Catalyst aluminum chloride

Triaryl phosphates are produced by reaction of phosphoms oxychloride with phenoHc compounds at 100—200°C with magnesium or aluminum chloride catalyst. Past use of cresols and xylenols from coal tar or petroleum is replaced for lower toxicity and cost by synthetic phenoHcs, primarily isopropyl phenol, /-butyl phenol, and phenol itself A range of viscosities is achieved by selection and proportioning of the phenols and their isomers used for the starting material. 

Isopropylnaphthalenes can be prepared readily by the catalytic alkylation of naphthalene with propjiene. 2-lsopropylnaphthalene [2027-17-0] is an important intermediate used in the manufacture of 2-naphthol (see Naphthalenederivatives). The alkylation of naphthalene with propjiene, preferably in an inert solvent at 40—100°C with an aluminum chloride, hydrogen fluoride, or boron trifluoride—phosphoric acid catalyst, gives 90—95% wt % 2-isopropylnaphthalene however, a considerable amount of polyalkylate also is produced. Preferably, the propylation of naphthalene is carried out in the vapor phase in a continuous manner, over a phosphoric acid on kieselguhr catalyst under pressure at ca 220—250°C. The alkylate, which is low in di- and polyisopropylnaphthalenes, then is isomerized by recycling over the same catalyst at 240°C or by using aluminum chloride catalyst at 80°C. After distillation, a product containing >90 wt % 2-isopropylnaphthalene is obtained (47). 

Nonregenerable aluminum chloride catalyst is employed with various carriers ia a fixed-bed or Hquid contactor. Platinum or other metal catalyst processes that utilize fixed-bed operation can be either regenerable or nonregenerable. The reaction conditions vary widely, between 40—480°C and 1035— 6900 kPa (150—1000 psi), depending on the particular process and feedstock. 

Aluminum Chloride-Based All lation. The eadier alkylation processes were variations of the Eriedel-Craft reaction on an aluminum chloride catalyst complex in a Hquid-phase reactor (27), including those developed by Dow Chemical, BASE, Monsanto, and Union Carbide in cooperation with Badger. The Union Carbide-Badger process was the one most widely used during the 1960s and 1970s, with 20 plants built worldwide. 

Cumene as a pure chemical intermediate is produced in modified Friedel-Crafts reaction processes that use acidic catalysts to alkylate benzene with propylene (see Alkylation Friedel-CRAFTSreactions). The majority of cumene is manufactured with a soHd phosphoric acid catalyst (7). The remainder is made with aluminum chloride catalyst (8). 

Alkylation. Ethylbenzene [100-41 -4] the precursor of styrene, is produced from benzene and ethylene. The ethylation of benzene is conducted either ia the Hquid phase ia the preseace of a Eriedel-Crafts catalyst (AlCl, BE, EeCl ) or ia the vapor phase with a suitable catalyst. The Moasanto/Lummus process uses an aluminum chloride catalyst that yields more than 99% ethylbenzene (13). More recently, Lummus and Union Oil commercialized a zeoHte catalyst process for Hquid-phase alkylation (14). Badger and Mobil also have a vapor-phase alkylation process usiag zeoHte catalysts (15). Almost all ethylbenzene produced is used for the manufacture of styrene [100-42-5] which is obtained by dehydrogenation ia the preseace of a suitable catalyst at 550—640°C and relatively low pressure, <0.1 MPa (<1 atm). 

To reduce pollution, Dow developed a new catalyst system from the mor-denite-zeolite group to replace phosophoric acid or aluminum chloride catalysts. The new catalysts eliminates the disposal of acid wastes and handling corrosive materials. 

McAfee of Gulf Refining Co. discovered that a Friedel-Crafts aluminum chloride catalyst could catalytically crack heavy oil. 

The alkylation proceeds with aluminum chloride or hydrofluoric acid as catalyst, by which the importance of aluminum chloride diminishes. Today approximately 70% of all manufacturers use the HF process [4]. In addition, LAB is produced by the alkylation of secondary chloroparaffins (Wibarco in Germany) and by the alkylation of olefins (EniChem Augusta in Italy) over an aluminum chloride catalyst [12]. 

The color of the derivative alkylbenzenesulfonic acid is clearly better. The solubility characteristics remain good. An olefin from the Pacol-Olex process (C, 0/13 olefin) is used as a starting olefin. The DeFine step is employed to reduce the diolefin content to <0.5%. With such an olefin an LAB is obtained over an aluminum chloride catalyst with a linear content of >99% and from which the sulfonation product has a biodegradability (DOC) comparable to that of other LABs[122,123].Table 25 gives typical physical-chemical data about different LAB types. 

In this section, the reactivities of organosilicon compounds for the Friedel-Crafts alkylation of aromatic compounds in the presence of aluminum chloride catalyst and the mechanism of the alkylation reactions will be discus.sed, along with the orientation and isomer distribution in the products and associated problems such as the decomposition of chloroalkylsilanes to chlorosilanes.. Side reactions such as transalkylation and reorientation of alkylated products will also be mentioned, and the insertion reaction of allylsilylation and other related reactions will be explained. 

The results of these alkylation reactions with allyidichlorosilane (1) in the presence of aluminum chloride catalyst are summarized in Table II. 

Monoalkylation products, 3-aryl-1,1 -dichloro-1 -silabutanes, were obtained from the alkylation of aromatic compounds with I in the presence of aluminum chloride catalyst in good isolated yields (60-80%) along with small amounts of higher alkylation products. Dialkylation products were obtained in yields ranging from 2 to 8% when a 5-fold excess of the aromatic compounds with respect to 1 was used. The amount of dialkylated products can be further reduced by using a greater excess of the aromatic compounds. 

To prepare multifunctionalized symmetric organosilicon compounds by the polyalkylation of benzene. (2-chloroethyi)trichlorosilane and (3-chloropropyl)tri-chlorosilane were reacted with benzene. Polyalkylations of benzene with (2-chloroethyl)silane and (3-chloropropyl)silane were carried out in the presence of aluminum chloride catalyst at a reaction temperature of 80 C. The reaction of benzene with excess (2-chloroethyI )trichlorosilanes afforded pcralkylated product, hexakis(2-(trichlorosilyl)ethyl)benzene in good yield (70%). ... 

The alkylation of benzene with ((w,a -dichloroalkyl)silanes was also studied in the presence of aluminum chloride catalyst. The alkylation gave diphenylated products, (w.w-diphenylalkyl)chlorosilanes in fair to good yields (Eq. (12)). 

In the alkylation of benzene with (dichloroalkyl)chlorosilanes in the presence of aluminum chloride catalyst, the reactivity of (dichloroalkyl)silanes increases as the spacer length between the C—Cl and silicon and as the number of chloro-groups on the silicon of (dichloroalkyl)chlorosilanes decreases as similarly observed in the alkylation with (cD-chloroalkyl)silanes. The alkylation of benzene derivatives with other (dichloroalkyl)chlorosilanes in the presence of aluminum chloride gave the corresponding diphenylated products in moderate yields.Those synthetic data are summarized in Table XI. 

The alkylation of halogen-substituted benzenes such as fluorobenzene and dichlorobenzenes with other (dichloroalkyl)silanes in the presence of aluminum chloride catalyst afforded isomeric mixtures of the corresponding (dihalogen-substituted phenyl)alkylsilanes in moderate yields (Eq. (13)). These results are summarized in Table Xll. 

In extension of the alkylation reactions to polychlorobenzenes, polychlorinated benzenes such as 1,2,4-trichlorobenzene and 1,2,., 4-tetrachlorobenzene were alkylated with (l,2-dichloroethyl)trichlorosilanes in the presence of aluminum chloride catalyst. Although the electron-withdrawing chlorine substituents on the ring deactivated the electrophilic substitution reaction, the alkylation... 

The reaction was carried out in the presence ol 20 moWi aluminum chloride catalyst. 

The mechanism for the production of 9-((chlorosilyl)alkyl)(luorenes from the Friedel-Crafts alkylation reaction of biphenyl with (l,2-dichloroethyl)silane in the presence of aluminum chloride as catalyst is outlined in Scheme 4. At the beginning stage of the reaction, one of two C—Cl bondsof (1,2-dichloroethyl)silane (CICH2—CICH—SiXi) interacts with aluminum chloride catalyst to give intermediate 1 (a polar +C-CI - ( +C-C1—Al CI3) or a carbocation C AICU ... 

Sometimes a catalyst promoter or accelerator, ethyl chloride, is added to the feed to speed up the reaction. The ethyl chloride actually works on the aluminum chloride catalyst, not the reactants. Its like offering a supervisor a bonus. He doesn t do any more work, but he gets more work done. 

The PEB can be and usually is fed to a separate reactor (not shown) where it reacts with-more benzene at 250—300°F in the presence of an aluminum chloride catalyst to produce additional EB via the transallcylation route. The catalyst is removed from the reaction mixture before it is passed into the separation section. 

Allylchlorosilanes also react with naphthalene to give isomeric mixtures of poly-alkylated products. However, it is difficult to isolate and purify the products for characterization because the products possess similar boiling points. The alkylation of anthracene with allylchlorosilanes or vinylchlorosilanes is not possible because of the deactivation of aluminum chloride catalyst by complex formation with anthracene. 

Cycloalkenes such as cyclohexene, 1-methylcyclohexene, cyclopentene, and nor-bornene are hydrosilylated with triethylsilane in the presence of aluminum chloride catalyst in methylene chloride at 0 °C or below to afford the corresponding hydrosilylated (triethylsilyl)cycloalkanes in 65-82% yields [Eq. (23)]. The reaction of 1-methylcyclohexene with triethylsilane at —20 °C occurs regio- and stereoselectively to give c/i-l-triethylsilyl-2-methylcyclohexane via a tra x-hydrosilylation pathway. Cycloalkenes having an alkyl group at the double-bonded carbon are more reactive than non-substituted compounds in Lewis acid-catalyzed hydrosilylations. ... 

Linear alkylbenzenes are made from -paraffms (Cio-Cu) by either partial dehydrogenation to olefins and addition to benzene with HF as catalyst (60%) or chlorination of the paraffins and Friedel-Crafts reaction with benzene and an aluminum chloride catalyst (40%). See Chapter 24 for more information. 

The process involves first separating mixed butane compounds by distillation to isobutane and n-butane. The n-butane is then mixed with hydrogen, heated and passed through a reactor containing a platinum catalyst or an HC1 activated aluminum chloride catalyst. The n-butane is isomerized to isobutane and separated. 

A report that JV-(3-halopropyl)benzylamines cyclize to tetrahydro-2-benzazepines in hot decalin in the presence of an aluminum chloride catalyst is incorrect 4-methyltetra-hydroisoquinolines are the major products (>60%) along with only minor amounts (<20%) of the seven-membered heterocycle (80JOC2000). 

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