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United States Patent Office Patented Mar 3,238,235 United States Patent Office Patented Mar. 1, 1966 1. 2 3,238,235 FLUORNATED AMIDO CARBOXYLIC ACDS CF3IC Flic-N-CH.C-OH AND SALTS THEREOF Murray Hauptschein, Glenside, and Sameeh S. Toukan, Levittown, Pa., assignors to Pennsalt Chemicals Corpo 5 ration, Philadelphia, Pa., a corporation of Pennsylvania CFC Flic-N-CH-C-OH No Drawing. Filed Apr. 29, 1963, Ser. No. 276,160 12 Claims. (C. 260-404) CFC Full-N-CHé OH This invention relates to fluorinated compounds having O valuable surface properties and more specifically is con CF3 O O cerned with certain new derivatives of long chain per CFCFC Flic-N-CHCHC OH fluorinated carboxylic acids which possess such surface properties in a particularly high degree. (F. O It is known that relatively long chain perfluorinated 15 CFCFCFal -N-CH,OH,C OH carboxylic acids and salts thereof, e.g. perfluorooctanoic acid and its ammonium and metal salts, have unusual (F. O Surface properties. They are known for example to CFCFCF -N-CHCHé OH reduce the surface tension of aqueous systems to un usually low values and thus have valuable uses as ultra 20 O O performance surfactants in such systems. According to CF (CFle C -N-CHCH, O this invention, certain new derivatives of certain high members of such acids have been found to display sur F. face properties which are superior in a marked and 'sur CF, CFCFC-N-CEIC OF prising degree to the acids themselves, to the salts of 25 Hs such acids, as well as to compounds of similar types derived from perfluorinated sulfonic acids. (F 9 The new compounds of the invention may be repre CFaCFCF); C-N-CBC OEI sented by the general formula 3 30 O O CF3 O C.F.-N-R-E-OM CFCFC Flic-N-OH.c OE CH3 where CFan1 is a perfluoroalkyl group which may have O O a straight or branched chain and which has a chain 35 CFC File-N-ch, OH length of at least seven carbon atoms; where n is an CH3 integer having a value ranging from 8 to 13; where R is CF3 O O hydrogen or an alkyl group (which may be straight or - branched) having from 1 to 4 carbon atoms; where R' CFCFC F.C-N-H OE is an alkylene radical or a monohydroxyalkylene radical 40 CH3 (which may be straight or branched) having from 1 to 6 carbon atoms and where M is hydrogen, an alkali metal F. ( ) or ammonium. CFCFC FC-N-Hc OH Of particular value are compounds of the above type CH3 where the perfluoroalkyl group C, Fani contains from 45 O O 10 to 12 carbon atoms. Despite the very low solubility - || of such compounds in aqueous systems they display re CF3IC Flac-N-Hc OE markably superior surface properties when employed in CE such systems. Of particular value also are compounds of CF3 O O the above type where R is hydrogen or an alkyl group 50 C Fé FC Flt-N-OH, OE containing from 1 to 2 carbon atoms; and those in which &H, R’ is an alkylene radical having from 1 to 3 carbon atoms. Typical examples of the new compounds of the inven CF3 O O C FéHIC Flé-N-OH, OE tion shown in the form of the free acid are the following: 55 &H, F. O O CF3 CFCFls -N-CH-C-OH CFC Flé-N-OH, oh (F 9 60 &H, CF3 CFC Flic-N-CH-C-OH CF's O O F. C Fé FC Fil-N-CHCHCH.) OE CFCFC Fé-N-CHé-OH &H, 3,238,235 4. acid halide or a perfluorinated halosulfate with a primary - CF3. O Chion amine. The amide thus produced is then reacted with CF.CFCF-C-N-CH-COH metallic sodium in an organic solvent such as toluene to form a sodium derivative which is then reacted with a CIN CH, chloro or bromo ester to form an ester derivative which CF3 CH O is then hydrolyzed to provide the desired end product. CF.CFCF-C-N-CH-coh| || This method may be illustrated by the preparation of ce CH, 0 cificNCH.cooH pH C2H starting with the chlorosulfate CFOSOCl in accordance F. H, 9 with the following: CF.CFCF-C-N-CH-coh (a) The new compounds of the invention may be prepared 5 CgF19 OSOC - 3C2H5NH2 --> O by the direct reaction of the acid fluoride or the acid | chloride of a perfluorinated carboxylic acid of the proper CsF17 CNBC2H5 -- C2H5NEISONHCH -- HCl +2HF chain length with an amino acid. This reaction may be (b) O O illustrated by the reaction of perfluorononanoic acid toluene fluoride with glycine in accordance with the following: 20 CsF17 CNHCH5 -- Na - C6F1, CN (Na) CH (c) O (diethylene glycol O O | dinnethyl ether) cifier -- NH2CH2COOH --> CF&NHCHCOOH + HF CslF 17 CN (Na) C2H5 -- BrCHCOO CEI - - - - - The reaction is preferably carried out by dissolving or suspending the perfluoro acid fluoride in an anhydrous 25 cificNCHC OOC2H Solvent and mixing the solution slowly with a suspension CH5 of the amino acid in the same solvent and then refluxing (d) O mild alkaline hydrolysis (NaOH) the mixture for several hours. The amino acid may be CsF17CNCF2COO CEI5 - - - - added slowly to the perfluoro acid fluoride or conversely, 30 2H5 the acid fluoride may be added slowly to the amino acid. O O The reaction mixture is filtered to remove insoluble ma acidification terial which generally includes excess amino acid and its circNCH.cooN --> CSF1, CNCHCOOE hydrogen fluoride salt, after which the amide product CEis Hs may be isolated by evaporation of the solvent and purified 35 After preparation of the free acid as described above, if necessary by crystallization, or similar techniques. the alkali metal salts such as the ammonium salt, potas Suitable anhydrous solvents include e.g. diethylether, di sium salt, Sodium salt, lithium salt, etc. may be readily methoxyethane, CHOCH2CHOCH, tetrahydrofuran, prepared, preferably by dissolving the free acid in a sol trichlorotrifluoroethane and benzene. Reaction tempera vent such as isopropanol, ethanol or methanol, and titrat tures of from 0° C. to 150° C. and more usually from 20 40 ing the solution to its equivalence point with a solution of C. to 100 C. will generally be used. Sufficient amino acid the alkali metal hydroxide preferably in a solvent such is employed to insure high conversion of the perfluoro as ethanol, methanol, or an aqueous alcoholic solution. acid fluoride, molar ratios of the amino acid to the per The salt is readily recovered by evaporation of the solvent fluoro acid fluoride of from 1:1 to about 3:1 being gen and drying at a temperature range of 40-80 C. erally preferred. Reaction may be generally carried out The ammonium salt may be readily prepared by pass most conveniently at atmospheric pressure and reaction ing ammonia gas through a solution of the free acid in a times of from about 10 minutes to 10 hours are generally Solvent such as diethyl ether, methanol, isopropanol, satisfactory. CF2CCFCl2 or acetone, after which the solvent is evap The compounds of the invention may also be prepared orated to recover the ammonium salt. by the direct reaction of an amino acid with a perfluoro 50 The perfluorinated carboxylic acid fluorides used to pre inated halosulfate of the formula CF2n OSOZ where n pare the compounds of the invention may be obtained is an integer ranging from 9 to 14 and where Z is chlorine in a variety of ways. Perfluorinated acid fluorides con or fluorine. This method may be illustrated by the reac taining up to 10 carbon atoms may be prepared by the tion of perfluorononyl chlorosulfate with glycine in ac electrochemical fluorination of the corresponding hydro cordance with the following: carbon carboxylic acid in liquid hydrogen fluoride as O described for example in U.S. Patent 2,519,983 of Simons. CF190SO2Cl -- 3NH2CH2COOH -> C.F. bNHCHCOOH The perfluorinated acid fluorides may also be obtained by the reaction of perfluorinated iodides with fuming sulfuric - HOOCCHNHSONHCHCOOH -- 2HF -- HCl acid as described in co-pending application Serial No. This reaction is carried out preferably by dissolving or 60 212,137, filed July 24, 1962, now abandoned, of Murray suspending the perfluoroinated halosulfate in an anhy Hauptschein and Chester L. Parris for Preparation of drous solvent and the solution then mixed with a sus Fluorinated Organic Compounds. The fluorinated iodide. pension of the amino acid in the same solvent followed precursors may be prepared by telomerization procedures. by refluxing for sufficient time to insure complete reac Such as by the reaction of perfluoroisopropyl iodide. tion. Insoluble material is then removed by filtration after (CFa)CFI or perfluoroethyl iodide CFCFI with tetra which the crude product is isolated by evaporation of the fluoroethylene to produce telomers of the formula solvent followed sometimes by recrystallization. (CF3)2CFICFCFal. I and CFCFCFCFI If desired a tertiary amine, e.g. triethylamine or pyridine respectively. may be added to the reaction mixture in either of the The perfluoroinated chlorosulfates or fluorosulfates may 70 be prepared by the reaction of perfluorinated iodides with above methods of synthesis to act as a scavenger for the chlorosulfonic or fluorosulfonic acid following the proce hydrogen halide liberated during the reaction. dures described in detail in co-pending application Serial Another less preferred procedure for the preparation of No. 735,702, filed May 16, 1958, now abandoned, of the compounds of the invention involves the initial Murray Hauptschein and Milton Braid for Halogenated preparation of an amide by the reaction of a perfluorinated 5 Organic Compounds.
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