Guerbet Alcohols

All lation. CPD can be multiply alkylated in high yields using alkyl haUdes, oxo alcohols, and Guerbet alcohols (35—36). After hydrogenation of the diene products, these so-called multiply alkylated cyclopentanes (6), where R = C Hg -C20 and m = 2-6, have been demonstrated to be useful as synthetic lubricants. 

Linear Guerbet alcohol. bBranched Guerbet alcohol. 

Branched dodecyl alcohol derived from the oxidation of branched olefins from petroleum feedstocks. bLinear Guerbet alcohol, branched Guerbet alcohol. 

R is mostly derived from natural fatty alcohols and is generally between C6H13 and C18H37. Sometimes R is partly unsaturated. On behalf of special applications R can also be derived from branched fatty alcohols, such as oxoalcohols or Guerbet alcohols. 

VDC polymer degradation and, 25 717 2-Alkyl-alcohols. See Guerbet alcohols Alkylalkanolamines, 2 140 Alkylaluminum compounds, 2 285 Alkylaluminum halides, 2 358 Alkylaluminum reagents, in triorganotin preparation, 24 815-816 Alkyl amino acids, protonated, 17 780 Alkylaminomethanols, 12 112 AT-Alkyl amino propionates, 24 148... 

Guerbet alcohols cosmetic applications, 2 21 in cosmetic molded sticks, 7 840t major producers, 2 27t Guerbet process, 2 27t, 43 Guerbet reaction, 10 558 Guest-host LCDs, 15 115 Guest-host mode LCD systems, 9 339 Guggenheim process, for sodium nitrate, 22 846-848... 

Other alcohols used in the surfactant industry, although of minor importance, are the Guerbet alcohols obtained by self-condensation of lower alcohols to yield products in the range of 16-26 carbons with a high degree of branching. 

In 1899 R. C. Guerbet discovered the self-condensation reaction of alcohols, which, via the aldehyde as an intermediate, lead to branched structures (2-alkyl alcohols) (Fig. 4.21) - the Guerbet alcohols. Starting with fatty alcohols from vegetable sources, such as octanol and decanol, the corresponding C1(, and C2o alcohols are produced (2-hexyldecanol and 2-octyldecanol, respectively). The reaction is carried out under alkali catalysis and high temperatures (>200 °C). Over the years, both products have proven to be efficient emollients, but are also used for other applications, such as plasticizers or components for lubricants (Fig. 4.21). 

The second alcohol family is Guerbet alcohols which have been known for over 100 years when Marcel Guerbet synthesised these beta branched primary alcohols. The process is a modified Aldol reaction as shown below ... 

This is very simplified there are potential side reactions to be minimised and complicated purification steps before the final alcohol is available for use. Therefore, they are expensive which probably accounts for their underutilisation but they have some very interesting physical properties. The alcohols are liquid up to C2o, whereas the saturated linear alcohols are all solids. The only liquid linear long chain alcohols are unsaturated and lack the oxidative stability of the Guerbet alcohols. 

During the last 10 years, Sasol has introduced a complete range of Guerbet alcohols under the trade name IsofolR with chain lengths from C32 to C2o, C24, C2s and C32. Other uses suggested are in the various ester products (mentioned later in this chapter) where they should give low irritation and be more effective products if they can be cost competitive. 

Guerbet alcohols were previously used by the author [1] to prepare controlled molecular weight polyesters derived from succinic acid and used in skin care formulations. 

The alcohols can be oxidized to the corresponding acids. Guerbet alcohols, acids, their esters, sulfates, and ether sulfates are used as lubricants, cosmetic additives, and surfactants. Their synthesis, characterization, and applications have been reviewed (93). 

Figure 15. (a) Guerbet alcohol from lauryl alcohol (12 0). (b) Estollde from meadowfoam acids (20 1 5c). 

Exxal Guerbet Alcohols, Exxon Corporation, Houston, Texas, 1988. 

Hwang, H.S. S.Z. Erhan. Synthetic lubricant basestocks from epoxidized soybean oil and Guerbet alcohols. Ind. Crop Prod. 2006,23, 311—317. 

Guerbet Alcohols. 1. Surface and Instantaneous Interfacial Tensions, J. Phys. Chem. 95 ... 

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