EP1322737A2 - Detergents de sulfonate d'alkyltoluene - Google Patents

Detergents de sulfonate d'alkyltoluene

Info

Publication number
EP1322737A2
EP1322737A2 EP01971233A EP01971233A EP1322737A2 EP 1322737 A2 EP1322737 A2 EP 1322737A2 EP 01971233 A EP01971233 A EP 01971233A EP 01971233 A EP01971233 A EP 01971233A EP 1322737 A2 EP1322737 A2 EP 1322737A2
Authority
EP
European Patent Office
Prior art keywords
component
composition according
group
water
sulfonates
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP01971233A
Other languages
German (de)
English (en)
Inventor
George A. Smith
Prakasa R. Anantaneni
Samir S. Ashrawi
Raeda M. Smadi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Huntsman Specialty Chemicals Corp
Huntsman Petrochemical LLC
Original Assignee
Huntsman Specialty Chemicals Corp
Huntsman Petrochemical LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US09/665,642 external-priority patent/US6995127B1/en
Application filed by Huntsman Specialty Chemicals Corp, Huntsman Petrochemical LLC filed Critical Huntsman Specialty Chemicals Corp
Publication of EP1322737A2 publication Critical patent/EP1322737A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0047—Detergents in the form of bars or tablets
    • C11D17/006—Detergents in the form of bars or tablets containing mainly surfactants, but no builders, e.g. syndet bar
    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0047—Detergents in the form of bars or tablets
    • C11D17/0065—Solid detergents containing builders
    • C11D17/0073—Tablets

Definitions

  • This invention relates generally to detergent compositions and cleaning
  • compositions having enhanced detergency and cleaning capabilities comprising
  • an alkylated benzene such as toluene or
  • ethylbenzene are utilized as an aromatic compound that is further alkylated and
  • Saponification is essentially a process whereby
  • aqueous alkali metal hydroxide is mixed with an ester (such as an animal fat or
  • salt(s) of the carboxylic acid(s) from which the ester was derived which salt(s) are
  • alkali salts of the carboxylic acid(s) include as part of their molecular structure a
  • hydrophilic portion i.e., the carboxylate function, which is highly attracted to water
  • Such salts also include a hydrophobic portion as part of their molecular
  • a clean substrate which may typically comprise a
  • the hydrocarbyl substituent may typically
  • alkylbenzene sulfonates each of which have different solubilization capabilities
  • detergent materials made from sulfonation of the 2-phenyl alkyl materials have
  • 2-phenyl alkyl isomer products may be represented structurally, in the case of the
  • alkylbenzenes as:
  • alkylbenzenes results from such alkylation.
  • the present invention is a linear alkyltoluenes of this invention.
  • the present invention is a linear alkyltoluenes of this invention.
  • alkyltoluenes derived from the alkylation of toluene, preferably using olefins having a
  • alkylbenzene is but one possible structural isomer resulting from the alkylation of
  • the detergent range This may be due to resonance stabilization which permits
  • linear alkylbenzenes or "LAB's”.
  • linear alkyltoluenes as well, and linear alkyltoluenes may be
  • LAT's referred to as "LAT's”.
  • surfactant molecules generally comprise a hydrophobic
  • hydrophobic group increases in molecular
  • the surfactant becomes less soluble
  • solubility ofan ionic surfactant is plotted against temperature, a complex graph results.
  • linear alkyltoluene sulfonate surfactants are provided.
  • the detergent range olefin may attach itself in either an
  • alkyl group on the ring are themselves ortho, para directors.
  • the present invention provides a method and catalyst for LAT
  • 2-toluyl alkyltoluenes may be used.
  • the present invention provides detergent compositions and
  • alkyltoluenes in which the hydrocarbon groups that are bonded to the toluene nucleus
  • the detergent range may comprise any number of carbon atoms in the detergent range, and in one
  • the invention further provides detergent compositions and formulations which
  • surfactant component that comprises a mixture of the following:
  • a first alkyltoluene sulfonate component comprising 2-toluyl alkyltoluene
  • a second surfactant component which may comprise: a) alkylbenzene
  • a position other than the alkyl group's 2 position comprise at least 60 % of all
  • alkylbenzene sulfonate isomers present; b) alkylbenzene sulfonates in which isomers
  • alkyl group's 2 position comprise at least 70 % of all alkylbenzene sulfonate isomers
  • alkyltoluene sulfonates in which isomers having the toluene nucleus attached to a
  • linear alkyl group at a position other than the alkyl group's 2 position comprise at least
  • alkyltoluene sulfonates 60 % of all alkyltoluene sulfonate isomers present; e) alkyltoluene sulfonates in which
  • alkyl group's 2 position comprise at least 70 % of all alkyltoluene sulfonate
  • Branched alkyltoluene sulfonates may be introduced into a formulated product
  • feedstock used in the alkylation reaction of the toluene nucleus may be replaced by
  • isomers comprise any amount less than 50.0 % of the total alkyltoluene sulfonate
  • branched isomers comprise any amount less than
  • isomers comprise any amount less than 2 .00% of the total alkyltoluene sulfonate
  • lower activity isomers isomers other
  • the second surfactant component may
  • the benzene ring attached to a linear alkyl group at a position other than the alkyl group's 2 position comprise at least 50 % of all alkylbenzene sulfonate isomers
  • the second surfactant component in another preferred form of the invention, the second surfactant component
  • alkyltoluene sulfonates may comprise alkyltoluene sulfonates or alkylbenzene sulfonates in which isomers
  • alkyl group's 2 position comprise at least 40 % of all alkylbenzene sulfonate isomers
  • the second alkylbenzene sulfonate in another preferred form of the invention, the second alkylbenzene sulfonate
  • component may comprise alkyltoluene sulfonates or alkylbenzene sulfonates in which
  • alkyl group's 2 position comprise at least 30 % of all alkylbenzene sulfonate
  • embodiment of the invention may contain sulfonated 2-phenyl alkyltoluenes in an
  • alkyltoluene component in another form of the invention, an alkyltoluene sulfonate
  • component may contain sulfonated 2-phenyl alkyltoluenes in an amount of at least
  • component may contain sulfonated 2-phenyl alkyltoluenes in an amount of at least
  • component may contain sulfonated 2-phenyl alkyltoluenes in an amount of at least 60.00 % by weight based upon the total weight of the sulfonated alkyltoluene
  • component may contain sulfonated 2-phenyl alkyltoluenes in an amount of at least
  • component may contain sulfonated 2-phenyl alkylbenzenes in an amount of at least
  • detergents a mixture of sulfonated alkylbenzenes and sulfonated alkyltoluenes useful
  • sulfonated alkyltoluenes are useful as a component in forming detergent and cleaning
  • compositions useful in a wide variety of applications as later illustrated in the specification are particularly useful in a wide variety of applications as later illustrated in the specification.
  • a slip stream of reactants may be
  • the retrofitted plant can produce higher 2-phenyl isomer LAB or LAT at
  • a slip stream of reactant is drawn and sent
  • the invention in one broad respect, is directed at cleaning formulations
  • formulations comprise an alkyltoluene
  • the invention in another broad respect is a process useful for the production of
  • mono-alkyltoluene comprising: contacting toluene with an olefin containing from about 8 to about 30 carbons in the presence of fluorine-containing mordenite under conditions
  • this invention is a process for the production of linear
  • alkyltoluene comprising: a) contacting toluene and an olefin having about 8 to about
  • alkyltoluene stream b) contacting toluene and an olefin having about 8 to about 30
  • alkyltoluene stream and the second linear alkyltoluene stream form a third linear
  • alkyltoluene stream as well as the mono-sulfonation product made from this process.
  • this invention is a process useful for the production of
  • linear alkyltoluene comprising: combining a product from a conventional linear
  • alkylbenzene alkylation reactor with a product from a linear alkyltoluene alkylation
  • this invention is a process for the production of
  • linear alkyltoluene comprising: a) dehydrogenating a paraffin to form an olefin; b)
  • Such process may optionally include the steps of: g) distilling the toluene-free
  • alkyltoluene product and removing a bottoms stream containing any heavies.
  • this invention is a process useful for the production of
  • monoalkyltoluene comprising: introducing a feed comprising olefin having about 8 to
  • toluene refluxes to furtlier contact the fluorine-containing mordenite.
  • this invention relates to mordenite useful for
  • the invention relates to a chemical mixture that
  • alkyltoluenes which mixture contains a higher concentration of sulfonated 2-toluyl
  • alkyltoluenes than previously available using prior art methods and catalysts.
  • the invention comprises formulations for finished
  • laundry detergents enzyme-free powdered laundry detergents, and the like, as it has
  • the invention is a method useful for the preparation of
  • fluorine-containing mordenite comprising contacting a mordenite having a silica to
  • alumina molar ratio in a range from about 10:1 to about 100:1 with an aqueous
  • fluorine is produced, collecting the fluorine-containing mordenite by filtration, and drying.
  • the fluorine treated mordenite catalyst advantageously produces high
  • FIGS. 1 and 2 has the advantage that rising toluene from the reboiler
  • this invention advantageously produces only low amounts of dialkyltoluene, which is
  • the invention provides solid salts of alkyltoluene sulfonates
  • solid salts may contain various cations necessary for charge balance.
  • the invention comprises finished detergent compositions
  • components comprising: a) an alkyltoluene sulfonate surfactant component
  • n is equal to any integer between 4 and 16, wherein one and only one of R,
  • R 2 , R 3 , R 4 and R 5 is a sulfonate group, and wherein one and only one of R l5 R 2 , R 3 , R 4
  • R 5 is a substituent group selected from the group consisting of methyl and ethyl
  • components is selected from the group consisting of: fatty acids, alkyl sulfates, an
  • salts alkali sulfates, enzymes, hydrotropes, dyes, fragrances, preservatives,
  • alkylphenol ethoxylates fatty acid amides, alpha olefin sulfonates, paraffin sulfonates,
  • betaines chelating agents, tallowamine ethoxylates, polyetheramine ethoxylates,
  • the mordenite catalyst of the present invention is useful as a catalyst in the
  • LAT is useful as starting material to produce sulfonated LAT, which itself is
  • Meq/g means milliequivalents of titratable acid per gram of catalyst, which is
  • Acidity is generally determined by
  • olefin conversion is about 95 percent or more in the
  • selectivity to the 2-phenyl isomer is about 70 % or more in the
  • Detergent range means a molecular species which contains an alkyl group that
  • sulfonated or not means a hydrocarbon comprising between 7 and 16 carbon atoms
  • Branched alkyl when referring to a hydrocarbon or alkyl chain that is part of
  • alkylbenzene or alkyltoluene whether the alkylbenzene or alkyltoluene is sulfonated
  • hydrocarbon comprising between 4 and 16 carbon atoms linked to one
  • straight chain may have a hydrogen atom and any alkyl group otlier than a methyl group
  • Branched alkylbenzene means a molecular species which comprises a
  • Branched alkyltoluene means a molecular species which comprises a branched
  • Branched alkylbenzene sulfonate means a water-soluble salt of a branched
  • alkylbenzene that has been sulfonated.
  • Branched alkyltoluene sulfonate means a water-soluble salt of a branched
  • alkyltoluene that has been sulfonated, regardless of the isomeric position of the sulfonate
  • 2-phenyl alkylbenzenes means a benzene ring having at least one alkyl
  • alkyl group attached to it, wherein the alkyl group comprises any number of carbon atoms
  • 2-phenyl alkyltoluenes means a toluene molecule having, in addition to its
  • group comprises any number of carbon atoms between 7 and 16 (including every
  • phenyl alkyltoluene is synonymous with2-tolyl alkylbenzene.
  • 2-tolyl alkylbenzene means a toluene molecule having, in addition to its
  • group comprises any number of carbon atoms between 7 and 16 (including every
  • Sulfonated 2-phenyl alkylbenzenes means 2-phenyl alkylbenzenes as
  • sulfonate group on the ring with respect to the location of the alkyl group; however, it is most common and preferred that the sulfonate group is attached to the benzene ring
  • Sulfonated 2-phenyl alkyltoluenes means 2-phenyl alkyltoluenes as defined
  • the sulfonate group is attached to the benzene ring in the para-
  • LAB means a mixture linear alkylbenzenes which comprises a benzene ring
  • LAT means a mixture linear alkyltoluenes which comprises a toluene
  • alkyl chain in the detergent range in the detergent range.
  • LAB sulfonates means LAB which has been sulfonated to include an acidic
  • ammonium hydroxides alkylammonium hydroxides, or any chemical agent known by
  • LAT sulfonates means LAT which has been sulfonated to include an acidic
  • ammonium hydroxides alkylammomum hydroxides, or any chemical agent known by
  • 2-phenyl isomer means LAB or LAT sulfonates of 2-phenyl alkylbenzenes
  • sulfonated aromatic alkylate means a chemical compound which comprises a
  • FIG. 1 shows a representation of a first continuous reactive distillation column
  • FIG. 2 shows a representation of a second continuous reactive distillation column
  • FIG. 3 shows a representative process scheme for one embodiment of this invention
  • FIG. 4 shows another representative process scheme for one embodiment of this
  • FIG. 5 shows graphic data of a total detergency study conducted on cloth swatches
  • FIG. 6 shows the turbidity of solutions containing conventional alkylbenzene surfactant in aqueous solutions of differing hardness
  • FIG. 7 shows the turbidity of solutions containing alkylbenzene surfactant having a 2- phenyl isomer content of about 80% in aqueous solutions of differing hardness;
  • FIG. 8 shows the turbidity of aqueous solutions having a constant water hardness in the presence of different mixtures which each contain different amounts of linear alkylbenzene sulfonates and linear alkyltoluene sulfonates in which the 2-pheny isomer
  • alkylbenzene sulfonates and the alkyltoluene sulfonates is greater than 80% by weight based upon the total weight of all sulfonates present.
  • the catalysts used to prepare the linear alkyltoluenes of this invention is a
  • Mordenite is a type of zeolite.
  • invention is prepared from hydrogen mordenite (typically having 0.1 percent or less of
  • silica-alumina molar ratio of from about 10:1 to about 100:1. More
  • the starting mordenite has a silica/alumina molar ratio of from about 10:1 to
  • this invention show a fluorine content of from about 0.1 to about 4 percent by weight
  • the aqueous solution used to treat the mordenite may contain a range of HF
  • the HF concentration is a minimum of about 0.1 percent by
  • the HF concentration on the upper end is about 10 percent by weight or less.
  • the aqueous HF solution may be prepared by diluting commercially available
  • the treatment is carried out by adding mordenite powder or pellets to
  • a stirred aqueous HF solution at a temperature of from about 0 ° C to about 50 ° C.
  • stirring and contacting is continued for a time sufficient to achieve the desired level of
  • gaseous hydrogen fluoride Preferably said fluoride-treated mordenite would be calcined
  • agents to hydrofluoric acid and hydrogen fluoride include ammonium fluoride, fluorided
  • the HF-treated mordenite of this invention generally has about 0.1 percent by
  • the weight or more of fluorine based on the total weight of the mordenite.
  • the weight or more of fluorine based on the total weight of the mordenite.
  • fluorine-containing mordenite contains about 4 percent by weight or less fluorine.
  • fluorine-containing mordenite most typically contains about 1 percent by weight of
  • the mordenite can be used in the practice of this invention as a powder, in pellet form, as granules, or as extrudates.
  • the mordenite can be formed into pellets or extrudates using binders well known to those of skill in the art, such as alumina, silica
  • toluene is alkylated with olefin to form LAT.
  • the reactants are water and
  • the olefins employed in the practice of this invention have from about 8 to
  • the olefin be monounsaturated. It is most preferred that the olefin be an alpha-olef ⁇ n
  • Olefins in the 10 to 14 carbon number range are typically available from the
  • dehydrogenation reactor into which was fed a C 10 to C 14 mixture typically comprises a
  • the olefin content of said olefm-paraffin mixture may be
  • FIG. 1 a feed mixture of toluene and olefin, generally at a toluene-to-olefin molar ratio range of about 1 :1 to 100:1 flows
  • reactants can be mixed via an in-line mixer prior to introducing the reactants into the
  • the lengths may be made of two lengths of 1.1 inch internal diameter tubing, the lengths being 9.5
  • thermocouple 38 which monitors temperature to provide
  • thermocouple 30 which connects to bottoms temperature controller 28 which activates
  • the system may be flushed with nitrogen which enters via line
  • catalyst bed 32 so as to drive off water from the fluorine-containing mordenite.
  • Residual water from the feed mixture or which otherwise enters the system is
  • water trap 24 upon being liquefied at condenser 21 (along with benzene vapor). If the feed is very dry (free of water) the water trap 24 may not be needed.
  • the water trap 24 is optional.
  • Condenser 21 is cooled via coolant such as water entering
  • water in water trap 24 may
  • LAT product may be removed from the system via line 47, using either gravity or
  • valve 44 is
  • dip tube 46 which is optional, is employed to slightly increase the
  • a pressure generator 56 may be optionally employed to raise the pressure of
  • control mechanisms for heat shutoff 50 and pump shutoff 52 are
  • control mechanisms are optional and may be included so that the
  • the bed is maintained at the reflux temperature of toluene
  • the temperature of the catalyst bed is above about
  • reaction rates and about 250 °C or less to avoid degradation of reactants and products
  • the temperature is
  • the process may be operated at a
  • olefin vaporize the temperature varying depending on olefin, and generally being from
  • the reboiler will vary over time, but is generally set initially to have a toluene-to-olefin
  • the rate of introduction of feed into the catalyst bed may vary, and is generally at a
  • liquid hourly space velocity (LHSV) of about 0.05 hr “1 to about 10 hr "1 , more typically
  • the catalyst bed is generally from about 1 : 1 to about 100:1.
  • toluene In commercial toluene
  • alkylation operations it is common to run at mole ratios of from about 2:1 to about 20:1,
  • olefins as an olefm-paraffin mixture comprising 5% to 20% olefin content. Said olefm-
  • paraffin mixtures are normally generated commercially through dehydrogenation of the corresponding paraffin starting material over a noble metal catalyst.
  • Another continuous reactive distillation apparatus is depicted in FIG. 2.
  • the feed mixture enters the reactor via feed inlet 114.
  • the feed mixture falls
  • thermowell 133 monitors the temperature of said catalyst bed 132.
  • the catalyst bed 132
  • electric heater 140 heats the contents of reboiler 142 such that heated vapors of toluene
  • bottoms LAB product may be removed from reboiler 142 by opening bottoms valve 144
  • thermocouples 138, 130, and 165 The system includes
  • Level control activator 150 activates
  • bottoms level control valve 151 to open when the liquids level in the reboiler rises to the
  • level control activator 150 The Line 160 connects level control activator 150 to the system
  • FIG. 1 and FIG.2 show single catalyst bed
  • An example of such a second catalyst is HF-treated
  • Such a catalyst may also be used as montmorillonite clay having about 0.5% fluoride.
  • a clay such as montmorillonite clay having about 0.5% fluoride.
  • Such a catalyst may also be used as montmorillonite clay having about 0.5% fluoride.
  • the fluorine-containing mordenite of this invention generally produces LAT
  • chloride alkylation catalysts This may be affected by withdrawing a slip stream of
  • a typical HF process produces about 16-18% of the 2-phenyl isomer.
  • 2-phenyl isomer may be adjusted by the amount of reactants sent to the mordenite
  • zeolites include various zeolites, alumina-silica, various clays, as well as other catalysts.
  • FIG. 3 depicts a representative, non-limiting scheme for practice of this
  • dehydrogenation apparatus 210 is then pumped into a conventional alkylation reactor
  • dehydrogenated paraffin feed may ofcourse be supplied from any provider.
  • LAT product from alkylation unit 230 may thereafter be purified by a
  • alkylation effluent is delivered to a toluene column 240 by way
  • FIG. 3 is depicted in FIG. 3 as representative of a typical
  • paraffin column 250 where any paraffin present is distilled off, with the distilled
  • dialkylates and olefin derivatives are withdrawn from refining column 260 via
  • reactor 220 is used in conjunction with the conventional alkylation reactor 230.
  • toluene/dehydrogenated paraffin feed is taken from line 214 and pumped through
  • mordenite reactor 220 may be fed toluene and
  • effluent from reactor 220 may, in the alternative if no unreacted
  • olefin is present, be sent directly to toluene column 240, for later combination with
  • columns 240, 250, and 260 may be maintained at conditions (e.g., pressure and temperature) well known to
  • FIG. 4 depicts an alternative configuration to that shown in FIG. 3.
  • FIG. 4 depicts an alternative configuration to that shown in FIG. 3.
  • one of the mordenite reactors may be in operation
  • olefin feed (dehydrogenated paraffin) is supplied via line 301, with toluene
  • the admixed reactants may be any aromatic feed stock being provided via line 302.
  • the admixed reactants may be any aromatic feed stock being provided via line 302.
  • a portion of the mixed stream may be withdrawn via line 304a for
  • withdrawn may be varied depending on the desired level of 2-phenyl isomer in the
  • mordenite 320, 321 may be fed to the first alkylation reactor 330, particularly if the
  • second alkylation reactor 34 is not employed in the process.
  • the slip stream reactants may optionally be sent to dewatering unit 317 by
  • water is distilled from the reactants in dewatering tower 310. Rising vapor
  • Effluent from heat exchanger 312 is advanced to water trap 318 via line 311b.
  • Dewatered reactants may be removed via
  • heat exchanger 315 may serve
  • one of the catalyst beds may be regenerated, as by calcination for
  • regeneration heater 350 which may be connected to the
  • the reactors 320 and 321 may optionally be run simultaneously.
  • catalyst employed may vary depending on a variety of considerations such as type
  • second conventional reactor 340 or optionally may be sent to a purification section
  • FIG. 4 effluent from the second conventional alkylation reactor is advanced to a
  • the second alkylation reactor may be used to react unreacted
  • example 2 illustrates LAB production from paraffin
  • Example 9 shows how virtually no alkylation activity is observed with a
  • the example illustrates the preparation of a hydrogen fluoride-modified
  • This example illustrates the preparation of linear alkylbenzenes using a
  • dodecene (10 g) was injected into the flask and the solution allowed to reflux for 3
  • filtrate liquid flashed to remove unreacted benzene, and the bottoms liquid analyzed by
  • Alkylation was conducted in a process unit as shown in FIG. 1. Alkylation was conducted by first charging 500 ml of a benzene/paraffin
  • dehydrogenate mix (10:1 molar ratio, benzene/C 10 -C 14 olefin) to the reboiler and 250 cc
  • Example 9 the alkylation unit was charged with 250 cc of untreated, calcined,
  • the recovered mordenite showed by analysis: Acidity: 0.29 meq/g; H 2 O: 2.1%>
  • This example also illustrates the preparation of linear alkylbenzene from paraffin
  • the reboiler temperature was typically in the range of 122-188 ° C, the column
  • This example also illustrates the preparation of linear alkylbenzenes from
  • paraffin dehydrogenate using a hydrogen fluoride-treated mordenite catalyst.
  • glassware unit of FIG. 1 complete with catalyst column, reboiler, condenser and
  • the liquid feed comprised a benzene plus C 10 -C 14 paraffin dehydrogenate mix in a 5:1
  • paraffin dehydrogenate was conducted using the stainless-steel unit of FIG. 2, complete
  • Example B mordenite of Example B was charged to the column.
  • the liquid feed comprised benzene plus C 10 -C 14 paraffin dehydrogenate mix in a 10:1 molar ratio of benzene/C 10 -
  • the LHSV varied from 0.2 to 0.4 hr "1 .
  • Alkylation was conducted over a range of column and reboiler temperatures and
  • CBV-20A hydrogen fluoride-treated mordenite
  • Example B but having a much higher loading of HF (fluoride content 4.8%).
  • C12-Linear alkyltoluene is prepared by using mordenite, CBV20A, a
  • reaction was conducted in a 2L round-bottom flask equipped with a mechanical
  • ClO-linear alkyltoluene is prepared by using mordenite, CBV20A,
  • reaction apparatus is the same as the one used in
  • Example 10 above. About 50 grams of freshly calcined (1000° F) catalyst is stirred
  • Linear light alkyltoluene (LLAT) is prepared by using mordenite CBV20A
  • the reactor setup is the same as for Example 10 above. About 50 grams of
  • toluene azeotrope is removed to make the reaction completely anhydrous.
  • About 600 grams of a hydrocarbon mix containing about 10% olefins and 90 % paraffins is
  • reaction mixture is cooled, filtered, and the excess toluene is removed to obtain a
  • soap and detergent molecules including the LAB sulfonate materials of the prior art.
  • a chelating agent such as borax, zeolites, citric acid, or EDTA or one of its sodium
  • Krafft temperature which is in the range of between about 15°C to 30° C
  • isomer content in the range of between about 30.00% and 80.00 % have been observed
  • LAT materials is particularly dependent upon the alkyl chain length in the LAT
  • formulators may in many instances omit a chelating agent from their
  • blending and raw material quantities may be passed on to the public.
  • alkylbenzene sulfonates of this invention having a 2-phenyl isomer content of about

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Abstract

L'invention concerne des compositions détergentes qui utilisent des alkyltoluènes sulfonés comme agents tensio-actifs, les alkyltoluènes sulfonés présentant une teneur en isomères d'alkyltoluènes 2-phényle sulfonés supérieure à ce qu'on pouvait jusqu'alors trouver dans des tensio-actifs d'alkyltoluènes sulfonés existants. Les compositions de nettoyage selon l'invention sont plus efficaces comme agents nettoyants que leurs homologues déjà existants qui contiennent des alkyltoluènes sulfonés renfermant une plus faible concentration des isomères d'alkyltoluènes 2-phényle, du fait d'une augmentation inattendue de la tolérance à la dureté de l'eau de minéraux normalement associés à une précipation de l'agent détergent actif. L'invention concerne également des sels sulfonés solides d'alkyltoluènes, dont des formulations nettoyantes sèches contenant lesdits sels. Les alkyltoluènes peuvent être combinés à des tensio-actifs d'alkylbenzène pour produire des mélanges détergents présentant une meilleure résistance à la dureté de l'eau, une température de Krafft inférieure et une meilleure performance de nettoyage qu'il n'était jusqu'alors possible.
EP01971233A 2000-09-19 2001-09-19 Detergents de sulfonate d'alkyltoluene Withdrawn EP1322737A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US665642 1991-03-06
US09/665,642 US6995127B1 (en) 1996-02-08 2000-09-19 Alkyl toluene sulfonate detergent
PCT/US2001/029396 WO2002024845A2 (fr) 2000-09-19 2001-09-19 Detergents de sulfonate d'alkyltoluene

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EP1322737A2 true EP1322737A2 (fr) 2003-07-02

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EP (1) EP1322737A2 (fr)
KR (1) KR20040002842A (fr)
CN (1) CN1622990A (fr)
AU (1) AU2001291141A1 (fr)
CA (1) CA2422723A1 (fr)
MX (1) MXPA03002349A (fr)
NO (1) NO20031227L (fr)
WO (1) WO2002024845A2 (fr)
ZA (1) ZA200301979B (fr)

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US7090882B2 (en) 2003-06-12 2006-08-15 Cargill, Incorporated Antimicrobial salt solutions for food safety applications
CA2584152A1 (fr) * 2004-10-25 2006-05-04 Huntsman Petrochemical Corporation Detergents de carburant et d'huile
ES2378018T3 (es) † 2009-09-14 2012-04-04 The Procter & Gamble Company Composición detergente
CN102728202A (zh) * 2012-07-02 2012-10-17 长春市新瑞科贸有限责任公司 一种高效多元复合清塔剂
CA3041722A1 (fr) 2016-11-09 2018-05-17 Pepsico, Inc. Machines, procedes et systemes de fabrication de boisson gazeuse
JP7372921B2 (ja) * 2017-12-20 2023-11-01 ハンツマン ペトロケミカル エルエルシー 芳香族系ポリエーテルアミンアルコキシレート
CN113403150B (zh) * 2021-06-22 2022-07-05 河南省紫风养护发展有限公司 一种烟厂空调管道清理消杀方法
CN113861846B (zh) * 2021-10-18 2023-02-10 艾品美化妆品(上海)有限公司 一种机洗餐具催干剂及其制备方法

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ID26172A (id) * 1997-07-21 2000-11-30 Procter & Gamble Proses pembuatan surfaktan-surfaktan alkilbenzenasulfonat dan produk-produknya
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WO2000040551A1 (fr) * 1999-01-06 2000-07-13 The Procter & Gamble Company Procede de fabrication d'un tensioactif a base d'alkyl-benzene sulfonate lineaire et compositions de nettoyage contenant ces compositions
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Publication number Publication date
WO2002024845A3 (fr) 2002-07-11
NO20031227D0 (no) 2003-03-17
CN1622990A (zh) 2005-06-01
NO20031227L (no) 2003-05-08
ZA200301979B (en) 2004-04-08
CA2422723A1 (fr) 2002-03-28
WO2002024845A2 (fr) 2002-03-28
AU2001291141A1 (en) 2002-04-02
MXPA03002349A (es) 2003-10-15
KR20040002842A (ko) 2004-01-07

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