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Abstract
The aim of present work was to check the possibility of microwave irradiation application for benzylic oxidation of diphenylmethane. The investigations were carried out using tert-butyl hydroperoxide (TBHP) both under conventional and microwave conditions. The catalysts tested were chlorides of transition d-metals: FeCl3·6H2O, CoCl2·6H2O, NiCl2·6H2O, CrCl3·6H2O, CuCl2·2H2O, ZnCl2 and iodine. From all studied metal catalysts, FeCl3·6H2O, CoCl2·6H2O, NiCl2·6H2O, CrCl3·6H2O showed the best catalytic activity.
CAS No.: 75-91-2
EC No.: 200-915-7
Synonyms:
TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; TERT-BUTYL HYDROPEROXIDE; 75-91-2; Tert-Butyl hydroperoxide; T-Butyl hydroperoxide; tert-Butylhydroperoxide; Perbutyl H; t-Butylhydroperoxide; 2-Hydroperoxy-2-methylpropane; Cadox TBH; 1,1-Dimethylethyl hydroperoxide; Hydroperoxide, 1,1-dimethylethyl; tert-Butyl hydrogen peroxide; Terc. butylhydroperoxid; Hydroperoxyde de butyle tertiaire; Hydroperoxide, tert-butyl; Slimicide DE-488; Tertiary butyl hydroperoxide; Trigonox a-75; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; Trigonox A-W70; Tert-Butyl hydroperoxide-70; NSC 672; Tertiary-butyl hydroperoxide; 1,1-Dimethylethylhydroperoxide; tert-Butyl-hydroperoxide; Caswell No. 130BB; Dimethylethyl hydroperoxide; Trigonox A-75 [Czech]; T-Hydro; tBuOOH; t-BuOOH; UNII-955VYL842B; terc.Butylhydroperoxid [Czech]; CCRIS 5892; HSDB 837; terc. Butylhydroperoxid [Czech]; EINECS 200-915-7; DE 488; DE-488; BRN 1098280; Hydroperoxyde de butyle tertiaire [French]; AI3-50541; CHEBI:64090; 955VYL842B; Hydroperoxide, 1,1-dimethylethyl-; tert-Butyl Hydroperoxide (70% Solution in Water); TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; Tert-Butyl hydroperoxide, 70% solution in water; tert-Butyl hydroperoxide, >90% with water [Forbidden]; terc.Butylhydroperoxid; tert Butylhydroperoxide; Kayabutyl H; tert-BuOOH; tBOOH; Perbutyl H 69; Perbutyl H 69T; Perbutyl H 80; Luperox TBH 70X; t-butyl-hydroperoxide; terbutyl hydroperoxide; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; tert-butyhydroperoxide; tert-C4H9OOH; Trigonox A-W 70; t-butyl hydrogenperoxide; t-butyl-hydrogenperoxide; tert.-butylhydroperoxide; tert.butyl hydroperoxide; tertiarybutylhydroperoxide; tertbutylhydrogen peroxide; t-butyl hydrogen peroxide; tert.-butyl hydroperoxide; ACMC-1BM3U; DSSTox_CID_4693; tert-butylhydrogen peroxide; EC 200-915-7; DSSTox_RID_78866; DSSTox_GSID_31209; tertiary butyl hydro peroxide; Hydroperoxide,1-dimethylethyl; KSC377C1B; Trigonox A-80 (Salt/Mix); UN 2093 (Salt/Mix); UN 2094 (Salt/Mix); TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; USP -800 (Salt/Mix); CHEMBL348399; NSC672; DTXSID9024693; tert-Butyl hydroperoxide (8CI); WLN: QOX1&1&1; CTK2H7110; tert-Butyl hydroperoxide solution; tert-Butyl-hydroperoxide solution; NSC-672; 2-Methyl-prop-2-yl-hydroperoxide; KS-00000X6A; ZINC8585869; CC(C)([OH+][O-])C; Tox21_200838; ANW-43954; Aztec t-butyl Hydroperoxide-70, Aq; MFCD00002130; tert-Butyl hydroperoxide solution, CP; AKOS000121070; LS-1679; 2-$l^{1}-oxidanyloxy-2-methylpropane; NCGC00090725-01; NCGC00090725-02; NCGC00090725-03; NCGC00258392-01; Hydroperoxide, 1,1-dimethylethyl (9CI); SC-46818; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; tert-Butyl Hydroperoxide (70% in Water); tert-Butyl hydroperoxide, >90% with water; B3153; FT-0657109; 22991-EP2284165A1; 22991-EP2298755A1; 22991-EP2305684A1; 22991-EP2305825A1; 22991-EP2308492A1; 22991-EP2311850A1; 22991-EP2315502A1; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; 22991-EP2380874A2; 72702-EP2292610A1; 72702-EP2308492A1; 81228-EP2289887A2; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; 81228-EP2289888A2; 81228-EP2295401A2; 81228-EP2305687A1; 84903-EP2281821A1; 84903-EP2305808A1; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; 101542-EP2277880A1; 101542-EP2289887A2; 101542-EP2289888A2; 101542-EP2292610A1; 101542-EP2301934A1; Q286326; J-509597; tert-Butyl hydroperoxide solution, ~5.5 M in decane; F1905-8242; tert-Butyl hydroperoxide solution (Tert-Butyl hydroperoxide), 70% in H2O; tert-Butyl hydroperoxide solution, 5.0-6.0 M in decane; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; tert-Butyl hydroperoxide solution, 5.0-6.0 M in nonane; Luperox(R) TBH70X, tert-Butyl hydroperoxide solution, 70 wt. % in H2O; tert-Butyl hydroperoxide solution, ~80% in di-tert-butyl peroxide/water 3:2; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; tert-Butyl hydroperoxide solution, packed in FEP bottles, ~5.5 M in decane (over molecular sieve 4??); tert-Butyl hydroperoxide solution, packed in FEP bottles, ~5.5 M in nonane (over molecular sieve 4 ??); TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; TERT-BUTYL HYDROPEROXIDE; 75-91-2; Tert-Butyl hydroperoxide; T-Butyl hydroperoxide; tert-Butylhydroperoxide; Perbutyl H; t-Butylhydroperoxide; 2-Hydroperoxy-2-methylpropane; Cadox TBH; 1,1-Dimethylethyl hydroperoxide; Hydroperoxide, 1,1-dimethylethyl; tert-Butyl hydrogen peroxide; Terc. butylhydroperoxid; Hydroperoxyde de butyle tertiaire; Hydroperoxide, tert-butyl; Slimicide DE-488; Tertiary butyl hydroperoxide; Trigonox a-75; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; Trigonox A-W70; Tert-Butyl hydroperoxide-70; NSC 672; Tertiary-butyl hydroperoxide; 1,1-Dimethylethylhydroperoxide; tert-Butyl-hydroperoxide; Caswell No. 130BB; Dimethylethyl hydroperoxide; Trigonox A-75 [Czech]; T-Hydro; tBuOOH; t-BuOOH; UNII-955VYL842B; terc.Butylhydroperoxid [Czech]; CCRIS 5892; HSDB 837; terc. Butylhydroperoxid [Czech]; EINECS 200-915-7; DE 488; DE-488; BRN 1098280; Hydroperoxyde de butyle tertiaire [French]; AI3-50541; CHEBI:64090; 955VYL842B; Hydroperoxide, 1,1-dimethylethyl-; tert-Butyl Hydroperoxide (70% Solution in Water); TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; Tert-Butyl hydroperoxide, 70% solution in water; tert-Butyl hydroperoxide, >90% with water [Forbidden]; terc.Butylhydroperoxid; tert Butylhydroperoxide; Kayabutyl H; tert-BuOOH; tBOOH; Perbutyl H 69; Perbutyl H 69T; Perbutyl H 80; Luperox TBH 70X; t-butyl-hydroperoxide; terbutyl hydroperoxide; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; tert-butyhydroperoxide; tert-C4H9OOH; Trigonox A-W 70; t-butyl hydrogenperoxide; t-butyl-hydrogenperoxide; tert.-butylhydroperoxide; tert.butyl hydroperoxide; tertiarybutylhydroperoxide; tertbutylhydrogen peroxide; t-butyl hydrogen peroxide; tert.-butyl hydroperoxide; ACMC-1BM3U; DSSTox_CID_4693; tert-butylhydrogen peroxide; EC 200-915-7; DSSTox_RID_78866; DSSTox_GSID_31209; tertiary butyl hydro peroxide; Hydroperoxide,1-dimethylethyl; KSC377C1B; Trigonox A-80 (Salt/Mix); UN 2093 (Salt/Mix); UN 2094 (Salt/Mix); TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; USP -800 (Salt/Mix); CHEMBL348399; NSC672; DTXSID9024693; tert-Butyl hydroperoxide (8CI); WLN: QOX1&1&1; CTK2H7110; tert-Butyl hydroperoxide solution; tert-Butyl-hydroperoxide solution; NSC-672; 2-Methyl-prop-2-yl-hydroperoxide; KS-00000X6A; ZINC8585869; CC(C)([OH+][O-])C; Tox21_200838; ANW-43954; Aztec t-butyl Hydroperoxide-70, Aq; MFCD00002130; tert-Butyl hydroperoxide solution, CP; AKOS000121070; LS-1679; 2-$l^{1}-oxidanyloxy-2-methylpropane; NCGC00090725-01; NCGC00090725-02; NCGC00090725-03; NCGC00258392-01; Hydroperoxide, 1,1-dimethylethyl (9CI); SC-46818; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; tert-Butyl Hydroperoxide (70% in Water); tert-Butyl hydroperoxide, >90% with water; B3153; FT-0657109; 22991-EP2284165A1; 22991-EP2298755A1; 22991-EP2305684A1; 22991-EP2305825A1; 22991-EP2308492A1; 22991-EP2311850A1; 22991-EP2315502A1; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; 22991-EP2380874A2; 72702-EP2292610A1; 72702-EP2308492A1; 81228-EP2289887A2; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; 81228-EP2289888A2; 81228-EP2295401A2; 81228-EP2305687A1; 84903-EP2281821A1; 84903-EP2305808A1; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; 101542-EP2277880A1; 101542-EP2289887A2; 101542-EP2289888A2; 101542-EP2292610A1; 101542-EP2301934A1; Q286326; J-509597; tert-Butyl hydroperoxide solution, ~5.5 M in decane; F1905-8242; tert-Butyl hydroperoxide solution (Tert-Butyl hydroperoxide), 70% in H2O; tert-Butyl hydroperoxide solution, 5.0-6.0 M in decane; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; tert-Butyl hydroperoxide solution, 5.0-6.0 M in nonane; Luperox(R) TBH70X, tert-Butyl hydroperoxide solution, 70 wt. % in H2O; tert-Butyl hydroperoxide solution, ~80% in di-tert-butyl peroxide/water 3:2; TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit; tert-Butyl hydroperoxide solution, packed in FEP bottles, ~5.5 M in decane (over molecular sieve 4??); tert-Butyl hydroperoxide solution, packed in FEP bottles, ~5.5 M in nonane (over molecular sieve 4 ??); TERT-BUTYL HYDROPEROXIDE; TERT-BÜTİL HİDROPEROKSİT; tert-bütil hidroperoksit
TERT-BUTYL HYDROPEROXIDE
Abstract
Abstract Image
The current study evaluates the protective effects of tangeretin, a representative polymethoxyflavone (PMF) mainly isolated from the peels of citrus fruits, against tert-butyl hydroperoxide (t-BHP)-induced oxidative damage in HepG2 cells and the potential mechanisms of this protection. Tangeretin suppressed t-BHP-induced oxidative damage, as evaluated by cell viability, reactive-oxygen-species (ROS) levels, lactate dehydrogenase (LDH) leakage and glutathione (GSH) levels. Further mechanistic studies showed that tangeretin up-regulated the expression of heme oxygenase 1 (HO-1) and NAD(P)H quinone oxidoreductase 1 (NQO1). Moreover, tangeretin induced antioxidant-responsive-element (ARE)-dependent luciferase activation, nuclear factor (erythroid-derived 2)-like 2 (Nrf2) nuclear translocation, and mitogen-activated-protein-kinase (MAPK) phosphorylation. Results in the study indicate that the protective effects of tangeretin may be at least partly due to its capacity to up-regulate the antioxidant enzymes NQO1 and HO-1 via the MAPK–Nrf2–ARE signaling pathway. Tangeretin may play an effective protective role in liver injury.
Preparation method for mixture containing tert-butyl hydroperoxide
Abstract
The invention relates to a preparation method for a mixture containing tert-butyl hydroperoxide, which belongs to the technical field of organic peroxide preparation. The method includes the following steps that: (A) tert-butyl alcohol and sulfuric acid are added into a first reactor and stirred for reaction and the reaction temperature is controlled, so that tert-butyl hydrogen sulfate esterified solution is obtained; (B) hydrogen peroxide and recycled mother solution are added into a second reactor and stirred and the stirring temperature is controlled, so that mixed solution is obtained; (C) the tert-butyl hydrogen sulfate esterified solution and the mixed solution are added into a third reactor and stirred for reaction and the reaction temperature is controlled, so that reaction product is obtained; (D) the reaction product is led into a liquid-separating tank to separate liquid, so that upper oleic-phase mixture containing the tert-butyl hydroperoxide and lower aqueous-phase mother solution containing sulfuric acid and hydrogen peroxide are obtained, moreover, the lower aqueous-phase mother solution containing the sulfuric acid and the hydrogen peroxide returns to the step B and is mixed with the hydrogen peroxide, and the upper oleic phase is the mixture containing the tert-butyl hydroperoxide. The invention prevents the discharge of industrial sewage, so that the environment is protected, and energy and materials are saved, so that the preparation cost is reduced.
tert-Butyl hydroperoxide is a flammable liquid and a highly reactive oxidizing agent. Pure TBHP is shock sensitive and may explode on heating. Carbon dioxide or dry chemical extinguishers should be used for fires involving tert-butyl hydroperoxide.
Reactivity and Incompatibility
tert-Butyl hydroperoxide and concentrated aqueous solutions of TBHP react violently with traces of acid and the salts of certain metals, including, in particular, manganese, iron, and cobalt. Mixing anhydrous tert-butyl hydroperoxide with organic and readily oxidized substances can cause ignition and explosion. TBHP can initiate polymerization of certain olefins.
Storage and Handling
tert-Butyl hydroperoxide should be handled in the laboratory using the "basic prudent practices" described in Chapter 5.C supplemented by the additional precautions for work with reactive and explosive substances (Chapter 5.G). In particular, tert-butyl hydroperoxide should be stored in the dark at room temperature (do not refrigerate) separately from oxidizable compounds, flammable substances, and acids. Reactions involving this substance should be carried out behind a safety shield.
Accidents
In the event of skin contact, immediately wash with soap and water and remove contaminated clothing. In case of eye contact, promptly wash with copious amounts of water for 15 min (lifting upper and lower lids occasionally) and obtain medical attention. If tert-butyl hydroperoxide is inhaled or ingested, obtain medical attention immediately.
In the event of a spill, remove all ignition sources, soak up the tert-butyl hydroperoxide with a spill pillow or noncombustible absorbent material, place in an appropriate container, and dispose of properly. Respiratory protection may be necessary in the event of a large spill or release in a confined area. Cleanup of anhydrous tert-butyl hydroperoxide and concentrated solutions requires special precautions and should be carried out by trained personnel working from behind a body shield.
Disposal
Excess tert-butyl hydroperoxide and waste material containing this substance should be placed in an appropriate container, clearly labeled, and handled according to your institution's waste disposal guidelines.
Abstract
The aim of present work was to check the possibility of microwave irradiation application for benzylic oxidation of diphenylmethane. The investigations were carried out using tert-butyl hydroperoxide (TBHP) both under conventional and microwave conditions. The catalysts tested were chlorides of transition d-metals: FeCl3·6H2O, CoCl2·6H2O, NiCl2·6H2O, CrCl3·6H2O, CuCl2·2H2O, ZnCl2 and iodine. From all studied metal catalysts, FeCl3·6H2O, CoCl2·6H2O, NiCl2·6H2O, CrCl3·6H2O showed the best catalytic activity.
Keywords: microwave irradiation, benzylic oxidation, tert-butyl hydroperoxide, d-metal chlorides
tert-Butyl hydroperoxide
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tert-Butyl hydroperoxide
Skeletal formula of tert-butyl hydroperoxide
Ball-and-stick model of the tert-butyl hydroperoxide molecule
Names
Preferred IUPAC name
2-Methylpropane-2-peroxol[1]
Systematic IUPAC name
tert-Butyl hydroperoxide
Identifiers
CAS Number
75-91-2 check
3D model (JSmol)
Interactive image
Abbreviations Tert-Butyl hydroperoxide
Beilstein Reference 1098280
ChEMBL
ChEMBL348399 check
ChemSpider
6170 check
ECHA InfoCard 100.000.833 Edit this at Wikidata
EC Number
200-915-7
MeSH tert-Butylhydroperoxide
PubChem CID
6410
RTECS number
EQ4900000
UNII
955VYL842B ☒
UN number 3109
CompTox Dashboard (EPA)
DTXSID9024693 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties
Chemical formula C4H10O2
Molar mass 90.122 g·mol−1
Appearance Colorless liquid
Density 0.935 g/mL
Melting point −3 °C (27 °F; 270 K)
Boiling point 37 °C (99 °F; 310 K) at 2.0 kPa
Solubility in water miscible
log P 1.23
Acidity (pKa) 12.69
Basicity (pKb) 1.31
Refractive index (nD) 1.3870
Thermochemistry
Std enthalpy of
formation (ΔfH⦵298) −294±5 kJ/mol
Std enthalpy of
combustion (ΔcH⦵298) 2.710±0.005 MJ/mol
Hazards
Safety data sheet [1]
GHS pictograms GHS02: Flammable GHS05: Corrosive GHS06: Toxic GHS08: Health hazard GHS09: Environmental hazard GHS03: Oxidizing
GHS Signal word Danger
GHS hazard statements H226, H242, H302, H311, H314, H317, H331, H341, H411
GHS precautionary statements P220, P261, P273, P280, P305+351+338, P310
NFPA 704 (fire diamond)
[2]
NFPA 704 four-colored diamond
444OX
Flash point 43 °C (109 °F; 316 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒ verify (what is check☒ ?)
Infobox references
tert-Butyl hydroperoxide (tBuOOH) is an organic peroxide widely used in a variety of oxidation processes, for example Sharpless epoxidation.[3] It is normally supplied as a 69–70% aqueous solution.
Contents
1 Application
2 Synthesis and production
3 Safety
4 See also
5 References
Application
Industrially, tert-butyl hydroperoxide is used as a radical polymerization initiator. For example, its reaction with propene yields propylene oxide and the byproduct t-butanol which can dehydrate to isobutene and convert to MTBE.
Synthesis and production
Many synthetic routes are available, including:[4]
Reaction of hydrogen peroxide with isobutylene or tert-butyl alcohol in the presence of sulfuric acid
Auto-oxidation of isobutane with oxygen
Safety
tert-butyl hydroperoxide is an exceptionally dangerous chemical that is highly reactive, flammable and toxic. It is corrosive to skin and mucous membranes and causes respiratory distress when inhaled. [5]
A solution of tert-butyl hydroperoxide and water with a concentration of greater than 90% is forbidden to be shipped according to US Department of Transportation Hazardous Materials Table 49 CFR 172.101.
In some sources it also has an NFPA 704 rating of 4 for health, 4 for flammability, 4 for reactivity and is a potent oxidant,[6] however other sources claim lower ratings of 3-2-2 or 1-4-4.[7][8]
See also
Di-tert-butyl peroxide
Abstract
(A) Tert-Butyl hydroperoxide is widely used as an epoxidizing agent, both synthetically and industrially. Tert-Butyl hydroperoxide has been used to effect regiospecific, stereospecific, and asymmetric epoxidations. 8 Zhang and Yamamoto showed that asymmetric epoxidation of allylic alcohols can be carried out using Tert-Butyl hydroperoxide with a vanadium catalyst and 95% ee was obtained. 9 (B) Styrene can be epoxidized by Tert-Butyl hydroperoxide to styrene oxide with high selectivity and in high yield using barium oxide (with or without gallium oxide support) as a simple, inexpensive and reusable solid catalyst. 10 trans-Stilbene can be epoxidized by Tert-Butyl hydroperoxide using a Au/TiO 2 catalyst. 11 (C) The epoxidation of α,β-unsaturated ketone and aldehyde compounds is accomplished by Tert-Butyl hydroperoxide in the presence of catalytic amounts of Ti(Oi-Pr) 4 or diaryl-2-pyrrolidinemethanols. 12 The epoxides have been obtained in good yields and with ee values of 80-90%. 13 (D) Manganese(III) acetate catalyzed allylic oxidation of alkenes to the corresponding enones was investigated and showed excellent regioselectivity. 14 Some new strategies have been reported for a useful transformation of the allylic oxidation of alkenes to carbonyl compounds, such as the protocols using Tert-Butyl hydroperoxide catalyzed by transition-metal ion centers (Cr, Ru, Cu, Co, Pd). 15 (E) The palladium-catalyzed allylic alkylation (the Trost-Tsuji reaction) is one of the most important reactions for constructing C-C bonds in modern organic synthesis. Recently, Chao-Jun Li and co-workers found that when a catalytic amount of CuBr and a stoichiometric amount of Tert-Butyl hydroperoxide were used the desired product was obtained in higher yield. 16 (F) In the presence of a catalytic amount of CuI and inorganic bases such as NaHCO 3, the aldehydes with amine hydrochloride salts gave the amide under mild conditions in good yield. The method can be used as the strategy for amide bond formation. 17 (G) Oxidative cleavage of the C=C bond to afford ketone or aldehyde products with Tert-Butyl hydroperoxide as the oxidant can be catalyzed by AuCl. This oxidation reaction proceeds under mild conditions in water, a variety of functional groups are tolerated. 18 (H) Copper-catalyzed oxidative esterification of aldehydes with β-dicarbonyl compounds was developed using Tert-Butyl hydroperoxide as an oxidant. In general, the enol esters were synthesized in good yields (up to 87%) and high stereoselectivity under the optimized reaction conditions. 19.
1 Tert-butyl hydroperoxide decomposition in the presence of initiators (tert-butyl peroxide (t BuOOtBu), azodiisobutyronitrile(AIBN)) and catalysts (Mo 2 B 5 , MoB, Mo 2 B, MoSi 2 , VB 2 , VSi 2) was studied. Our experiments suggest that the introduction of radicals may reduce the catalytic activity. The mechanism of the initial stage of tert-butyl hydroperoxide decomposition and reaction rate equation are proposed.
Abstract
Abstract Image
The current study evaluates the protective effects of tangeretin, a representative polymethoxyflavone (PMF) mainly isolated from the peels of citrus fruits, against tert-butyl hydroperoxide (t-BHP)-induced oxidative damage in HepG2 cells and the potential mechanisms of this protection. Tangeretin suppressed t-BHP-induced oxidative damage, as evaluated by cell viability, reactive-oxygen-species (ROS) levels, lactate dehydrogenase (LDH) leakage and glutathione (GSH) levels. Further mechanistic studies showed that tangeretin up-regulated the expression of heme oxygenase 1 (HO-1) and NAD(P)H quinone oxidoreductase 1 (NQO1). Moreover, tangeretin induced antioxidant-responsive-element (ARE)-dependent luciferase activation, nuclear factor (erythroid-derived 2)-like 2 (Nrf2) nuclear translocation, and mitogen-activated-protein-kinase (MAPK) phosphorylation. Results in the study indicate that the protective effects of tangeretin may be at least partly due to its capacity to up-regulate the antioxidant enzymes NQO1 and HO-1 via the MAPK–Nrf2–ARE signaling pathway. Tangeretin may play an effective protective role in liver injury.
Preparation method for mixture containing tert-butyl hydroperoxide
Abstract
The invention relates to a preparation method for a mixture containing tert-butyl hydroperoxide, which belongs to the technical field of organic peroxide preparation. The method includes the following steps that: (A) tert-butyl alcohol and sulfuric acid are added into a first reactor and stirred for reaction and the reaction temperature is controlled, so that tert-butyl hydrogen sulfate esterified solution is obtained; (B) hydrogen peroxide and recycled mother solution are added into a second reactor and stirred and the stirring temperature is controlled, so that mixed solution is obtained; (C) the tert-butyl hydrogen sulfate esterified solution and the mixed solution are added into a third reactor and stirred for reaction and the reaction temperature is controlled, so that reaction product is obtained; (D) the reaction product is led into a liquid-separating tank to separate liquid, so that upper oleic-phase mixture containing the tert-butyl hydroperoxide and lower aqueous-phase mother solution containing sulfuric acid and hydrogen peroxide are obtained, moreover, the lower aqueous-phase mother solution containing the sulfuric acid and the hydrogen peroxide returns to the step B and is mixed with the hydrogen peroxide, and the upper oleic phase is the mixture containing the tert-butyl hydroperoxide. The invention prevents the discharge of industrial sewage, so that the environment is protected, and energy and materials are saved, so that the preparation cost is reduced.
tert-Butyl hydroperoxide is a flammable liquid and a highly reactive oxidizing agent. Pure TBHP is shock sensitive and may explode on heating. Carbon dioxide or dry chemical extinguishers should be used for fires involving tert-butyl hydroperoxide.
Reactivity and Incompatibility
tert-Butyl hydroperoxide and concentrated aqueous solutions of TBHP react violently with traces of acid and the salts of certain metals, including, in particular, manganese, iron, and cobalt. Mixing anhydrous tert-butyl hydroperoxide with organic and readily oxidized substances can cause ignition and explosion. TBHP can initiate polymerization of certain olefins.
Storage and Handling
tert-Butyl hydroperoxide should be handled in the laboratory using the "basic prudent practices" described in Chapter 5.C supplemented by the additional precautions for work with reactive and explosive substances (Chapter 5.G). In particular, tert-butyl hydroperoxide should be stored in the dark at room temperature (do not refrigerate) separately from oxidizable compounds, flammable substances, and acids. Reactions involving this substance should be carried out behind a safety shield.
Accidents
In the event of skin contact, immediately wash with soap and water and remove contaminated clothing. In case of eye contact, promptly wash with copious amounts of water for 15 min (lifting upper and lower lids occasionally) and obtain medical attention. If tert-butyl hydroperoxide is inhaled or ingested, obtain medical attention immediately.
In the event of a spill, remove all ignition sources, soak up the tert-butyl hydroperoxide with a spill pillow or noncombustible absorbent material, place in an appropriate container, and dispose of properly. Respiratory protection may be necessary in the event of a large spill or release in a confined area. Cleanup of anhydrous tert-butyl hydroperoxide and concentrated solutions requires special precautions and should be carried out by trained personnel working from behind a body shield.
Disposal
Excess tert-butyl hydroperoxide and waste material containing this substance should be placed in an appropriate container, clearly labeled, and handled according to your institution's waste disposal guidelines.
Abstract
The aim of present work was to check the possibility of microwave irradiation application for benzylic oxidation of diphenylmethane. The investigations were carried out using tert-butyl hydroperoxide (TBHP) both under conventional and microwave conditions. The catalysts tested were chlorides of transition d-metals: FeCl3·6H2O, CoCl2·6H2O, NiCl2·6H2O, CrCl3·6H2O, CuCl2·2H2O, ZnCl2 and iodine. From all studied metal catalysts, FeCl3·6H2O, CoCl2·6H2O, NiCl2·6H2O, CrCl3·6H2O showed the best catalytic activity.
Keywords: microwave irradiation, benzylic oxidation, tert-butyl hydroperoxide, d-metal chlorides
tert-Butyl hydroperoxide
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tert-Butyl hydroperoxide
Skeletal formula of tert-butyl hydroperoxide
Ball-and-stick model of the tert-butyl hydroperoxide molecule
Names
Preferred IUPAC name
2-Methylpropane-2-peroxol[1]
Systematic IUPAC name
tert-Butyl hydroperoxide
Identifiers
CAS Number
75-91-2 check
3D model (JSmol)
Interactive image
Abbreviations Tert-Butyl hydroperoxide
Beilstein Reference 1098280
ChEMBL
ChEMBL348399 check
ChemSpider
6170 check
ECHA InfoCard 100.000.833 Edit this at Wikidata
EC Number
200-915-7
MeSH tert-Butylhydroperoxide
PubChem CID
6410
RTECS number
EQ4900000
UNII
955VYL842B ☒
UN number 3109
CompTox Dashboard (EPA)
DTXSID9024693 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties
Chemical formula C4H10O2
Molar mass 90.122 g·mol−1
Appearance Colorless liquid
Density 0.935 g/mL
Melting point −3 °C (27 °F; 270 K)
Boiling point 37 °C (99 °F; 310 K) at 2.0 kPa
Solubility in water miscible
log P 1.23
Acidity (pKa) 12.69
Basicity (pKb) 1.31
Refractive index (nD) 1.3870
Thermochemistry
Std enthalpy of
formation (ΔfH⦵298) −294±5 kJ/mol
Std enthalpy of
combustion (ΔcH⦵298) 2.710±0.005 MJ/mol
Hazards
Safety data sheet [1]
GHS pictograms GHS02: Flammable GHS05: Corrosive GHS06: Toxic GHS08: Health hazard GHS09: Environmental hazard GHS03: Oxidizing
GHS Signal word Danger
GHS hazard statements H226, H242, H302, H311, H314, H317, H331, H341, H411
GHS precautionary statements P220, P261, P273, P280, P305+351+338, P310
NFPA 704 (fire diamond)
[2]
NFPA 704 four-colored diamond
444OX
Flash point 43 °C (109 °F; 316 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒ verify (what is check☒ ?)
Infobox references
tert-Butyl hydroperoxide (tBuOOH) is an organic peroxide widely used in a variety of oxidation processes, for example Sharpless epoxidation.[3] It is normally supplied as a 69–70% aqueous solution.
Contents
1 Application
2 Synthesis and production
3 Safety
4 See also
5 References
Application
Industrially, tert-butyl hydroperoxide is used as a radical polymerization initiator. For example, its reaction with propene yields propylene oxide and the byproduct t-butanol which can dehydrate to isobutene and convert to MTBE.
Synthesis and production
Many synthetic routes are available, including:[4]
Reaction of hydrogen peroxide with isobutylene or tert-butyl alcohol in the presence of sulfuric acid
Auto-oxidation of isobutane with oxygen
Safety
tert-butyl hydroperoxide is an exceptionally dangerous chemical that is highly reactive, flammable and toxic. It is corrosive to skin and mucous membranes and causes respiratory distress when inhaled. [5]
A solution of tert-butyl hydroperoxide and water with a concentration of greater than 90% is forbidden to be shipped according to US Department of Transportation Hazardous Materials Table 49 CFR 172.101.
In some sources it also has an NFPA 704 rating of 4 for health, 4 for flammability, 4 for reactivity and is a potent oxidant,[6] however other sources claim lower ratings of 3-2-2 or 1-4-4.[7][8]
See also
Di-tert-butyl peroxide
Abstract
(A) Tert-Butyl hydroperoxide is widely used as an epoxidizing agent, both synthetically and industrially. Tert-Butyl hydroperoxide has been used to effect regiospecific, stereospecific, and asymmetric epoxidations. 8 Zhang and Yamamoto showed that asymmetric epoxidation of allylic alcohols can be carried out using Tert-Butyl hydroperoxide with a vanadium catalyst and 95% ee was obtained. 9 (B) Styrene can be epoxidized by Tert-Butyl hydroperoxide to styrene oxide with high selectivity and in high yield using barium oxide (with or without gallium oxide support) as a simple, inexpensive and reusable solid catalyst. 10 trans-Stilbene can be epoxidized by Tert-Butyl hydroperoxide using a Au/TiO 2 catalyst. 11 (C) The epoxidation of α,β-unsaturated ketone and aldehyde compounds is accomplished by Tert-Butyl hydroperoxide in the presence of catalytic amounts of Ti(Oi-Pr) 4 or diaryl-2-pyrrolidinemethanols. 12 The epoxides have been obtained in good yields and with ee values of 80-90%. 13 (D) Manganese(III) acetate catalyzed allylic oxidation of alkenes to the corresponding enones was investigated and showed excellent regioselectivity. 14 Some new strategies have been reported for a useful transformation of the allylic oxidation of alkenes to carbonyl compounds, such as the protocols using Tert-Butyl hydroperoxide catalyzed by transition-metal ion centers (Cr, Ru, Cu, Co, Pd). 15 (E) The palladium-catalyzed allylic alkylation (the Trost-Tsuji reaction) is one of the most important reactions for constructing C-C bonds in modern organic synthesis. Recently, Chao-Jun Li and co-workers found that when a catalytic amount of CuBr and a stoichiometric amount of Tert-Butyl hydroperoxide were used the desired product was obtained in higher yield. 16 (F) In the presence of a catalytic amount of CuI and inorganic bases such as NaHCO 3, the aldehydes with amine hydrochloride salts gave the amide under mild conditions in good yield. The method can be used as the strategy for amide bond formation. 17 (G) Oxidative cleavage of the C=C bond to afford ketone or aldehyde products with Tert-Butyl hydroperoxide as the oxidant can be catalyzed by AuCl. This oxidation reaction proceeds under mild conditions in water, a variety of functional groups are tolerated. 18 (H) Copper-catalyzed oxidative esterification of aldehydes with β-dicarbonyl compounds was developed using Tert-Butyl hydroperoxide as an oxidant. In general, the enol esters were synthesized in good yields (up to 87%) and high stereoselectivity under the optimized reaction conditions. 19.
1 Tert-butyl hydroperoxide decomposition in the presence of initiators (tert-butyl peroxide (t BuOOtBu), azodiisobutyronitrile(AIBN)) and catalysts (Mo 2 B 5 , MoB, Mo 2 B, MoSi 2 , VB 2 , VSi 2) was studied. Our experiments suggest that the introduction of radicals may reduce the catalytic activity. The mechanism of the initial stage of tert-butyl hydroperoxide decomposition and reaction rate equation are proposed.
