US3843564A - Detergent compositions and methods of obtaining them - Google Patents

Detergent compositions and methods of obtaining them Download PDF

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US3843564A
US3843564A US00115488A US11548871A US3843564A US 3843564 A US3843564 A US 3843564A US 00115488 A US00115488 A US 00115488A US 11548871 A US11548871 A US 11548871A US 3843564 A US3843564 A US 3843564A
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products
hydrocarbons
sulfonates
group
ammonia
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J Weisang
C Marty
J Maurin
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Compagnie Francaise de Raffinage SA
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/37—Mixtures of compounds all of which are anionic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
    • C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
    • C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
    • C07C5/333—Catalytic processes
    • C07C5/3335—Catalytic processes with metals
    • C07C5/3337—Catalytic processes with metals of the platinum group
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/16—Sulfonic acids or sulfuric acid esters; Salts thereof derived from divalent or polyvalent alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds

Definitions

  • a detergent composition with linear side chains and consequent biodegradability being a mixture of orthodialkyl benzene sulfonates, alkenyl sulfonates, and hydroxy alkyl sulfonates with unexpectedly desirable foaming characteristics in aqueous solution.
  • alkyl sulfate biodegradable detergent compositions Processes for manufacturing these compositions from normal paraffinic stock of a certain carbon range.
  • the present invention relates to biodegradable detergent compositions and also to economic methods of manufacturing said compositions.
  • alkyl benzene sulfonates obtained by alkylation of benzene by propylene tetramer, followed by sulfonation and neutralization with the use of an alkaline base, constitute good detergents.
  • their biodegradability properties are poor due to branching in the hydrocarbon chains.
  • the alkyl benzene sulfonates having linear side chains undergo much more complete biological degradation. Consequently, they are tending to replace the alkyl benzene sulfonates with branched side chains.
  • the hydrocarbons used in the preparation of the linear alkyl benzene sulfonates are obtained by catalytic alkylation of benzene by a linear olefin or by a normal monochloroparaffin.
  • the cost of these processes is very high, on the one hand, because the cost of the alkylation process proper and, on the other hand, due to the fact that two raw materials must be prepared, namely, the benzene and the linear olefin or normal monochloroparaffin.
  • An object of the present invention is to produce high quality detergent compositions having good ecological properties, including biodegradability, starting from a single raw material.
  • compositions can be obtained from specific hydrocarbons, namely, by sulfonation and then neutralization, or by sulfation and then neutralization, followed by a sulfonation and a neutralization.
  • a preferred embodiment of the present invention is a method of obtaining biodegradable sulfonate detergent compositions by carrying out in a stream of hydrogen a nonisomerizing catalytic dehydrogenation of normal parafiins having between 14 and 24 carbon atoms, eliminating the hydrogen and the cracking products of the said normal parafiins from the effiux, subjecting the olefin and aromatic hydrocarbons, resulting from the dehydrogenation, to a sulfonation by sulfuric anhydride in gaseous state, and neutralizing and hydrolyzing with an alkaline base the products resulting from the sulfonation.
  • Another embodiment of the present invention is a similar method for obtaining biodegradable detergent sulfonate and sulfate compositions wherein the olefin and aromatic hydrocarbons subjected to the sulfonation are at least in part composed of the hydrocarbons remaining after a sulfation by concentrated sulfuric acid of at least a part of the olefin hydrocarbons resulting from the dehydrogenation of the normal paraffins and by the fact that the products resulting from the sulfation are neutralized and hydrolyzed by an alkaline base.
  • Still another preferred embodiment of the present invention is a biodegradable detergent composition containing, as active products, primarily orthodialkyl benzene sulfonates, alkenyl sulfonates and hydroxy alkyl sulfonates of an alkali metal or ammonium ion.
  • the alkyl and alkenyl radicals are linear and contain between 1 and 18 carbon atoms in the case of the ortho-dialkyl benzene sulfonates and between 14 and 24 carbon atoms in the case of the alkenyl sulfonates and the hydroxy alkyl sulfonates.
  • alkyl aryl sulfonates have satisfactory foam stability.
  • alkenyl sulfonates and hydroxyalkyl sulfonates produce foams of such quantity and stability, it is usual to include with them additives adapted to break the foam.
  • Still another embodiment of the present invention 1ncludes biodegradable detergent compositions containing active products which are primarily alkyl sulfates of an alkali metal or ammonium ion, the alkyl radicals being linear and containing between 14 and 24 carbon atoms.
  • the charge of normal paraffin which is subjected to the dehydrogenation can be prepared by various methods.
  • a fraction rich in normal parafiins can be subjected to an extractive crystallization in urea or to a selective absorption on molecular sieves.
  • extractive crystallization with urea is, however, the method preferred by the applicants.
  • the preferred fraction is that which consists of normal paraffins having between 15 and 21 carbon'atoms.
  • the catalytic dehydrogenation of normal paraifins is carried out in the presence of hydrogen under pressure. This gas is introduced with the charge.
  • the hydrogen can be recovered in the elflux and be recycled to the dehydrogenation reactor.
  • the composition of the catalyst used is not critical, and this constitutes one of the advantages of the process.
  • One such catalyst consists of metals having dehydrogenating properties deposited on a support, such as alumina. However, it is necessary that the catalyst is not isomerizing, and in order to obtain this property, the acid sites of the support, should the latter contain any, are neutralized for this purpose. It is advantageous to employ a catalyst consisting of chromium oxide and potassium oxide deposited on alumina.
  • the catalyst consisting of platinum, lithium, and arsenic deposited on alumina.
  • the conditions under which the dehydrogenation is effected depend on the catalyst used.
  • the temperature is generally between 250 C. and 500 C.
  • the rate of conversion of the normal parafiins can be substantial.
  • the method of the invention does not make it necessary to obtain solely olefin hydro carbons.
  • the efilux of the dehydrogenation reactor is formed of hydrogen, unreacted normal paraffins and aromatic and olefin hydrocarbons, as well as traces of naphthenes and cracking products. After separation of the hydrogen, it is advantageous to eliminate the cracking products from this effiux. This can be effected in simple fashion by distillation.
  • a distinctive characteristic of the invention resides in the fact that the aromatic and olefin hydrocarbons coming from the dehydrogenation of the normal paraflins are subjected simultaneously to a sulfonation reaction or to a sulfation reaction followed by a sulfouation reaction. These reactions may be effected either on the mixture of unreacted normal paraffins, ole-fin and aromatic hydrocarbons and naphthenes, or on a mixture containing only olefin and aromatic hydrocarbons.
  • the dehydrogenation efilux after removal of the hydrogen and the cracking products is subjected to a sulfonation in a reactor at room temperature by gaseous sulfuric anhydride, diluted in a gas, which latter does not react with the products of the reaction under the operating conditions (this is true of nitrogen and air).
  • the sulfonation is effected, for instance, by causing the sulfuric anhydride to sweep over a thin film of hydrocarbons or by bubbling sulfuric anhydride into the liquid mass of hydrocarbons.
  • the resultant products After sulfonation, the resultant products 'are subjected to neutralization by soda at ordinary temperature. Thereupon, by an alkaline hydrolysis in an autoclave by means of excess soda, at a temperature between 150 C. and 260 C., the sultones are transformed into sulfonates. By settling, there is obtained an aqueous phase containing the sodium sulfonates and an organic phase which contains primarily the normal paraffins which did not react upon the dehydrogenation and small quantities of naphthenes and olefin and aromatic hydrocarbons. This organic phase is recycled to the dehydrogenation reactor.
  • a second embodiment of the method of the invention consists in sulfating the efllux of the dehydrogenation reactor, which has been freed of the hydrogen and cracking products, by contact with sulfuric acid of a concentration 1 of more than 90 percent at room temperature or lower for short periods of contact, and then neutralizing the resultant products with soda at room temperature and effecting an alkaline hydrolysis with soda at the temperature of 80 C., preferably on the organic phase obtained 4 of recovering the hydrocarbons to be recycled; they simply separate out after the alkaline hydrolysis.
  • the third and fourth embodiments of the invention are similar to the first and second embodiments, respectively; however, the charge subjected to the sulfonation or sulfation is previously treated so as to remove the normal paraffins and the traces of naphthenes which are recycled to the dehydrogenation reactor. This separation can be effected by selective absorption on molecular sieves. The volume of the organic phase collected after hydrolysis of the sulfonates is much less than that obtained with the first and second embodiments of the invention. This volume is recycled to the sulfonation reactor.
  • the aqueous phase which contains the sulfates, as well as the aqueous phase which contains the sulfonates, may contain traces of hydrocarbons. These traces are extracted by means of a suitable solvent, for instance, a mixture of ether and normal pentane or a mixture of ether, normal pentane and isopropyl alcohol
  • a suitable solvent for instance, a mixture of ether and normal pentane or a mixture of ether, normal pentane and isopropyl alcohol
  • the sodium alkyl sulfates obtained are colorless liquids.
  • the number of carbon atoms in these sulfates is larger than the number of carbon atoms in the sulfate at present available on the market since the sulfates comprise, in accordance with the invention and depending on the fraction from which one starts, between 14 and 24 carbon atoms which form a nonbranched chain.
  • the sodium sul-fonate composition obtained consists of a mixture of ortho-dialkyl benzene sulfonates, alkenyl sulfonates and hydroxy alkyl sulfonates.
  • the sulfonates are obtained in the form of a powder.
  • This phase may be carried out in a spray tower into which the solution of sulfonates are introduced against a counter-current of hot air. Furthermore, this apparatus has the advantage of effecting the removal of oil.
  • a gas oil rich in normal paratfins and having between 15 and 21 carbon atoms is introduced through the line 1 into a urea selective extraction unit 2.
  • This unit 2 has not been shown in detail in the figure.
  • the dewaxed gas oil is collected via the line 3a.
  • the normal parafiins are in-. troduced into a nonisomerizing dehydrogenation reactor 6 via the line 3, the recycled hydrocarbons (which are composed primarily of normal parafiins and traces of naphthenes) via the line 4, and the hydrogen via the line 5.
  • the dehydrogenation catalyst consists of platinum, lithium, and arsenic deposited on an alumina support in quantities, expressed in percent of the weight of the catalyst, of 0.75,.0.50, and 0.36, respectivelyfThe hourly space speed of the liquid charge is equal to l.
  • the molar ratio of hydrogen to hydrocarbons is equal to 5. The operation is carried out at a temperature of 450 C., the pressure being slightly more than 1 bar. V After separation of the hydrogen at 7, a part thereof is recycled via the line 5, while the cracking products composed primarily of hydrocarbons having a number of carbon atoms of between 6 and 15 are removed at the top of a column 8 and evacuated through the line 9.
  • a part of the distillation residue is introduced through the line 10 into a sulfation reactor 11.
  • the sulfuric acid of a concentration of 98 percent is introduced into the reactor through the line 12.
  • the time of contact between the sulfuric acid and the charge is 5 minutes.
  • the temperature of the reactor is fixed at 5 C. .
  • the effiux is then introduced into a neutralization reactor 13 into which soda of a concentration of 4 N is introduced through the line 14.
  • the neutralization is effected at room temperature.
  • the efllux is then subjected to alkaline hydrolysis in the reactor 15 for a period of three hours at a temperature of 80 C.
  • the sodium alkyl sulfates are recovered via the line 17. They can be subjected to a de-oiling, which has not been shown in the diagram.
  • the organic phase discharged through the line 18 from the decantation vessel, as well as the distillation residue coming from the column 8 which circulates in the line 19, are introduced into a sulfonation reactor 20.
  • a stream of nitrogen,'containing 1 percent by weight sulfuric anhydride in gaseous form, is introduced into the liquid mass of the hydrocarbons via the line 21.
  • the efilux from the sulfonation reactor is introduced into a neutralization reactor 23 into which soda of a concentration of 4 N is introduced through the line 24. The neutralization is effected at room temperature.
  • a variant of the embodiment of the method described in the diagram consists in placing a settling vessel between the neutralization reactor 13 and the hydrolysis reactor 15. There is thus recovered an aqueous phase which is is composed of sulfates and an organic phase which is subjected to hydrolysis in the reactor 15. After hydrolysis of the sulfuric diesters, an aqueous phase 17, consisting of sulfates, and an organic phase 18 are collected in the settling vessel 16, the organic phase being subjected to sulfonation.
  • the effiux from the dehydrogenation reactor is subjected to sulfation at a temperature of 5 C. by means of 98 percent sulfuric acid.
  • the contact time is short (5 minutes) so as to avoid the formation of polymers.
  • the molar ratio of sulfuric acid to olefins to be sulfated is equal to 1.5.
  • the conversion rate of the olefin hydrocarbons (which are the only ones ones to react with the sulfuric acid) is equal to 52 percent, including less than 5 percent polymers.
  • the total yield of sodium alkyl sulfates per 100 g. of olefins converted is equal to 75 percent (after neutralization of the sulfuric monoester with 4 N soda at room temperature and hydrolysis of the sulfuric diester by a 4 N soda solution in excess for 3 hours).
  • the aqueous phase obtained is composed primarily of a solution of sodium alkyl surfates, the alkyl radical being linear and having 18 carbon atoms.
  • the organic phase is subjected to a sulfonation reaction.
  • a gaseous stream containing 1.2 percent sulfuric anhydride in nitrogen is bubbled into the said organic phase at a temperature of 22 C.
  • the time of reaction is 1 /2 hours.
  • the sulfonic acids obtained are then neutralized with 4 N soda at room temperature.
  • akaline hydrolysis is then effected in an autoclave by means of soda solution at a temperature of 250 C. for 1 hour.
  • the organic phase which contains the normal octadecane which has not been converted as well as the naphthenes, can be recycled into the dehydrogenation reactor.
  • the aqueous phase is composed primarily of sodium alkenyl sulfonates, sodium hydroxy alkyl sulfonates and sodium ortho-dialkyl benzene sulfonates.
  • the total conversion of the olefin and aromatic hydrocarbons after sulfonation, neutralization and hydrolysis is equal to 96 percent;
  • the aqueous phase can be subjected to a de-oiling in order to extract therefrom the traces of dissolved hydrocarbons.
  • This extraction can be effected by means of a mixture of ethyl ether and normal pentane.
  • the dehydration yields a biodegradable detergent powder.
  • This powder contains dissodium sulfate formed upon the neutralization with the soda. The latter may be separated. However, it is not necessary to do so, since sodium sulfate is a substance which is contained in the composition of wash powders.
  • EXAMPLE II mina These three metals have been deposited in the form of nitrates in such a manner that after calcination at 800 0., they have the following weight percent composition, referred to the alumina: 4.97% chromium, 3.03% copper, and 1.00% potassium.
  • the hourly space velocity of the normal octadecane measured in liquid state is equal to l; the temperature of the catalyst is 440 C.
  • the molar ratio of hydrogen to normal octadecane is equal to 5.
  • the conversion of the normal octadecane introduced into the nonisomerizing dehydrogenation reactor is equal to 19 percent. For 100 g. of normal octadecane charged, there are collected 12.8 g.
  • olefin hydrocarbons and 5.9 g. of aromatic hydrocarbons.
  • the olefin hydrocarbons, as well as the aromatic hydrocarbons collected, are subjected simultaneously to sulfonation by bubbling a gaseous stream of sulfuric anyhdride in nitrogen, the molar concentration of sulfuric anhydride in nitrogen being equal to 1 percent.
  • the excess soda is neutralized by sulfuric acid. Evaporation is effected until a dry product is obtained.
  • a wash powder of the following composition was prepar-ed with the product of the invention:
  • Ys luminance of the cloth impregnated with the standard soilage.
  • Yt luminance of the support cloth not impregnated with the standard soilage.
  • the detergent power DP in percent was calculated by means of the following formula:
  • the culture broth used in the tests comprises between 2 and 4x10 microorganisms per mm. It was prepared by aerobic fermentation, in a rich nutrient medium, of microorganisms taken from the water of the Seine River at the point of discharge of the large Clic'hy sewer in Paris.
  • the detergent content of the microorganism cultures is determined in accordance with the method of Longwell and Manisoe, the principle of which is as follows: a colored complex is formed with methylene blue; it is extracted with chloroform and a calorimetric measure is effected by comparison with a standard'product.
  • the biodegradation rate T at the end of 7 days is given by the formula:
  • Hydroxyalkyl sulfonates 47 Other 1 2 Total 10 In the commercial production the percentage composition for each will range from to 60% for alkyl aryl sulfonates, 8% to 45% for alkenyl sulfonates, and 20% to 72% for hydroxyalkyl sulfonates.
  • a method for producing alkyl sulfates and mixtures of olefinic snlfonates and also orthodialkyl benzene sulfonates having detergent and biodegradable properties with superior foam stability comprises the steps of:
  • step (f) Subjecting the remaining efilux from step (b) not utilized in step (c) and the organic phase from step (e) to sulfonation;
  • step (g) Neutralizing the sulfonation products from step (f) by addition of an alkaline base selected from the group consisting of alkali metal hydroxides and ammonia;
  • a method for producing alkyl sulfates and mixtures of olefinic sulfonates and also orthodialkyl benzene sulfonates having detergent and biodegradable properties With superior foam stability comprises the steps of:
  • step (f) Subjecting the remaining efllux from step (b) not utilized in step (c) and the organic phase from step (e) to sulfonation;
  • step (g) Neutralizing the sulfonation products from step (if) by addition of an alkaline base selected from the group consisting of alkali metal hydroxides and ammonia;

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
US00115488A 1970-02-16 1971-02-16 Detergent compositions and methods of obtaining them Expired - Lifetime US3843564A (en)

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AT (1) AT314050B (enExample)
BE (1) BE762757A (enExample)
CH (2) CH540888A (enExample)
DE (1) DE2106507A1 (enExample)
FR (1) FR2079877A5 (enExample)
GB (1) GB1311245A (enExample)
LU (1) LU62592A1 (enExample)
NL (1) NL7101977A (enExample)
SE (1) SE373598B (enExample)
ZA (1) ZA71966B (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4006111A (en) * 1972-07-12 1977-02-01 Lever Brothers Company Production of alkane: olefin sulfonate mixtures by sequential sulfonation and sulfitation

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2232665A (en) * 1989-05-31 1990-12-19 Exxon Chemical Patents Inc Sulphonic acid derivatives and their use as emulsifiers
EP2186783A3 (en) * 2010-01-27 2010-09-01 Shell Internationale Research Maatschappij B.V. Process for the preparation of olefins
EP2186784A3 (en) * 2010-01-27 2010-09-01 Shell Internationale Research Maatschappij B.V. Process for the preparation and recovery of olefins
EP2186785A3 (en) * 2010-01-27 2010-09-01 Shell Internationale Research Maatschappij B.V. Process for the separation of olefins from paraffins
US9108906B2 (en) 2012-03-22 2015-08-18 Uop Llc Production of alkane sulfonates

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4006111A (en) * 1972-07-12 1977-02-01 Lever Brothers Company Production of alkane: olefin sulfonate mixtures by sequential sulfonation and sulfitation

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FR2079877A5 (enExample) 1971-11-12
SE373598B (sv) 1975-02-10
ZA71966B (en) 1972-04-26
DE2106507A1 (de) 1971-09-02
NL7101977A (enExample) 1971-08-18
LU62592A1 (enExample) 1971-02-19
GB1311245A (en) 1973-03-28
CH540888A (fr) 1973-08-31
AT314050B (de) 1974-03-11
CH540334A (fr) 1973-09-28

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