (2003)

(Matrix presented) A μ-oxo-iron(III) dimer, [((phen)2(H 2O)FeIII)2(μ-O)](ClO4) 4, is an efficient epoxidation catalyst for a wide range of alkenes, including terminal alkenes, using peracetic acid as the oxidant. Low catalyst loadings, in situ catalyst preparation from common reagents, fast reaction times (5 min at 0°C), and enhanced reaction performance at high substrate concentrations combine to create a temporally and synthetically efficient procedure for alkene epoxidation.

METHOD FOR PRODUCING EPOXY COMPOUND

-

Paragraph 0089-0091, (2021/11/05)

The invention provides a method for producing an epoxy compound by hydrogen peroxide using an organic compound having a carbon-carbon double bond as a raw material, wherein a by-product is suppressed from being generated and the epoxy compound is produced in a high yield. In particular, the invention provides a method for producing an epoxy compound involving oxidizing a carbon-carbon double bond in an organic compound with hydrogen peroxide in the presence of a catalyst, wherein the catalyst comprises a tungsten compound; a phosphoric acid, a phosphonic acid or salts thereof; and an onium salt having an alkyl sulfate ion represented by formula (I) as an anion: wherein R1 is a linear or branched aliphatic hydrocarbon group having 1 to 18 carbons, which may be substituted with 1 to 3 phenyl groups.

SO2F2-Mediated Epoxidation of Olefins with Hydrogen Peroxide

Ai, Chengmei,Zhu, Fuyuan,Wang, Yanmei,Yan, Zhaohua,Lin, Sen

, p. 11928 - 11934 (2019/10/02)

An inexpensive, mild, and highly efficient epoxidation protocol has been developed involving bubbling SO2F2 gas into a solution of olefin, 30% aqueous hydrogen peroxide, and 4 N aqueous potassium carbonate in 1,4-dioxane at room temperature for 1 h with the formation of the corresponding epoxides in good to excellent yields. The novel SO2F2/H2O2/K2CO3 epoxidizing system is suitable to a variety of olefinic substrates including electron-rich and electron-deficient ones.

Safe, environment-friendly and controllable synthetic process of di-epoxide

-

Paragraph 0152-0168, (2019/10/01)

The invention relates to the field of synthesis of epoxide, and more specifically, relates to a safe, environment-friendly and controllable synthetic process of di-epoxide. The synthetic process of the di-epoxide at least comprises the following steps: mixing diolefin, carboxylic acids, basic salt and solvent, and cooling; dropwise adding a hydrogen peroxide solution for 1-12 h; standing for layering to obtain a lower layer organic phase-1, washing the organic phase-1 with a cleaning solution, and standing for layering to obtain a lower layer organic phase-2; purifying. The reaction system ofthe synthetic process is simple, environmentally friendly, safe and controllable, is low in production cost, and can meet the requirements of technical economy; the prepared di-epoxide is high in purity and yield and low in solvent content, chroma and halogen content, and is suitable for large-scale industrial production.

Regioselective Cleavage of Electron-Rich Double Bonds in Dienes to Carbonyl Compounds with [Fe(OTf)2(mix-BPBP)] and a Combination of H2O2 and NaIO4

Spannring, Peter,Yazerski, Vital A.,Chen, Jianming,Otte, Matthias,Weckhuysen, Bert M.,Bruijnincx, Pieter C. A.,Klein Gebbink, Robertus J. M.

, p. 3462 - 3466 (2015/08/06)

A method for the regioselective transformation of dienes to carbonyl compounds has been developed. Electron-rich olefins react selectively to yield valuable aldehydes and ketones. The method is based on the catalyst [Fe(OTf)2(mix-BPBP)] with an oxidant combination of H2O2 (1.0 equiv.) and NaIO4 (1.5 equiv.); it uses mild conditions and short reaction times, and it outperforms other olefin cleavage methodologies. The combination of an Fe-based catalyst, [Fe(OTf)2(mix-BPBP)], and the oxidants H2O2 and NaIO4 can discriminate between electronically different double bonds and oxidatively cleave the electron-rich bond in dienes to yield aldehydes and ketones in a regioselective manner. The reaction requires mild conditions (0-50 C) and short reaction times (70 min).

2,2,2-Trifluoroacetophenone: An organocatalyst for an environmentally friendly epoxidation of alkenes

Limnios, Dimitris,Kokotos, Christoforos G.

, p. 4270 - 4276 (2014/06/09)

A cheap, mild, fast, and environmentally friendly oxidation of olefins to the corresponding epoxides is reported using polyfluoroalkyl ketones as efficient organocatalysts. Namely, 2,2,2-trifluoroacetophenone was identified as an improved organocatalyst for the epoxidation of alkenes. Various olefins, mono-, di-, and trisubstituted, are epoxidized chemoselectively in high to quantitative yields utilizing 2-5 mol % catalyst loading and H2O 2 as the green oxidant.

Liquid-phase synthesis of cyclic diene diepoxides using metal halides and hydrogen peroxide

Alimardanov, Kh. M.,Sadygov,Garibov,Abdullaeva, M. Ya.

, p. 1302 - 1308 (2013/02/21)

Optimal conditions were found for induced hydroxyhalogenation of cyclic dienes (tetrahydroindene, 4-vinylcyclohexene and 5-vinyl- and 5-cyclohexenylbicyclo[2.2.1]hept-2-enes) in the system [MHlg-HA or HHlg]-H 2O2 (or NaClO). Dehydrohalogenation of the chloro- and bromohydrins thus obtained with powdered potassium carbonate gave the corresponding diepoxy derivatives, and their hydrolysis led to mixtures of stereoisomeric tetrahydric alcohols. Pleiades Publishing, Ltd., 2012.

Designing the synthesis of catalytically active Ti-β by using various new templates in the presence of fluoride anion

Sasidharan, Manickam,Bhaumik, Asim

experimental part, p. 16282 - 16294 (2012/01/14)

Crystallization of large-pore Ti-β by using a variety of diquaternary ammonium derivatives of dibromoalkane and amines such as triethylamine, 1,4-diazabicyclo[2,2,2]octane (DABCO), and quinuclidine as structure-directing agents (SDA) is described. The size of hydrophobic bridging alkyl-chain length of the template [R3N+-(CH2)x-N +R3](OH-)2 directs the final crystalline product: Ti-β, Ti-ZSM-12, Ti-nonasil or Ti-ZSM-5, as x gradually changes from 6 to 1, in the fluoride medium under hydrothermal conditions. A dense phase such as Ti-nonasil (clathrasil type) is crystallized as the size of hydrophobic bridging alkyl-chain length decreases. The use of F- anions as a mineralizer and Ti4+ as a heteroatom in the synthesis gel also influences the selectivity of final crystalline product. The phase purity and incorporation of Ti4+ into the lattice of β (BEA) and ZSM-12 frameworks are confirmed using XRD, UV-visible, FT-IR, 29Si NMR spectroscopes, elemental analysis (ICP), surface area measurements and catalytic test reactions. The morphology of Ti-β samples is dependent on the nature of the structure-directing agent as revealed by the scanning electron microscopic (SEM) observations. The catalytic activity in the epoxidation of 4-vinyl-1-cyclohexene is increased with the amount of tetrahedral Ti4+ atoms in the framework. The new templates can be effectively used for preparation of catalytically active Ti-β with the minimum number of framework defect sites.

Regioselective epoxidation of different types of double bonds over large-pore titanium silicate Ti-β

Sasidharan, Manickam,Bhaumik, Asim

experimental part, p. 60 - 67 (2010/12/18)

Regioselective epoxidation of different types of double bonds located within the cyclic and acyclic parts of bulky olefins has been investigated using large-pore titanium silicate Ti-β in the presence of dilute aqueous H 2O2 as oxidant under mild liquid-phase conditions. Our experimental results revealed that side-chain vinylic double bonds are selectively epoxidized than those in the cyclohexene-ring. The epoxidation tendency of various bulky olefins with different positional and/or geometric isomers over Ti-β follows the order: terminal -CC- > ring -CC- ≈ bicyclic ring -CC- > allylic C - H bond. Unlike 4-vinyl-1-cyclohexene, epoxidation of an equimolar mixture of cyclohexene and 1-hexene under identical conditions using Ti-β exhibits completely different selectivity and product distributions. Steric factor and accessibility of reactants to active Ti-sites are responsible for the observed regioselectivity of bulky alkenes.

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