19686-73-8Relevant articles and documents
Cycloaddition of carbon dioxide to 1,2-epoxypropane catalyzed by tetra-t-butylphthalocyaninatoaluminium(III) hydroxide
Kasuga, Kuninobu,Kato, Takao,Kabata, Naohiko,Handa, Makoto
, p. 2885 - 2888 (1996)
Carbon dioxide was fixed as propane-1,2-diol carbonate (PDC) with 1,2-epoxypropane (EP) catalyzed by Al(OH) {pc(t-Bu)4} in the presence of such a quaternary ammonium halide (HAX) as [HO(CH2)2N(CH3)2(C4H 9)]X (X=Cl, Br, I). Although the yield was scarcely affected by the structure of HAX, it was dependent on the kind of halide ion. While PDC was formed in chloroform or dichloromethane, the yield decreased extremely in DMSO or pyridine, and PDC was not prepared in methanol. Although halohydrin was formed in a chloroform solution of EP, Al(OH){pc(t-Bu)4}, and HAX, it was not an intermediate. The formation of a hexa-coordinate complex of Al(OH){pc(t-Bu)4} with HAX and EP was spectroscopically confirmed, and the complex catalyzed the preparation of PDC from carbon dioxide and EP.
O-phenylenediamine as a new catalyst in the highly regioselective conversion of epoxides to halohydrins with elemental halogens - A reinvestigation
Soroka, Miroslaw,Goldeman, Waldemar
, p. 169 - 174 (2006)
In contrast to a previous report, o-phenylenediamine is not a catalyst in the ring opening reaction of epoxides by means of bromine or iodine. The o-phenylenediamine is just a reactant which reacts with iodine to give phenazine-2,3-diamine and hydrogen iodide, or with bromine to give a mixture of brominated and polymerized products as well as hydrogen bromide. The hydrogen halogenides are in fact the real epoxide ring opening reactants. Springer-Verlag 2006.
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Malinowski,Wolkowa,Morosowa
, p. 117 (1949)
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Method for preparing halogen propanol and epoxypropane
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Paragraph 0098; 0099; 0110; 0111; 0129; 0130, (2017/05/19)
The invention provides a method for preparing halogen propanol. The method comprises the following steps (1) halogen alcoholization: adding halogen hydride, H2O2, propylene and an HTS molecular sieve into a reaction device, and carrying out halogen alcoholization reaction to obtain the halogen propanol. The invention also provides a method for preparing epoxypropane with a halogenohydrin method. The method comprises the following steps: (1) halogen alcoholization: adding halogen hydride, H2O2, propylene and an HTS molecular sieve into the reaction device, and carrying out the halogen alcoholization reaction to obtain halogen propanol; (2) saponification: carrying out saponification reaction on halogen propanol and a hydroxide of alkali metal in step (1), and separating to obtain the epoxypropane and alkali halide metal salt; optionally (3) electroosmosis: carrying out bipolar membrane electroosmosis on the alkali halide metal salt obtained in step (2) to obtain the hydroxide of alkali metal and the halogen hydride. According to the methods, the halogen propanol or the epoxypropane can be prepared at extremely high selectivity and yield, and the discharging of waste water and waste residues can be drastically lowered.
H2TPP organocatalysis in mild and highly regioselective ring opening of epoxides to halo alcohols by means of halogen elements
Torabi, Parviz,Azizian, Javad,Zomorodbakhsh, Shahab
experimental part, p. 5508 - 5519 (2012/08/28)
We found that elemental iodine and bromine are converted to trihalide nucleophiles (triiodine and tribromide anion, respectively) in the presence of catalytic amounts of meso-tetraphenylporphyrins (H2TPP). Therefore a highly regioselective method for the synthesis of β-haloalcohols through direct ring opening of epoxides with elemental iodine and bromine in the presence of H2TPPs as new catalysts is described. At room temperature a series of epoxide derivatives were converted into the corresponding halohydrins resulting from an attack of trihalide species anion atoms at the less substituted carbon atom. This method occurs under neutral and mild conditions with high yields in various aprotic solvents, even when sensitive functional groups are present.