DE1200809B - Process for the production of chloromethanesulfonyl chloride - Google Patents

Process for the production of chloromethanesulfonyl chloride

Info

Publication number
DE1200809B
DE1200809B DEV24681A DEV0024681A DE1200809B DE 1200809 B DE1200809 B DE 1200809B DE V24681 A DEV24681 A DE V24681A DE V0024681 A DEV0024681 A DE V0024681A DE 1200809 B DE1200809 B DE 1200809B
Authority
DE
Germany
Prior art keywords
production
chloromethanesulfonyl chloride
chloride
mol
trithiane
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
DEV24681A
Other languages
German (de)
Inventor
Dr Zaki El-Hewehi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Filmfabrik Wolfen VEB
Original Assignee
Filmfabrik Wolfen VEB
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 Filmfabrik Wolfen VEB filed Critical Filmfabrik Wolfen VEB
Priority to DEV24681A priority Critical patent/DE1200809B/en
Publication of DE1200809B publication Critical patent/DE1200809B/en
Pending legal-status Critical Current

Links

Classifications

    • 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
    • C07C303/16—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 oxidation of thiols, sulfides, hydropolysulfides, or polysulfides with formation of sulfo or halosulfonyl groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von Chlormethansulfochlorid Es ist bekannt, durch Einleiten von Chlor in eine Suspension von s-Trithian (Trithioformaldehyd) in Wasser Chlormethansulfochlorid herzustellen (vgl.Process for the preparation of chloromethanesulfonyl chloride It is known by introducing chlorine into a suspension of s-trithiane (trithioformaldehyde) to produce chloromethanesulfonyl chloride in water (cf.

Journal of organic Chemistry« Bd. 5 [1940], S. 81; Bd. 14 [1949], S. 272 und die deutsche Patentschrift 836 492) entsprechend dem Schema C3HBS3 + 7 Cla + 5H2O 2 Cl-CH2SO2Cl + CH2O + S + 10 HC1 Dieses Verfahren ist unwirtschaftlich, weil das verwendete Chlor nur zum Teil zur Herstellung des gewünschten Produktes ausgenutzt wird, und außerdem zeitraubend, denn die Chlorierung erfordert eine geraume Zeit.Journal of Organic Chemistry "Vol. 5 [1940], p. 81; Vol. 14 [1949], P. 272 and the German patent specification 836 492) according to the scheme C3HBS3 + 7 Cla + 5H2O 2 Cl-CH2SO2Cl + CH2O + S + 10 HC1 This process is uneconomical, because the chlorine used is only partially used to produce the desired product is exploited, and also time consuming, because the chlorination requires a considerable amount of time Time.

Es wurde gefunden, daß man Chlormethansullochlorid in vorteilhafter Weise herstellen kann, indem man eine Suspension von s-Trithian in konzentrierter Salzsäure mit einem Alkalichlorat entweder in fester Form oder als wäßrige Lösung umsetzt. Vorzugsweise arbeitet man bei etwa +10° C. Das Chlormethansulfochlorid scheidet sich dabei als Ö1 ab und ist leicht durch Extraktion mit einem organischen Lösungsmittel, wie Methylenchlorid, Chloroform, Tetrachlorkohlenstoff, Ather oder Benzol, zu gewinnen. It has been found that chloromethanesullochloride is more advantageous Way can be prepared by making a suspension of s-trithiane in concentrated Hydrochloric acid with an alkali chlorate either in solid form or as an aqueous solution implements. It is preferable to work at about + 10 ° C. The chloromethanesulfonyl chloride separates out as oil and is easily extracted with an organic one Solvents such as methylene chloride, chloroform, carbon tetrachloride, ether or Benzene, to win.

Nach dem Auswaschen des Chiorwasserstoffes wird der das rohe Chlormethansulfochlorid enthaltende Extrakt entweder mit Trockenmitteln (z. B. Natriumsulfat) oder aber durch azeotrope Destillation getrocknet und anschließend destilliert.After washing out the hydrogen chloride, it becomes the crude chloromethanesulfonyl chloride containing extract either with desiccants (e.g. sodium sulfate) or else dried by azeotropic distillation and then distilled.

Beispiel 1 13,8 g (0,1 Mol) s-Trithian werden in 500 mol konzentrierter Salzsäure suspendiert. Unter Rühren und Wasserkühlung gibt man portionsweise 40,9 g (0,3 Mol) Kaliumchlorat hinzu, wobei sich das Reaktionsgemisch gelb färbt. Nach einiger Zeit scheidet sich ein gelbliches Ö1 ab. Das Rühren wird 5 Stunden fortgesetzt, danach wird mit Äther extrahiert, die Ätherschicht mit verdünnter Natriumbicarbonatlösung und anschließend mit Wasser gewaschen, über Natriumsulfat getrocknet und der Äther ab destilliert. Man erhält ein schwach gelbes Ö1, das bei Kr.15 = 700 C als farblose, stechend riechende Flüssigkeit übergeht. D. = = 1,638. Example 1 13.8 g (0.1 mol) of s-trithiane are concentrated in 500 mol Hydrochloric acid suspended. 40.9 are added in portions while stirring and cooling with water g (0.3 mol) of potassium chlorate are added, the reaction mixture turning yellow. To For some time a yellowish oil separates out. Stirring is continued for 5 hours, then it is extracted with ether, the ether layer with dilute sodium bicarbonate solution and then washed with water, dried over sodium sulfate and the ether distilled off. A pale yellow oil is obtained, which at Kr.15 = 700 C as a colorless, pungent smelling liquid passes over. D. = = 1.638.

Die Ausbeute beträgt 15,4 g (entsprechend 51,60/0 der Theorie, berechnet auf s-Trithian). The yield is 15.4 g (corresponding to 51.60 / 0 of theory, calculated on s-Trithian).

Beispiel 2 13,8 g (0,1 Mol) s-Trithian werden in 500 mol konzentrierter Salzsäure suspendiert, wonach unter Rühren 106,5 g (1 Mol) Natriumchlorat portionsweise zugegeben werden. Nach Sstündigem Rühren wird das ausgeschiedene Ö1 abgetrennt, die wäßrige Schicht mehrfach mit Benzol extrahiert. Die mit dem Ö1 vereinigten Auszüge werden dann mit Wasser und Natriumbicarbonatlösung säurefrei gewaschen und anschließend im Vakuum destilliert, wobei mit dem Benzol die enthaltene Feuchtigkeit azeotrop entfernt wird. Example 2 13.8 g (0.1 mol) of s-trithiane are concentrated in 500 mol Suspended hydrochloric acid, after which, with stirring, 106.5 g (1 mol) of sodium chlorate in portions be admitted. After stirring for an hour, the precipitated oil is separated off, the aqueous layer extracted several times with benzene. The extracts associated with the Ö1 are then washed acid-free with water and sodium bicarbonate solution and then distilled in vacuo, the moisture contained azeotropically with the benzene Will get removed.

Ausbeute: 18,4 g (entsprechend 61,7°/o der Theorie). Yield: 18.4 g (corresponding to 61.7% of theory).

Claims (1)

Patentanspruch: Verfahren zur Herstellung von Chlormethansulfochlorid, dadurchgekennzeichn et, daß man eine Suspension von s-Trithian in konzentrierter Salzsäure mit einem Alkalichlorat entweder in fester Form oder als wäßrige Lösung umsetzt. Claim: Process for the production of chloromethanesulfonyl chloride, durchgekennzeichn et that a suspension of s-trithiane in concentrated Hydrochloric acid with an alkali chlorate either in solid form or as an aqueous solution implements.
DEV24681A 1963-10-07 1963-10-07 Process for the production of chloromethanesulfonyl chloride Pending DE1200809B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEV24681A DE1200809B (en) 1963-10-07 1963-10-07 Process for the production of chloromethanesulfonyl chloride

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEV24681A DE1200809B (en) 1963-10-07 1963-10-07 Process for the production of chloromethanesulfonyl chloride

Publications (1)

Publication Number Publication Date
DE1200809B true DE1200809B (en) 1965-09-16

Family

ID=7581364

Family Applications (1)

Application Number Title Priority Date Filing Date
DEV24681A Pending DE1200809B (en) 1963-10-07 1963-10-07 Process for the production of chloromethanesulfonyl chloride

Country Status (1)

Country Link
DE (1) DE1200809B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000010966A1 (en) * 1998-08-25 2000-03-02 Degussa Aktiengesellschaft Method for the production of sulfonyl halogenides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000010966A1 (en) * 1998-08-25 2000-03-02 Degussa Aktiengesellschaft Method for the production of sulfonyl halogenides
US6291710B1 (en) 1998-08-25 2001-09-18 Degussa Ag Process for preparing sulfonyl halides

Similar Documents

Publication Publication Date Title
DE1200809B (en) Process for the production of chloromethanesulfonyl chloride
DE1227914B (en) Process for the preparation of 3- (1, 2-dithia-cyclopentyl) -5-pentanoic acid
DE1931486C3 (en) Process for the preparation of 1,4-diacetoxybutene- (2) from dichlorobutenes
DE962073C (en) Process for the production of 1,2-epoxycyclooctane
DE1291328B (en) Process for the production of propylene oxide
DE1170923B (en) Process for the preparation of 1, 2-dichloro-propanol- (3)
DE2011078B2 (en) Process for purifying hexetidine
DE896193C (en) Process for the production of ª ‡ -chloracrolein
DE2703640A1 (en) PROCESS FOR THE PRODUCTION OF AROMATIC METHYLENE DIOXY COMPOUNDS
DE2346317C3 (en) Process for the preparation of dinitroanthraquinones
DE942926C (en) Process for the production of 11ª ‡ -oxy-17ª ‡ -methyltestosterone or 11ª ‡ -oxy-10-normethyl-17ª ‡ -methyltestosterone
DE962162C (en) Process for the production of concentrated formic acid from its alkali salts
DE1189975B (en) Process for the preparation of beta, beta'-dicyandiaethyl ether
DE1909523C3 (en) Process for the production of benzoyl chloride and benzotrichloride
DE835139C (en) Process for the production of ª-chloro-ª-acetobutyrolactone
DE334298C (en) Process for the preparation of formic acid esters
AT89800B (en) Process for the concentration of aqueous acetic acids.
DE932612C (en) Process for the production of carbon tetrachloride
DE524435C (en) Process for the preparation of chloro-3-butanol-1 and its esters
DE708371C (en) Process for the production of chlorine or bromovinyl methyl ketone
AT235277B (en) Process for the preparation of 3- (1'-tetralyl) -propanol- (1)
DE368160C (en) Process for the production of sulfur chloride (S Cl)
DE604640C (en) Process for the production of vinyl esters
AT160457B (en) Process for the processing of used esterification baths.
DE1004155B (en) Process for the production of 1,4-dichlorobutane from 1,4-dioxybutane