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United States Patent U.S. Cl. 260-633 Claims ABSTRACT OF THE DISCLOSURE Novel alkali metal fiuorocarbinolates are produced by a novel method which involves reacting a great variety of; ketones and substituted ketones with an alkali metal fluoride. The resulting fluorocarbinolates are then converted to fiuorinated esters by reaction with an acid halide. Because the resulting esters have a fluorine on the rat-carbon of the alcohol moiety, they are useful as oil and water repellants for fabrics. By using the halide of an unsaturated acid in the reaction, the resulting esters can be made into homoor copolymers which are useful for the production of oil and water resistant coatings on a variety of fabrics made from both natural and synthetic fibers.
This application is a division of Ser. No. 623,483, filed I an. 9, 1967, now Patent No. 3,419,602, which in turn is a division of Ser. No. 398,129, filed Sept. 21, 1964, now Patent No. 3,384,628.
A non-exclusive, irrevocable, royalty-free license in the invention herein described, throughout the world for all purposes of the United States Government, with the power to grant sublicenses for such purposes, is hereby granted to the Government of the United States of America.
This invention relates to and has among its objects the provision of novel processes for preparing fiuorinated compounds, the provision of the products as new compositions of matter, and procedures for treating fibrous materials, especially textiles, with the compounds. Further objects of the invention will be evident from the following description wherein parts and percentages are by weight unless otherwise specified.
In conventional practice, if it is desired to convert a ketone to an ester the following procedure is used: The ketone is reduced to an alcohol and the alcohol is esterified with an acid halide.
Acid halide I Ac0(|3H* radical, that is, a fluorocarbinol group wherein the hydrogen of the hydroxyl radical is replaced by alkali metal. Thus:
Then, the intermediate is reacted with an organic acid halide to form an ester, as follows:
AcO+F wherein Ac is the acyl radical of an organic acid.
By this simple two-step synthesis, many diflerent kinds of fiuorinated esters can be produced in yields as high as of the theoretical. The reactions may be further examplified by the following formulas which depict the synthesis of heptafluoroisopropyl acrylate from hexafluoroacetone:
0 F 3 0 F3 Acryloyl 0 0 F3 03F chloride 4|) I o: C O-C-F CH =OH -0C-F C F 3 C F3 F 3 It is evident from the above formulas that the key step in the synthesis is the reaction of the ketone with the alkali metal fluoride. This reaction not only changes the ketone function to an alcohol function without requiring use of a reducing agent, but also adds a fluorine group which carries over to the ester; that is, the ester contains a florine group on the alpha carbon atom of the alcohol moiety. This is an unusual type of structure which gives the products especially useful properties. For example, the products can be used to provide oiland water-repellent finishes on textiles and the repellency attained is substantially greater than that achieved with the corresponding compounds wherein the same position is occupied by hydrogen.
The process of the invention is by no means limited to the example above but is of great versatility and, generically, can be applied to any aliphatic (open-chain or closed-chain) ketone which contains at least two fluorine groups adjacent to the carbonyl group. In other words, the carbon atoms connected to the carbonyl group must contain at least two fluorine atomsdistributed on these carbon atoms symmetrically of asymmetrically. These fluorine groups are a critical item to activate to the carbonyl group so that it will undergo the desired transformation when contacted with the alkali metal fluoride. Especially good results are obtained when the carbon atoms adjacent to the carbonyl radical contain halogen radicals (i.e., F. Cl, Br, or I) in addition to the minimum of two fluorine groups. In this connection it may be noted that although halogens of higher atomic weight than fluorinei.e., Cl, Br. and Iare not effective by themselves to activate the carbonyl group, they can be employed to supplement the activating influence of fluorine groups. Beyond the positions adjacent to the carbonyl group, the structure of the ketone is of no criticality to the process and available sites may be occupied, for example, by hydrogen or halogen. In other words, the critical itemfor the process aspect of this invention is that the starting compound contain a carbonyl group activated by adjacent fiuorine atoms as explained hereinabove; the remainder of the starting compound is not material to the process. Of course, this remainder may be limited in accordance with certain parameters to provide particular desired characteristics in the ester products. However, such limitation concerns the character of the ester product, not the operation of the process.
Typical examples of ketones to which the proces of the invention may be applied and the corresponding caster products are given below by way of illustration but not 5 F limitation: fi
H nn Ester (Product) (Ac is an acyl C (CFDWF HwFz) I Ketone (Starting compound) radical of an organic acid) F u I ii CF (CFr)n-C-(CFz)n,CF CF (CFz)n(|3-(CFz)n,CF H(OFz)nCCF(CFa)2 H(CF (|]-CF(CF Wherein n and n are each a number from 0 to 10 R- -C uF2n+1 RC-CnF2n+1 H Ac? (C F3) F-C-C F( Fm (C F920 FOO F (C Fs)2 L Wherein R represents an alkyl group containing 1 to 18 carbon atoms or 11L a cycloalkyl group such as cyclopropyl, cyclobutyl, or cyclohexyl.
It is also within the broad scope of the invention to E utilize, as the starting material, ketones containing more CF -(CF2)n-CCF(CF3)2 CF (CFz)nCCF(CFa)2 than one carbonyl group. By adjustment of the proportions of reactants in line with usual stoichiometrical relatlonships, diesters are produced. Typical in this category wherein n is a number from O to 18 are the following:
Ketone Ester (Ac is acyl group of an organic acid) 0 1O AcO (IJAc (CFa)zCFC-CCF(CFa)2 (CF3)2CFCI-(l]-CF(CF3)2 F F I(I) (H) Ac? Ac([) (CFa)2CFC(CF2)aC-CF( Q)2 a)2C l 2)a([3CF(CFQ);
Ester (Product) (A0 is an acyl Ketone (Starting compound) radical of an organic acid) Whcrclu n is a number from 3 to 10 Compounds containing other halogen atoms in addition to fluorine (Y is Cl, Br, or I) Whereln n is a number from 0 to 18 Generically, a preferred class of ketones which may be used in the process of the invention and the intermediates and the esters formed therefrom may be represented by the following structures:
(B) Alkali metal (A) Ketone fluorocarbinolate (C) Ester R R R R R 114.11 RJHQ O( 3 BIO-A l AeOC JF R( 3-lt RCR RCIR It It t Wherein each R represents a member of the group consisting of hydrogen halogen, alkyl, haloalkyl, cycloalkyl, and halocycloalkyl and wherein at least two of the Rs are fluorine. Ac represents an acyl radical of an organic acid, M represents an alkali metal.
The fluorocarbinolates and the esters responding to the structure given above in columns B and C are new compounds, not heretofore prepared or described.
As noted above, in the first step of the synthesis the fiuoroketone is reacted with an alkali metal fluoride. As the latter reagent, potassium fluoride is generally preferred, but the fluorides of sodium, cesium, and rubidium may also be used. The reaction is generally conducted in an inert solvent for the ketone, for example, acetonitrile, dioxane, tetrahydrofuran, tetramethylene sulphone, diglyme (an abbrevated name for dimethyl ether of diethylene glycol), etc. The alkali metal fluoride is only slightly soluble in these solvents and the disappearance of undispersed alkali metal fluoride during the reaction supplies a useful indication of formation of the desired intermediate (which is soluble). The temperature of reaction is not critical. Generally, temperatures over 35 C. are avoided to pre vent decomposition of t
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