Detergent alkylate

Beilstein Handbook Reference) AI3-00435 Alkane Alkylate P 1 Benzene, dodecyl- BRN 1909107 CCRIS 2291 Detergent alkylate Detergent Alkylate No. 2 Dodecane, 1-phenyl- Dodecylbenzene n-Dodecylbenzene EINECS 204-591-8 HSDB 937 Laurylbenzene Marlican Nalkylene 500 NSC 102805 Phenyidodecan Ucane alkylate 12. Liquid mp 3° bp = 328° d = 0.8551 insoluble in H2O. 

This material is produced via synthesis derived from early work by Berlnger et. al (10.11). The key to solubility of the ionic material lies in the nature of the dodecylbenzene used. Linear alkylate (detergent alkylate) dodecylbenzene is a mixture of at least two dozen isomers of several distinct compositions normally ranging from CgHj Ph to Cj H2gPh. The bis (dodecylphenyl) iodonium salt derived from this mixture therefore includes over 400 separate compounds, so that the catalyst behaves like a supercooled fluid due to the freezing point depression phenomenon, and can therefore be dispersed in relatively nonpolar epoxysilicone media. (This catalyst remains immiscible in non-functional dimethylsilicones, however). 

Detergent alkylate Detergent alkylate, hard. See Dodecylbenzene... 

CAS 123-01-3 EINECS/ELINCS 204-591-8 Synonyms Detergent alkylate Detergent alkylate, hard 1-Phenyldode-cane... 

Dimethylbenzyl N-alkyl detergents - 191 Dimethylbutane - 356 Dimethyl carbinol (see Isopropyl alcohol) Dimethylchloroacetyl - 526 Dimethyidistearyl ammonium chloride -192 Dimethyl ether (methyl ether) -128,156, 157,... 

A wide class of aiyl-based quaternary surfactants derives from heterocycles such as pyridine and quinoline. The Aralkyl pyridinium halides are easily synthesized from alkyl halides, and the paraquat family, based upon the 4, 4 -bipyridine species, provides many interesting surface active species widely studied in electron donor-acceptor processes. Cationic surfactants are not particularly useful as cleansing agents, but they play a widespread role as charge control (antistatic) agents in detergency and in many coating and thin film related products. 

The salts of monoalkyl sulphates are frequently encountered as commercial detergents (for example, dreft, gardinol and pentrone ) they are usually sodium salts, the alkyl components contain 12 or more carbon atoms, and give colloidal solutions. They are hydrol3 sed by boiling with dilute sodium hydroxide solution ... 

The detergent range alcohols and their derivatives have a wide variety of uses ia consumer and iadustrial products either because of surface-active properties, or as a means of iatroduciag a long chain moiety iato a chemical compound. The major use is as surfactants (qv) ia detergents and cleaning products. Only a small amount of the alcohol is used as-is rather most is used as derivatives such as the poly(oxyethylene) ethers and the sulfated ethers, the alkyl sulfates, and the esters of other acids, eg, phosphoric acid and monocarboxyhc and dicarboxyhc acids. Major use areas are given ia Table 11. 

The most widely used alkyl sulfate in shampoo preparation is lauryl sulfate. The alkyl component of this sulfate ranges from C-10 to C-18 with a predominance of the C-12 (lauryl) component. By distillation of the fatty alcohol, certain cuts can be obtained which offer the best effects in foaming, cleansing, and rinsing properties for the alkyl sulfate preparation. The range which appears to be most desirable is between C-12 and C-16. Lauryl sulfate detergents are available in various salt forms with the sodium, ammonium, and triethanolamine types being used most frequently in shampoos. 

A.lkyl Sulfosuccinate Half Asters. These detergents are prepared by reaction of maleic anhydride and a primary fatty alcohol, followed by sulfonation with sodium bisulfite. A typical member of this group is disodium lauryl sulfosucciaate [26838-05-1]. Although not known as effective foamers, these surfactants can boost foams and act as stabilizers when used ia combination with other anionic surfactants. In combination with alkyl sulfates, they are said to reduce the irritation effects of the latter (6). 

Fatty Held—Peptide Condensates. These proteia detergents are reaction products of fatty acid chlorides and hydrolyzed proteias. They are used ia shampoos because of their mildness on skin, hair, and to eyes when used alone or ia combination with alkyl surfactants (8). 

A.lpha-Olefm Sulfonates. Sulfonation of alpha-olefins yields a mixture of alkene sulfonates, hydroxyalkane sulfonates, and some amount of various disulfonates. These detergents are excellent foamers with good detergency properties. They are unaffected ia hard water and thek effects are considered superior to the alkyl ether sulfates (9). 

Detergents are metal salts of organic acids used primarily in crankcase lubricants. Alkylbenzenesulfonic acids, alkylphenols, sulfur- and methjiene-coupled alkyl phenols, carboxyUc acids, and alkylphosphonic acids are commonly used as their calcium, sodium, and magnesium salts. Calcium sulfonates, overbased with excess calcium hydroxide or calcium carbonate to neutralize acidic combustion and oxidation products, constitute 65% of the total detergent market. These are followed by calcium phenates at 31% (22). 

Uses. Magnesium alkyls are used as polymerization catalysts for alpha-alkenes and dienes, such as the polymerization of ethylene (qv), and in combination with aluminum alkyls and the transition-metal haUdes (16—18). Magnesium alkyls have been used in conjunction with other compounds in the polymerization of alkene oxides, alkene sulfides, acrylonitrile (qv), and polar vinyl monomers (19—22). Magnesium alkyls can be used as a Hquid detergents (23). Also, magnesium alkyls have been used as fuel additives and for the suppression of soot in combustion of residual furnace oil (24). 

Alkylation. Benzene and phenol feedstocks are readily alkylated under Friedel-Crafts conditions to prepare extensive families of alkylated aromatics. These materials generally are intermediates in the production of surfactants or detergents such as linear alkylbenzenesulfonate (LABS) and alkylphenolethoxylate (APE). Other uses include the production of antioxidants, plasticizers, and lube additives. 

Vista, Huntsman, and other linear alkylben2ene (LAB) producers feed chlorinated paraffins to an alkylation reactor to produce detergent alkylate without prior separation of the unreacted paraffins. Large amounts of paraffins must be recycled in these processes. 

Emulsifiers. Removing the remover is just as important as removing the finish. For water rinse removers, a detergent that is compatible with the remover formula must be selected. Many organic solvents used in removers are not water soluble, so emulsifiers are often added (see Emulsions). Anionic types such as alkyl aryl sulfonates or tolyl fatty acid salts are used. In other appHcations, nonionic surfactants are preferred and hydrophilic—lipophilic balance is an important consideration. 

Most of the industrially important alkyl aromatics used for petrochemical intermediates are produced by alkylating benzene [71-43-2] with monoolefins. The most important monoolefins for the production of ethylbenzene, cumene, and detergent alkylate are ethylene, propylene, and olefins with 10—18 carbons, respectively. This section focuses primarily on these alkylation technologies. 

Detergent All late. In the 1940s, sodium dodecylben2ene sulfonate [25155-30-0] (DDES) produced by the alkylation of ben2ene with propylene tetramer followed by sulfonation with oleum [8014-95-7] (H2SO4 mixture with sulfur trioxide) or sulfur trioxide and then neutrali2ation... 

A simplified flow diagram for a typical UOP linear detergent alkylation unit is shown in Figure 7. The design of this unit is similar to a unit that produces branched-chain detergent alkylate. 

Fig. 7. UOP linear detergent alkylate process Rx = reactor S = settler HR = HF regenerator HS = HF stripper BC = benzene column ...

PC = paraffin column DC = detergent alkylate column VE = vacuum ejector. 

Future Developments. The most recent advance in detergent alkylation is the development of a soHd catalyst system. UOP and Compania Espanola de Petroleos SA (CEPSA) have disclosed the joint development of a fixed-bed heterogeneous aromatic alkylation catalyst system for the production of LAB. Petresa, a subsidiary of CEPSA, has announced plans for the constmction of a 75,000 t/yr LAB plant in Quebec, Canada, that will use the UOP / -paraffin dehydrogenation process and the new fixed-bed alkylation process (85). 

Table 3 shows typical properties of linear detergent alkylates produced via AIQ., HP, and new UOP Detal catalyst systems (86,87). 

Catalysts. Nearly aU. of the industrially significant aromatic alkylation processes of the past have been carried out in the Hquid phase with unsupported acid catalysts. For example, AlCl HF have been used commercially for at least one of the benzene alkylation processes to produce ethylbenzene (104), cumene (105), and detergent alkylates (80). Exceptions to this historical trend have been the use of a supported boron trifluoride for the production of ethylbenzene and of a soHd phosphoric acid (SPA) catalyst for the production of cumene (59,106). 

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