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United States Patent (19 11) 4,192,810 W 45) Mar United States Patent (19 11) 4,192,810 W 45) Mar. 11, 1980 54 PREPARATION OF VICINAL EPOXIDES OTHER PUBLICATIONS A. L. Shapiro et al., Jour. Org. Chem., USSR, vol. 5 75 Inventor: Yulin Wu, Bartlesville, Okla. (1969) pp. 200-203. 73) Assignee: Phillips Petroleum Company, Primary Examiner-Norma S. Milestone Bartlesville, Okla. 57 ABSTRACT Vicinal epoxides having 2 to 30 carbon atoms per mole 21) Appl. No.: 934,667 cule are prepared by heating the corresponding carbon ate esters having the general formula 22 Filed: Aug. 17, 1978 Related U.S. Application Data R---RO O 62) Division of Ser. No. 845,183, Oct. 25, 1977, Pat. No. V / 4,111,965, which is a division of Ser. No. 459,628, Apr. C 10, 1974, Pat. No. 4,069,234. I O 51) Int. Cl’............................................ C07D 301/02 52 U.S. Cl. ................................................ 260/348.16 in the presence of a catalytic amount of a catalyst se 58 Field of Search .................................... 260/348.16 lected from the group consisting of phosphonium ha lides, sulfonium halides, sulfoxonium halides and metal salts selected from the group consisting of the halides, 56) References Cited sulfates and carboxylates having 1 to 20 carbon atoms of FOREIGN PATENT DOCUMENTS iron, tin, manganese and zinc. 893037 5/1944 France ................................ 260/348.16 47-15951 12/1972 Japan ..................................... 260/340.2 8 Claims, No Drawings 4,192,810 2 PREPARATION OF WICNAL EPOXDES This is a divisional application of application Ser. No. R---R 845,183, filed Oct. 25, 1977, now U.S. Pat. No. OHOH 4,111,965, which is a divisional of application Ser. No. 459,628, filed Apr. 10, 1974, now U.S. Pat. No. wherein each R and R' are hydrogen or a hydrocarbyl 4,069,234. radical having from 1 to 10 carbon atoms. This invention relates to the preparation of vicinal Examples of suitable carbonate esters which can be epoxides. 10 employed in the process of this invention include the Vicinal epoxides are well known in the art as mono cyclic carbonate esters of the following vicinal diols: mers in the preparation of resins of various types rang 1,2-ethanediol; 1,2-propanediol; 1,2,3,4-tetrahydro-1,2- ing from epoxy adhesive applications to elastomeric napthalenediol; 3,3-dimethylcyclobutane-1,2-diol; solvent-resistant polymers for use in making tubing, 3,3,4,4-tetramethylcyclobutane-1,2-diol; 2,3-dimethyl shoe soles and the like. Such epoxides can be prepared 15 2,3-butanediol; 2-methyl-2,3-butanediol; 2-methyl-1,2- by the direct oxidation of an olefin or by treatment of propanediol; 2,3-butanediol; 2-phenyl-1,2 -ethanediol; the corresponding halohydrin with line. 1,2-butanediol; 1,2-pentanediol; 1-phenyl-1,2- It is an object of this invention to provide a novel butanediol; 2-phenyl-1,2-pentanediol; and 1-(2-methyl process for the preparation of vicinal epoxides. phenyl)cyclohexane-1,2-diol. Other objects, aspects and advantages of the inven 20 The carbonate esters of vicinal diols are well known tion will become obvious from the following descrip in the art. Such esters can be prepared by the reaction of tion and the appended claims. a vicinal chlorohydrin with an alkali metal carbonate, In accordance with the present invention, it has been bicarbonate or sesquicarbonate under pressure of car discovered that vicinal epoxides having 2 to 30 carbon bon dioxide as disclosed in U.S. Pat. No. 2,766,258, J. D. atoms per molecule having the general formula 25 Malkemus, issued Oct. 9, 1956. Such esters can also be prepared by the reaction of a vicinal chlorohydrin with R" R' . an alkali metal alkyl carbonate as disclosed in U.S. Pat. R-C-C- No. 2,784,201, H. C. Chitwood, issued Mar. 5, 1957. V / Catalysts suitable for use in the process of this inven O 30 tion are selected from one of the following: wherein each R and each R" are individually selected A. Phosphonium halides having the formula R'4PX, from the group consisting of hydrogen and hydrocarbyl wherein R' is selected from the group consisting of radical groups having 1 to 10 carbon atoms and wherein hydrogen, alkyl, cycloalkyl, aryl, alkenyl, cycloalkenyl both R" radicals can represent a divalent aliphatic hy 35 and combinations thereof having from 1 to 10 carbon drocarbon radical which together with the oxirane atoms and X is a halide selected from the group consist group ing of chlorine, bromine and iodine; B. sulfonium halides having the formula R'3SX wherein R'' and X are as given above; C. sulfoxonium halides having the formula N / (R"3S-PO)--X- wherein R" and X are as given above; O and D. Metal salts selected from the group consisting of in said epoxide can form a cycloaliphatic nucleus, are the halides, sulfates and carboxylates having 1 to 20 prepared by heating the corresponding carbonate ester, 45 carbon atoms of iron, tin, manganese and zinc. having the general formula Examples of suitable catalysts include methyltri phenylphosphonium bromide, ethyltriphenylphos phonium bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tetraphenylphos Ram C-C-R 50 phonium bromide, tetraphenylphosphonium chloride, O O triphenylbenzylphosphonium chloride, allyldiethylsul V / fonium chloride, allyldimethylsulfonium bromide, ben C zyldiethylsulfonium chloride, benzyldimethylsulfonium O iodide, benzylethylvinylsulfonium chloride, tert-butyl 55 dimethylsulfonium chloride, tert-butylmethylpropylsul wherein R and R' are as defined above, in the presence fonium iodide, trimethylsulfonium bromide, diisopen of a catalytic amount of a catalyst selected from the tylmethylsulfonium iodide, diphenyl-2,5-xylylsulfonium group consisting of phosphonium halides, sulfonium bromide, cyclooctyldimethylsulfonium iodide, tri halides, sulfoxonium halides and certain metal salts, phenylsulfonium iodide, trimethylsulfoxonium iodide, each as hereinafter defined, under epoxide forming 60 trimethylsulfoxonium bromide, trimethylsulfoxonium conditions. As used herein, the term "hydrocarbyl' chloride, ethyldimethylsulfoxonium bromide, ferric includes alkyl, cycloalkyl, aryl, aralkyl and alkaryl radi chloride, stannic chloride, stannous chloride, manga cal groups. nese sulfate, zinc acetate, zinc benzoate, ferrous sulfate, The carbonate esters from which the vicinal epoxides stannous sulfate, stannic bromide, manganese iodide, are prepared according to the process of the present 65 zinc chloride, ferrous chloride, manganese acetate, stan invention are the carbonate esters of vicinal diols con nous acetate and the like. taining from 2 to 30 carbon atoms per molecule and The amount of catalyst employed in the process of corresponding to the general formula this invention is a catalytic amount, generally from 0.01 4,192,810 3 4. to 50 weight percent of the starting carbonate ester. In a presently preferred embodiment, from 0.1 to 10 EXAMPLE II weight percent of catalyst is employed. A series of runs was carried out using the compounds Reaction conditions vary according to starting mate listed below to determine, qualitatively, whether propy rials and catalyst. In general, the process is conducted at 5 lene oxide was obtained from propylene carbonate. a temperature which will allow for decomposition of Reaction conditions were essentially the same as used in the cyclic carbonate ester to the desired vicinal epoxide Example I, except that each run had a duration of 0.5 to without undesirable side reactions, for a time sufficient 1 hour. Results of these runs are shown in the following to provide essentially complete conversion. table: The temperature employed in the process of this 10 invention can be in the range of 25' to 300° C. In a presently preferred embodiment the temperature is in Compound Decomposition to the range of 100 to 250 C. Run quantity (g) propylene oxide 4. PdCl2, No The reaction time is generally within the range of 0.5 5 5 Ag2CO3, 1 No to 24 hours. It is preferred that the reaction time be in 6 CuCl2. 2H2O, No. the range of 1.5 to 5 hours. 7 Znbenzoate)2, 0.3 Yes The process of this invention can be conducted at any 8 Znacetate), 0.3 Yes suitable pressure, ranging from subatmospheric to atmo 9 ZnO, 0.3 No 10 Mo(CO), 0.3 No spheric. It is preferred that the process be conducted at 20 MnSO, 0.3 Yes atmospheric pressure. 2 FeCl3, 0.3 Yes The process of this invention can be carried out in the 13 NiSO, 0.3 No presence or absence of a diluent. If desired, an inert 4. SnC, O.3 Yes diluent can be employed in an approximate amount 5 SnCl2, 0.3 Yes ranging from 10 to 2000 weight percent of the starting 25 carbonate ester. Suitable inert diluents include hydro In each of the above runs which gave no indication of carbons such as benzene, toluene, decane and cyclohex propylene oxide formation, the receiver was rinsed with ane, ethers such as 1,2-dimethoxyethane and tetrahy a small volume of acetone to recover any material drofuran and cyclic sulfones such as sulfolane. In a which might have been collected. The acetone wash presently preferred embodiment the process of this liquid was analyzed by GLC for the presence of propy invention is carried out in the absence of diluent in lene oxide. In those runs showing negative results, no order to simplify recovery procedures. bubble formation was noted in the reaction vessel, as The process of this invention can be carried out as a would be expected from the formation of carbon diox batch or continuous process. ide as the co-product with propylene oxide. Those runs The following examples illustrate the invention. 35 showing positive results were observed to form bubbles EXAMPLE I during the reaction period. Reasonable variations and modifications of this in A 50 ml round-bottom flask equipped with stirring vention will be apparent to those skilled in the art in means was charged with 30 g (0.294 mol) of propylene view of this disclosure.
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