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United States Patent Office Patented Sept 3,205,257 United States Patent Office Patented Sept. 7, 1965 2 diols one can mention ethylene glycol, propylene glycol, 3,205,257 tetramethylene diol, decamethylene diol, pentamethylene BES9-(2-CYANOALKYL)FLUOREN-9.YLALKANE COMPOUND diol, hexamethylene diol, and the like. In producing the Henry E. Fritz, South Charleston, and David W. Peck, bis(9-fluorenyl)alkanes the concentration of diol in the Charleston, W. Va., assignors to Union Carbide Corpo charge can vary from about 0.1 mole or less to about 10 ration, a corporation of New York moles or more, per mole of fluorene compound charged, No Drawing. Fied Sept. 10, 1962, Ser. No. 222,694 with from about 0.5 to about 2.0 mole of diol per mole of 5 Caims. (CI. 260-465) fluorene compound being preferred. AS Stated above, an alkali metal hydroxide, such as This invention relates to novel fluorene derivatives. O lithium hydroxide, sodium hydroxide, potassium hydrox More particularly, this invention relates to bis9-(sub ide, and the like, is employed as a catalyst in producing stituted alkyl)fluoren-9-ylalkanes of the formula: the bis(9-fluorenyl)alkanes, with potassium hydroxide be ing preferred. The amount of alkali metal hydroxide used can vary from about 0.1 mole or less to about 1.0 5 mole or more per mole of fluorene compound charged, with from about 0.2 to about 0.5 mole of alkali metal hy -N droxide per mole of fluorene compound being preferred. ZCHRCH CnH2n CHCERZ, The reaction of diol with fluorene is conducted at a tem wherein it is an integer having a valve of from 2 to 10 perature of from about 175 C. or lower to about 275 C. and preferably from 2 to 6; Z is a cyano radical, a or higher, with temperatures of from about 220 C. to -COOR radical, or a -CHNHR2 radical; R is a hy about 250 C. being preferred. drogen atom or a methyl radical; R is a hydrogen atom, The bis(9-fluorenyl)alkane is readily recovered from an alkali metal atom, or an alkyl radical having from 1 the reaction mixture by slurrying the reaction mixture to about 10 carbon atoms; and R2 is a hydrogen atom or with water to dissolve unreacted diol and the alkali an alkanoyl radical having from 1 to about 5 carbon atoms 25 metal hydroxide and then filtering the insoluble bis(9- in the alkyl radical thereof. Thus, the compounds of fluorenyl)alkane from the aqueous slurry. If desired, this invention are novel bis9-(2-cyanoalkyl)fluoren-9- the bis(9-fluorenyl)alkane can be further purified by yl)alkanes; bis 9 - (2 - carboxyalkyl)fluoren-9-ylalkanes washing with water or methanol, or by recrystallization and their alkali metal salts or alkyl esters; bis(9-(N-alka from an organic solvent, for example, 1,4-dioxane. noyl-3-aminoalkyl)fluoren-9-ylalkanes; and bis(9 - (3- 30 Reaction of the bis(9-fluorenyl)alkane with a cyanoal aminoalkyl)fluoren-9-ylalkanes. kene such as acrylonitrile or methacrylonitrile produces The novel carboxyl and amino compounds of this in the bis9-(2-cyanoalkyl)fluoren-9-ylalkanes having the vention are useful in themselves as monomers for the formula: formation of new polymers, such as polyesters, polyam ides, and the like; while the cyano compounds are use ful as intermediates for the production of polymerizable monomers. For example, the cyano derivatives of this invention can be hydrolyzed to form dicarboxylic acids which are useful in the production of polyesters or poly NC CHRc?, CnH2n CHCHRCN amides. The cyano derivatives can also be hydrogenated 40 wherein in and R are as previously defined. As examples in the presence of an alkali metal alkanoate to produce N of these compounds one can mention 1,2-bis(9-(2-cyano aikanoylamino derivatives which can be hydrolyzed to ethyl)fluoren - 9-ylethane, 1,4-bis(9-(2-cyanoethyl)fluo form an amine derivative useful in the production of poly ren - 9-yl)butane, 1,10-bis(9-(2-cyanoethyl)fluoren-9-yl) amides, polyureas, and the like. decane, 1,2-bis(9-(2-cyanopropyl)fluoren-9-yl)ethane, 1, The novel bis9-(substituted alkyl)fluoren-9-ylalkanes 10-bis9-(2-cyanopropyl)fluoren - 9-ydecane, and the of this invention are all readily produced from the bis(9- like. fluorenyl)alkanes of the formula: As indicated, the bis(9-(2-cyanoalkyl)fluoren-9-yl alkanes are produced by the cyanoalkylation of a bis(9- fluorenyl)alkane with a cyanoalkene such as acrylonitrile or methacrylonitrile. The cyanoalkylation can be carried 50 out at from about 10° C. to about 50° C., preferably from about 20° C. to about 35° C., in the presence of a solvent for the bis(9-fluorenyl)alkane, for example, benzene, (U) (UO dioxane, pyridine, acetonitrile, tert-butyl alcohol, etc. wherein n is as previously defined. The bis(9-fuorenyl) The mole ratio of cyanoalkene to bis(9-fluorenyl)alkane alkanes are produced by reacting a fluorene with a diol in 5 5 can vary from about 0.5:1 or less to about 5:1 or more, the presence of an alkali metal hydroxide as a catalyst. with ratios of from about 2:1 to about 3:1 preferred. By the term "fluorene' is meant both fluorene and fluo The cyanoalkylation is assisted by a basic catalyst, such rene compounds which are substituted on the aromatic as the oxides, hydroxides, alkoxides, hydrides, cyanides, rings with alkyl, aryl, alkaryl, aralkyl, alkoxy, aryloxy, or amides of sodium or potassium. Quaternary ammo alkaryloxy, and aralkoxy radicals having up to 10 carbon 60 nium hydroxides such as benzyltrimethylammonium hy toms. As examples of suitable fluorene compounds, one droxide are particularly preferred as catalysts. In gen can mention fluorene, 1-methylfluorene, 2-methylfluo eral, the basic catalysts are employed in the cyanoalkyla rene, 3-methylfluorene, 4-methylfluorene, 5-methylfluo tion reaction in an amount varying from about 0.5 to rene, 6-methylfluorene, 7-methylfluorene, 8-methylfluo about 10 weight percent, based upon the cyanoalkene, with rene, 2-hexylfluorene, 2-phenylfluorene, 2-(1-naphthyl) from about 1 to about 5 weight percent preferred. Al fluorene, 2-(2-methylphenyl)fluorene, 2-benzylfluorene, though the reactants can be charged in any order, it is 2 - methoxyfluorene, 2 - phenoxyfluorene, 2-(2-methyl preferred to gradually add the cyanoalkene to a stirred phenoxy) fluorene, 2-benzyloxyfluorene, and the like. mixture of catalyst, bis(9-fluorenyl)alkane and solvent. The diols employed to produce the bis(9-fluorenyl)al The bis(9-(2-cyanoalkyl)fluoren-9-ylalkanes are solids kanes are represented by the formula HOCH26p 70 which can be recovered from the reaction mixture by wherein n is as defined above. As examples of suitable filtration. Additional bis 9-(2-cyanoalkyl)fluoren-9-yl) 3,205,257 4. alkane can be recovered from the filtrate by admixing procedures known to those skilled in the art, such as re the filtrate with water, whereupon the bis 9-(2-cyano fluxing the selected acid and alcohol in the presence of alkyl)fluoren-9-ylalkane dissolved in the filtrate precipi an acid catalyst, for example, p-toluene sulfonic acid, to tates out and can be recovered by filtration. The bis(9-(2- produce the ester, which is recovered by conventional cyanoalkyl)fluoren-9-ylalkane can then be purified by procedures. conventional procedures. The bis(9 - (N-alkanoyl-3-aminoalkyl)fluoren-9-yl)al The bis(9-(2-carboxyalkyl)fluoren-9-ylalkanes and the kanes of this invention have the formula: alkali metal salts and alkyl esters thereof of this inven tion have the formula: 10 RéNHCHCHRó?,YYYYX C.H. HCHRCH-NHCR wherein n and R are as previously defined and R3 is an Riooc CHR off, C.E. CHCHRCOOR1 5 alkyl radical of from 1 to 5 carbon atoms. As examples wherein n, R and Rare as defined above. of these compounds one can mention 1,2-bis 9-(N-acetyl As examples of the novel dicarboxylic acids one can 3-aminopropyl)fluoren-9-yl)ethane, 1,4-bis(9-(N-acetyl-3- mention 1,2-bis(9-(2-carboxyethyl)fluoren-9-ylethane, 1, aninopropyl)fluoren-9-yl)butane, 1,10-bis(9-(N-acetyl-3- 4-bis(9-(2-carboxyethyl)fluoren-9-yl-butane, 1,10-bis 9 aminopropyl)fluoren-9-ylethan, 1,2-bis9-(N-valeryl-3- (2-carboxyethyl)fluoren-9-yl) decane, 1,2-bis(9-(2-carbox 20 aminopropyl)fluoren-9-yl)ethane, 1,2-bis 9-(N-acetyl-3- ypropyl)fluorei - 9-yl)ethane, 1,10-bis(9-(2-carboxypro amino-2-methylpropyl)fluoren-9-ylethane, and the like. pyl)fluoren-9-yl) decane, and the like. These dicarboxyic The bis 9 - (N-alkanoyl-3-aminoalkyl)fluoren-9-ylal acid compounds are readily produced by the hydrolysis of kanes of this invention are produced, for example, by hy the corresponding bis(9-(2-cyanoalkyl)fluoren-9-yl)al drogenation of a mixture of a bis(9-(2-cyanoalkyl)fluoren kane compound or by the reaction of an alkali metal 9-yllalkane, an alkanoic acid anhydride and an alkali acrylate or alkali metal methacrylate with a bis(9-fluor metal alkanoate in contact with hydrogenation catalyst. enyl)alkane followed by acidification of the resulting di The alkanoic acid anhydrides suitable for use in pro alkali metal salt. ducing the bis(9-(N-alkanoyl-3-aminoalkyl)fluoren-9- The hydrolysis of the bis 9-(2-cyanoalkyl)fluoren-9-yl) ylalkanes of this invention are the anhydrides of lower alkane to form the bis(9-(2-carboxyalkyl)uuoren-9-y 30 alkanoic acids such as acetic acid, propionic acid, butyric alkane can be conducted by methods known to those acid, pentanoic acid, and the like.
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