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DE405384C - Process for the preparation of dipolyoxyalkyl ethers of dithioalkylenes - Google Patents

Process for the preparation of dipolyoxyalkyl ethers of dithioalkylenes

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Publication number
DE405384C
DE405384C DEF51543D DEF0051543D DE405384C DE 405384 C DE405384 C DE 405384C DE F51543 D DEF51543 D DE F51543D DE F0051543 D DEF0051543 D DE F0051543D DE 405384 C DE405384 C DE 405384C
Authority
DE
Germany
Prior art keywords
dithioalkylenes
ethers
dipolyoxyalkyl
preparation
fuel
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.)
Expired
Application number
DEF51543D
Other languages
German (de)
Inventor
Dr Carl Josef Muller
Dr Karl Thiess
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.)
Hoechst AG
Original Assignee
Hoechst AG
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 Hoechst AG filed Critical Hoechst AG
Priority to DEF51543D priority Critical patent/DE405384C/en
Application granted granted Critical
Publication of DE405384C publication Critical patent/DE405384C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups

Landscapes

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

Description

Verfahren zur Darstellung von Dipolyoxyalkyläthern der Dithioalkylene. Es wurde gefunden, daß die bisher un- bekannten 1)iliolvotyalkvläther der Dithio- , alkvIene der allreineinen Formel R-S-Rr-S z. BÄthvlendithiodiglykol, leicht herstel-lbRa=r sind durch Einwirkung der Alkvien<iinierkap- tane auf die Chlorlivdrine mehrwertiger Alkohole oder der llerkaptane mehr-,vertiger Alkohole auf die Alkvlendihalogenide. In dieser Formel soll kennzeichnen: IZ und R_ den Rest eines mehrwertigen aliphatischen Alkohols und R1 eine Alkylengruppe, wie z. B. -CH4--, -CH., - CH.,- usw, Die Reak- tion wird zweckmäßig unter Verwendung der Salze, z. B. \atriumsalze der llerkaptane, durchgeführt. Die hier gekennzeichneten Dipolvoxyalkvläther können als Lösungs- mittel für Farbstoffe usw. oder als Weich- rnachungsmittel Verwendung finden. Beispiele. r. i Mol. Äthvlenchlorid wird irn gleichen Gewicht Sprit gelöst und bei 5o bis 6o° mit einer alkoholischen Lösung von 4. 1lol. ha- litrrrrsulfh_vdrat versetzt und bis zur Beendi- aung der Reaktion zum Sieden erhitzt (vgl. Berichte 2o, 46o). Sodann -,werden 2 1101. reines :@tlivlenchlorhvdrin nach und nach zu- gegeben und nach ungefähr ''- Stunde auf dem Dainpfhade erwärmt. Das au.-eschiedene haliumchlorid wird abfiltriert und der Sprit a l> lestillic#rt. \aclinoclirnali"erI3eliztrr,lltiri#,niit Sprit hinterhleibt das -@thvlendithiodiglvlcc (OHCH=-CH,- S-CH.-CH= S-CH_-CH.- OH als klares (5l, das in Sprit leicht, in Rasse ziemlich leicht und in Ä-tlier unlöslich ist. 2. 2 llol. a-lIonochlorhvdrin (Givcerin chlorh@-(Irin) «-erden mit 2 11o1. eine alkoholischen _\`atriumsulfhrdratlösung zun Sieden erhitzt (vgl.Liebigs Annalen i2.t'r22) .Nach Beendigung der .Schwefelwasserstoti=- entwicklung wird r 11o1. 1lethvlenclilor:d zu- gegeben und noch kurzeZeit erwärmt. Weiter- behandlung wie in Beispiel i. Das erhalten( Produkt, (las llethvlendithiodigt_vcerin CH, - S_ [CH_CH(OH)C ist ein dickflüssiges Öl von syrupartiger Konsistenz das in Wasser und Sprit leicht, in Äther un- löslich ist. Bei der Destillation iui Vakutin- «-erden nur Zersetzungsprodukte erhalten. 3. r 11o1. Dithiodiglykol (dargestellt durcl- Umsetzung von 2 lIol. :1thv lenchlorhvdrirr mit i 11o1. Natriumdisultfid) wird mit einer Lösung von 2 IIoI. alkoholischer Schwefel- kaliumlösung auf dem Danipfhade erwärmt. ach eini-er Zeit wird an-esäuert und der entstehende #,-chwefehN-asserstott aus der Lösung verjagt. Nach \etrtralisatinrt mit \atronlatr#,e lä ßt inan i \Iol. Äthvlenchlorid zufließen und erwärmt noch kurze Zeit. Sprit und Wasser «-erden alrdestilliert und vom Kochsalz und Schwefel filtriert. Das ge- wonnene ()l ist identisch rnit denn nach Bei- .spiel r erhaltenen Produkt. Process for the preparation of dipolyoxyalkyl ethers of dithioalkylenes. It was found that the hitherto un- known 1) iliolvotyalkvläther of the dithio- , alkvenes of the all-pure formula RS-Rr-S z. BÄthvlendithiodiglykol, easy to manufacture lbRa = r are encapsulated by the action of the alkali tane on the Chlorlivdrine more valuable Alcohols or the llerkaptane poly-, vertiger Alcohols on the alkylene dihalides. In this formula should indicate: IZ and R_ the remainder of a polyvalent aliphatic Alcohol and R1 is an alkylene group, such as z. B. -CH4--, -CH., - CH., - etc., The Rea- tion is expedient using the Salts, e.g. B. \ atrium salts of the llerkaptans, carried out. The ones marked here Dipole voxy alkylene can be used as a solution agent for dyes etc. or as a softener Find remedies use. Examples. r. 1 mole of ethylene chloride is the same Weight of fuel dissolved and at 5o to 6o ° with an alcoholic solution of 4.1lol. Ha- litrrrrsulfh_vdrat and until the end the reaction is heated to the boil (cf. Reports 2o, 46o). Then -, will be 2 1101. pure: @tlivlenchlorhvdrin gradually increasing given and up after about an hour warmed up the Dainpfhade. The deceased halium chloride is filtered off and the fuel a l> lestillic # rt. \ aclinoclirnali "erI3eliztrr, lltiri #, niit Fuel leaves that - @ thvlendithiodiglvlcc (OHCH = -CH, - S-CH .- CH = S-CH_-CH.-OH as clear (5l, which is easy in fuel, in race is quite light and insoluble in a-tlier. 2. 2 llol. a-lIonochlorhvdrin (Givcerin chlorh @ - (Irin) «earths with 2 11o1. one alcoholic _ \ `atrium sulfate solution Boiling heated (see Liebigs Annalen i2.t'r22) .After the .Sulfur water stoti = - development becomes r 11o1. 1lethvlenclilor: d to- given and warmed up for a short time. Further- treatment as in example i. That received ( Product, (las llethvlendithiodigt_vcerin CH, - S_ [CH_CH (OH) C is a thick oil with a syrupy consistency that easily in water and fuel, un- is soluble. In the case of distillation in the vacuum «- only decomposition products are obtained. 3. r 11o1. Dithiodiglycol (shown by Implementation of 2 lIol. : 1thv lenchlorhvdrirr with i 11o1. Sodium disultfide) is used with a Solution of 2 IIoI. alcoholic sulfur Potassium solution warmed up on the Danipfhade. oh, some time is acidified and the resulting #, - chwefehN-asserstott from the Solution chased away. According to \ etrtralisatinrt with \ atronlatr #, e lets inan i \ Iol. Ethylene chloride flow in and heats up for a short time. Fuel and water "earth distilled and dated Table salt and sulfur filtered. The GE- won () l is identical to because according to both .spiel r received product.

Claims (1)

PATEN T-ANSPRUCII: Verfahren zur Darstellung von Dipoly- oxyalk1-läthern der DithioalkyIene, ge-
kennzeichnet durch Einwirkung der Alkylenmerkaptane auf Chlorh%-drine mehrwertiger Alkohole oder der illerkaptane mehrwertiger Alkohole auf Alkylendihalogenide. PATEN T-ANSPRUCII: Process for the representation of dipoly- oxyalk1 ethers of the dithioalkylenes,
is characterized by the action of the alkylene mercaptans on chlorine-drine of polyhydric alcohols or the illerkaptans of polyhydric alcohols on alkylene dihalides.
DEF51543D 1922-04-11 1922-04-11 Process for the preparation of dipolyoxyalkyl ethers of dithioalkylenes Expired DE405384C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF51543D DE405384C (en) 1922-04-11 1922-04-11 Process for the preparation of dipolyoxyalkyl ethers of dithioalkylenes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF51543D DE405384C (en) 1922-04-11 1922-04-11 Process for the preparation of dipolyoxyalkyl ethers of dithioalkylenes

Publications (1)

Publication Number Publication Date
DE405384C true DE405384C (en) 1924-10-31

Family

ID=7104700

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF51543D Expired DE405384C (en) 1922-04-11 1922-04-11 Process for the preparation of dipolyoxyalkyl ethers of dithioalkylenes

Country Status (1)

Country Link
DE (1) DE405384C (en)

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