WO2020187893A1 - Procédé de production d'acide alcane sulfonique dans des conditions superacides - Google Patents

Procédé de production d'acide alcane sulfonique dans des conditions superacides Download PDF

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Publication number
WO2020187893A1
WO2020187893A1 PCT/EP2020/057245 EP2020057245W WO2020187893A1 WO 2020187893 A1 WO2020187893 A1 WO 2020187893A1 EP 2020057245 W EP2020057245 W EP 2020057245W WO 2020187893 A1 WO2020187893 A1 WO 2020187893A1
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Prior art keywords
solvent
alkane
acid
sulfonic acid
superacid
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PCT/EP2020/057245
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English (en)
Inventor
Timo Ott
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Basf Se
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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
    • C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
    • C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide

Definitions

  • the present invention refers to a method for the production of alkane sulfonic acid, in which SO 3 and an alkane are contacted with each other in the presence of a solvent, said solvent does constitute a superacid and the combination of said solvent with one or more of the reactants also gives rise to a superacid.
  • alkane sulfonic acids and especially methane sulfonic acid are known in the prior art.
  • Possible is the production of alkane sulfonic acids by direct sul- fonation of the alkane. This is already disclosed in US 2,493,038, where SO 3 and CH 4 are re acted in the presence of a sulfonation catalyst, which is a metal or sulfate of a metal in group II- B of the periodic table, particularly mercury.
  • a sulfonation catalyst which is a metal or sulfate of a metal in group II- B of the periodic table, particularly mercury.
  • a superacid is an acid with an acidity greater than that of 100% pure sulfuric acid, which has a Hammett acidity function (Ho) of -12.
  • a superacid is a medium in which the chemical potential of the proton is higher than in pure sulfuric acid. Consequently, the pK a value is negative.
  • the present application therefore provides for a method for producing alkane sulfonic acids in which SO 3 and an alkane are contacted with each other in the presence of a solvent, wherein said solvent does constitute a superacid and/or the combination of said solvent with SO 3 and/or the alkane sulfonic acid does give rise to a superacid,
  • a superacid is an acid with an acidity greater than that of 100% pure sulfuric acid, which has a Hammett acidity function (Ho) of -12.
  • a superacid is a medium in which the chemical potential of the proton is higher than in pure sulfuric acid. Consequently, the pK a value is negative.
  • the solvent alone or the combination of solvent and SO 3 or the combination of solvent and alkane sulfonic acid or the combination of solvent and SO 3 and alkane sulfonic acid constitutes a super acid, meaning that it has a pK a value of less than -3, i.e. , the pK a value is more negative.
  • the acidity is therefore of course higher.
  • the method is a method for the production of methane sulfonic acid.
  • the present invention provides for a method for manufacturing alkane sulfonic acids, especially methanesulfonic acid, comprising the following steps:
  • the solvent according to the present invention is selected such that the solvent alone does con stitute a super acid. It may be, that in the reactor, in which the educts and the solvent react with each other, the solvent and SO 3 react with each other in any kind, or interact with each other. Also, such a reaction or interaction of the solvent with SO 3 does give rise to a super acid ac cording to the present invention. The same is true for the combination of the solvent and the alkane sulfonic acid which is formed during the reaction in the reactor. Thus, the solvent alone does constitute a super acid. Also or alternatively, the combination of the solvent and SO 3 does give rise to a super acid. Further, the combination of the solvent and the alkane sulfonic acid does give rise to super acid.
  • the combination of the solvent with SO 3 and the alkane sul fonic acid does give rise to super acid within the meaning of the present invention. It is within the meaning of the present invention that as soon as either the solvent alone constitutes a su per acid or the solvent in combination with SO 3 or the solvent in combination with alkane sul fonic acid or the solvent in combination with SO 3 and alkane sulfonic acid gives rise to a super acid, the solvent is within the scope of the present claims.
  • a super acid is an acid with an acid strength stronger than that of pure H 2 SO 4 . Therefore, in the meaning of the present invention a super acid means an acid with a pK a value less than -3.
  • the method of the present invention is suitable to produce different kinds of alkane sulfonic ac ids.
  • the alkane which is used as educt and from which the respective alkane sulfonic acid is formed is a short chain methane with 1 to 10 C atoms which can be linear or non-linear.
  • the alkane is selected from methane, ethane, propane, butane, and pentane.
  • the alkane is methane so that the alkane sulfonic acid being formed according to the method of the present invention is methane sulfonic acid.
  • the reaction between SO 3 and the alkane in the present solvent usually takes place in a high- pressure autoclave.
  • the pressure at which SO 3 and alkane are contacted with each other is preferably in a range of from 1 bar to 200 bar, especially from 50 bar to 150 bar, preferably from 80 bar to 120 bar.
  • the temperature during the reaction is preferably within a range of from 0 °C to 100° C, espe cially from 15 °C to 80° C, especially preferred from 20 °C to 70° C, preferably from 35 °C to 60° C.
  • the temperature at which SO 3 and alkane are contacted with each other is below 70 °C, especially below 65 °C, preferably below 60 °C and especially pre ferred below 55 °C. If the temperature is around 0 °C or 10 °C, the reaction time increases tre mendously so that for an economically process the temperature is preferably 20 °C or above, especially 25 °C or above, especially preferred 30 °C or above.
  • the solvent used in a method according to the present invention is liquid under the respective conditions.
  • SO 3 is provided as liquid so it is homogenously distributed in the solvent.
  • the alkane is added either as a gas or as liquid depending on the length of the C chain.
  • a pressure reactor is therefore usually necessary.
  • a pressure reactor is sufficient.
  • gaseous alkanes for example methane
  • a pressure of 1 bar to 100 bar is set.
  • Solvents which preferably are used in the method of the present invention are selected from the group comprising fluoroantimonic acid, carborane acids, magic acid, fluorosulfuric acid, hydro gen fluoride, triflic acid, or mixtures of two or more of them. These solvents are all superacids.
  • a solvent constituting superacid conditions within the meaning of the present invention is also a combination of two or more solvents, wherein a first solvent does not constitute a superacid, but a second solvent constituting a superacid is added to said first solvent and the combination of said first and said second solvent give rise to a superacid.
  • Magic acid is a super acid consisting of a mixture most commonly in a 1 :1 molar ratio, of fluorosulfuric acid (HSO 3 F) and antimony pentafluoride (SbFs).
  • Fluoroantimonic acid is an inor ganic compound with the chemical formula FhFSbFe (also written H 2 F[SbFe], 2HF SbF 5 , or simply HF-SbF 5 ).
  • Fluorosulfuric acid (lUPAC name: sulfurofluoridic acid) is the inorganic compound with the chemical formula HSO 3 F.
  • Triflic acid also known as trifluoromethanesulfonic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF 3 SO 3 H.
  • the reaction speed is improved depending on the acidity of the solvent or the acidity of the reaction mixture.
  • the method of the present invention comprises the following steps: a. Providing sulfur trioxide SO 3 ;
  • a compound which initializes the reaction between SO 3 and the alkane at the described reaction conditions.
  • This compound may be provided in pure form or solved in a suitable solvent with the proviso that preferably this solvent again does not constitute a super acid and the combination of said solvent with SO 3 and/or the alkane sulfonic acid does not give rise to super acid. If this solvent does not constitute a superacid itself and/or in combination with SO 3 and/or alkane sulfonic acid, the amount of said solvent is to be controlled the conditions inside the reactor are still superacid.
  • this solvent is the same as used in the reaction as a whole. If such a compound is added, the initial molar ratio between this compound and SO3 is in the range of 1 :50 to 1 :10000, preferably 1 :100 to 1 :500, particularly 1 :150.
  • the compound added at step f) of the method according to the above preferred embodiment may be a compound being known to initialize the reaction between an alkane and SO 3 to form alkane sulfonic acid under super acid conditions. Therefore, the compound added at step f) is preferably selected from the group consisting of organic or inorganic peroxides being stable at room temperature, compounds with a heterogeneously or homogenously cleavable bond, stable cations as well as mixtures of two or more of them. Suitable compounds are for example dis- closed in PCT/EP2017/080495, EP 18157127.4, EP 18196493.3, EP 18196498.2, and EP 18196520.3, EP 18196520.3, the contents of which is enclosed herein in its entirety.
  • Higher alkyl group within the meaning of the present invention means an alkyl group with 1 to 10 carbon atoms.
  • ALK is methyl, ethyl, propyl, butyl, isopropyl or isobu tyl, especially methyl or ethyl, particularly methyl.
  • X is preferably hydrogen, alkali or alkaline earth metal. Particularly, X is hydrogen.
  • the compound added to initialize the reaction between SO 3 and alkane is CH 3 -SO 2 -O-O-H.
  • the compound added in step f) of the preferred embodiment is an organic peroxo- acid which, where appropriate, comprises functional groups.
  • the peroxoacid accord ing to the invention can be described by the formula R-O-O-H.
  • the peroxoacid comprises at least one organic peroxoacid of sulfur, phosphorus, silicon, boron, ni trogen or carbon. Any suitable peroxoacid of said elements can be used.
  • the peroxoacids are typically derived from the corresponding oxoacid of the respective element.
  • the peroxoacid group is selected from the group consisting of -SO2-O-O-X, -CO-O-O-X, -P0(0H)-0-0-X, PS(0H)-0-0-X, wherein X is H, Li, Na and/or K.
  • the organic peroxoacid comprises at least one additional functional group.
  • the additional functional group may particularly be selected from the group consisting of carbon double bonds, carbon triple bonds, aryl groups, heteroaryl groups and functional groups comprising heteroatoms, especially functional groups comprising O, S, N, P, Si, B, Se, Te, F, Cl, Br, I, Mg or Li atoms.
  • Particularly preferred are aryl groups, halogen atoms, such as F, Cl, Br, I, and siloxane groups.
  • the functional groups, particularly aryl groups may be further derivatized and may contain fur ther functional groups. Examples of functional groups according to the invention comprise par ticularly phenyl groups, carbonyl groups, ether groups, thioether groups, thioketone groups and halide groups.
  • Suitable organic peroxoacids according to the invention are peroxybenzoic acid and trifluoroperacetic acid. Any of the aforementioned examples may be derivatized and/or sub stituted with side chains, particularly with alkyl groups, aryl groups or halogen atoms.
  • the organic peroxoacid used as a catalyst according to the invention may be obtainable by a reaction of the corresponding oxoacid with a peroxide. More preferably, the peroxoacid may be obtainable by a reaction of the corresponding oxoacid with hydrogen peroxide or a salt thereof. Without the intention of being bound by theory, the reaction of an oxoacid with hydrogen perox ide can for example be described by
  • organic peroxoacid is used as compound, it is only suitable if it does not give rise to superacid conditions in the reactor at which the reaction takes place. This may be controlled by selecting the compound carefully or by using it in only small amounts.
  • the compound is an inorganic peroxoacid or a salt thereof, wherein the peroxoacid is stable at room temperature.
  • Stability at room temperature is particu larly to be understood as stability in a reaction solvent comprising sulfur trioxide and an alkane, especially methane. This solvent may be sulfuric acid.
  • the peroxoacid according to the inven tion must be stable enough in order to act as catalyst in the production of alkanesulfonic acids and not to decompose. Said decomposition may particularly take place by the release of reac tive oxygen species such as superoxide anions (O2-).
  • stability of the peroxoacid catalysts of the present invention for example means the absence of the release of reactive ox ygen species such as superoxide anions.
  • the peroxoacid comprises at least one peroxoacid of boron, silicon, phosphorus, carbon, nitrogen or sulfur. Any suitable peroxoacid of said elements can be used.
  • the peroxoacids are typically derived from the corresponding oxoacid of the respective ele ment.
  • the peroxoacid used as a catalyst according to the invention is obtainable by a reac tion of the corresponding oxoacid with a peroxide. More preferably, the peroxoacid is obtainable by a reaction of the corresponding oxoacid with hydrogen peroxide. Without the intention of be ing bound by theory, the reaction of an oxoacid with hydrogen peroxide can for example be de scribed by
  • the peroxoacid used according to the invention comprises a poly- protic acid.
  • the peroxoacid may consist of one or more polyprotic acids.
  • Said poly- protic peroxoacid comprises one or more peroxy groups, which can be described by -O-O-X, wherein X may be hydrogen and/or an alkaline and/or alkaline-earth metal. More preferably X is hydrogen, lithium, sodium and/or potassium. Most preferably, X is hydrogen.
  • the peroxoacid comprises one or more hydroxyl groups in addition to the one or more peroxy groups.
  • Said hydroxyl groups may be present in form of a salt, i.e., the groups can be described by -O-X, wherein X may be hydrogen, an alkaline metal and/or an alkaline-earth metal. Most preferably X is hydrogen.
  • X is hydrogen.
  • the replacement of hydrogen with an alkaline-(earth) metal may be particularly necessary to stabilize the peroxo acid as required by the invention.
  • the reaction product of phosphoric acid (H3PO4) with hydrogen peroxide is used as stable inorganic peroxoacid according to the invention.
  • H3PO4 phosphoric acid
  • H3BO3 reaction product of boric acid
  • KHSO5 potassium peroxomonosulfate
  • said preferred peroxoacids are particularly suita ble as catalyst in the preparation of alkanesulfonic acids from alkanes and sulfur trioxide.
  • inorganic peroxoacid is used as compound, it is only suitable if it does not give rise to superacid conditions in the reactor at which the reaction takes place. This may be controlled by selecting the compound carefully or by using it in only small amounts.
  • the compound is a compound comprising a heterolytically cleavable bond between an atom selected from the group consisting of nitrogen, phosphor sulfon oxygen and an atom selected from the group consisting of nitrogen, phosphor and sulfur.
  • a heterolytically cleavable bond in the sense of the present invention is especially a chemical bond -X-Y- between two atoms X and Y, which may be broken in such a way that the remain- ing fragments are not two radicals with unpaired electrons. Particularly, the electrons of the bond are unequally partitioned between atoms X and Y upon cleavage of the bond.
  • the atoms X and Y of the heterolytically cleavable bond may additionally be bound to the same or different radicals.
  • the bond between X and Y may be polarized. Polarization of the bond may enable or favor heterolytical cleavage of the bond.
  • Polarization may, for example, be accomplished by choosing two different elements for atoms X and Y, especially elements with different electro negativities. Polarization of the bond may also be accomplished by choosing different radicals, to which atoms X and Y are additionally bound. These measures may be combined, when X and Y are different and bound to at least two different additional radicals.
  • any com pound comprising heterolytically cleavable bonds in the aforementioned sense can be em ployed according to the invention. Such compounds are cheaply available from commercial dis tributors.
  • the heterolytically cleavable bond is a single bond or a double bond.
  • the heterolytically cleavable bond may also be a triple bond.
  • Particularly preferred are single bonds. If a double bond is cleaved, it could be that the bond is cleaved completely. Within the scope of the present invention it is also that a single bond remains and only one bond cleaves heterolytically. The same is of course true for the triple bond.
  • the bond is preferably heterolytically cleavable under acidic conditions. Particularly preferred are bonds, which are heterolytically cleavable under superacid conditions.
  • Heterolytic cleavage of the bond of the inventive catalyst preferably generates a cation and/or an anion. If the cleavage of the bond is catalyzed by an acid, particularly H + , the anion may for mally react with the acid upon cleavage. In this case, only a cation and a neutral compound are generated.
  • the compound, which is used as catalyst according to the invention is preferably selected from the group consisting of R 1 -N-N-R 2 , R 1 -N-0-R 2 ,
  • the atom X and/or the atom Y which form the heterolytically cleavable bond, may each be directly bound to an atom E selected from S, P, Si, B, N and C.
  • said atom may additionally be bound to up to three further radicals R 3 , R 4 and R 5 .
  • the place of the radicals R 3 , R 4 and R 5 can alternatively be filled with oxygen or sulphur atoms, which are double bonded to E, or groups YZ, which primarily corre spond to OH and SH groups and their derivates.
  • the inventive catalyst compound may there fore, for example, be a derivate of an oxoacid of sulfur, phosphorus, silicon, boron, nitrogen or carbon.
  • R 1 and/or R 2 are selected from the group consisting of -S0 2 -R 3 , -SO2OH, -CO-R 3 , -PO(OH)-R 3 ,
  • Each of the aforementioned radicals R 1 , R 2 , R 3 , R 4 and R 5 may preferably be individually select ed from the group consisting of alkyl radicals, alkyl radicals substituted with one or more func tional groups, siloxane radicals or any other suitable inorganic or organic radical.
  • Preferred alkyl radicals are branched or unbranched alkyl radicals with a carbon number of 1 to 20, especially 1 to 10, particularly methyl, ethyl, propyl, butyl, isopropyl, isobutyl or higher alkyl radicals.
  • the aforementioned additional functional groups may particularly be selected from the group consisting of carbon double bonds, carbon triple bonds, aryl groups, heteroaryl groups and functional groups comprising heteroatoms, especially functional groups comprising O, S, N, P, Si, B, Se, Te, F, Cl, Br, I, Mg or Li atoms.
  • aryl groups such as F, Cl, Br, I, and siloxane groups.
  • the functional groups, particularly aryl groups may be further derivatized and may contain fur ther functional groups.
  • Examples of functional groups according to the invention comprise par ticularly phenyl groups, carbonyl groups, ether groups, thioether groups, thioketone groups and halide groups.
  • the compound added in step f) of the preferred method is a cation being stable under super acid conditions. If the cation is stable, stability in this context means that it is able to react with the alkane but does not decompose within 24 h at room tem perature (20 °C), i.e. the half-life time ti/2 at room temperature is at least 24 h, preferably at least 30 h, especially at least 48 h.
  • Stable cations are formed prior to their use, i.e. prior to their addition into the reactor in which the reaction between alkane and sulfur trioxide takes place.
  • one type of cation is used alone and not together with another type of cation.
  • the cation is produced in situ during the production of the alkane sulfonic acid.
  • a compound is added to the reaction and the cation is formed according to the above shown reaction (R2).
  • Suitable compounds to be used are halogens, especially I2 and Br2, inter halogen compounds, especially l-Br, or solid elements of the 15 th or 16 th group of the peri odic table of elements, especially S, Se, Te, P, As, Sb.
  • halogens or interhalogens are used as compounds, the bond between the halogens breaks heterolytically. Iodine would thus react to HI and G, bromine to HBr and Br + , and the interhalo gen either to HI and Br + or to HBr and G.
  • the reactive cation would be G or Br + , which is formed in situ, and afterwards reacts with the alkane to the alkane cation as schematically shown above in (R1).
  • solid elements of the 15 th or 16 th group of the periodic table may form oligomer ic or polymeric cationic compounds, i.e., sulfur will form an oligomer S n -S + , wherein n may for example be in the range of from 0 to 10, preferably from 2 to 10, or in another range. Said S n -S + would be the reactive compound. Similar compounds may also occur with the other elements. Alternatively, they can form cations without polymerisation/oligomerisation. To sum up all possi ble cations of S, Se, Te, As, Sb and P, they are summarized with S + , Se + , Te + , As + , Sb + , and P + respectively. Additionally, also Silicon may be added to the reaction solution forming Si + as cati on.

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Abstract

La présente invention concerne un procédé de production d'acide alcane sulfonique, dans lequel du SO3 et un alcane sont mis en contact l'un avec l'autre en présence d'un solvant, ledit solvant ne constitue pas un superacide et la combinaison dudit solvant avec un ou plusieurs des réactifs donne également naissance à un superacide.
PCT/EP2020/057245 2019-03-21 2020-03-17 Procédé de production d'acide alcane sulfonique dans des conditions superacides WO2020187893A1 (fr)

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EP19164459 2019-03-21

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2493038A (en) 1946-05-31 1950-01-03 Houdry Process Corp Reaction of methane with sulfur trioxide
EP1558353B1 (fr) 2002-11-05 2016-06-15 Alan K. Richards Conversion anhydre de methane et d'autres alcanes legers en methanol et d'autres derives au moyen de trajets de radicaux et de reactions en chaine produisant un minimum de dechets
WO2018096138A1 (fr) * 2016-11-28 2018-05-31 Grillo-Werke Ag Sulfonation d'alcanes sans solvant
WO2018146153A1 (fr) 2017-02-07 2018-08-16 Grillo-Werke Ag Procédé de production d'acides alcanesulfoniques

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2493038A (en) 1946-05-31 1950-01-03 Houdry Process Corp Reaction of methane with sulfur trioxide
EP1558353B1 (fr) 2002-11-05 2016-06-15 Alan K. Richards Conversion anhydre de methane et d'autres alcanes legers en methanol et d'autres derives au moyen de trajets de radicaux et de reactions en chaine produisant un minimum de dechets
WO2018096138A1 (fr) * 2016-11-28 2018-05-31 Grillo-Werke Ag Sulfonation d'alcanes sans solvant
WO2018146153A1 (fr) 2017-02-07 2018-08-16 Grillo-Werke Ag Procédé de production d'acides alcanesulfoniques

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