Linear alkyl benzene production

Hydrogen fluoride is an important catalyst used in the majority of the installed linear alkyl benzene production in the world. The process involves dehydrogenation of n-paraffins to olefins, and subsequent reaction with benzene using HF as catalyst. 

The production of linear alkyl benzenes (LABs) is carried out on a large scale for the production of surfactants. The reaction involves the reaction between benzene and a long-chain alkene such as dodec-l-ene and often gives a mixture of isomers. Greco et al. have used a chloroaluminate(III) ionic liquid as a catalyst in the preparation of LABs [83] (Scheme 5.1-53). 

Based on petrochemicals, linear alkyl benzene sulfonates (LAS) are the most important surfactants. First description can be found in patents from the mid-1930s [2] using Fischer-Tropsch synthesis and Friedel-Crafts reactions. With the beginning of the 1950s the importance of the class of surfactants rose. The main use is in household and cleaning products. 

Figure 4.6. General scheme for the synthesis of linear alkyl benzenes, precursors to surfactants. Control over pore size of the catalyst can suppress the second alkylation almost completely. Given the ease with which the pore size can be chosen, one can design an effective catalyst for any particular reaction, and allow the selective and clean production of the desired mono-alkyl product, thus eliminating much of the waste associated with the process.

Neutral oil products,< -j N-paraffin Spray oils, Transformer oils, Turbine oils, Machine oils, Benzene, Cumene, Gas oils, Linear alkyl benzene. 

A wide range of anionic surfactants (Fig. 23) has been classified into groups, including alkyl benzene sulfonates (ABS), linear alkyl benzene sulfonates (LAS), alcohol sulfates (AS), alcohol ether sulfates (AES), alkyl phenol ether sulfates (APES), fatty acid amide ether sulfates (FAES), alpha-olefin sulfates (AOS), paraffin sulfonates, alpha sulfonated fatty acids and esters, sulfonated fatty acids and esters, mono- and di-ester sulfosuccinates, sulfosuccinamates, petroleum sulfonates, phosphate esters, and ligno-sulfonates. Of the anionic surfactants, ABS and LAS continue to be the major products of anionic surfactants [314, 324]. Anionic surfactants have been extensively monitored and characterized in various environmental matrices [34,35,45,325-329]. 

The large demand for benzene is due to its use as a starting material in the production of polystyrene, acrylonitrile styrene butadiene rubber, nylons, polycarbonates and linear alkyl benzene detergent. All of these final chemical products that are suitable to form into consumer goods have multiple chemical transformations in various industrial processes to obtain them from benzene. Because the production of benzene does not involve a liquid adsorptive process on a zeolite, these processes are not described here but can be found in other sources. However, it is important to note that benzene is typically a large byproduct from an aromatics... 

C10-C14 long paraffin dehydrogenation is a key-step for linear alkyl benzene (LAB) production. However, this reaction, which requires monofunctional catalysis, is implemented on Pt-Sn catalysts deposited on controlled acidity alumina. It is generally associated with several secondary reactions, among which aromatic formation is extremely problematic it is catalyzed by a metallic phase (M) or by residual support (A) activity. Indeed, on the one hand, these arylaromatics are very good coke precursors and are consequently responsible for a large part of the... 

Other interesting products that can be obtained from waste plastics using combined thermal and catalytic processes are alkylaromatic compounds, which possess industrial applications as automatic transmission fluids (ATF), detergents (linear alkyl benzenes, LAB), and improvers of cetane number in diesel fuels [104]. The process uses as raw material the olefins generated in a previous step of thermal and catalytic cracking, which represent a cheaper source of olefins alternative to the currently existing ones. No special details about the conditions applied for the olefin production are indicated, the emphasis being focused on the alkylation step. Alkylation catalysts comprise conventional Lewis... 

Linear alkyl benzenes (LAB) are starting compounds for making linear alkyl benzene sulfonates, which are widely used biodegradable surfactants. U.S. 5,012,021 (to UOP) describes a process for making LAB and U.S. 5,196,574 and U.S. 5,344,997 (also to UOP) give yields for several catalysts. Estimate the cost of production of the LAB and determine which catalyst is the best. 

The UOP Paeol process for selective long-chain paraffin dehydrogenation to produee linear mono-olefins is shown in Fig. 15 in combination with the UOP detergent alkylation process. The Pacol process consists of a radial-flow reactor and a product recovery section. Worldwide, more than 2 million metric tons per year of linear alkyl benzene is produced employing this process. 

Fig. 6 Energy summary for the production of surfactants short tail pentosides (FO APP fusel oil alcohols APP) and glucosides (Pc BuOH APG petrochemical Butanol APG) and linear alkyl benzene sulfonate (LAS)...

Linear alkyl benzene (LAB) is manufactured by catalytic dehydrogenation of C10-C13 n-parafifins, followed by alkylation with benzene. High product selectivity, and reasonable catalyst life, in the dehydrogenation reaction, are obtained at the expense of conversion, by adjusting reaction parameters. Proper choice of reaction parameters is thus of paramount importance in this reaction. The present study, was carried out with n-decane, as model feed, and a promoted Pt/ALOs catalyst. A composite Box-Wilson experimental design was adopted to develop an empirical model for predicting monoene yield as a function of reaction conditions. Further, the model was used for determination of optimum reaction parameters. 

BP Chemicals studied the use of chloroaluminates as acidic catalysts and solvents for aromatic alkylation [43]. At present, the AICI3 existing technology (based on red oil catalyst) is still used industrially, but continues to suffer from poor catalyst separation and recycle [44]. The aim of the work was to evaluate the AlCls-based ionic liquids, with the emphasis placed on the development of a clean and recyclable system for the production of ethylbenzene (benzene/ethene alkylation) and synthetic lubricants (alkylation of benzene with 1-decene). The production of linear alkyl benzene (LAB) has also been developed by Akzo [45]. The eth)4benzene experiments were run by BP in a pilot loop reactor similar to that described for the dimerization (Fig. 5.4-8). 

The operation of bubbling sulphonators with surface exposure times of 10 milliseconds for typical bubble size ranges do not appgar to be prone to inter facial temperatures in the region of 100 u above datum. However, the industrial sulphonation of linear alkyl benzenes presents an interesting problem of associated severe discolouration and the formation of malodourous compounds when sulphonation is carried out at high gas composition of SO. The productivity of sulphonators is limited by these factors and the role of localised high temperatures in the absorption process has yet to be fully appreciated. 

As in the all-purpose cleaners, specialty cleaners generally have a combination of surfactants for most effective cleaning. These are usually combinations of anionic and nonionic surfactants. However, as was noted in the discussions above, there are times when solely nonionic surfactants are needed. Over the past 20 years, the household cleaners have gradually made more and more use of amine oxide, betaines, and more specialized nonionics. Amine oxides were always well used in hypochlorite-containing products, but are now used in other cleaners as well. However, the use of linear alkyl benzene sulfonates, alkyl sulfates, and ethoxylated alkyl sulfates are still very prevalent. As stated before, the main choice of surfactant is dictated by the other chemistry in the cleaner—acid, alkaline, bleach, and quats. 

These middle-chain esters are quite similar to those of the fatty acids derived from palm kernel oil and coconut oil. The alkene by-products, with the double bond near the end of the chain, can be transformed into useful linear C12-C14 alcohols by hydroformylation, or transformed into linear alkyl benzene sulfonates. 

Stepan was the first to develop and conunercialize a continuous falling film SO3 sulfonation process. The design is a multitubular unit. The company operates about 12 falling film SO3 sulfonation units in the United States, not only for the production of linear alkyl benzene sulfonates, but substantial amounts of fatty alcohol and fatty alcohol ethoxylates are also sulfated. Other key commercial reactor designs are by Chemithon, Ballestra SpA, Lion, Mazzoni SpA, and Meccaniche Modeme. Several features are common to all falling-film systems. Fatty alcohol and alcohol ethoxylates are reacted at a rate of about 0.3 kg/h/mm with SO3 concentration at about 2-3%. Liquid residence times are estimated at 10-30 s and most units operate with gas velocities in the range of hurricane wind velocities (121-322 km/h). ° Linear alcohols and linear alcohol ethoxylates are by far the easiest to sulfate. Caution is required with branched alcohols as color and conversion can suffer. 

A variety of organic molecules are used in practice as a base material for detergents, either based on mineral oil, crude oil resources or from natural products. The most important organic feedstocks are Linear Alkyl Benzene (LAB), Primary Alcohols (PA), Primary Alcohol Ethers (PAE) and Alpha-Olefms (AO). 

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