PRODUCT AND PROCESS DEVELOPMENT Sulfonation with Sulfur Trioxide

Gilbert, Everett E.; Veldhuis, Benjamin

doi:10.1021/ie50551a033

Cited by 9 publications

(3 citation statements)

References 2 publications

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“…Addition of liquid S03 to the undiluted liquid hydrocarbon gives unsatisfactory results with the long-chain compounds, apparently because of removal of the alkyl group by destructive dealkylation (203,207). Unlike benzene or toluene, dodecylbenzene forms almost no sulfone, but it does give by-product sulfonic anhydride (201) 2RSO3H + S03 -* (RS02)20 + h2so4 It is noteworthy that sulfones and anhydrides are both, in the over-all sense, formed by a dehydration process, which results differently depending upon the size of the substituting alkyl group. Steric factors also differ.…”

Section: Rate CC [Arh][s03][hx]mentioning

confidence: 99%

The Reactions of Sulfur Trioxide, and Its Adducts, with Organic Compounds.

Gilbert¹

1962

Chem. Rev.

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173

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Section: Rate CC [Arh][s03][hx]mentioning

confidence: 99%

The Reactions of Sulfur Trioxide, and Its Adducts, with Organic Compounds.

Gilbert¹

1962

Chem. Rev.

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173

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“…A pressure drop of about 5 p. 8 Heat exchanger back pressure at 15 gallons per minute in sulfonation of dodecylbenzene. A pressure drop of about 5 p. 8 Heat exchanger back pressure at 15 gallons per minute in sulfonation of dodecylbenzene.…”

Section: Mist Filtration From Recycledmentioning

confidence: 99%

Sulfonation with Sulfur Trioxide

Carlson¹,

Flint²,

Gilbert³

et al. 1958

Ind. Eng. Chem.

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lwll ,ears ago, GeneralChemical Division introduced stabilized liquid trioxide as an article of commerce, under the trademark Sulfan. Since then, the used for this reagent have grown rerqarkably. Process development work is being accelerated to utilize it as an efficient reagent for making important household and industrialproducts. I/EC reportedthe first laboratory process in 1953 (10). Here is the 100-fold pilot plant scale-upbuilt because laboratory results looked so good. ?%is has paid off too, the pilot plant since serving 'as the prototype for several coltlrnercid. insfa ~ 4 PUOT PLANT study of the sulfonation of one commercial brand of dodecylknm e with vaporized sulfur trioxide has bcm reported as showing promise (4).The Gndings of the present study c o n h that conduaion, and they have been extended to other available brands of the hydrocarbon. From the standpoint of engineering, a different technique of beat removal haa hen employed, and the hrst data are reported on recycle of the air d as the carrier gas for the vaporized sulfur trioxide. A remedy is advanced for a factor Cited earlier as a disadvantage for the use of sultur trioxide with this hydrocarbon-formation of sulfonic acid anhydride leading to objectionable "acid drift."A similar study was made of the sulfation of several grades of lauryl alcohol.In addition, the reaction of& trioxide with thm other products was considered to a minor extent: toluene, a petroleum lubricant raffmate, and a polyether alcohol made by condensing e,thylene oxide with aq alkylated phenol. General Factors Underlying Plan# DesignThe Thinking behind Plant Dcsign: Simplicity. A majoro maximuq simplicity d d 276 I NW-AND -R I M Q y M l S R Y with acceptable product quality. This involved the me, wherever poapible, of inexpensive, readily available e q u i p ment. Design simplicity was inherent in the fact that the pilot plant, in its initial form, was a direct scale-up of the laboratory flask sulfonator 0pe;ation (70), which comprised two ordinary laboratory reaction flasks, one for vaporiza-, tion of the sulfur trioxide and the other for the reaction proper. The m n t i a l pilot plant components, shown in generalized schematic form in Figures 1,2, and 3, were an air dryer, sulfur trioxide vaporizer, and kettlea for sulfonation and ncntrdization. Photographs of this pilot plant have been published [for airdrymg and metering system, sulfur trioxide vaporizer, and neutralization kettle (5), and for sulfonation kettle @)I. ~e n b i l i t y . Flexibility was wsential,

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“…Digestion for a longer period leads to darker color without further reduction of oil. Sulfonates prepared with sulfur trioxide must be processed to remove sulfonic acid anhydride (9). A statement in the literature (13) to the effect that anhydride is not formed during sulfonation of detergent alkylate with sulfur trioxide in the Votator is concluded to be incorrect on the basis of the present work.…”

Section: Variables Affecting Product Qualitymentioning

confidence: 70%