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United States Patent (19) 11) Patent Number: 4,605,521 Eubanks Et Al

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United States Patent (19) 11) Patent Number: 4,605,521 Eubanks Et Al United States Patent (19) 11) Patent Number: 4,605,521 Eubanks et al. 45) Date of Patent: Aug. 12, 1986 (54) PROCESS FOR THE PREPARATION OF 56 References Cited ORGANIC NTRILES FROM ORGANIC CARBOXYLECACID PRIMARY AMIDES U.S. PATENT DOCUMENTS 3,317,585 5/1967 Herschmann .................... 260/465.2 (75) Inventors: Robert J. I. Eubanks; James G. Primary Examiner-Dolph H. Torrence Pacifici, both of Batesville, Ark. Attorney, Agent, or Firm-Clyde L. Tootle; J. Frederick (73) Assignee: Eastman Kodak Company, Thomsen Rochester, N.Y. 57 ABSTRACT (21) Appl. No.: 717,926 This invention relates to a process for the preparation of organic nitriles. More particularly, the invention relates 22) Fied: Mar. 29, 1985 to a process for the preparation of organic nitriles by reacting organic carboxylic acid primary amides with a 51 Int. Cl." ............................................ C07C 120/10 dehydrating agent in the presence of a catalytic amount (52) U.S. Cl. ..................................... 558/313; 546/286 of a particular quaternary ammonium salt. (58) Field of Search ................. 260/465 B, 465.2, 464; 546/286 12 Claims, No Drawings 4,605,521 1 2 The quaternary ammonium salt used in a catalytic PROCESS FOR THE PREPARATION OF amount has the formula: ORGANIC NTRILES FROM ORGANC CARBOXYLIC ACID PRIMARY AMIDES DESCRIPTION This invention relates to a process for the preparation of organic nitriles. More particularly, the invention relates to a process for the preparation of organic ni wherein triles by reacting organic carboxylic acid primary am O R1, R2, R3, and R4 are each independently selected ides with a dehydrating agent in the presence of a cata from alkyl of from 1 to 18 carbon atoms, alkylaryl of lytic amount of a particular quaternary ammonium salt. from 7 to 18 carbon atoms, arylalkyl of from 7 to 18 The organic nitriles are used in many organic synthe carbon atoms, and aryl of from 6 to 18 carbon atoms and sis processes. Such compounds have been well known 15 X is an anion such as hydroxyl, halogen, hydrogen in the art for many years. Such organic nitriles can be sulfate, perchlorate, hydroxide anion and the like. The prepared by reacting an aliphatic, cycloaliphatic or quaternary ammonium salts in which R1, R2 and R3 aromatic carboxylic acid primary amide with a dehy each independently contain 1 to 4 carbon atoms and R4 drating agent such as thionyl chloride. Other dehydrat contains 1 to 4 carbon atoms or a benzyl group are ing agents are known in the art such as, for example, 20 preferred. Such preferred quaternary ammonium salts phosphorous pentoxide, acetic anhydride and the like. include tetraethylammonium chloride, tetraethylammo Generally, the preferred dehydrating agent is thionyl nium bromide, tetraethylammonium hydroxide, benzyl chloride since it can be easily handled and forms gase triethylammonium chloride, benzyltriethylammonium ous by products, hydrogen chloride and sulfur dioxide, hydroxide, benzyltriethylammonium bromide, and which allows relatively simple workups. The use of 25 ethyltrimethylammonium chloride, ethyltrimethylam thionyl chloride however in many reactions reacts monium hydroxide, propyltrimethylammonium hy slowly, requires long reaction times, elevated reaction droxide, butyltrimethylammonium hydroxide, tetraeth temperatures and large excesses of thionyl chloride for ylammonium bromide, tetrabutylammonium bromide, dehydration reactions. The use of large excesses of tetrabutylammonium hydroxide, tetraethylammonium thionyl chloride in dehydration reactions is undesirable 30 acetate, and mixtures thereof. Such salts are disclosed as since any unreacted thionyl chloride must be removed being useful as catalysts in heterogeneous reactions in before the product is isolated and recovered. In addi U.S. Pat. No. 3,992,432. tion, the use of an excess amount of thionyl chloride in The quaternary ammonium salts of this process gen combination with high reaction temperatures and long erally are employed in a catalytic amount, that is, any 35 amount which exhibits a favorable comparison in the stripping times at temperatures greater than 60° C. will reaction as compared to the use of the dehydrating rapidly darken organic nitriles and increase residual agent alone. Typically this amount will be about 0.01 sulfur content which is also undesirable. mol percent to about 0.1 mol percent of the organic acid In an attempt to eliminate or reduce the above unde primary amide reactant, preferably 0.02 to 0.05 mol sirable aspects, catalysts such as N,N-dimethylforma percent, most preferably about 0.03 mol percent. mide (DMF) have been widely used in preparing a Suitable organic carboxylic acid primary amides use variety of organic nitriles. The DMF catalyst provides ful in the present invention can be aliphatic, cycloali dehydration reactions at shorter reaction times, at lower phatic, heterocyclic or aromatic carboxylic acid pri temperatures and with a less amount of thionyl chlo mary amides. The aliphatic carboxylic acid primary ride. However, relatively large amounts of DMF are 45 amides can be straight or branched chain acid primary necessary. Moreover, when DMF is exposed to thionyl amides containing 2 to 22 carbon atoms. The organic chloride and other such dehydration agents such as carboxylic acid primary amides such as the longer chain. phosphorous pentoxide and the like, there is formed length or high molecular weight are generally slower N,N-dimethylcarbamoyl chloride (DMCC) which is a reacting than the short chain aliphatic acid primary proven-carcinogen in mice and a possible carcinogen in 50 amides. The aliphatic, cycloaliphatic, heterocyclic, and humans. Therefore, when dehydration processes are aromatic carboxylic acid primary amides can be substi carried out where DMCC may be produced there are tuted or unsubstituted. Substituents include any substit procedures which must be carried out to ensure that uent which does not hinder the dehydration, block the there is no human exposure in the work place to the dehydration or which react more easily with the car DMCC. Therefore, dehydration processes where DMF 55 boxyl primary amide group thereby preventing forma is present and could form DMCC during the dehydra tion of the organic nitrile. Suitable substituents include, tion which could result in human exposure to such for example, alkyl groups, phenyl groups, nitro groups, formed DMCC are highly undesirable. cyano groups, halogens and the like. Examples of such Therefore, it would be an advance in the state of the aliphatic, cycloaliphatic, heterocyclic and aromatic art to provide a dehydration process to prepare organic carboxylic acid primary amides are acetamide, propana nitriles in high yields and efficiency where DMCC was mide, butanamide, isobutanamide, stearamide, benza not formed in the dehydration process and only a small mide, pentamide, 3-methylbutamide, hexanamide, hep amount of catalyst is required. tamide, octamide, nonamide, decamide, undecamide, In accordance with the present invention, it has been dodecamide, tetradecamide, hexadecamide, heptadeca found that the use of a quaternary ammonium salt as a 65 mide, octadecamide, eicosanoic acid amide, cyclo catalyst in the dehydration of organic carboxylic acid propanecarboxylic acid amide, cyclopentanecarboxylic primary amides to form organic nitriles provides a acid amide, cyclohexanecarboxylic acid amide, benza highly efficient and safe dehydration process. mide, p-toluic acid amide, m-toluic acid amide, 1-naph 4,605,521 3 4. thalene carboxylic acid amide, phenyl acetic acid am 95%) and high purity which can be used without fur ide, p-chlorobenzoic acid amide, p-nitrobenzoic acid ther purification. amide, m-nitrobenzoic acid amide, p-methylbenzoic The process of this invention therefore provides the acid amide, p-methoxybenzoic acid amide, 3,4-dime desired organic nitrile product in good yield and purity thoxybenzoic acid amide, nicotinamide and the like. without the use of long reaction times, large excesses of The dehydration reaction can be carried out in the dehydrating agent, elevated reaction temperatures or presence or absence of a solvent depending on the reac the preparation of possibly carcinogens. tants employed. The process is a homogeneous process. The novel process of the present invention therefore Generally the organic carboxylic acid amide used in the provides organic nitriles which are useful as intermedi present invention are liquids and are miscible with the 10 dehydrating agents, such as thionyl chloride, and the ates in the synthesis of organic compounds and other quaternary ammonium salt. It may be desirable in dehy useful materials in a unique and efficient manner. drating the organic carboxylic acid primary amides The invention will be further illustrated by the fol which have high melting points to carry out the dehy lowing Examples although it will be understood that dration in non-polar organic solvents such as heptane, 15 these Examples are included merely for purposes of hexane, benzene, toluene and the like. The solvent after illustration and are not intended to limit the scope of the dehydration can, if desired, be recovered by conven invention. tional stripping methods. Suitable dehydration agents include phosgene, oxyal EXAMPLE 1 oyl chloride, oxyaloyl bromide, oxyaloyl iodide, phos 20 A homogeneous mixture of benzamide (1.0 mol) and phorous trichloride, phosphorous tribromide, phospho benzyltriethylammonium chloride (0.02 mol percent) rous triiodide, thionyl chloride, thionyl bromide, thio was
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