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United States Patent Office Patented Apr 3,658,869 United States Patent Office Patented Apr. 25, 1972 1. 2 Separation difficulties of organic solvent media since the 3,658,869 1-hydrocarbylthio-aldoximes precipitate out of the aque PROCESS FOR PREPARING SULFUR CONTAINING ALDOX MES ous medium, being only slightly soluble in water. Further Samuel B. Soloway, Modesto, Calif., and Herbert P. more, the use of water as the reaction medium obviates Rosinger, Kent, England, assignors to Shell Oil Com any need for changing solvent systems or for isolating the pany, New York, N.Y. intermediate halogenation product. This reduction in op No Drawing. Continuation-in-part of application Ser. No. erating steps leads to the higher yields necessary for 645,511, June 12, 1967. This application Aug. 25, 1969, commercial operations. The improved process of the Ser. No. 852,899 invention has consistently produced yields of at least 80% Claims priority, application Great Britain, June 13, 1966, O While a similar process using organic solvents seldom pro 26,258/66 duced yields of about 50%. The costs are also greatly Int, C. C07 131/00 reduced not only because of the use of water but also in U.S. C. 260-453 R 9 Claims the elimination of added costs connected with handling toxic, volatile organic solvents. Since the chlorination of the aldoxime is carried out in ABSTRACT OF THE DISCLOSURE an aqueous medium it is essential that the aldoxime re Process for preparing 1-hydrocarbythio-aldoximes in an actant be at least substantially soluble in water. The crude aqueous reaction medium by the halogenation of an al reaction mixture from the chlorination then is reacted doxime followed by reaction with a mercaptain in the with the mercaptan. In this step, it is essential that the presence of a base, said 1-hydrocarbylthio-aldoximes are intermediate 1-haloaldoxime not be solid (i.e., that it be known compounds which are useful as oil additives, anti liquid) and it be soluble in water to at least some extent. oxidants, accelerators for curing rubber, and as chemical It is then feasible to carry out the two steps of the reac intermediates. tion in sequence without isolating the intermediate, and Without the use of organic solvents or organic extraction This application is a continuation-in-part of Ser. No. techniques. 645,511, filed June 12, 1967, now abandoned. The 1 - hydrocarbylthio-aldoximes prepared by the FIELD OF THE ENVENTION process of this invention can be described by the formula: The invention relates to an improved process for pre paring 1-hydrocarbylthio-aldoximes. 30 DESCRIPTION OF THE PRIOR ART in which each R and R1 is hydrocarbyl, preferably alkyl 1-hydrocarbylthio-aldoximes of the formula or alkenyl, of up to 5 carbon atoms each, or such radicals Substituted with non-reactive functional groups. R-i-NoH The aldoximes and mercaptans used in the process of SR 35 this invention are described by the formulae wherein R and R1 are hydrocarbyl are known compounds. These compounds have been previously prepared in an R-CH-NOH organic reaction medium by the halogenation of an al and RSH in which R and R are alkyl or alkenyl of doxime followed by reaction with a mercaptain to form 40 up to 5 carbon atoms, or such radicals substituted with the 1-hydrocarbylthioaldoxime. This method is described non-reactive functional groups. By non-reactive functional in Can. J. Chem. 42, 2393 (1964). groups are meant those groups that do not prevent the The use of organic solvents for this process produces formation of the 1-hydrocarbylthioaldoximes under the re many problems, especially when commercial quantities of action conditions of this process. Functional groups that the 1-hydrocarbylthioaldoximes are prepared. For one may reduce the yields of 1-hydrocarbylthio-aldoximes are, thing, the separation problems of the 1-hydrocarbylthio 45 therefore, included in this definition. Suitable functional aldoximes are complicated by the use of organic solvents groups include halogens, i.e., fluorine, chlorine, bromine or since these compounds are soluble in the organic solvents. iodine, as well as cyano, nitro, carboxyl, hydroxy and the The separation entails the use of costly distillation tech like. niques, solvent extraction processes or the like p isolate Examples of Suitable R and R radicals, which may be the final product. This process is even more complicated 50 straight or branched-chain, include the alkyls such as when different organic solvents are used in the halogena methyl, ethyl, propyl, isopropyl, butyl, tert-butyl and tion and hydrocarbylthiolation steps. In many cases, scal hexane; the alkenyls such as vinyl, 2-propenyl, 3-butenyl. ing-up the process results in reduced yields through ex As previously indicated, these radicals may be suitably traction and decomposition losses of intermediates and Substituted with non-reactive functional groups such as final product. Additionally, the use of organic solvents 55 halogen, cyano, etc. increases the cost and introduces safety hazards in prepar Illustrative alkanaldoximes include acetaldoxime, pro ing the 1 - hydrocarbylthio-aldoximes on a commercial pionaldoxime, n-butyraldoxime, isobutyraldoxime, n-valer Scale. This process, then, has not been commercially at aldoxime and the alkenaldoximes such as 1-vinylform tractive. aldoxime, 2-vinylacetaldoxime, 3-vinylacetaldoxime and 60 the like. SUMMARY OF THE INVENTION The mercaptains (thiols) used in this invention include Surprisingly, We have found that the use of an aqueous the alkyl mercaptans such as methyl mercaptan, ethyl reaction medium for the preparation of 1-hydrocarbyl mercaptan, propyl mercaptan, isopropyl mercaptan, butyl thio-aldoximes avoids the difficulties of the prior art mercaptan, isobutyl mercaptan, pentyl mercaptan, hexyl process. Accordingly, this invention involves a process of 65 mercaptan, decyl mercaptan and the like; the alkenylmer preparing 1-hydrocarbylthio-aldoximes in an aqueous re captains such as vinylthio, 1 - propene - 3 - thiol, 1-butene action medium by reaction of a halogen with an aldoxime 4 - thiol, 1 - butene - 3 - thiol, 1 - pentene - 5 - thiol, 1 to form a halogenation product followed by reaction of pentene - 3 -thiol, 1 - hexene - 5 - thiol, 1-hexene-6-thiol, said halogenation product with a mercaptan in the pres 1-decene-10-thiol, 1-decene - 5 - thiol and the like; the ence of a base. O aromatic mercaptans, i.e., those in which the R groups The use of the aqueous reaction medium avoids the contain aromatic Substituents, such as benzenethiol, 1 3,658,869 3 4 naphthalenethiol, p - methylbenzenethiol, p-ethylbenzene lower temperatures as with the halogenation may be en thiol, benzylthiol, phenethylthiol and the like. ployed, however. The base employed, which may be organic or inorganic, The formation of the 1-hydrocarbylthio-aldoxime is should be of sufficient basicity to neutralize the halogen rapid after the two aqueous reaction mixtures have been halide produced by the halogenation and form a salt of mixed. Any excess base present should usually be neutra the mercaptain. lized before recovering the 1-hydrocarbylthio-aldoxime Suitable organic bases include the aliphatic, aromatic or since they are less soluble in a neutral or slightly acidic heterocyclic amines such as methylamine, butylamine, di solution. The 1-hydrocarbylthio-aldoxime, which precipi ethylamine, dipropylamine, triethylamine, tripropylamine, tates out of solution, can then be separated by conven benzylamine, S-phenylethylamine, aniline, o-toluidine, O tional techniques such as filtration, purified by Washing pyridine, piperidine and the like. with cold water and dried. The inorganic bases include the alkali and alkaline While the process can be operated by batchwise proce earth metal carbonates such as lithium, sodium and potas dures, it is well suited to continuous operation. A con sium carbonate, calcium carbonate and the like; the alkali venient mode of operation is that in which at least the metal carbonates and hydroxides such as sodium bicar 5 halogenation step is carried out continuously by continual bonate, potassium bicarbonate, lithium hydroxide, sodium injection of halogen into a flowing stream of the aqueous hydroxide, potassium hydroxide and the like and other aldoxime mixture. Preferably the injected halogen is bases such as ammonia. caused to flow countercurrent to the flowing stream of The halogenation of the aldoxime is conveniently per aqueous aldoxime solution. This can be conveniently ac formed by passing the solid, liquid or gaseous halogen, 20 complished by injecting the halogen continuously into a i.e., chlorine, bromine or iodine, into an aqueous reaction vertical column from an inlet at least partway down the medium containing the aldoxime. column while the aqueous solution of aldoxime flows The temperatures employed are determined mainly by downwardly through the column. The halogenation prod the reaction rate and yield of the intermediate halogena uct can then be continuously mixed with an aqueous alka tion produce desired. The yields tend to decrease at the 25 line solution of the salt of the mercaptan. As previously lower end of the temperature range (the freezing point indicated it is generally immaterial whether the base is of the aqueous medium sets the ultimate lowest tempera present in the initial aqueous aldoxime mixture or added ture that can be used) and at the upper end. In general, later, provided that it is present when the mercaptain addi however, the temperature may range from about -30 tion takes place. C. to 75 C. Better results are obtained in the range of 30 The aldoxime used as starting materials in the process about -20° C. to 50 C., with temperatures of -10 C. may conveniently be prepared by reacting the appropriate to 30 C. being particularly suitable. Best results are ob aldehyde with hydroxylamine salts, optionally in the pres tained when the temperature is maintained between about ence of an alkali metal carbonate. Another method in -5 C., and 5 C. Internal and/or external cooling may volves reacting the aldehyde in a water medium with so be employed to maintain the temperature in a suitable 35 dium nitrite, sodium bisulfite, and sulfur dioxide.
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