Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus esters
Patent
1997-03-20
1999-03-16
Ambrose, Michael G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Phosphorus esters
C07F 902
Patent
active
058832807
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a process for the preparation of a phosphoric monoester through the phosphorylation of an organic hydroxyl compound. More particularly, the present invention relates to a process for the preparation of a phosphoric monoester which can easily provide a phosphoric ester mixture having a high phosphoric monoester purity, a reduced orthophosphoric acid content and good odor.
2. Description of the Related Art
Phosphoric esters of organic hydroxyl compounds are used in a wide field as a detergent, a textile treating agent, an emulsifying agent, a rust inhibiter, a liquid ion exchanger and a medicament.
Although the reaction of an organic hydroxyl compound with phosphorus pentaoxide has been known as an industrial process for the preparation of phosphoric esters in the prior art, the product of the reaction comprises mainly a nearly equimolar mixture of a phosphoric monoester represented by the following formula (A) and a phosphoric diester represented by the following general formula (B) (hereinafter, this mixture is referred to as "sesquiphosphate"): ##STR1## wherein R represents a linear or branched alkyl or alkenyl group having 6 to 30 carbon atoms.
There are great differences in properties between a phosphoric monoester and a phosphoric diester. To give an explanation about, e.g., alkali metal salts and alkanolamine salts of long-chain alkyl phosphates, phosphoric monoester salts are soluble in water, excellent in foaming power and detergency, less toxic and lowly irritant to the skin to be useful as an excellent detergent, while phosphoric diester salts are little soluble in water and exhibit little foaming power or rather have defoaming properties, and accordingly they can not be used as high foaming detergents. Therefore, when sesquiphosphate salts are employed, the above performances inherent in phosphoric monoester salts can not be exhibited, and, therefore, sesquiphosphate salts are unusable as substitutes for phosphoric monoester salts.
Under these circumstances, the development of a process by which a phosphoric ester mixture having a high phosphoric monoester content can be prepared on an industrial scale safely and easily has been eagerly expected and the following processes have been reported to answer this expectation: phosphorus oxychloride and hydrolyzing the obtained monoalkyl phosphorodichloridate; and thereafter adding phosphorus pentaoxide to the obtained mixture to conduct phosphorylation with the amount of water preliminarily added being 0.5 to 3 mol per mol of phosphorus pentaoxide; orthophosphoric acid and phosphorus pentaoxide; condensed phosphoric acid (polyphosphoric acid); phosphorus pentaoxide in the presence of water while blowing steam into the reaction system; and phosphorylating agent mixture comprising phosphorus pentaoxide, phosphoric acid and a polyphosphoric acid under such a condition that phosphoric acid components are excess, adding an organic hydroxyl compound to the obtained reaction mixture to make up to a stoichiometric amount and conducting 21, 1982, assignee: Kao Corporation)!.
However, these processes have respective disadvantages as will now be described, being unsatisfactory as industrial processes for the preparation of phosphoric ester mixtures.
The process (1) gives hydrogen chloride as a by-product to be significantly problematic in the corrosion of equipment and the disposal of hydrochloric acid. Further, this process involves the formation of an alkyl chloride as a by-product, so that it is difficult to enhance the phosphoric monoester content of the reaction product.
According to the processes (2) and (3), the ratio of the phosphoric monoester to the phosphoric diester in the reaction product can be enhanced by increasing the amount of water or orthophosphoric acid used. However, the use of a large amount of water or orthophosphoric acid remarkably lowers the degree of conversion of phosphorus to give a remarkably increased amount of orthophosphoric acid. The contamina
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Patent Abstracts of Japan, vol. 11, No. 214 (C-434) Jul. 10, 1987, & JP,A 62 033 190 (Miyoshi Oil & Fat Co. Ltd.) Feb. 13, 1987.
Aimono Kiyoshi
Shibata Kengo
Tsuyutani Shinji
Ambrose Michael G.
Kao Corporation
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