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United States Patent Office Patented Dec 3,014,059 United States Patent Office Patented Dec. 19, 1961 i 2 hereinafter and the novelty of which will be particularly 3,014,059 pointed out and distinctly claimed. PREPARATION OF DAKOXY BORANES Jack D. Bush, Kansas City, Mio., Richard A. Carpenter, This invention is based on the discovery that dialkoxy Prairie Village, Kans, and William H. Schechter, boranes, such as dimethoxy borane, can be produced in Zelienople, Pa., assignors, by direct and mesne as substantial yields and in a relatively short time by heat signments, to Caliery Chemical Company, Pittsburgh, ing together a mixture of a trialkyl borate, such as tri Pa., a corporation of Pennsylvania methyl borate, and a hydride compound of the group No Drawing. Fied July 6, 1954, Ser. No. 44,636 consisting of hydrides, borohydrides, and alkoxy sub 14 Claims. (C. 260-462) stituted borohydrides of alkali and alkaline earth metals, O and separating the dialkoxy borane thus formed by any This invention relates to new and useful improvements suitable method such as distillation or extraction. In in processes for preparing dialkoxy boranes, HB(OR)2, carrying out this reaction a ratio of trialkyl borate to and more particularly to a process for preparing a di hydride is maintained which favors the formation of a alkoxy borane by the reaction of a trialkyl borate and a dialkoxy borane and a tetraalkoxy borate according to compound of the group consisting of hydrides, borohy 5 one of the following equations: drides, and alkoxy substituted borohydrides, of alkali and alkaline earth metals. (1) MH-I-2xB(OR)=xHB(OR)--MB(OR) Dialkoxy boranes, HB(OR)2, in general and dimethoxy ... O borane, HB(OCH3)2, in particular are compounds of some considerable importance as intermediates in the 20 preparation of diborane. Dimethoxy borane dissociates into diborane and trimethyl borate according to the equa where R is a lower hydrocarbon radical, M is an alkali tion: 6HB(OCH) = BH6-4B(OCH3). The manufac or alkaline earth metal, x is the valence of M, and in ture of diborane by use of the intermediate compound is an integer from 1 to 4. dimethoxy borane offers a relatively inexpensive source From the above mentioned reaction it should be espe of diborane which does not require the use of expensive cially noted that a proportion of trialkyl borate is al boron halides. In the past, dialkoxy boranes such as di ways maintained in excess of the amount which favors methoxy borane have been prepared by the dissociation the formation of the trialkoxy borohydride or borohy of an alkoxyborohydride such as sodium trimethoxy dride. borohydride into dimethoxy borane and sodium meth 30 In one experiment molten sodium trimethoxyborohy oxide. The production of dimethoxy borane by this dride NaBH(OCH3) was maintained at a temperature process is uncertain and generally produces sodium boro of 240 to 250 C. in a glass flask and vapors of tri hydride and sodium tetramethoxy borate as the principal methyl borate B(OCH3)3 were bubbled through the reaction products. Another process for preparing di molten trimethoxyborohydride at atmospheric pressure. methoxy borane is the reaction of trimethyl borate and 35 The trimethyl borate vapors, which had passed through the diborane. This reaction, however, is merely the reversal molten trimethoxyborohydride were condensed and found of the reaction which is proposed using dimethoxy borane upon analysis to contain about 5% by weight of di to produce diborane. It is obvious therefore that this methoxy borane HB(OCH3)2. The dimethoxy borane process would have little or no utility for making di was identified by specific chemical and physical tests, in methoxy borane unless the dimethoxy borane so manu 40 cluding the boiling point, active hydrogen analysis, and factured were intended for a purpose other than the identification of hydrolysis products. In view of the fact production of diborane. that sodium trimethoxyborohydride is known to dissociate It is therefore one object of this invention to provide and produce small quantities of dimethoxyborane at ele a new and improved process for preparing dialkoxy vated temperatures, further tests were run to determine boranes. 45 whether or not the trimethyl borate vapors were merely Another object of this invention is to provide an im acting as a sweep gas to carry out from the flask any proved process for preparing dialkoxy boranes from the dimethoxy borane which was formed. In these further reaction of trialkyl borates and metal hydride compounds. tests molten trimethoxyborohydride maintained at the Another object is to provide an improved process for same temperature and under the same pressure conditions preparing dialkoxy boranes from the reaction of trialkyl 50 was swept with dry, oxygen-free, nitrogen gas and no di borates and compounds of the group consisting of hy methoxy borane was produced. drides, borohydrides, and alkoxyborohydrides of alkali In another experiment sodium trimethoxy borohydride and alkaline earth metals. was dissolved in tetraethylene glycol dimethyl ether, Another object is to provide an improved process for CHO(CHO)4CH3, and the solution heated to 200 to preparing dialkoxyboranes by distillation of a mixture 55 230° C. in a glass flask. Trimethyl borate was bubbled of a trialkyl borate and a compound of the group con through the heated solution for about 2 days and a 35% sisting of hydrides, borohydrides, and alkoxy borohy yield (based on trimethoxyborohydride reacted) of di drides of alkali and alkaline earth metals. methoxy borane was obtained. In another experiment, a Another object is to provide a new and improved solution of sodium borohydride in the same solvent and process for preparing dimethoxy borane. 60 at the same temperature was treated with trimethyl borate Another object is to provide an improved process for under the conditions above mentioned and produced preparing dimethoxy borane by distillation from a mix about a 35% yield of dimethoxy borane. Other experi ture of trimethyl borate and a compound of the group ments with solvents indicate that this reaction will proceed consisting of hydrides, borohydrides, and methoxyboro satisfactorily in solvents having a boiling point above 65 the boiling point of dimethoxy borane and preferrably hydrides of alkali and alkaline earth metals. carried out in the temperature range from about 30° C. Other objects will become apparent from time to time to 270° C. with the yields varying slightly in different throughout the specification and claims as hereinafter solvents. The temperature range of 65 to 270° C. has related. been preferred in most experiments. This invention comprises the new and improved process 70 In another experiment sodium hydride and trimethyl for preparing dialkoxy boranes in general and dimethoxy borate were charged into a distillation pot on top of which borane in particular which will be described more fully there was provided a 4 foot section of a 1% inch diameter 3,014,059 3 4. distillation column packed with /8 inch Raschig rings. by Wartik and Schaeffer to the committee on inorganic The column was heated to a point at which the pot was nomenclature of the American Chemical Society and ten maintained at approximately 70° C. and the top of the tatively approved by said committee, except that in naming distillation column was maintained at about 30° C. After the borohydrides the nomenclature proposed by Schlesin maintaining the column at total reflux for about 2 hours 5 ger has been followed. a sample of 5 to 6 cc. of pure dimethoxy borane was Although there have been described the best known obtained from the top of the column. A similar experi embodiments of this invention as required by patent laws ment was carried out in the same apparatus but using it is to be understood that within the scope of the claims sodium trimethoxy borohydride instead of sodium hydride appended hereto this invention may be practiced other and a small quantity of pure dimethoxy borane was ob wise than as specifically described. tained after a few hours operation at total reflux. Having thus described this invention and the manner In still another experiment sodium hydride and trimeth in which it is to be performed what we desire to claim yl borate were charged into a distillation pot and main and secure by Letters Patent of the United States is: tained at total reflux for one day. After this period at 1. A method of preparing a dialkoxy borane, total reflux the reflux ratio was set at about 10 to 1 and a HB(OR)2, where R is a lower alkyl radical, which com 17% concentration of dimethoxy borate in methyl borate prises reacting a trialkyl borate, B(OR), where R is a was obtained with a yield of dimethoxy borane of about lower alkyl radical, and a hydride compound of the group 70%. consisting of MH, and MBH(OR), where M is In another experiment 0.25 mol of sodium trimethoxy selected from the group consisting of alkali and alkaline borohydride was charged into the pot of a distillation earth metals, R is a lower alkyl radical, r is the valence of column with 4 mols of trimethyl borate. A packed dis M, and n is an integer from 1 to 4, in a molar proportion tillation column was used having a reflux ratio in excess of trialkyl borate to hydride of not less than the stoichi of 10 to 1 and the distillate was continuously removed. ometric amount required to produce dialkoxyborane by The distillation pot was maintained at a temperature of heating at a temperature of 30 to 270° C. and continu 65 to 70° C. and the still head temperature was main 2 5 ously removing and recovering the dialkoxy borane as it tained in the range of 25 to 40° C.
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