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United States Patent Office Patented June 16, 1953 - - - - - 2,642.456 UNITED STATES PATENT OFFICE N-CARBOXYALKYL-a-AMNO TOLUIC ACDS AND THEIR ALKYL ESTERs William S. Emerson, and Robert A. Heimsch, Dayton, Ohio, assignors to Monsanto Chemical Company, St. Louis, Mo., a corporation of Dela ware No Drawing. Application April 25, 1950, Serial No. 158,074 8 Claims. (C. 260-471) 1. 2 This invention relates to new aralkyl amino in which R is as defined above. As illustrative dicarboxylic acids and esters of the Same. Of compounds having this structure may be men The new dicarboxylic compounds are N-car tioned N-carboxymethyl-N-methyl-a-amino-2, boxyalkyl-a-amino toluic acids and their alkyl 3- or 4-toluic acid, methyl N-carbomethoxy esters having the general structure: . methyl-N-methyl-a-amino-4-toluate, butyl N 5 carbobutoxymethyl-N-methyl-a-amino-2-toluate, 2-ethylhexyl N-carbo (2-ethylhexyl)oxy-N-meth K C-CHN-Hcoor yl-a-amino-3-toluate, n octyl N-carbooctyloxy ROOC X Y. methyl-N-methyl-a-amino-4-toluate, isopropyl in which R is a member of the group consisting O N - carboisopropoxymethyl-N-methyl-a-amino-4- of hydrogen and alkyl groups of from 1 to 8 car tOluate, etc. bon atoms and X and Y are members of the Still another group of compounds provided by group consisting of hydrogen and alkyl groups of the present invention includes those obtainable from 1 to 4 carbon atoms. m - The present new aminodicarboxylic acids or by employing leucine or its alkyl esters as the their dialkyl esters are readily obtainable by con 5 amino acid compound and having the general tacting an a-halotoluic acid or an alkyl a-halo formula: . toluate with an a-amino acid or its ester, the reaction proceeding according to the scheme: X X-CHNHgico OR RO O.C. &HCHCH, & D-CH2 -- It cool a 20 (H, ROOC X in which R. is as defined above, e. g., N-(a-car boxy-at-isobutylmethyl)-a-amino-4-toluic acid. & D-chi-Hoo OR - HZ Depending upon the nature of the individual ROOC X Y. 25 reactants, the condensation may occur under in which Z is a member of the group consisting varying conditions of temperature and/or pres of chlorine, bromine and iodine, R is a member Sure. For optimum yields, however, it is advan of the group consisting of hydrogen and alkyl tageous to reflux the mixture of the toluic acid groups of from 1 to 8 carbon atoms, and X and Y Compound and the amino acid compound in a are members of the group consisting of hydrogen 30 Suitable Solvent. Also while the present amino and alkyl radicals of from 1 to 4 carbon atoms. dicarboxylic compounds are obtainable by con The toluic acid compounds which may be em ducting the reaction in the absence of any extra ployed include, e. g., a-chloro-4-toluic acid, a neous material, we have found that optimum bromo-2-toluic acid, a-iodo-3-toluic acid and yields are obtained by employing in the reaction alkyl esters of such acids in which the alkyl group 35 mixture a basically reacting material which serves has from 1 to 8 carbon atoms. As illustrative of to neutralize the hydrogen halide evolved during amino acid compounds which may be employed the condensation. Basically reacting materials may be mentioned glycine, sarcosine, a-alanine, Which may be employed include alkali and alkali leucine, isoleucine, norleucine, paline and esters. metal hydroxides, e. g., sodium, potassium, of the same with aliphatic alcohols of from 1 to 8 40 lithium, calcium, or magnesium hydroxide; basi cally reacting Salts. Such as sodium carbonate, carbonwhen atoms. employing glycine or its esters as the potassium acetate, etc. amino acid component there are obtained com As herein stated alkyl esters of the amino acids pounds having the general formula: may be used instead of the free... acids. Thus, reaction of an ester such as the ethyl ester of 45 Sarcosine With ethyl a-chloro-4-toluate will yield X X-CHNHOH.cook ethyl N-carboethoxymethyl-N-methyl-a-amino RO OC . in which R is a member of the group consisting 4-toluate, the methyl ester of sarcosline with a of hydrogen and alkyl radicals of from 1 to 8 bromo-3-toluic acid will yield N-carpomethoxy 50 methyl-N-methyl-a-amino-3-toluic acid, etc. carbon atoms, e.g., N-carboxymethyl-a-amino-4- Mixed esters are thus obtainable, e.g., condensa toluic acid, butyl N-carboxymethyl-a-amino-3- tion of the methyl ester of sarcosine with iso toluate, etc. propyl a-chloro-4-toluate will give isopropyl N with sarcosine or its esters, the compounds carbomethoxymethyl-N-methyl-a-amino-4- tol which are obtained have the general formula: uate. Dialkyl esters of the present dicarboxylic acids also are obtainable by esterifying the free acids ROOC X >-on H coor - With an unsubstituted, aliphatic saturated alcohol 2,642,456 3 4. of from 1 to 8 carbon atoms, preferably in the of elastomeric vinyl compositions. While many presence of an esterifying catalyst. The higher plasticizers will produce flexible compositions at alkyl esters, e. g., N-carboalkoxyalkyl-a-amino room temperature the flexibility of these com toluates in which the alkoxy group has from 4 to positions at low temperatures may vary consid 8 carbon atoms are more advantageously pre 5 erably, i. e., plasticized polyvinyl chloride com pared; however, by an interchange reaction positions that are flexible at room temperature Whereby a lower dialkyl ester of an N-carboxy-r often become very brittle and useless at low tem alkyl-a-aminotoluic acid, for example, the di peratures. Low temperature flexibility tests methyl ester is reacted with an unsubstituted, herein employed are according to the Clash-Berg aliphatic saturated alcohol of from 4 to 8 carbon method. This method determines the torsional atoms in the presence of an esterifying catalyst. flexibility of a plastic at various temperatures. Catalysts of general utility in the trans-esteri The temperature at which the vinyl chloride Com fication are basic materials, for example, potas position exhibits an arbitrarily established mini sium ethylate, metallic sodium, Sodium hydroxide, mum flexibility is defined as the Low Tempera Sodium methylate, etc. In both esterifying pro ture Flexibility of the composition. This value cedures, formation of the desired esters. Occurs to may also be defined as the lower temperature some extent at ordinary room temperatures; how limit of the plasticized composition's usefulness ever, in order to obtain good yields we prefer to as an elastomer. operate at refluxing temperatures while remov Water resistance.--The amount of water ing from the reaction zone either the water which 20 absorption and the amount of leaching that takes is given off during the direct esterification or the place when the piasticized composition is im lower alcohol generated in the interchange reac mersed in distilled water for 24 hours is deter tion. w mined. The present N-carboxyalkyl-a-aminotoluic The invention is further illustrated, but not acids and their lower alkyl esters are solids, or 25 limited, by the following examples: stable, highly boiling, viscous liquids, which may Eacomple 1 be advantageously employed in the chemical and allied industries for a wide variety of purposes. A Two hundred eight grams (1.1 moles of a number of the free acids, e. g., the N-carboxy chloro-4-toluyl chloride was hydrolyzed by heat methyl-N-methyl-a-amino-2-, 3- or 4-toluic acids ing with a mixture of 1500 cc. of water and 45 g. and the dialkyl esters thereof may serve as in of sodium hydroxide. To the resulting hydroly termediates in the production of synthetic fibers sis product (comprising a-chloro-4-toluic acid in of the polycarboxylamide type, and in the pro an aqueous solution of sodium chloride) there duction of non-ionic wetting-out and detersive was added a solution of 150 g. (1.2 moles) of agents. Sarcosine hydrochloride, 140 g. of . Sodium hy Dialkyl esters of the present N-carboxyalkyl droxide and 500 cc. of water, and the whole was a-aminotoluic acids in which the -alkyl groups refluxed for a time of 18 hours. At the end of have from 4 to 8 carbon atoms are highly efficient that time the reaction mixture was filtered and plasticizers for vinyl chloride polymers. A wide the filtrate was acidified with hydrochloric acid variety of plasticizers has been employed for the 40 to a pH of 2. Solid material was recovered by purpose of improving the physical properties of repeated subsequent filtration and evaporation vinyl chloride polymers. Particular attention has followed by filtration. When the volume of the been given to the improvement of flexibility and filtrate was reduced to about 200 cc. it was treat heat and light stability of Such plasticized com ed with an equal volume of acetone and filtered. positions. We have found that very good low All of the solids thus obtained were combined temperature flexibility is imparted to vinyl chlo and dried, a total of 507 g. of solids being ob ride polymers When the present esters are emi tained in this manner. The Solid product, thus ployed as plasticizers for Such polymers. obtained comprised a mixture of N-carboxy The present esters are valuable plasticizers for methyl-N-methyl-a-amino-4-toluic acid, sodium polyvinyl chloride and copolymers of at least 70 50 chloride and probably some sodium hydroxide. per cent by weight of vinyl chloride and up to 30 Methyl N-carbomethoxymethyl-N-methyl-a- per cent by Weight of an unsaturated monomer amino-4-toluate was prepared by refluxing the copolymerized therewith, for example vinyl ace 507 g.
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