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United States Patent Office Patented Dec 2,818,411 United States Patent Office Patented Dec. 31, 1957 2 the resulting solution to crystallize out the gamma pico line oxalate. By such a process it has been found that 2,818,411 substantially all of the gamma picoline in the mixture SEPARATION OF GAMMA PCOLINE can be crystallized out as the oxalic acid salt while the 5 beta picoline and 2,6-lutidine remain in solution. The Harold L. Dimond, Pittsburgh, Pa., assignor to Pittsburgh entire disclosure of the Williams et al. application is here Coke & Chemical Company, Pittsburgh, Pa., a corpo by incorporated by reference. ratiosa of Pennsylvania While the process recited in the Williams et al. appli No Drawing. Application June 21, 1955 cation is highly advantageous, it suffers from the dis Serial No. 517,053 O advantage that the gamma picoline is recovered by steam distillation of an alkaline solution or by other methods 8 Claims. (CI. 260-290) involving the production of a dilute, aqueous solution of gamma picoline. It has now been found that the formation of a dilute, The present invention relates to the separation of aqueous solution or other solvent solution of the gamma gamma picoline (4-methyl pyridine) from mixtures there picoline can be avoided and the gamma picoline can be of with other nitrogen bases such as beta picoline (3- recovered readily in good yields by heating the gamma methyl pyridine) and 2,6-lutidine (2,6-dimethyl pyridine) picoline-oxalic acid complex to 150-200 C. and recover by forming the gamma picoline-oxalic acid complex or ing the gamma picoline from the distillate. It would be salt. expected that dry distillation would cause a dissociation It is an object of the present invention to recover of the complex into oxalic acid and gamma picoline. gariana piccine from a gamma picoline-oxalic acid salt. From the properties of oxalic acid, it would also be ex it is an additional object to recover gamma picoline pected that it would sublime, and that it would be neces from said salt without employing large amounts of water sary to fractionate and separate the gamma picoline. Sur or other solvents. prisingly, it was found that this did not occur but instead A further object is to provide a practical and commer there was decomposition of the oxalic acid part of the cially attractive process for the isolation and recovery molecule resulting in a distillate composed principally of substantially pure gamma picoline from mixtures there of water, formic acid and gamma picoline, as well as of with beta picoline and/or 2,6-lutidine. gaseous products including carbon dioxide, some water, Yet another object is to prepare the gamma picoline 30 some gamma picoline and possibly also some carbon salt of oxalic acid in an improved manner. monoxide and hydrogen. The gamma picoline can be A still further object is to separate said salt from mix readily recovered by drying over a conventional dehy tures thereof with beta picoline and/or 2,6-lutidine in drating agent such as sodium hydroxide, and separating an improved manner. the liquid while the gaseous gamma picoline likewise can Still further objects and the entire scope of applicability be trapped and recovered. of the present invention will become apparent from the The present process gives a very high grade gamma detailed description given hereinafter; it should be under picoline (95-100% pure) in yields as high as 60-70% stood, however, that the detailed description and specific of theory. Based on the commercial beta, gamma picoline examples, while indicating preferred embodiments of the fraction which is processed with the oxalic acid approxi invention, are given by way of illustration only, since 40 mately 30% by weight is recovered as gamma picoline. various changes and modifications within the spirit and The oxalic acid used for the formation of the gamma scope of the invention will become apparent to those picoline oxalate composition is preferably anhydrous skilled in the art from this detailed description. or substantially so, although hydrates of the acid (e. g. Numerous procedures for the separation of gamma 71.5% to 98% oxalic acid) may be used with some de picoline from ternary or binary mixtures thereof, con crease in yields. The gamma picoline oxalate obtained, taining beta picoline and/or 2,6-lutidine, have been pro according to the present process, appears to be principally posed and some have been employed commercially. How that containing one mole of picoline per mole of oxalic ever, each of these procedures has left much to be de acid, although other base to acid compositions, such as sired from the standpoint of economical operation, ease one containing four moles of picoline per five moles of of operation, efficiency of recovery, and/or the realization oxalic acid or two moles picoline per three moles of oxalic if the base in sufficiently pure state as to be suitable for acid, may also be present. The quantity of oxalic acid further synthesis of valuable and useful products, such used for the salt formation can be varied but is preferably as isonicotinic acid. about the theoretical required to give a 1:1, 2:3, or 4:5 One such procedure has been described by Alan G. molar ratio of base to acid salt of the gamma picoline, Lidstone (Journal of The Chemical Society, 1940, part 1, i. e., from 1 to 1/2 moles of oxalic acid per mole of page 241), which involves separation of a mixture of gamma picoline in the mixture. Less oxalic acid than beta and gamma picolines from their admixture with that designated above may be used but, in such case, the 2,6-lutidine in the form of their oxalate salts, followed yield of gamma picoline is lowered. Likewise, an excess by separation of the beta and gamma picoline salts by of the acid over the preferred range stated may be em crystallization from alcohol. Fairly satisfactory results 60 ployed, but such excess causes gummy characteristics in can be obtained using the process described by Lidstone the crystalline oxalate salt composition. on a laboratory scale but, when employed in commercial Dissolution of the oxalic acid into the gamma picoline operations, the process is undesirable. This fact is indi containing mixture to form the gamma picoline oxalate, cated by the author himself, who states that treatment according to the invention, can be carried out in any of batches larger than one hundred grams at a time 85 convenient manner. For example, the acid may be added seriously diminishes the yield. to the picoline mixture with stirring until complete solu An improvement on the Lidstone procedure is described tion is obtained. Preferably, the mixture is warmed to in Williams and Hensel application Serial No. 350,762, between 50 C. and 110° C. before the acid is added filed April 23, 1953, and now Patent 2,728,771, December thereto, since this assists the dissolution, although such 27, 1955, wherein there is disclosed a process comprising 70 heating is not essential in view of the exothermic reaction dissolving oxalic acid in a mixture of gamma picoline which occurs as the oxalate is formed. with beta picoline and/or 2,6-lutidine and then cooling Cooling of the oxalic acid solution for the purpose of 2,818,411 3 4 crystallizing out the gamma picoline oxalate contained left in the reaction vessel after the 10% (or 80% with therein can be effected in any desirable fashion, e.g., with the hydrated oxalic acid recited above) distillation step an external water bath. Generally, the solution is per is completed. The yield of gamma picoline is based on mitted to reach equilibrium conditions before cooling al the amount equivalent to the oxalic acid employed since though this is not necessary. The temperature to which 5 the efficiency of the oxalic acid used is of primary con the solution is cooled for recovery of the oxalate may be cern. As previously set forth, more or less oxalic acid widely varied with satisfactory results but, normally, need can be employed than the mol for mol ratio with the only be sufficiently low to effect complete and otherwise gamma picoline which at present is preferred. Satisfactory crystallization, e. g., a temperature within The 10% distillation step can be omitted in some the range of 25 to 30° C. is usually sufficient. Preferably, 10 instances, especially if all reagents employed are anhy cooling is carried out slowly, for instance over a period drous, although even then it is preferred to employ this from 30 to 60 minutes, or even up to 3 hours, to permit distillation step. optimum crystallization of the desired salt. After the clear, homogeneous mixture has been purged After crystallization, the oxalate can be recovered by of its water, it is preferably cooled rapidly at first (e.g., filtration, preferably by centrifuging. with external cooling aids) to stop the distillation. The The formation of the gamma picoline-oxalic acid con cooling is then permitted to continue slowly during one plex can be used to recover gamma picoline in substan to three hours to 20 C. While rapid cooling may be tially pure form from any binary or ternary mixtures employed, slow cooling is preferred as it gives well thereof with beta picoline and 2,6-lutidine. As examples defined crystals and thus facilitates filtration. of such binary and ternary mixtures, there may be given 20 The white oxalate cake is next filtered and spun dry ternary "beta-gamma picoline fractions' derived from for 2 to 4 hours on a centrifuge to remove beta picoline coal tar bases and containing from 20% to 50% gamma and 2,6-lutidine.
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