Determination of Sulfonation Conditions of HAB as a By-product of Linear Alkylbenzene Production

Document Type: Research Paper

Authors

1 Chemical, Polymeric and Petrochemical Technology Development Research Division, Research Institute of Petroleum Industry (RIPI), Tehran, Iran

2 Development of Gas Processing and Transportation Technology Research Division, Research Institute of Petroleum Industry (RIPI), Tehran, Iran

Abstract

Heavy alkylated benzene (HAB), which is a by-product in linear alkylbenzene (LAB) production by UOP process, is separated by distillation from LAB and consists of a range of components such as polyalkylbenzenes, diphenylalkanes, alkyl tetralins, and alkylindans. The products of sulfonation of HAB or its distillation cuts are of wide industrial applications such as emulsifiers, dispersants in lubricating oils, anionic surfactants, and aqueous phase stable waterflooding.
The sulfonation of the HAB mixture using oleum as the sulfonating agent has been carried out and optimum reaction conditions have been defined based on the highest degree of sulfonation. Some light, average, and heavy distillation cuts were then sulfonated under optimum conditions. The degree of sulfonation of the fractions was found to be dependent on the composition of the mixture. 1HNMR spectroscopy was used to investigate the relationship between the ratio of aliphatic to aromatic protons of the compounds and the trend in sulfonation.

Keywords


      [1]     Bloch H. S., “A New Route to Linear Alkylbenzenes,” Oil & Gas J., 1967, 65, 79-81.

      [2]     Kistler J. P. and Marin P. D., “Emulsifiable Mixture of Oil Soluble Alkylbenzene Sulfonate Salts Having Two Different Molecular Weight Maxima,” U.S. Patent 4 140 642, 1979

      [3]     Eckard A., Weaver J. A. Jr., and Riff I., “Sodium Sulfonate Blends as Emulsifiers for Petroleum Oils,” U.S. Patent 6225267 B1, 2001.

      [4]     Sias R. C., “Preparation of Oil Soluble Sulfonic Acids Useful as Dispersant Additives,” U.S. Patent 3 703 475, 1971.

      [5]     Hampel M., Mauffret A., Pazdro K., and Blasco J., “Anionic Surfactant Linear Alkylbenzene Sulfonates (LAS) in Sediments from the Gulf of GdaƄsk (Southern Baltic Sea, Poland) and Its Environmental Implications,” Environ. Monit. Assess, 2012, 184, 6013-23.

      [6]     Brooker T. A., Robles E. S., and Somerville R. N. P., “Detergent Composition,” EP 2 451 911 A1, 2012.

      [7]     Al-Sabagh A. M., Abd-El-Bary H. M., El-Ghazawy R. A., Mishrif M. R., et al., “Surface Active and Thermodynamic Properties of Some Surfactants Derived from Locally Linear and Heavy Alkyl Benzene in Relation to Corrosion Inhibition Efficiency,” Materials and Corrosion, 2011, 62, 1015–1030.

      [8]     Kott K. L., Scheibel J. J., Severson R. G., Cripe T. A.,et al., “Hard Surface Cleaning Compositions Comprising Modified Alkylbenzene Sulfonates,” U.S. Patent, 6 342 473, 2002.

      [9]     Berna Tejero J. L., Goncalvez de Almeida J. L., and Serrano I. L., “Process to Obtain a Highly Soluble Linear Alkylbenzene Sulfonate,” U.S. Patent 8 158 819, 2012.

    [10]    Stokke K., “Sulfonate for Waterflooding,” U.S. Patent 4 435 295, 1984.

    [11]    Bahattin B. and Baysal M., “Determination of Sulfonation Conditions of Postdodecylbenzene,” Ind. Eng. Chem. Res., 1990, 29, 667–669.

    [12]    Le Coent J. L. and Tequi P., “Alkylaryl Sulfonate Detergent Mixture Derived from Linear Olefins,” U.S. Patent 8 293 698, 2012.

    [13]    Dehydag Deutsche Hydrierwerke, German Patent, 852-690, 1952.

    [14]    ASTM D4711-89, “Standard Test Method for Sulfonic and Sulfuric Acids in Alkylbenzene Sulfonic Acids,” American Society for Testing and Materials, West Conshohocken, PA, 1995.

    [15]    ASTM D500-95, “Standard Test Methods of Chemical Analysis of Sulfonated and Sulfated Oils,” American Society for Testing and Materials, West Conshohocken, PA, 1995.

    [16]    ASTM D-664-95, “Test Method for Acid Number of Petroleum Products by Potentiometric Titration,” American Society for Testing and Materials, West Conshohocken, PA, 1995.

    [17]    ASTM D-5236-99, “Test Method for Distillation of heavy Hydrocarbon Mixtures,” American Society for Testing and Materials, West Conshohocken, PA, 1999.