US2796429A - Alkyl aryl sulfonates - Google Patents

Alkyl aryl sulfonates Download PDF

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Publication number
US2796429A
US2796429A US430398A US43039854A US2796429A US 2796429 A US2796429 A US 2796429A US 430398 A US430398 A US 430398A US 43039854 A US43039854 A US 43039854A US 2796429 A US2796429 A US 2796429A
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alkyl
sodium
alkyl aryl
new
compositions
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US430398A
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Robert W F Kreps
Jacobus J Tjepkema
Pieter L Kooijman
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Shell Development Co
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Shell Development Co
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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
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds

Definitions

  • alkyl aryl sulfonates A variety of different alkyl aryl sulfonates have been suggested as detergents, wetting agents, dispersants and the like. Propylene tetramer benzene sulfonates and keryl benzene sulfonates are typical of the compounds which have gone into large scale use in these fields.
  • the present invention provides a dilferent type of alkyl aryl sulfonate which has now been found to give exceptionally advantageous results in all these applications and especially as detergents, particularly for cleaning dishes,
  • alkyl aryl sulfonic acids and their salts will be referred to generically as alkyl aryl sulfonates.
  • R1 The number of carbon atoms in R1 is not more than twice the number in R2, while R3 contains at least one but not more than the same number of carbon atoms of the larger R1 and R2.
  • alkyl benzene sulfonates of the foregoing formula in which the maximum difference between the number of carbon atoms in R1 and R2 is not more than two. It is also preferred to use compounds in which R1, R2 and R3 are straight chain, normal alkyl radicals.
  • Tertiary olefins corresponding to these halides and alcohols, for example, the dehydrohalogenation and dehydration products thereof, are also advantageous alkylating agents.
  • Especially suitable tertiary olefins are those of the formula wherein R4 is an alkyl radical having one less carbon atom than R1 in the previously indicated formulae, and R2 and R3 are alkyl radicals as above described.
  • R4 is an alkyl radical having one less carbon atom than R1 in the previously indicated formulae
  • R2 and R3 are alkyl radicals as above described.
  • alkyl aryl hydrocarbons for instance, lower hydrocarbons, by known methods. Using such agents, it is feasible to prepare alkyl aryl hydrocarbons of the required structure in a pure or substantially pure form. However, it is not necessary to use pure starting materials in large scale manufacture of the new compounds and, for reasons of economy, it may be desirable to employ starting mixtures which contain isomers and/ or homologues of specified compounds. Excellent results can be obtained with alkyl aryl sulfonates which contain at least 60%, on a molar basis, of sul fonates havingalkyl groups of the special structure characterizing the new compounds of the invention. Preferably not more than 25%, more preferably not more than 10%, of the alkyl aryl sulfonate molecules present should have a constitution different from that indicated above as essential. I I I
  • alkyl aryl hydrocarbon or mixture of hydrocarbons chosen as starting material can be sulfonated in various Ways.
  • alkali metal salts especially the sodium and potassium salts, are particularly useful as are also the ammonium and amine salts.
  • the mono-, diand triethanolamine salts are examples of amine salts which have been found to have special advantages.
  • Alkalineearth metal salts can also be used.
  • inorganic salts are particularly suitable.
  • suitable inorganic salts are sodium sulfate, sodium carbonate, sodium phosphates, for instance sodium pyrophosphate, more particularly sodium polyphosphates such as sodium trior tetra-polyphosphate, sodium tetrapyrophosphate and sodium hexametaphosphate and sodium silicates, for example, sodium metasilicate (NazO.SiO2), alkaline sodium silicate (NazO.2SiOz) and neutral sodium silicate (NazO.3SiOz). It is in many cases advantageous to add one or more phosphates and one or more silicates in combination.
  • compositions according to the invention may also contain so-called washing promoters.
  • washing promoters are cellulose or starch derivatives.
  • the sodium salt of carboxy methylcellulose has become particularly well-known.
  • Components which may also advantageously be added to the compositions according to the invention are bleaching agents, i. e. agents which have an oxidizing effect and/or the so-called optical bleaching agents, the effect of which is due to fluorescence.
  • peroxygen compounds such as persulfates, perborates and percarbonates, for example, are suitable as chemical, i. e. oxidizing, bleaching agents.
  • the new compositions can also contain other surfaceactive agents besides the alkyl aryl sulfonates of the invention. Most preferably, these are of the anionic and/or nonionic type. Alkyl sulfonates and alkyl sulfate salts having alkyl chains of 8 to 20 carbon atoms are typical of the anionic surface-active agents which can be used as well as alkyl aryl sulfonates which do not have the advantageous structure of the new compounds. Polyethylene glycol ethers and esters are examples of suitable nonionic surface-active agents which can be advantageously used in the new compositions.
  • the proportions of the various components in the new detergent compositions can be varied. These compositions can be in solid form, as powders, beads, flakes, bars, cakes and the like, or can be liquid solutions or gels such as are used as so-called liquid soap. These forms are most suitable for storage, transportation and sale of the new compositions, but the invention also includes these compositions in more dilute solutions such as are useful for washing and similar purposes.
  • the surface-active compounds present can be in the range of 3% to 75% by weight of the total solids, i. e. disregarding any liquids which may be present. In most cases, the content of surface-active compounds will, however, vary between 5% and 60% by weight of the total solids, particularly between and about 40% by weight.
  • the surface-active compounds are predominantly alkyl aryl sulfonatm having the unique structure of the new compounds of the invention and, most preferably, only the new alkyl aryl sulfonates are used. Very good results have been obtained with detergent compositions containing to 30% by weight, preferably to by weight, of the new alkyl benzene sulfonates as the sole surface-active components present.
  • Sodium phosphates are particularly advantageous in the new compositions when they are intended for use in aqueous solution.
  • the amount which will be used in such cases will be influenced by the hardness of the water which will be employed in making up the solutions.
  • phosphates preferably sodium tripolyphosphate and/orsodium pyrophosphate, are used in amounts about equal to about twice the weight of the surface-active compound or compounds present.
  • Sodium silicates are less effected by the hardness of the water used. They are added in amounts from about 20% to about 50% by weight of the surface-active components.
  • Sodium metasilicate, alkaline sodium silicate and neutral sodium silicate have been found to be suitable.
  • a washing promoter such as the sodium salt of carboxy methyl cellulose or the like
  • amounts preferably between about 5% and about 20%, especially about 10%, by weight of the surface-active compounds present are suitable.
  • compositions should preferably also contain: 4-10 parts by weight of sodium silicate (meta, alkaline or neutral silicate) and/or 1-4 parts by weight of the sodium salt of carboxy methylcel-lulose.
  • one or more bleaching agents preferably: 5-15 parts by weight of sodium perborate, if desired, in
  • alkyl aryl sulfonates to be employed according to the invention have a very good foaming effect, in some cases it may nevertheless be important to add an extra substance which has a foaming and/ or foam stabilizing effect. This is particularly the case with compositions intended (for domestic use.
  • Suitable foam promoters and stabilizers are, for example, fatty acid amides of ethanol amines such as lauryl ethanolamide, or sulfone-substituted amides such as lauryl sulfolanyl amide and the like whose use, for such purposes, is claimed in copending application of Morris and Sawyer, Serial No.
  • alkyl aryl sulfonates used in preparing these compositions were the following typical compounds having alkyl groups of the structure required in the new detergents of the invention, as shown by the number of carbon atoms in groups R1, R2 and R3 of the previously mentioned general formula.
  • compositions were also prepared corresponding to mixture No. 10 of Table II using a number of alkyl aryl sulfonates having structures which do not meet the requirements for the new compounds of the invention. These sulfonates are characterized below by the number of carbon atoms in their groups R1, R and & according to the preceding general formula, except that a zero indicates a hydrogen atom in place of an alkyl group.
  • compositions were tested in comparison with similar mixtures prepared with new alkyl benzene sulfonates of the invention.
  • the test compares the relative foaming powder of detergents in the presence of a form of dirt, tallow, which has an especially strong anti-foaming power.
  • the test was carried out with four liters of an aqueous solution of each of the detergents containing 0,05% by weight of alkyl aryl sulfonate dissolved in water having a hardness corresponding to 250 mg. of calcium carbonate per liter. Each solution was heated to 60 C. and stirred mechanically for 30 seconds to produce foam. Then, successive additions of 2 grams of tallow were made carefully so as to disperse the tallow without forming any new foam.
  • the invention offers considerable advantage over prior alkyl aryl sulfonates, particularly with respect to its application in washing operations.
  • Many variations can be made in the invention, however, since the new compounds are also effective as wetting agents, dispersants and emulsifiers as well as foaming agents. They can likewise be used in compositions containing biocidal compounds and can thus be employed for the control of harmful organisms. Still other changes can be made in the new compositions Without departing from the invention which is not restricted by any theory proposed in explanation of the improved results which are obtained nor by the details given by way of illustration in the foregoing examples.
  • Alkyl aryl monosulfonates of the benzene series having the general formula wherein M represents a cation, Ar is a divalent aromatic hydrocarbon radical of the henzene series, and R1, R2 and R3 are alkyl radicals, the total number of carbon atoms in the alkyl group being at least 13 but not more than 16 carbon atoms, the number of carbon atoms in group R1 having the maximum number of carbon atoms of said three alkyl radicals being not more than twice the number in group R2, and group R3 containing at least one but not more than the number of carbon atoms in group R1.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
US430398A 1953-05-29 1954-05-17 Alkyl aryl sulfonates Expired - Lifetime US2796429A (en)

Applications Claiming Priority (1)

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NL178695A NL178695B (is") 1953-05-29 1953-05-29

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US2796429A true US2796429A (en) 1957-06-18

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US (1) US2796429A (is")
BE (1) BE529128A (is")
CH (1) CH330486A (is")
FR (1) FR1105032A (is")
GB (1) GB770310A (is")
NL (1) NL178695B (is")

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2944028A (en) * 1956-09-12 1960-07-05 California Research Corp Sulfonate detergent compositions
US2956025A (en) * 1955-03-22 1960-10-11 California Research Corp Sulfonate detergent compositions with improved foam characteristics
US2956026A (en) * 1955-03-22 1960-10-11 California Research Corp Sulfonate detergent compositions
US3093590A (en) * 1956-08-08 1963-06-11 Purex Corp Ltd Trichlorocyanuric acid bleach with spray-dried base
US3238249A (en) * 1960-09-23 1966-03-01 Exxon Research Engineering Co Alkylbenzene sulfonate production via n-olefin dimerization
US3298912A (en) * 1963-10-02 1967-01-17 Emery Industries Inc Emulsifiable toxicant solution containing emulsifier of alkaryl sulfonic acid polyoxyalkylated polyamine salt
US3425940A (en) * 1966-06-30 1969-02-04 Exxon Research Engineering Co Non-staining liquid lubricant
EP1135354A4 (en) * 1998-12-01 2002-02-06 Exxonmobil Res & Eng Co BRANCHED ALKYL-AROMATIC SULFONIC ACID DISPERSION AGENTS FOR SOLVING ASPHALENES IN MINERAL OILS
US20060014650A1 (en) * 2004-07-15 2006-01-19 Chevron Oronite Company Llc Alkylxylene sulfonates for enhanced oil recovery processes

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2467170A (en) * 1947-10-15 1949-04-12 Du Pont Alkyl substituted aromatic sulfonates
US2500024A (en) * 1950-03-07 Aqueous detergent
US2525024A (en) * 1947-12-26 1950-10-10 Allied Chem & Dye Corp Process of producing alkyl benzene hydrocarbon sulfonates
US2681362A (en) * 1949-10-07 1954-06-15 Sun Oil Co Alkyl substituted benzene sulfonate

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2500024A (en) * 1950-03-07 Aqueous detergent
US2467170A (en) * 1947-10-15 1949-04-12 Du Pont Alkyl substituted aromatic sulfonates
US2525024A (en) * 1947-12-26 1950-10-10 Allied Chem & Dye Corp Process of producing alkyl benzene hydrocarbon sulfonates
US2681362A (en) * 1949-10-07 1954-06-15 Sun Oil Co Alkyl substituted benzene sulfonate

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2956025A (en) * 1955-03-22 1960-10-11 California Research Corp Sulfonate detergent compositions with improved foam characteristics
US2956026A (en) * 1955-03-22 1960-10-11 California Research Corp Sulfonate detergent compositions
US3093590A (en) * 1956-08-08 1963-06-11 Purex Corp Ltd Trichlorocyanuric acid bleach with spray-dried base
US2944028A (en) * 1956-09-12 1960-07-05 California Research Corp Sulfonate detergent compositions
US3238249A (en) * 1960-09-23 1966-03-01 Exxon Research Engineering Co Alkylbenzene sulfonate production via n-olefin dimerization
US3298912A (en) * 1963-10-02 1967-01-17 Emery Industries Inc Emulsifiable toxicant solution containing emulsifier of alkaryl sulfonic acid polyoxyalkylated polyamine salt
US3425940A (en) * 1966-06-30 1969-02-04 Exxon Research Engineering Co Non-staining liquid lubricant
EP1135354A4 (en) * 1998-12-01 2002-02-06 Exxonmobil Res & Eng Co BRANCHED ALKYL-AROMATIC SULFONIC ACID DISPERSION AGENTS FOR SOLVING ASPHALENES IN MINERAL OILS
US20060014650A1 (en) * 2004-07-15 2006-01-19 Chevron Oronite Company Llc Alkylxylene sulfonates for enhanced oil recovery processes
US7332460B2 (en) * 2004-07-15 2008-02-19 Chevron Oronite Company Llc Alkylxylene sulfonates for enhanced oil recovery processes

Also Published As

Publication number Publication date
BE529128A (is")
GB770310A (en) 1957-03-20
NL178695B (is") 1956-06-15
FR1105032A (fr) 1955-11-25
CH330486A (de) 1958-06-15

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