WO2009017498A1 - Procédé de fabrication d'un composé alkylarylé synthétique - Google Patents

Procédé de fabrication d'un composé alkylarylé synthétique Download PDF

Info

Publication number
WO2009017498A1
WO2009017498A1 PCT/US2007/074842 US2007074842W WO2009017498A1 WO 2009017498 A1 WO2009017498 A1 WO 2009017498A1 US 2007074842 W US2007074842 W US 2007074842W WO 2009017498 A1 WO2009017498 A1 WO 2009017498A1
Authority
WO
WIPO (PCT)
Prior art keywords
olefins
mixture
process according
aromatic compound
carbon atoms
Prior art date
Application number
PCT/US2007/074842
Other languages
English (en)
Inventor
Curt B. Campbell
Gilles Sinquin
Original Assignee
Chevron Oronite Company 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
Application filed by Chevron Oronite Company Llc filed Critical Chevron Oronite Company Llc
Priority to PCT/US2007/074842 priority Critical patent/WO2009017498A1/fr
Publication of WO2009017498A1 publication Critical patent/WO2009017498A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
    • C07C2/66—Catalytic processes
    • C07C2/70—Catalytic processes with acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/08—Halides
    • C07C2527/12—Fluorides
    • C07C2527/1206—Hydrogen fluoride

Definitions

  • the present invention is directed to a method of making an alkylated aromatic (i.e.. alkylaryl) compound by reacting an aromatic compound with a mixture of olefins selected from olefins having from about 8 to about 100 carbon atoms in the presence of a strong acid catalyst, whereby the reaction takes place in two reactors in series.
  • the alkylated aromatic compound may be used as an enhanced oil recovery alkylate.
  • Mikulicz et al. U.S. Patent No. 4,225,737, discloses a process for the alkylation of an aromatic hydrocarbon with an olefin-acting alkylating agent.
  • the aromatic hydrocarbon is commingled with a first portion of said alkylating agent in a first alkylation reaction zone at alkylation reaction conditions in contact with a hydrofluoric acid catalyst.
  • Boney, U.S. Patent No. 3.953.538 discloses an alkylation process in which a stream of an olefinic material is mixed with an acid stream and polymerized to cause formationi of a polymeric diluent for the high strength acid which is initially charged to the alkylation process.
  • Mehlberg et al. U.S. Patent No. 5,750,818 discloses a process for the liquid phase alkylation in an alkylation reactor of a hydrocarbon substrate with an olefinic alkylating agent in the presence of an acid alkylation catalyst at least one hydrocarbon having a lower boiling point than the hydrocarbon substrate and with a substantial stoichiometric excess of the hydrocarbon substrate over the alkylating agent to form a liquid product mixture.
  • U.S. Patent No. 6.551.967 discloses a low overbased alkaline earth metal alkylaryl sulfonate having a Total Base Number of from about 2 to about 30, a dialkylate content of 0% to about 25% and a monoalkylate content of about 75% to about 90% or more, wherein the alkylaryl moiety is alkyltoluene or alkylbenzene in which the alkyl group is a C 15 -C 21 branched chain alkyl group derived from a propylene oligomer are useful as lubricating oil additives.
  • U.S. Patent No. 6,054.419 discloses a mixture of alkyl aryl sulfonates of superalkalinized alkaline earth metals comprising (a) 50 to 85% by weight of a mono alkyl phenyl sulfonate with a C 14 to C40 linear chain wherein the molar proportion of phenyl sulfonate substituent in position 1 or position 2 is between 0 and 13% and (b0 15 to 50% by weight of a heavy alkyl aryl sulfonate, wherein the aryl radical is phenyl or not. and the alkyl chains are either two linear alkyl chains w ith a total number of carbon atoms of 16 to 40. or one or a plurality of branched alkyl chains with on average a total number of carbon atoms of 15 to 48.
  • the slug comprises a mixture of ( 1 ) from about 1 to about 10% of a sulfonate of a mixture of mono- and dialkyl-substituted aromatic hydrocarbon which has been obtained by the alkylation of an aromatic hydrocarbon with an olefinic hydrocarbon in the presence of a hydrogen fluoride catalyst: (2) a lower alkyl alcohol which possesses from about 3 to about 6 carbon atoms; and (3) a nonionic cosurfactant comprising an ethoxylated n-alcohol which possesses from about 12 to about 15 carbon atoms.
  • the present invention is directed to a process for alkylating an aromatic compound comprising
  • the present invention relates to a process for alkylating an aromatic compound.
  • Figure 1 discloses the alkylation process employed in the present invention.
  • Olefins refers to a class of unsaturated aliphatic hydrocarbons having one or more carbon-carbon double bonds, obtained by a number of processes. Those containing one double bond are called mono-alkenes. and those with two double bonds arc called dicnes. alkyldienes. or diolefins. Alpha olefins are particularly reactive because the double bond is between the first and second carbons. Examples are 1 -octene and l -octadecene. which are used as the starting point for medium-biodegradable surfactants. Linear and branched olefins are also included in the definition of olefins.
  • Linear Olefins refers to olefins which are straight chain, non-branched hydrocarbons with at least one carbon-carbon double bond present in the chain.
  • Double-Bond Isomerized Linear Olefins refers to a class of linear olefins comprising more than 5% of olefins in which the carbon-carbon double bond is not terminal (i.e., the double bond is not located between the first and second carbon atoms of the chain).
  • Partially branched linear olefins refers to a class of linear olefins comprising less than one alkyl branch per straight chain containing the double bond, wherein the alkyl branch may be a methyl group or higher. Partially branched linear olefins may also contain double-bond isomerized olefin.
  • branched Olefins refers to a class of olefins comprising one or more alkyl branches per linear straight chain containing the double bond, wherein the alkyl branch may be a methyl group or higher.
  • an alkylated aromatic compound in one preferred embodiment, is a process for preparing an alkylated aromatic compound, wherein said process comprises (a) reacting a first amount of at least one aromatic compound with a first amount of a mixture of olefins selected from olefins having from about 8 to about 100 carbon atoms, in the presence of a strong acid catalyst; and reacting the product of (a) with an additional amount of at least one aromatic compound and an additional amount of strong acid catalyst and. optionally, with an additional amount of a mixture of olefins selected from olefins having from about 8 to about 100 carbon atoms, wherein the resulting product comprises at least about 85 weight percent of a 1 , 2. 4 tri-alkylsubstituted aromatic compound.
  • At least one aromatic compound or a mixture of aromatic compounds may be used for the alkylation reaction in the present invention.
  • the at least one aromatic compound or the aromatic compound mixture comprises at least one of monocyclic aromatics, such as benzene, toluene, xylene, cumene or mixtures thereof.
  • the at least one aromatic compound or aromatic compound mixture may also comprise bi-cyclic and poly-cyclic aromatic compounds, such as naphthalenes.
  • the at least one aromatic compound or aromatic compound mixture is xylene, including all isomers (i.e., mcta -, ortho- and para-), a raffinate of xylene isomeri/ation. and mixtures thereof.
  • the at least one aromatic compound is ortho-xylene.
  • the at least one aromatic compound or the mixture of aromatic compounds employed in the present invention is prepared by methods that are well known in the art.
  • the olefins employed in this invention may be linear, isomerized linear, branched or partially branched linear.
  • the olefin may be a mixture of linear olefins, a mixture of isomerizcd linear olefins, a mixture of branched olefins, a mixture of partially branched linear or a mixture of any of the foregoing.
  • the olefins may be derived from a variety of sources. Such sources include the normal alpha olefins, linear alpha olefins, isomerized linear alpha olefins, dimerized and oligomerized olefins, and olefins derived from olefin metathesis. Another source from which the olefins may be derived is through cracking of petroleum or Fischer-Tropsch wax. The Fischer-Tropsch wax may be hydrotreated prior to cracking. Other commercial sources include olefins derived from paraffin dehydrogenation and oligomerization of ethylene and other olefins, mcthanol-to-olefin processes (methanol cracker) and the like.
  • the olefins may also be substituted with other functional groups, such as carboxylic acid groups, hcteroatoms, and the like, provided that such groups do not react with the strong acid catalyst.
  • the mixture of olefins is selected from olefins with carbon numbers ranging from about 8 carbon atoms to about 100 carbon atoms.
  • the mixture of olefins is selected from olefins with carbon numbers ranging from about 10 to about 80 carbon atoms, more preferred from about 14 to about 60 carbon atoms.
  • the mixture of olefins is selected from linear alpha olefins or isomerized olefins containing from about 8 to about 100 carbon atoms. More preferably, the mixture of olefins is selected from linear alpha olefins or isomerized olefins containing from about 10 to about 80 carbon atoms. Most preferably, the mixture of olefins is selected from linear alpha olefins or isomerized olefins containing from about 14 to about 60 carbon atoms.
  • the mixture of olefins contains a distribution of carbon atoms that comprise from about 40 to about 90 percent C 12 to C 20 and from about 4 percent to about 15 percent C 32 to C 58 . More preferably, the distribution of carbon atoms comprises from about 50 to about 80 percent C 12 to C 20 and from about 4 percent to about 15 percent C 32 to C 58 .
  • the mixture of branched olefins is preferably selected from polyolefins which may be derived from C 3 or higher monoolefins (i.e., propylene oligomers, butylenes oligomers, or co-oligomers etc.).
  • the mixture of branched olefins is either propylene oligomers or butylenes oligomers or mixtures thereof.
  • the mixture of linear olefins that may be used for the alkylation reaction is a mixture of normal alpha olefins selected from olefins having from about 8 to about 100 carbon atoms per molecule. More preferably the normal alpha olefin mixture is selected from olefins having from about 10 to about 80 carbon atoms per molecule. Most preferably, the normal alpha olefin mixture is selected from olefins having from about 12 to about 60 carbon atoms per molecule. ⁇ n especially preferred range is from about 14 to about 60.
  • the normal alpha olefins are isomerizcd using at least one of two types of acidic catalysts, solid or liquid.
  • a solid catalyst preferably has at least one metal oxide and an average pore size of less than 5.5 angstroms. More preferably, the solid catalyst is a molecular sieve with a one- dimensional pore system, such as SM-3. M ⁇ PO- 1 1. SAPO-1 1 , SSZ-32, ZSM-23, MAPO-39, SAPO-39, ZSM-22 or SSZ-20.
  • Other possible acidic solid catalysts useful for isomerization include ZSM-35, SUZ-4, NU-23, NU-87 and natural or synthetic ferrierites.
  • a liquid type of isomerization catalyst that can be used is iron pentacarbonyl (Fc(CO) 5 ).
  • the process for isomerization of normal alpha olefins may be carried out in batch or continuous mode.
  • the process temperatures may range from about 50°C to about 250°C.
  • a typical method used is a stirred autoclave or glass flask, which may be heated to the desired reaction temperature.
  • a continuous process is most efficiently carried out in a fixed bed process. Space rates in a fixed bed process can range from 0.1 to 10 or more weight hourly space velocity.
  • the isomerization catalyst is charged to the reactor and activated or dried at a temperature of at least 150°C under vacuum or flowing inert, dry gas. After activation, the temperature of the isomerization catalyst is adjusted to the desired reaction temperature and a flow of the olefin is introduced into the reactor. The reactor effluent containing the partially-branched, isomerized olefins is collected.
  • the resulting partially- branched, isomerized olefins contain a different olefin distribution (i.e., alpha olefin, beta olefin; internal olefin, tri-subslituted olefin, and vinylidene olefin) and branching content that the unisomerizcd olefin and conditions are selected in order to obtain the desired olefin distribution and the degree of branching.
  • olefin distribution i.e., alpha olefin, beta olefin; internal olefin, tri-subslituted olefin, and vinylidene olefin
  • the alkylated aromatic compound may be prepared using strong acid catalysts (Bronsted or Lewis acids).
  • strong acid refers to an acid having a pK a of less than about 4.
  • strong acid is also meant to include mineral acids stronger than hydrochloric acid and organic acids having a Hammett acidity value of at least minus 10 or lower, preferably at least minus 12 or lower, under the same conditions employed in context with the herein described invention.
  • the I lammett acidity function is defined as: where B is the base and BH its protonated form.
  • pK BH is the dissociation constant of the conjugate acid and BH 7B is the ionization ratio; lower negative values of H o correspond to greater acid strength.
  • the strong acid catalyst is selected from a group consisting of hydrochloric acid, hydrofluoric acid, hydrobromic acid, sulfuric acid, perchloric acid, trifluoromethane sulfonic acid, fluorosulfonic acid, and nitric acid. Most preferred, the strong acid catalyst is hydrofluoric acid.
  • the alkylation process may be carried out in a batch or continuous process.
  • the strong acid catalyst may be recycled when used in a continuous process.
  • the strong acid catalyst may be recycled or regenerated when used in a batch process or a continuous process.
  • the strong acid catalyst may be regenerated after it becomes deactivated (i.e.. the catalyst has lost all or some portion of its catalytic activity). Methods that are well known in the art may be used to regenerate the deactivated hydrofluoric acid catalyst.
  • the alkylation process is carried out by reacting a first amount of at least one aromatic compound or a mixture of aromatic compounds with a first amount of a mixture of olefin compounds in the presence of a strong acid catalyst, such as hydrofluoric acid, in a first reactor in which agitation is maintained, thereby producing a first reaction mixture.
  • a strong acid catalyst such as hydrofluoric acid
  • the resulting first reaction mixture is held in a first alkylation /one under alkylation conditions for a time sufficient to convert the olefin to aromatic alkylate (i.e., a first reaction product).
  • the first reaction product is removed from the alkylation zone and fed to a second reactor wherein the first reaction product is reacted with an additional amount of at least one aromatic compound or a mixture of aromatic compounds and an additional amount of strong acid catalyst and, optionally, with an additional amount of a mixture of olefin compounds, wherein agitation is maintained.
  • a second reaction mixture results and is held in a second alkylation zone under alkylation conditions for a time sufficient to convert the olefin to aromatic alkylate (i.e., a second reaction product).
  • the second reaction product is fed to a liquid-liquid separator to allow hydrocarbon (i.e., organic) products to separate from the strong acid catalyst.
  • the strong acid catalyst may be recycled to the reactor(s) in a closed loop cycle.
  • the hydrocarbon product is further treated to remove excess un-reacted aromatic compounds and, optionally, olefinic compounds from the desired alkylate product.
  • the excess aromatic compounds may also be recycled to the reactor(s).
  • the reaction takes place in more than two reactors which are located in series.
  • the second reaction product is fed to a third reactor wherein the second reaction product is reacted with an additional amount of at least one aromatic compound or a mixture of aromatic compounds and an additional amount of strong acid catalyst and, optionally, with an additional amount of a mixture of olefin compounds, wherein agitation is maintained.
  • a third reaction mixture results and is held in a third alkylation zone under alkylation conditions for a time sufficient to convert the olefin to aromatic alkylate (i.e., a third reaction product).
  • the reactions take place in as many reactors as necessary to obtain the desired alkylated aromatic reaction product.
  • the total charge mole ratio of hydrofluoric acid to the mixture of olefin compounds is about 1.0 to 1 for the combined reactors.
  • the charge mole ratio of hydrofluoric acid to the mixture of olefin compounds is no more than about 0.7 to 1 in the first reactor and no less than about 0.3 to I in the second reactor.
  • the total charge mole ratio of the aromatic compound to the mixture of olefin compounds is about 7.5 to 1 for the combined reactors.
  • the charge mole ratio of the aromatic compound to the mixture of olefin compounds is no less than about 1 .4 to 1 in the first reactor and is no more than about 6.1 to 1 in the second reactor.
  • reactor configurations may be used for the reactor zone. These include, but are not limited to. batch and continuous stirred tank reactors, reactor riser configurations, ebulating bed reactors, and other reactor configurations that are well known in the art. Many such reactors are known to those skilled in the art and are suitable for the alkylation reaction. Agitation is critical for the alkylation reaction and can be provided by rotating impellers, with or without baffles, static mixers, kinetic mixing in risers, or any other agitation devices that are well known in the art.
  • the alkylation process may be carried out at temperatures from about 0°C to about 100°C.
  • the process is carried out under sufficient pressure that a substantial portion of the feed components remain in the liquid phase.
  • a pressure of 0 to 150 psig is satisfactory to maintain feed and products in the liquid phase.
  • the residence time in the reactor is a time that is sufficient to convert a substantial portion of the olefin to alkylate product.
  • the time required is from about 30 seconds to about 30 minutes. ⁇ more precise residence time may be determined by those skilled in the art using batch stirred tank reactors to measure the kinetics of the alkylation process.
  • the at least one aromatic compound or mixture of aromatic compounds and the mixture of olefins may be injected separately into the reaction /one or may be mixed prior to injection. Both single and multiple reaction /ones may be used with the injection of the aromatic compounds and the mixture of olefins into one, several, or all reaction zones. The reaction zones need not be maintained at the same process conditions.
  • the hydrocarbon feed for the alkylalion process may comprise a mixture of aromatic compounds and a mixture olefins in which the molar ratio of aromatic compounds to olefins is from about 0.5: 1 to about 50: 1 or more.
  • the molar ratio of aromatic compounds to olefin is > 1.0 to 1
  • an excess of aromatic compounds is used to increase reaction rate and improve product selectivity.
  • the excess un-rcactcd aromatic in the reactor effluent can be separated, e.g. by distillation, and recycled to the reactor.
  • the product of the presently claimed invention is a tri-alkylsubstitutcd alkylated aromatic compound.
  • the resulting product comprises at least about 80 weight percent of a 1 , 2. 4 tri-alkylsubstituted aromatic compound. More preferred, the resulting product comprises at least about 85 weight percent, even more preferred at least about 90 weight percent of a 1 , 2, 4 tri-alkylsubstitutcd aromatic compound.
  • the alkylated ortho-xylenes of Examples 1 -3 were prepared in a continuous alkylation pilot plant using hydrofluoric acid (HF) in which two alkylation reactors ( 1. 15 liter volume each) were in series followed by a 25 liter settler to separate the organic phase from the HF phase. All equipment was maintained under a pressure of 5 bar and the reactors and settler were jacketed to allow temperature control.
  • the alkylation reactors were configured such that the orlho-xylene, normal alpha olefins (NAO) and HF could be fed to each reactor at a specified rate.
  • NAO normal alpha olefins
  • the organic phase was removed through a valve and allowed to expand to atmospheric pressure.
  • the HF acid phase was separated and neutralized with caustic.
  • the resulting organic phase was then distilled under vacuum to remove the excess ortho-xylene.
  • the olefin used to make this feed was a blend of commercial C 14 -C 30+ cuts.
  • the distribution of olefins in the feed is shown in Table A.
  • the feed mixture was stored under dry nitrogen during use. Because of the waxy nature of the alpha olefin, the alkylation feed mixture was heated to 50°C to keep all the olefin in solution. O-Xylene was also stored under dry nitrogen during use.
  • Table I summarizes the HF alkylation conditions for Examples 1 -3 and the aromatic alkylates' chemical properties.
  • the infrared spectrum of a sample of alkylated ortho-xylene product was obtained using an infrared spectrometer (Thermo model 4700) equipped with a rebounce diamond attenuated reflectance cell.
  • the absorbancc spectrum of the sample between 600 and 1000 cm-1 was displayed and the peaks at about 780. 820, and 880 cm-1 were integrated.
  • the relative percentage area of each peak was calculated and the percent 1. 2, 3 - alkyl aromatic content is represented by the relative area percentage of the 780 cm " 1 peak.
  • Quantitative 13 C NMR spectra were obtained on a 300 Ml Iz Varian Gemini NMR (75 MHz carbon) using about 1 .0 g of sample dissolved in about 3.0 mL of 0.5 M chromium (acac) 3 in chloroform-d contained in a 10 mm NMR tube.
  • the transmitter pulse sequence (delay (2.2 s).
  • 90 pulse acquisition (0.853 s) was employed with the decoupler (WALTZ- 16) gated off during the delay and on during acquisition.
  • the relaxation delay was always more than four times the longest Tl . We believe this is sufficient to allow residual NOE to die away between pulse excitations even though the decoupler duty cycle is above the recommended 5- 10% range for quantitative experiments. Integration of the 13 C NMR spectrum was carried out with no base-line correction.
  • the integrated peak intensity for the quartcmary carbons (Q) on the aromatic ring carbons substituted with the long chaing alkyl group and the methane (benzylic) carbons (M) of the long chain alkyl groups where the long chain alkyl group is attached to the aromatic ring are used to calculate the percent alkyl attachment position.
  • the integrals for each aromatic carbon is the same. Sum the integrals for each of the Q and M peaks and calculate the percentage attachment from both the aromatic quarternary (Q) and aliphatic methine (M) integrals of the assigned peaks. For example, the amount of 2-attachment from the integration of the aromatic quaternary carbons would equal the integral for the 145.475 ppm signal divided by the total of the integrals for the 145.475 ppm peak plus the integral for the 143.502 ppm peak plus the integral for the 143.86 ppm peak.
  • the aliphatic methine carbons provide the 2-. 3-, 4-, and >4- alkyl attachment while the aromatic quaternary carbons provide only the 2-. 3-. and 4- alkyl attachment values. The attachment values determined by the aliphatic methine and the aromatic quaternary carbons agree reasonably well.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention porte sur un procédé d'alkylation d'un composé aromatique comprenant les opérations consistant à : (a) la faire réagir une première quantité d'au moins un composé aromatique avec une première quantité d'un mélange d'oléfines ayant d'environ 8 à environ 100 atomes de carbone, en présence d'un catalyseur acide fort ; (b) faire réagir le produit de (a) avec une quantité supplémentaire d'au moins un composé aromatique et d'une quantité supplémentaire d'un catalyseur acide fort et, facultativement, avec une quantité supplémentaire d'un mélange d'oléfines choisies parmi les oléfines ayant d'environ 8 à environ 100 atomes de carbone, le produit résultant comprenant au moins environ 8 à au moins environ 100 atomes de carbone, au moins environ 80 pour cent en poids d'un composé aromatique 1,2,4-trialkylsubstitué.
PCT/US2007/074842 2007-07-31 2007-07-31 Procédé de fabrication d'un composé alkylarylé synthétique WO2009017498A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/US2007/074842 WO2009017498A1 (fr) 2007-07-31 2007-07-31 Procédé de fabrication d'un composé alkylarylé synthétique

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2007/074842 WO2009017498A1 (fr) 2007-07-31 2007-07-31 Procédé de fabrication d'un composé alkylarylé synthétique

Publications (1)

Publication Number Publication Date
WO2009017498A1 true WO2009017498A1 (fr) 2009-02-05

Family

ID=40304593

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2007/074842 WO2009017498A1 (fr) 2007-07-31 2007-07-31 Procédé de fabrication d'un composé alkylarylé synthétique

Country Status (1)

Country Link
WO (1) WO2009017498A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4225737A (en) * 1979-04-23 1980-09-30 Uop Inc. Alkylation process
US20070142665A1 (en) * 2005-12-21 2007-06-21 Chevron Oronite Company Llc Method of making a synthetic petroleum sulfonate

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4225737A (en) * 1979-04-23 1980-09-30 Uop Inc. Alkylation process
US20070142665A1 (en) * 2005-12-21 2007-06-21 Chevron Oronite Company Llc Method of making a synthetic petroleum sulfonate

Similar Documents

Publication Publication Date Title
AU2006327205B2 (en) A method of making an alkylated aromatic using acidic ionic liquid catalyst
US7449596B2 (en) Method of making a synthetic petroleum sulfonate
US7732651B2 (en) Method of making an alkylated aromoatic using acidic ionic liquid catalyst
US20090163669A1 (en) Method of making a synthetic alkylaryl sulfonate
US7495140B2 (en) Method of making a synthetic alkylaryl compound
US7964745B2 (en) Method of making a synthetic alkylaryl sulfonate
CA2780903A1 (fr) Procede de fabrication d'un alkylaryl sulfonate synthetique
US8148591B2 (en) Method of making a synthetic alkylaryl compound
WO2009017498A1 (fr) Procédé de fabrication d'un composé alkylarylé synthétique
WO2009017497A2 (fr) Procédé de fabrication d'un alkylaryl sulfonate synthétique
WO2002074720A2 (fr) Procede de mono-alkylation permettant de preparer des tensioactifs anioniques

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 07799934

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 07799934

Country of ref document: EP

Kind code of ref document: A1