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WO2009017497A2 - Procédé de fabrication d'un alkylaryl sulfonate synthétique - Google Patents

Procédé de fabrication d'un alkylaryl sulfonate synthétique Download PDF

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Publication number
WO2009017497A2
WO2009017497A2 PCT/US2007/074800 US2007074800W WO2009017497A2 WO 2009017497 A2 WO2009017497 A2 WO 2009017497A2 US 2007074800 W US2007074800 W US 2007074800W WO 2009017497 A2 WO2009017497 A2 WO 2009017497A2
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Prior art keywords
olefins
mixture
process according
aromatic compound
carbon atoms
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WO2009017497A3 (fr
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Curt B. Campbell
Gilles Sinquin
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Chevron Oronite Co LLC
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Chevron Oronite Co LLC
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Publication of WO2009017497A3 publication Critical patent/WO2009017497A3/fr
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    • 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
    • C07C303/14—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 sulfoxidation, i.e. by reaction with sulfur dioxide and oxygen with formation of sulfo or halosulfonyl groups

Definitions

  • the present invention is directed to a method of making a synthetic alkylaryl sulfonate that is derived by sulfonating an alkylated aromatic 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 wells.
  • the alkylated aromatic compound may be used as an enhanced oil recovery alkylate.
  • 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.
  • 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 aoubt 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 alkylben/cne 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 w herein the molar proportion of phenyl sulfonate substituent in position 1 or position 2 is between 0 and 13% and (b ⁇ 1 5 to 50% by weight of a heavy alkyl aryl sulfonate, wherein the aryl radical is phenyl or not. and the alkvl chains are either two linear alkyl chains with 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.
  • U.S. Patent No. 4,536.301 discloses a surfactant slug used to recover residual oil in subterranean reservoirs.
  • 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.
  • U.S. Patent No. 6,989,355 discloses an under-neutralized alkylxylene sulfonic acid composition for enhanced oil recovery processes.
  • This invention is also directed to a method for enhancing the recovery of oil from a subterranean reservoir which method employs the underncutralized alkylxylene sulfonic acid compositions of the present invention.
  • the under-neutralized alkylxylene sulfonic acid compositions are employed in an aqueous media.
  • the method optionally employs suitable co-surfactants, such as alcohols, alcohol ethers, polyalkylene glycols, poly (oxyalkylene)glycols and/or poly(oxyalkylene)glycol ethers.
  • the present invention is directed to a process for preparing a synthetic alkylaryl sulfonate comprising
  • the present invention relates to a process for preparing a sulfonated alkylated aromatic.
  • Figure 1 discloses the alkylation process employed in the manufacture of the synthetic alkylaryl sulfonate of 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 arc called mono-alkenes. and those with two double bonds are called dienes. alkyldienes. or diolefins. Alpha olefins are particularly reactive because the double bond is between the first and second carbons. Examples arc 1 -octene and 1 -octadecenc, 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 - The term “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.
  • a process for preparing a synthetic alkylaryl sulfonate comprising (a) reacting a first amount of at least one aromatic compound with a fist 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; (b) 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-alkyl substituted aromatic compound; (c) sulfonating the product of (b); and (d) neutralizing the product of (c) with a source of alkali or alkaline earth metal or ammonia.
  • 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., meta -, ortho- and para-), a raftlnatc of xylene isomerization, and mixtures thereof.
  • the at least one aromatic compound is ortho-xylene.
  • the al 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 isomerized 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 hydrotrcatcd prior to cracking. Other commercial sources include olefins derived from paraffin dehydrogenation and oligomerization of ethylene and other olefins, methanol-lo-olefin processes (methanol cracker) and the like.
  • the olefins may also be substituted with other functional groups, such as carboxylic acid groups, heteroatoms. and the like, provided that such groups do not react with the strong acid catalvst.
  • 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 comprises 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 monoolcfins (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. An especially preferred range is from about 14 to about 60.
  • the normal alpha olefins are isomerized 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 si/.e 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. MAPO-I 1 , S ⁇ PO-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 (Fe(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-substituted olefin, and vinylidene olefin) and branching content that the unisomerized 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-substituted 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 Hammctt acidity function is defined as:
  • 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 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- rcacted 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 wells.
  • 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 1 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 I 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 v ⁇ ell 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 lime 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.
  • a 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 zone or may be mixed prior to injection. Both single and multiple reaction zones 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 alkylation 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.
  • excess aromatic compounds can be separated, e.g. by distillation, and recycled to the reactor.
  • An intermediate product of the presently claimed invention is a tri-alkylsubstitutcd alkylated aromatic compound.
  • the resulting intermediate 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-alkylsubstituted aromatic compound.
  • the product prepared by the process described herein i.e., alkylated aromatic compound: 1.2.4 tri-alkylsubstitutcd alkylbenzene; 1 ,2.3 tri-alkylsubstitutcd alkylbenzene and mixtures thereof) is further reacted to form a sulfonate.
  • Sulfonation of the alkylaryl compound may then be performed by any method known to one of ordinary skill in the art.
  • the sulfonation reaction is typically carried out in a continuous falling film tubular reactor maintained at about 55°C.
  • the alkylaryl compound is placed in the reactor along with the sulfur Irioxide diluted with air, sulfuric acid, chlorosulfonic acid or sulfamic acid, thereby producing alkylaryl sulfonic acid.
  • the alkylaryl compound is sulfonated w ith sulfur trioxide diluted with air.
  • the charge mole ratio of sulfur trioxide to alkylate is maintained at about 0.8 to 1 .1 : 1 .
  • Neutralization of the alkylaryl sulfonic acid may be carried out in a continuous or batch process by any method known to a person skilled in the art to produce alkylaryl sulfonates.
  • an alkylaryl sulfonic acid is neutralized with a source of alkali or alkaline earth metal or ammonia.
  • the source is an alkali or alkaline earth metal; more preferably, the source is an alkaline earth metal hydroxide, such as but not limited to. calcium hydroxide or magnesium hydroxide.
  • 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 ( 1.1 5 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 ortho-xylene, normal alpha olefins (NAO) and HF could be fed to each reactor at a specified rate.
  • the CMR in Reactor is the cumulative ratio, which includes Reactor 1 reactants.
  • the olefin used to make this feed was a blend of commercial C 14 -C 30+ cuts. I he distribution of olefins in the feed is shown in Table 2. Table 2 Olefin Feedstock Distribution
  • 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.
  • Sulfonation of the alkylxylene was performed in a continuous falling film flow reactor by contacting the alkylxylene with a stream of air and sulfur trioxide.
  • the molar ratio of the alkylxylene to sulfur trioxide ranged from was about 1 .
  • Detailed values are given in Table 3.
  • the reactor jacket was maintained around 60°C.
  • the sulfonic acid product was titrated potentiometrically w ith a standardized cyclohexylamine solution to determine the weight percent of the sulfonic acid (as HSO 3 ) and the sul furic acid (H 2 SO 4 ) in the samples. Results are shown in fable 3.
  • alkyl ortho-xylene sulfonic acids were converted to their corresponding sodium salt by treatment with one equivalent of aqueous NaOH (50 % aqueous NaOH solution).
  • the salts were evaluated by the Fresh lnterfacial Tension (FIT) Method. This procedure was as follows: 1 ) A 3.0 wt% stock solution of alkyl ortho-xylene sodium sulfonate was prepared in distilled water;
  • the sodium sulfonate/co-solvent solutions were each placed in the capillary of a Temco Model 501 Tensiometer followed by approximately 2 ⁇ l of Minas crude oil (pre-heated so to be well above its Wax Appearance Temperature (WAT)). The samples were heated to 200°F, spun in the
  • fable 4 summarizes the FIT measurements of the alkyl ortho-xylene sodium sulfonates. Without surfactant, FIT measurements for Minas crude are on the order of 10-20 dynes/cm. FIT measurements for the alkyl ortho-xylene sodium sulfonates of this invention are all less than 0.01 dynes/cm. Such surfactants are considered to be useful in recovering oil in low salinity reservoirs. Optimal salinity is the salinity where the interfacial tension is lowest, which in Examples 4-7 is 0.2 % NaCl.
  • 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 absorbance 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 MHz 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 (WAI.T/-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 quarternary 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.

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Abstract

L'invention porte sur un procédé de préparation d'un sulfonate de pétrole synthétique 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, en présence d'un catalyseur acide fort, le produit résultant comprenant au moins environ 80 pour cent en poids d'un composé aromatique 1,2,4-trialkylsubstitué; (c) sulfoner le produit de (b); et (c) neutraliser le produit de (b) par un hydroxyde de métal alcalin ou alcalino-terreux ou de l'ammoniac.
PCT/US2007/074800 2007-07-31 2007-07-31 Procédé de fabrication d'un alkylaryl sulfonate synthétique Ceased WO2009017497A2 (fr)

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CN106166467A (zh) * 2015-05-22 2016-11-30 中国石油天然气股份有限公司 石油磺酸盐加碱装置及两段加碱的方法

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CN106166467A (zh) * 2015-05-22 2016-11-30 中国石油天然气股份有限公司 石油磺酸盐加碱装置及两段加碱的方法

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