WO2011107465A1 - Procédé pour la préparation d'acide 4-chlorobenzènesulfonique et de 4,4'-dichlorodiphénylsulfone - Google Patents

Procédé pour la préparation d'acide 4-chlorobenzènesulfonique et de 4,4'-dichlorodiphénylsulfone Download PDF

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Publication number
WO2011107465A1
WO2011107465A1 PCT/EP2011/053010 EP2011053010W WO2011107465A1 WO 2011107465 A1 WO2011107465 A1 WO 2011107465A1 EP 2011053010 W EP2011053010 W EP 2011053010W WO 2011107465 A1 WO2011107465 A1 WO 2011107465A1
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WO
WIPO (PCT)
Prior art keywords
acid
reaction
chlorobenzenesulfonic acid
dichlorodiphenyl sulfone
chlorobenzenesulfonic
Prior art date
Application number
PCT/EP2011/053010
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German (de)
English (en)
Inventor
Patrick Deck
Heiner Schelling
Florian Garlichs
Original Assignee
Basf Se
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 Basf Se filed Critical Basf Se
Priority to EP11708016A priority Critical patent/EP2542522A1/fr
Priority to BR112012021587A priority patent/BR112012021587A2/pt
Priority to KR1020127025928A priority patent/KR20130043620A/ko
Priority to JP2012555397A priority patent/JP2013521248A/ja
Priority to CN2011800124916A priority patent/CN102791679A/zh
Publication of WO2011107465A1 publication Critical patent/WO2011107465A1/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
    • C07C303/22—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 from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/39—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing halogen atoms bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings

Definitions

  • the invention relates to a process for the preparation of 4-chlorobenzenesulfonic acid from 2-chlorobenzenesulfonic acid and / or 3-chlorobenzenesulfonic acid comprising the reaction of 2-chlorobenzenesulfonic acid and / or 3-chlorobenzenesulfonic acid to 4-chlorobenzenesulfonic acid in the presence of sulfuric acid at a temperature of 100 to 300 ° C.
  • the present invention relates to a process for the preparation of 4,4'-dichlorodiphenyl sulfone comprising said process for the preparation of 4-chlorobenzenesulfonic acid.
  • 4,4'-dichlorodiphenyl sulfone is used in particular as a monomer in the synthesis of polyarylene ether sulfones.
  • polyether sulphone polymerization of 4,4'-dihydroxydiphenysulfone with 4,4'-dichlorodiphenyl sulfone
  • polysulfone polymerization of bisphenol A with 4,4'-dichlorodiphenyl sulfone
  • polyphenylene sulfone polymerization of 4,4 '. Dihydroxybiphenyl with 4,4'-dichlorodiphenyl sulfone).
  • 4,4'-dichlorodiphenyl sulfone is thus a central building block for the production of these engineering plastics.
  • Processes for the preparation of 4,4'-dichlorodiphenylsulfone are known in the art.
  • the known processes comprise, in particular, the preparation starting from monochlorobenzene and a sulfonating agent via 4-chlorobenzenesulfonic acid as intermediate, which is generally not isolated.
  • DE 2252571 describes the synthesis of dichlorodiphenyl sulfone from monochlorobenzene and sulfuric acid at temperatures of 220 to 260 ° C in a pressure reactor and with removal of the water of reaction formed.
  • No. 2,593,001 describes a continuous process for preparing diaryl sulfones by reacting aromatic sulfonic acids with aromatics, wherein the reaction water is continuously removed from the reaction zone by the aromatic compound added in countercurrent gas.
  • US 2,971,985 discloses the synthesis of dichlorodiphenyl sulfone using SO3, dimethyl sulfate and monochlorobenzene.
  • dichlorodiphenylsulfone isomers may e.g. be worked up by crystallization with / from alcohols, so as to obtain increased purities of the desired 4,4'-dichlorodiphenylsulfone.
  • EP-A 279387 this type of purification by recrystallization is described.
  • the unwanted isomers can be discarded after discharge from the process. This can be done by removing part of the mother liquor
  • the yield of the known processes for the preparation of 4,4'-dichlorodiphenyl sulfone should be increased by converting by-produced 2,4 'and / or 3,4'-dichlorodiphenyl sulfone into 4,4'-dichlorodiphenyl sulfone.
  • the process for the preparation of 4,4'-dichlorodiphenyl sulfone from monochlorobenzene comprises the process according to the invention for the preparation of 4-monochlorobenzenosulfonic acid from 2-chlorobenzenesulfonic acid and / or 3-chlorobenzenesulfonic acid.
  • the process according to the invention for the preparation of 4-monochlorobenzenesulfonic acid from 2-chlorobenzenesulfonic acid and / or 3-chlorobenzenesulfonic acid comprises the reaction of 2-chlorobenzenesulfonic acid and / or 3-chlorobenzenesulfonic acid to 4-chlorobenzenesulfonic acid in the presence of sulfuric acid at a temperature of 100 to 300 ° C.
  • Monochlorobenzenesulfonic acid can be present as 2-chlorobenzenesulfonic acid, 3-chlorobenzenesulfonic acid or 4-chlorobenzenesulfonic acid or as a mixture of two or three of the abovementioned compounds.
  • a mixture comprising at least two of the aforementioned isomers is referred to in the context of the present invention as the isomer mixture of monochlorobenzenesulfonic acid.
  • the present invention can be carried out starting from 2-chlorobenzenesulfonic acid or starting from 3-chlorobenzenesulfonic acid, the reaction starting from 2-chlorobenzenesulfonic acid being preferred.
  • the conducting the process starting from a mixture comprising 2-chlorobenzenesulfonic acid and 3-chlorobenzenesulfonic acid and optionally 4-chlorobenzenesulfonic acid, ie starting from an isomer mixture.
  • the process can also be carried out starting from a mixture of 4-chlorobenzenesulfonic acid on the one hand and 2-chlorobenzenesulfonic acid and / or 3-chlorobenzenesulfonic acid on the other hand.
  • Particularly preferred is the reaction starting from an isomeric mixture of monochlorobenzenesulfonic acid comprising 2-chlorobenzenesulfonic acid.
  • the reaction is carried out starting from an isomer mixture of monochlorobenzenesulfonic acid comprising 4-chlorobenzenesulfonic acid, this is carried out while increasing the proportion of 4-chlorobenzenesulfonic acid in the isomer mixture.
  • the temperature in the reaction of 100 to 300 ° C.
  • the temperature of the invention can be adjusted in different ways.
  • the starting compounds monochlorobenzenesulfonic acid and sulfuric acid can be mixed at the appropriate temperature.
  • Essential to the invention is the achievement of a temperature within the range of 100 to 300 ° C.
  • the temperature affects the selectivity and rate of formation of 4-chlorobenzenesulfonic acid.
  • the temperature of the reaction is preferably from 150 ° C to 250 ° C, in particular from 170 ° C to 210 ° C, particularly preferably from 180 to 200 ° C.
  • the selectivity of the formation of 4-chlorobenzenesulfonic acid is particularly high.
  • the speed of education is sufficiently high.
  • the duration of the reaction can vary over a long period of time.
  • the duration of the implementation is understood as the time within which the conditions according to the invention are fulfilled.
  • the period of the reaction is preferably from 5 minutes to 12 hours, especially from 15 minutes to 3 hours, more preferably from 30 minutes to 2 hours.
  • the amount of sulfuric acid used can vary over a wide range. However, it has proved advantageous with respect to the yield of 4-chlorobenzenesulfonic acid, if the molar ratio of sulfuric acid to monochlorobenzenesulfonic acid is at least 1.
  • the sulfuric acid is Nem molar ratio to the amount of monochlorobenzenesulfonic acid from 1 to 100, in particular from 2 to 20, particularly preferably from 3 to 15 used.
  • the concentration of the sulfuric acid used is preferably from 75 to 93% by weight, in particular from 80 to 90% by weight, particularly preferably from 83 to 87% by weight, based on the total weight of the sulfuric acid used. Compliance with these concentration ranges leads to a high yield of 4-chlorobenzenesulfonic acid and to a sufficiently high reaction rate.
  • the indication of the weight% of the sulfuric acid is to be understood in the usual way relative to the total weight of sulfuric acid and water contained in the sulfuric acid. The difference to 100 wt .-% thus comes from water whose presence in the specified range favors the formation of 4-chlorobenzenesulfonic acid.
  • reaction is carried out in the context of the process according to the invention in the sulfuric acid.
  • the reaction is carried out in liquid phase in sulfuric acid.
  • the reaction is carried out in the absence of other liquid compounds than the sulfuric acid and the starting compounds.
  • the reaction is preferably carried out with intensive mixing. Suitable methods of mixing are all customary processes, in particular stirring. The mixing can be carried out before and / or during the reaction. Furthermore, all processes known to those skilled in the art for carrying out reactions in the liquid phase are suitable for carrying out the reaction, the reaction conditions being taken into account with regard to the selection of the materials of a reactor. Preferred embodiments for carrying out the reaction are stirred tank reactors or static mixers with subsequent residence time reactor.
  • the described process for the preparation of 4-chlorobenzenesulfonic acid is integrated into a process for the preparation of 4,4'-dichlorodiphenyl sulfone starting from monochlorobenzene. This increases the yield of the process for producing 4,4'-dichlorodiphenyl sulfone.
  • an object of the present invention is a process for the preparation of 4,4'-dichlorodiphenyl sulfone starting from monochlorobenzene comprising the process according to the invention for the preparation of 4-chlorobenzenesulfonic acid. It may be all in the process for the preparation of 4-chlorobenzenesulfonic acid described preferred embodiments are advantageously integrated into the process for the preparation of 4,4'-dichlorodiphenylsulfone. All that is required is that the process for the preparation of 4,4'-dichlorodiphenyl sulfone via 4-chlorobenzenesulfonic acid proceeds as an intermediate.
  • the process for the preparation of 4,4'-dichlorodiphenyl sulfone comprises at least the following steps:
  • step (b) at least partial removal of 4,4'-dichlorodiphenyl sulfone from the mixture obtained in step (a), (c) cleavage of 2,4'-dichlorodiphenyl sulfone and / or 3,4'-dichlorodiphenyl sulfone and optionally 4,4'- Dichlorodiphenylsulfone in a mixture of isomers of Mobenlorbenzolsulfonkla in the presence of sulfuric acid,
  • step (d) simultaneously or subsequently reacting the isomer mixture obtained in step (c) from monochlorobenzenesulfonic acids to 4-chlorobenzenesulfonic acid according to the process of the invention for preparing 4-chlorobenzenesulfonic acid from 2-chlorobenzenesulfonic acid and / or 3-chlorobenzenesulfonic acid, and (e) at least partially Recycling of the 4- obtained in step (d)
  • Said step (a) relates to the reaction of monochlorobenzene to a mixture of 4,4'-dichlorodiphenyl sulfone and at least one compound selected from 2,4'-dichlorodiphenyl sulfone and 3,4'-dichlorodiphenyl sulfone.
  • Corresponding methods are known to the person skilled in the art.
  • the preparation of 4,4'-dichlorodiphenyl sulfone by reaction of 4-chlorobenzenesulfonic acid with monochlorobenzene in a countercurrent column, wherein the water of reaction is continuously stripped by the at the bottom of the column gaseously added aromatics overhead.
  • 4,4'-dichlorodiphenyl sulfone can be added at the top of the column 4- chlorobenzenesulfonic acid or sulfuric acid. The latter first reacts with monochlorobenzene in the column with monochlorobenzenesulfonic acid, which subsequently likewise reacts with monochlorobenzene to give dichlorodiphenylsulfone.
  • the preparation of dichlorodiphenyl sulfone is carried out using SO3, dimethyl sulfate and monochlorobenzene. It is first allowed to react at moderate conditions SO3 with dimethyl sulfate in a molar ratio of 2 to 1. Part of the SO3 reacts with dimethyl sulfate to the corresponding pyrosulfate. The remaining SO3 remains dissolved in the resulting liquid.
  • step (a) the work-up of the reaction product or of the reaction products can then optionally be carried out in a manner known to those skilled in the art. Working up is followed by the recovery and optionally purification of the product 4,4'-dichlorodiphenylsulfone understood. Corresponding methods depend on the manner in which step (a) is carried out and are likewise known to the person skilled in the art.
  • the separation of the reaction mixture is carried out by adding water and separating the two resulting liquid phases.
  • the aqueous phase contains unreacted monochlorobenzenesulfonic acids.
  • the water is evaporated off and the monochlorobenzenesulphonic acid recovered as starting material.
  • dichlorodiphenyl sulfone can then be isolated.
  • a corresponding method is described, for example, in US Pat. No. 4,937,387, the content of which is hereby fully incorporated by reference.
  • step (a) the separation of 4,4'-dichlorodiphenyl sulfone takes place.
  • Step (c) to (e) serve inter alia to increase the yield of step (a).
  • step (c) it is possible to separate in an intermediate step 2-chlorobenzenesulfonic acid, 3-chlorobenzenesulfonic acid and / or 4-chlorobenzenesulfonic acid and to feed only the incorrect isomers of 4,4'-dichlorodiphenyl sulfone to step (c) and to recycle the separated monochlorobenzenesulfonic acids in the process. turn.
  • step (b) and before carrying out step (c) the separation of chlorobenzene is preferably carried out.
  • Corresponding processes for the separation of chlorobenzene are known to the person skilled in the art, in which case the distillation is particularly suitable. In this way it can be prevented that as a result of the further reaction unwanted additional chlorobenzenesulfonic acid is formed from monochlorobenzene.
  • step (c) the cleavage of 2,4'-dichlorodiphenyl sulfone and / or 3,4'-dichlorodiphenyl sulfone in the presence of sulfuric acid to form an isomeric mixture of monochlorobenzenesulfonic acids.
  • the sulfuric acid used in step (c) has a concentration of 90 to 100 wt .-%, particularly preferably from 93 to 100 wt .-%, in particular from 94 to 98 wt .-%, most preferably 96 wt .-% based on the total weight of the sulfuric acid used.
  • the reaction is carried out in the sulfuric acid in the liquid phase.
  • step (c) can vary over a wide range. However, it is advantageous to carry out the cleavage with sulfuric acid at a temperature of at least 100 ° C, since the speed of the cleavage is otherwise too low. Preferably, step (c) is carried out at a temperature of 100 ° C to 300 ° C, especially from 140 ° C to 250 ° C, more preferably from 160 ° C to 230 ° C.
  • the duration of the reaction according to step (c) can vary over a wide period of time.
  • the duration of the implementation is understood as the time within which the conditions according to the invention are fulfilled.
  • the period of the reaction is preferably from 5 minutes to 12 hours, especially from 15 minutes to 3 hours, more preferably from 30 minutes to 2 hours.
  • the amount of sulfuric acid used can vary over a wide range. However, it has proved to be advantageous if the molar ratio of acid to dichlorodiphenyl sulfone is at least 1. Sulfuric acid is preferably used in a molar ratio to the amount of dichlorodiphenyl sulfone of from 1 to 100, in particular from 2 to 20, particularly preferably from 3 to 15.
  • the reaction of step (c) is preferably carried out with thorough mixing in suitable vessels and / or reactors. Corresponding methods are known to the person skilled in the art and are carried out under consideration of the present reaction conditions.
  • step (d) Simultaneously with or subsequent to step (c) takes place in the context of step (d), the inventive reaction of the isomer mixture to 4-chlorobenzenesulfonic acid.
  • step (d) the inventive reaction of the isomer mixture to 4-chlorobenzenesulfonic acid.
  • Corresponding embodiments have been described above. In principle, all embodiments designated as preferred may be used.
  • Step (d) is preferably carried out subsequent to step (c), adjusting the reaction conditions.
  • step (d) and step (c) simultaneously.
  • the conditions of step (c) are set in the latter case so that the process according to the invention for the preparation of 4-monochlorobenzenesulphonic acid is carried out simultaneously starting from 2-monochlorobenzenesulphonic acid and / or 3-monochlorobenzenesulphonic acid.
  • the skilled person will in this case choose the duration of the combined step (c) and (d), respectively, by adding the said preferred reaction times. Simultaneous performance of steps (c) and (d) is equivalent to sequential performance under identical conditions.
  • step (c) it is preferred to carry out first step (c) and then step (d), wherein the two steps differ in the reaction conditions.
  • step (d) then takes place by changing the reaction conditions.
  • step (c) there is thus a transition from step (c) to step (d) in that, starting from step (c), the desired conditions are adapted to the conditions required according to step (d).
  • the adaptation of the conditions preferably relates to the concentration of sulfuric acid which in step (d) is preferably from 80 to 90% by weight, in particular from 82 to 88% by weight, particularly preferably from 83 to 87% by weight.
  • the concentration of the sulfuric acid used in step (c) is preferably from 90 to 100% by weight, particularly preferably from 93 to 100% by weight, in particular from 94 to 97% by weight, very particularly preferably 96% by weight ,
  • the adjustment of the concentration of sulfuric acid is carried out in particular by dilution with water, d. H. Adding water.
  • step (c) it is also possible to isolate the reaction effluent resulting from step (c) and then use it in step (d). However, it is preferable to perform step (d) following step (c).
  • step (e) the at least partial recycling of the 4-chlorobenzenesulfonic acid obtained in step (d) is then preferably carried out after separation with renewed reaction in step (a).
  • the recovered 4-chloro Benzenesulfonic acid used to increase the yield of 4,4'-dichlorodiphenylsulfone.
  • the separation of 4-chlorobenzenesulfonic acid is preferably carried out by extraction or precipitation and more preferably by crystallization.
  • Comparative Example 1 1 g (3.5 mmol) of 2,4-dichlorodiphenyl sulfone was suspended in 10 ml (18.4 g, corresponding to 180 mmol) of concentrated sulfuric acid (96% by weight) and stirred at 170 ° C. for 3 h.

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

Abstract

L'invention concerne un procédé pour la préparation d'acide 4-chlorobenzènesulfonique à partir d'acide 2-chlorobenzènesulfonique et/ou d'acide 3-chlorobenzènesulfonique comprenant la transformation d'acide 2-chlorobenzènesulfonique et/ou d'acide 3-chlorobenzènesulfonique en acide 4-chlorobenzènesulfonique en présence d'acide sulfurique à une température de 100 à 300°C. De plus, la présente invention concerne un procédé pour la préparation de 4,4'-dichlorodiphénylsulfone comprenant le procédé mentionné pour la préparation d'acide 4-chlorobenzènesulfonique.
PCT/EP2011/053010 2010-03-05 2011-03-01 Procédé pour la préparation d'acide 4-chlorobenzènesulfonique et de 4,4'-dichlorodiphénylsulfone WO2011107465A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP11708016A EP2542522A1 (fr) 2010-03-05 2011-03-01 Procédé pour la préparation d'acide 4-chlorobenzènesulfonique et de 4,4'-dichlorodiphénylsulfone
BR112012021587A BR112012021587A2 (pt) 2010-03-05 2011-03-01 processo para preparar um composto
KR1020127025928A KR20130043620A (ko) 2010-03-05 2011-03-01 4-클로로벤젠술폰산 및 4,4''-디클로로디페닐술폰의 제조 방법
JP2012555397A JP2013521248A (ja) 2010-03-05 2011-03-01 ４−クロロベンゼンスルホン酸及び４，４’−ジクロロジフェニルスルホンの製造法
CN2011800124916A CN102791679A (zh) 2010-03-05 2011-03-01 制备4-氯苯磺酸和4,4’-二氯二苯砜的方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP10155591 2010-03-05
EP10155591.0 2010-03-05

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WO2011107465A1 true WO2011107465A1 (fr) 2011-09-09

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PCT/EP2011/053010 WO2011107465A1 (fr) 2010-03-05 2011-03-01 Procédé pour la préparation d'acide 4-chlorobenzènesulfonique et de 4,4'-dichlorodiphénylsulfone

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EP (1) EP2542522A1 (fr)
JP (1) JP2013521248A (fr)
KR (1) KR20130043620A (fr)
CN (1) CN102791679A (fr)
BR (1) BR112012021587A2 (fr)
WO (1) WO2011107465A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018024675A (ja) * 2011-12-15 2018-02-15 ソルベイ スペシャルティ ポリマーズ ユーエスエー， エルエルシー ジハロジアリールスルホンの異性体の混合物からハロアリール化合物を製造する方法
US10745348B2 (en) 2015-06-09 2020-08-18 Vertellus Holdings Llc Process for making diaryl sulfones

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US2593001A (en) 1950-01-31 1952-04-15 Stauffer Chemical Co Process for manufacture of a diphenyl sulfone
US2971985A (en) 1958-07-05 1961-02-14 Roussel Uclaf Process for the preparation of 4, 4'-dichlorodiphenylsulfone
DE2252571A1 (de) 1972-10-16 1974-05-09 Ici Ltd Verfahren zur herstellung von di-4-chlorphenylsulfon
EP0279387A1 (fr) 1987-02-17 1988-08-24 BASF Aktiengesellschaft Procédé pour la séparation de 4,4'-dichlorodiphénylsulfone
US4876390A (en) 1988-08-19 1989-10-24 Uop Process for separating dichlorodiphenylsulfone isomers
US4937387A (en) 1986-09-05 1990-06-26 Amoco Corporation Processes for preparing diaryl sulfones
EP0592875A1 (fr) * 1992-10-06 1994-04-20 Ube Industries, Ltd. Procédé de préparation de dichlorodiphénylsulfone

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US3632642A (en) * 1968-10-07 1972-01-04 Chris Craft Ind Inc Production of arylsulfonyl chlorides
DE3835562A1 (de) * 1988-10-19 1990-05-03 Basf Ag Verfahren zur herstellung von bis-(4-chlorphenyl)-sulfon
DE4234307A1 (de) * 1992-10-12 1994-04-14 Heidelberger Druckmasch Ag Einrichtung zur störungsfreien Produktförderung in Falzapparaten

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US2593001A (en) 1950-01-31 1952-04-15 Stauffer Chemical Co Process for manufacture of a diphenyl sulfone
US2971985A (en) 1958-07-05 1961-02-14 Roussel Uclaf Process for the preparation of 4, 4'-dichlorodiphenylsulfone
DE2252571A1 (de) 1972-10-16 1974-05-09 Ici Ltd Verfahren zur herstellung von di-4-chlorphenylsulfon
US4937387A (en) 1986-09-05 1990-06-26 Amoco Corporation Processes for preparing diaryl sulfones
EP0279387A1 (fr) 1987-02-17 1988-08-24 BASF Aktiengesellschaft Procédé pour la séparation de 4,4'-dichlorodiphénylsulfone
US4876390A (en) 1988-08-19 1989-10-24 Uop Process for separating dichlorodiphenylsulfone isomers
EP0592875A1 (fr) * 1992-10-06 1994-04-20 Ube Industries, Ltd. Procédé de préparation de dichlorodiphénylsulfone

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Title
E.N. KRYLOV ET AL.: "Hydrolysis of Aromatic Sulfonic Acids under Thermodynamic Control", JOURNAL OF ORGANIC CHEMISTRY OF USSR (ZHURNAL ORGANICHESKOI KHIMII), vol. 19, 1983, MAIK NAUKA, pages 1129 - 1133, XP008136364, ISSN: 0514-7492 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018024675A (ja) * 2011-12-15 2018-02-15 ソルベイ スペシャルティ ポリマーズ ユーエスエー， エルエルシー ジハロジアリールスルホンの異性体の混合物からハロアリール化合物を製造する方法
US10745348B2 (en) 2015-06-09 2020-08-18 Vertellus Holdings Llc Process for making diaryl sulfones

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JP2013521248A (ja) 2013-06-10
BR112012021587A2 (pt) 2016-09-13
CN102791679A (zh) 2012-11-21
EP2542522A1 (fr) 2013-01-09
KR20130043620A (ko) 2013-04-30

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