Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus esters
Patent
1995-02-21
1996-07-23
Ramsuer, Robert W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Phosphorus esters
C07F 909
Patent
active
055391419
DESCRIPTION:
BRIEF SUMMARY
This application was filed under 35 U.S.C. .sctn.371 and was based upon PCT International Application No. PCT/EP93/01497, which was filed on Jun. 14, 1993.
The present invention relates to mixed boric acid/phosphoric acid esters of polyols as well as to preparation and use thereof.
Preparation of both boric acid esters and phosphoric acid esters has been known for a long time from e.g. standard publications on technical chemistry.
In Ullmann: Encyclopaedia der technischen Chemie, 4th Edition, Vol. 8, page 653, there is described e.g. the preparation of boric acid esters. According to this publication, the preparation starts directly from boric acid or boron trioxide and the respective alcohol. The water resulting from the reaction is removed by azeotropic distillation from the equilibrium reaction mixture. Used as water entrainers are benzene, toluene, xylene or an excess of primary aliphatic alcohols. The boric acid esters are used, for instance, as oxidation inhibitors in additives for oils and fuels, and as hydraulic and brake fluids. Boron-modified phenolic resins of phenyl borates and formaldehyde are used as binders for flame-resistant molded articles such as brake liners. Methyl and ethyl borates are used in the preparation of sodium boranate.
According to the state of the art, phosphoric acid esters are prepared on an industrial scale by reacting alcohols with phosphorylating agents such as phosphoryl chloride, phosphorus pentoxide or polyphosphoric acids. Described in U.S. Pat. No. 4,100,231 is the esterification of orthophosphoric acid with alcohols in the presence of considerable quantities of alkali hydroxide.
While the reaction of phosphoryl chloride with alcohols under appropriate conditions allows the production of mono-, di- and triesters of phosphoric acid, alcoholysis of phosphorus pentoxide always leads to a "sesqui-phosphate" which consists of a substantially equimolar mixtures of mono- and diesters of phosphoric acid together with minor amounts of condensed phosphoric acid esters. Polyphosphoric acids subjected to alcoholysis provide mixtures which consist predominantly of monoesters next to a small proportion of diesters. With orthophosphoric acid, there will normally be formed nothing but monoesters.
Phosphoric acid esters constitute a broad class of materials which find use in many applications, e.g. as surfactants in detergents and cleaning agents, as plasticizers in various synthetic materials, as plant protectants, as anti-corrosive agents, for metal extraction, and as flame-proofing agents.
It is the object of the invention to modify the known phosphoric acid esters in a manner improving their properties and widening their range of use. Moreover, their preparation method shall be improved, especially with respect to usable starting materials and the ease of controlling the esterification reaction.
According to the invention, the above object is achieved by mixed boric acid/phosphoric acid esters of polyols which are obtainable by subjecting at Least one phosphorus(V)-compound capable of ester formation and at least one boron compound capable of ester formation simultaneously (i.e. in a one-pot reaction) to an esterification reaction with at least one and/or one polyol derivative capable of ester formation under the given conditions.
Preferably, this esterification reaction is conducted under continuous removal of the side products formed during reaction and of the optionally used solvent. This applies particularly when (as in a specifically preferred embodiment of the present invention) water is formed as a side product during esterification and, respectively, water is additionally used as a solvent.
As boron compound capable of ester formation, there may be used any compound which is known to undergo under appropriate conditions an esterification reaction with alcohols and, respectively, with derivatives thereof which are principally capable of ester formation. Specific examples of such compounds are B.sub.2 O.sub.3, boric acid (H.sub.3 BO.sub.3), metaboric acid (HBO.sub.2), as
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Dorn Karlheinz
Frankenfeld Klaus
Nagerl Hans-Dieter
Schlarb Sonja
Sommer Klaus
Ambrose Michael G.
Chemische Fabrik Budenheim Rudolf A. Oetker
Ramsuer Robert W.
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