Surfactants, even today, are the single most important cleaning ingredient in laundry and household cleaning products. Anionic surfactants, as a class, are the largest in terms of worldwide consumption and typically are used at levels as high as 30 to 40% of the detergent formulation. Evolution of this class sometimes called “mainframe surfactants” has always been slow due to the long development times and high capital investment costs in this multibillion pound a year commodity industry. Changes are often driven by changing consumer needs or habits such as the development of new fabric types which may require lower wash temperatures and gentle wash cycles or the fast paced society we now live in where shorter wash times are becoming the norm. All of the above factors have played a role in past developments of new anionic surfactants. As a result of the need for surfactants with properties that lend themselves to higher tolerance to precipitation with calcium and magnesium in hard water as well as improved cleaning in the colder wash temperatures and shorter wash cycle there has been in recent years several chemical developments which have led to the introduction of specific methyl and ethyl branched surfactants. Examples of such developments are described in the article by J. Scheibel, Journal of Surfactants and Detergents, “The Evolution of Anionic Surfactant Technology to Meet the Requirements of the Laundry Detergent Industry”, volume 7, number 4, October, 2004 (“Scheibel JSD Article” hereinafter) which defines the need and developments of these branched surfactant technologies. The technologies indicate the need for minimization of the branching to provide efficient surfactants with good biodegradability.
Highly branched surfactants have been derived from tetrapropylene and were called alkylbenzene sulfonates or “HARD ABS”. Hard ABS had very complex branching structures with 3 or 4 branches per molecule. The structure below illustrates one example of a hard ABS molecule. The illustration shows four branches with methyl and ethyl branching in quaternary as well as geminal branching.

Hard ABS was found to be significantly less biodegradable than linear alternatives. Alcohol es derived from these highly branched tetrapropylene feedstocks had similar problems as the hard ABS, including inhibited biodegradability. As such the hard ABS and related alcohol es had limited use in laundry or other consumer products.
One example of a currently marketed branched surfactants used in consumer products is a lightly branched alkyl sulfate and is called “HSAS” for highly soluble alkyl sulfate. HSAS is illustrated in the Scheibel JSD article and other external papers HSAS is derived from petroleum feedstocks. The material's light branching provides high solubility, hardness tolerance and good performance.

Thus, although this surfactant and others are designed to meet the needs of consumers today for cold water cleaning, the challenge remains to provide alternative branched surfactants from non petroleum sources for future sustainability for the detergent industry as well as other industries that rely on surfactant technology and prefer branched materials with the properties of HSAS.
Processes are disclosed herein to make the novel aldehydes, alcohols and surfactants useful in the formulation of consumer products such as personal care products and laundry and cleaning products.
USPTO Backgrounds
USPTO Backgrounds