Alkylation with propylene trimers

The synthesis of commercial nonylphenols generally proceeds through an alkylation reaction of phenols with propylene trimer [124], which itself has a spread of isomers [47]. The alkylation occurs preferentially at the para position of the phenol, but 3-6% of ortho-nonylphenol can be found in commercial products [125]. Also meta and disubstituted species have been mentioned [47]. A common feature of the isomers appears to be a dimethyl substitution of the a-carbon atom [83]. 

Chemical Identity of Nonylphenol Alkylation of Phenol with Propylene Trimer... 

Alkylphenol Ethoxylates (APE). The hydrophobes of most commercial APE are made by reacting phenol with either propylene trimer or diisobutylene to form nonylphenol or octylphenol. These products contain an aromatic moiety and extensive branching in their alkyl chains. It has been shown that APE biodegrade more slowly and less extensively than LPAE (3.15-20). The difference is more pronounced when the treatment system is operating under stress conditions such as low temperatures and high surfactant loadings. 

Alkylphenol. Alkylphenol is a common surfactant intermediate used to produce alkylphenol ethoxylates. Phenol reacts with an olefin thermally without a catalyst but with relatively poor yields. Catalysts for the reaction include sulfuric acid p-toluene sulfonic acid (PTSA), strong acid resins, and boron trifluoride (BF3). Of these, strong acid resins and BF3 are mostly widely used for the production of surfactant-grade alkylphenols. The most common alkylphenols are octylphenol, nonylphenol, and dodecylphe-nol. Mono nonylphenol (MNP) is by far the most common hydrophobe. It is produced by the alkylation of phenol with nonene under acid conditions. All commercially produced MNP is made with nonene based on propylene trimer. Because of the skeletal rearrangements that occur during propylene oligomerization, MNP is a complex mixture of branched isomers. 

Alkylated phenol. The most commonly used alkylated phenol ethoxylates (APE) have included octyl phenol ethoxylate and nonylphenol ethoxylates with 3-11 moles of EO, which were produced by alkylation of butylene dimer or propylene trimer onto phenol and subsequent ethoxylation. They had been used extensively in laundry and hard surfacecleaning applications in the nonionic form, and as the sulfated and phosphated derivatives of the low-mole ethoxylates in a variety of industrial applications. Concerns over the environmental impact of the partial metabolites generated during the waste treatment of these surfactants has prompted their elimination from European consumer product formulations, and their deformulation from most consumer products in North America and elsewhere in the world. 

Alkylation of phenol with nonene (propylene trimer and, therefore, it has a branched-chain alkyl group) produces 4-nonylphenol. It is principally used in the manufacture of a wide variety of surfactants but also of compounds used as antioxidants for rubber, other... 

Tris(nonylphenyl)phosphate (TNPP) is a common commercial phosphite. Note that this is not n-nonyl, hut rather a mixture of branched C9 isomers. Nonylphenol is commercially synthesized through Friedel-Crafts alkylation of phenol with nonene. Technical nonene ( propylene trimer ) is a mixture of predominantly C9-olefins with varying degrees of branching. The resulting nonylphenol is mainly a mixture of 4-substituted monoalkylphenols with various isomeric, branched nonyl groups [13]. Tris(2,4-di-t-butylphenyl)phosphite is another commonly used phosphite. 

The primary reactions in the alkylation of isobutane produce octanes from butylenes, heptanes from propylene, and nonanes from amylenes. Also, when dimer and trimer polymers of isobutylene are used with isobutane, the polymer is broken down during the reaction, and the resulting products are branched chain octanes similar to those produced when isobutylene is charged. Sulfuric acid consumption is somewhat higher for the diisobutylenes, however, and there are more side reactions than for isobutylene. 

The oleflnic hydrocarbon gases, propylene and the butylenes, are sent to polymerization and alkylation. Polymerization forms dimers and trimers of these olefins for use in gasoline blending or for petrochemicals. Alkylation is a more common process in which the olefins are reacted with isobutane. This step produces the more desirable isoparaffins for gasoline blending. 

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