Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
1999-06-21
2001-08-14
Michl, Paul R. (Department: 1714)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C560S190000, C560S205000, C524S296000
Reexamination Certificate
active
06274756
ABSTRACT:
This invention relates to esters and ethers of certain alcohols, to their uses, and to compositions comprising them. More especially, the invention relates to the use of the compounds as surfactants, synthetic lubricants or lubricant components and as plasticizers, to polymeric compositions plasticized by the esters, and to products made from the compositions. Certain of the compounds are novel.
The esters of 2-ethylhexanol, especially the phthalate, are among the most commonly used plasticizers. The alcohol is obtainable by, for example, subjecting propene to hydroformylation, dimerizing the resulting butanal by the aldol reaction, a term which is used throughout this specification, including the claims, as including the subsequent dehydration to an unsaturated aldehyde, and hydrogenating the resulting aldehyde to form a saturated alcohol.
The propene, produced for example by a steam cracking plant, has to be purified before hydroformylation, and its cost as feedstock is increased as a result.
Although the plasticizer esters derived from 2-ethylhexanol are widely used, for some purposes, for example where a lower volatility, or a stronger solvator for the polymer is needed, higher molecular weight esters, for example those based on C
9
to C
12
alcohols, are preferred. The C
9
esters presently available commercially are typically derived from an isomeric mixture of C
9
alcohols and the users' requirements for product consistency may result in manufacturing complexities.
These complexities result from variations in feed composition and reaction conditions in the process for the manufacture of the precursors to the alcohols. These precursors may be formed for example by oligomerizing a mixed C
3
to C
5
olefin feed, giving a mixture of linear and branched olefins, predominantly having six to ten carbon atoms, from which is distilled a mixed C
8
olefin, which is in turn hydroformylated (oxonated) and hydrogenated to form the isomeric C
9
alcohol mixture.
In other commercial processes, the C
9
alcohol precursors are typically obtained by dimerizing butene streams and oxonating the resulting C
8
olefin fraction. The butene stream itself contains a mixture of isomers, in proportions that may vary over a period, and the cobalt oxo process causes some isomerization. Thus the alcohols resulting from hydrogenation of the aldehyde form a reaction product of variable isomer distribution together with lower and higher homologues, necessitating further treatment if customers's product specifications are to be met. The processes for making other higher alcohols differ from those used in C
9
alcohol production but generally result in isomeric mixtures.
In a typical commercial process for the manufacture of a plasticizer ester, the alcohol is employed in excess over the acid, and alcohol is stripped from the ester product and recycled. Because of the recycling, less reactive isomers tend to become more concentrated in the reaction vessel as the reaction progresses, resulting in a change in the composition over time. In turn, the downstream users's quality control inspection of the incoming product is more onerous than if it were a single isomer.
Processing of thermoplastics containing a multi-isomer plasticizer may be more difficult to control in certain applications, resulting in a greater possibility of inconsistencies in properties between different batches of the final product.
This in turn may require the user to have tighter control over process variables, e.g., oven temperature ranges in motor vehicle paintshops and flooring material lines, than would otherwise be necessary, and also complicates material recycling.
Finally, effluent and environmental monitoring is more difficult; e.g., a single isomer material may have a minimum detectability an order of magnitude lower than a multi-isomer material.
There accordingly remains a need for an alternative route to commercially useful organic molecules, and more especially one that provides flexibility and a greater control of product structure, particularly the ability to produce single isomers if desired. There also remains a need for esters and ethers having enhanced properties for various uses.
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A.M. Koganovskii et al., “Kinetics of the ion exchange absorption of tetramethyloctanebenzene sulfonate ions and micelles by the resin”, Chemical Abstracts, vol. 68, No. 4, pp. 1585, Abstract No. 16449t, Jan. 22, 1968, Columbus, Ohio, US.
John A. Findlay et al, “Novel sulfated hydrocarbons from the sea cucumberCucumaria frondosa”,Chemical Abstracts, vol. 114, No. 17, p. 475, Abstract No. 161142k, Apr. 29, 1991, Columbus, Ohio, US.
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Caers Raphael Frans Ivo
Schlosberg Richard Henry
Exxon Chemicals Patents Inc.
Michl Paul R.
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