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United States Patent (19) 11) 4,308,215 Vaughan 45 Dec

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United States Patent (19) 11) 4,308,215 Vaughan 45 Dec United States Patent (19) 11) 4,308,215 Vaughan 45 Dec. 29, 1981 54 SULFONATION PROCESS 56) References Cited U.S. PATENT DOCUMENTS (75. Inventor: Ronald J. Vaughan, Orinda, Calif. 3,976,704 8/1976 Vaughan ... 260/645 (73) Assignee: Varen Technology, Marshallton, Del. OTHER PUBLICATIONS Gilbert "Sulfonation and Related Reactions' (1965) pp. (21) Appl. No.: 163,348 62-69. Weininger "Contemporary Org. Chem.” (1972) pp. 369, 22 Fied: Jun. 26, 1980 370. Primary Examiner-A. Siegel Related U.S. Application Data Attorney, Agent, or Firm-Charles J. Tonkin (63) Continuation-in-part of Ser. No. 915,656, Jun. 15, 1978, abandoned. 57 ABSTRACT A process for the sulfonation of organic compounds (51) Int. Cl. ............................................ CO7C 143/24 comprises contacting an organic compound with a sul 52) U.S. C. ................................ 260/505 S; 260/508; fonating agent while the organic compound and the 260/509; 260/510; 260/511; 260/512 R; sulfonating agent are substantially separated by a poly 260/504 R meric membrane containing pendant acidic groups. (58 Field of Search ............ 260/505 R, 505 S, 504 R, 260/508, 509, 510, 511, 512 R 13 Claims, No Drawings 4,308,215 2 pounds can be nitrated without the incorporation of SULFONATON PROCESS strong sulfuric acid in the nitrating agent. Such nitration reaction inherently is in an aqueous environment not This application is a continuation-in-part of my co only from the water in the usual aqueous nitric acid as pending application U.S. Ser. No. 915,656, filed June 15, the nitrating agent but also from the water produced in 1978 now abandoned. the nitration reaction. As is well known, a catalyst is necessary in nitration to create the nitronium ion as the FIELD OF THE INVENTION attacking agent in the reaction; without the catalyst the This invention relates to a process for the sulfonation reaction does not take place. On the other hand the of organic compounds with a sulfonating agent. O present sulfonation process is in a substantially anhy drous environment and the preferred sulfonating agent, BACKGROUND OF THE INVENTION sulfur trioxide, adds without generating water. As indi Sulfonation of aromatic hydrocarbons is a commer cated above the direct contact of sulfur trioxide to an cially important process for the production of cation aromatic compound gives a strongly exothermic reac exchange materials, anionic detergents, and lubricating 15 tion and excessive formation of by-products and char; oil additives. An example of such products is sodium for example, direct reaction of benzene with sulfur tri dodecylbenzenesulfonate, a principal ingredient of laun oxide was heretofore impractical because of excessive dry detergent formulations. by-product formation; and heretofore direct contact of . Sulfonation of the dodecylbenzene is done commer detergent alkylate with sulfur trioxide caused much cially either by heating the dodecylbenzene with 20% 20 prohibitive dealkylation. Many other differences be oleum or contacting it with vaporized sulfur trioxide. tween my patented nitration process and the present The oleum process generally involves, mixing the sulfonation process will be apparent to one skilled in the hydrocarbon with 20% oleum at 35-50 C. for 2 hours. art. After addition of a small amount of water to separate layers, neutralization of the organic layer with sodium 25 SUMMARY OF THE INVENTION hydroxide yields a product of 88-90% sodium dodecyl This invention relates to a process for the sulfonation benzenesulfonate and 10-12% sodium sulfonate. Sepa of organic compounds, especially organic aromatic ration and disposal of the sodium sulfate creates prob compounds. The compound to be sulfonated is con lems. tacted in a substantially non-aqueous environment with The processes utilizing sulfur trioxide involve lower 30 an anhydrous sulfonation agent across acid polymer cost reagents and yield a product which contains less membranes which substantially maintain the organic sodium sulfate. However, the reaction is very exother compound separate from the sulfonation agent. mic and somewhat more difficult to control. Liquid sulfur trioxide cannot be added directly to the aromatic DETAILED DESCRIPTION OF THE hydrocarbon without extensive charring and dealkyla 35 INVENTION tion of the alkylaromatic. Normally, sulfur trioxide is Any organic compound capable of being sulfonated used at a concentration of 5% in an inert gas such as dry may be readily sulfonated using the process of this in air or dry nitrogen. Efficient stirring of the viscous mass vention. For example, aromatic compounds are gener is required to promote gas-liquid contact throughout ally preferred for use in this invention, since they the reaction mass. This is particularly difficult at the end. readily undergo sulfonation to form products that are of a batch reaction because of the extremely viscous very useful. The aromatic or aliphatic compounds product. Although reaction occurs readily at low tem which may be sulfonated using the process of this inven perature, a temperature of about 50 C. is used to reduce tion may be hydrocarbons or substituted derivatives viscosity. Neutralization of the reaction mass yields a thereof. The aliphatic compounds should contain at product which is substantially sodium dodecylbenzene 45 least 2 carbon atoms and preferably from 3 to 20 carbon sulfonate in aqueous solution. atoms. The aromatic compounds preferably contain Membranes of various types have been used to carry from 6 to 40 carbon atoms. The substituted derivatives out certain separations of aqueous solutions. An exam of the aliphatic or aromatic hydrocarbons may be sub ple of this type of separation is the desalination of sea stituted with groups containing nitrogen, oxygen, sili water by forcing it under pressure through a membrane. 50 con, phosphorus, sulfur and/or halogen without ad It has now been found that certain membranes may be versely affecting the process of this invention. For ex used in non-aqueous environments and under conditions ample, this process may be used to sulfonate aromatic which permit the selective contacting of the reagents to compounds which contain one or more groups such as easily carry out reactions which hithertofore were diffi amino, nitroso, chloro, fluoro, bromo, silano, ether, cult to control. This discovery provides a simple and 55 hydroxy, and carboxy. Preferably the ratio of hydrocar efficient process for the sulfonation of organic com bon moiety to such polar groups should be high to pounds which avoids the problems associated with the minimize crossing of the membrane by these substituted known processes while providing a sulfonated product aromatic compounds. Control of diffusion in only one which is relatively free of undesirable by-products. direction, i.e., sulfur trioxide permeating through to the In my prior patent (U.S. Pat. No. 3,976,704) was organic reactant, can be supplemented by a pressure described and claimed a process of nitration of organic differential. compounds wherein the nitrating agent, usually aque Because of their commercial importance, aromatic ous nitric acid, and organic compound are substantially hydrocarbons are of particular interest for use in this separated by a polymeric membrane preferably com sulfonation process. For example, linear alkylbenzenes, prising sulfonic acid groups; when the preferred per 65 especially those with 10-16 carbon atoms in the alkyl fluorosulfonic acid polymer is used as the membrane, group, are sulfonated for use in laundry detergents, the sulfonic acid groups in the membrane supply the Aromatic petroleum fractions containing alkylben necessary catalytic acid and the organic aromatic com zenes, napthalenes and higher condensed aromatic sys 4,308,215 3 4. tems are sulfonated for use as detergents in lubricating of yield. Such a membrane provides a large surface area oils. for reaction and mixing. As indicated, the process is carried out in a substan The separating membrane must be substantially im tially anhydrous environment since it is recognized that permeable to the organic compound and substantially water exerts such a profound influence that sulfuric acid 5 permeable to the sulfonation agent at the temperature and free sulfur trioxide can be considered as having and conditions at which the reaction takes place. The opposite properties as sulfonating agents. For instance, polymeric membranes especially useful in the instant the rate of reaction of 97% sulfuric acid is slow and sulfonation process having the unique combination of requires heat for reaction completion whereas the rate permeability characteristics in the anhydrous reaction O environment, are polymers containing acid groups, salts of reaction with sulfur trioxide is instantaneous and is of acids and derivatives of acids. These polymers are exothermic throughout, the reaction readily going to known to form a semibiphasic cluster structure charac completion. terized by regions of concentrated ion groups or clus Suitable diluents are those which do not prevent ters in a matrix of fluorocarbon or hydrocarbon poly sulfonation. For example, sulfur trioxide may be diluted 15 mer phase. A model of ionic clustering is that the poly with sulfuric acid, sulfur dioxide, hydrochloric acid or meric ions separate from the fluorocarbon or hydrocar boron trifluoride. If the sulfonating agent is used with a bon backbone into approximately spherical clusters diluent, it will preferably be used at a concentration of which are connected by short narrow channels or 1 to 99%, more preferably 20 to 80%, of the sulfonating pores. The diameter of the ion clusters and the pores agent in the diluent. The preferred liquid sulfur trioxide 20 connecting the ion clusters are related to the Bragg can be used freshly distilled, or as the melted solid, or as Spacing, equivalent weight and water absorbed by the the common commercial product containing an anit dry polymer. Low angle X-ray scans of fluorocarbon polymerization stabilizer. and hydrocarbon polymers containing acid groups (sul In this process, the organic compound is sulfonated fonic, carboxylic and phosphonic) show that the aver with an anhydrous sulfonating agent.
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