EP1863786A1 - Procede de representation de 3,3,4,4-tetrachlortetrahydrothiophen-1,1-dioxyde - Google Patents

Procede de representation de 3,3,4,4-tetrachlortetrahydrothiophen-1,1-dioxyde

Info

Publication number
EP1863786A1
EP1863786A1 EP06723124A EP06723124A EP1863786A1 EP 1863786 A1 EP1863786 A1 EP 1863786A1 EP 06723124 A EP06723124 A EP 06723124A EP 06723124 A EP06723124 A EP 06723124A EP 1863786 A1 EP1863786 A1 EP 1863786A1
Authority
EP
European Patent Office
Prior art keywords
dioxide
reaction
phosphoryl chloride
chlorine
formula
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.)
Withdrawn
Application number
EP06723124A
Other languages
German (de)
English (en)
Inventor
Alexander Straub
Hans-Joachim Ressel
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.)
Bayer CropScience AG
Original Assignee
Bayer CropScience 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 Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1863786A1 publication Critical patent/EP1863786A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
    • C07D333/48—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom by oxygen atoms

Definitions

  • the present invention relates to a novel process for the preparation of the already known 3,3,4,4-tetrachlorotetrahydrothiophene dioxide.
  • This compound is required as an intermediate for the synthesis of 3,4-dichlorothiophene dioxide, which has fungicidal properties or can itself be used as a precursor for fungicides.
  • the presentation is described in J. Org. Chem. 1960, 20, 346.
  • a chlorine addition to sulfolene to 3,4-Dichlorsulfolan For the following raduclear substitution with chlorine more energetic conditions are necessary.
  • POCl 3 has excellent properties under the drastic reaction conditions investigated as the reaction medium. It may, for example, in conjunction with the chlorine introduced during the reaction itself chlorinating or catalyzing act on the chlorination.
  • the reaction is favored by the better solubility of chlorine in phosphoryl chloride and the binding capacity of phosphoryl chloride for the liberated hydrogen chloride.
  • the phosphoryl chloride can be recovered by simple distillation and recycled. It also allows the performance of photochemical chlorination in highly concentrated solution, because it has very good dissolution properties compared to sulfolene. It has been found that phosphoryl chloride has very good dissolution properties with respect to the educt and the product. This prevents precipitation during the reaction, which in turn would reduce light transmittance and thus slow down the chlorination in photocatalysis.
  • Suitable solvents for carrying out the first step of the process according to the invention are all conventional inert organic solvents.
  • Alkanes such as cyclohexane, methylcyclohexane, heptane, octane, petroleum ether or POCl 3 are preferably usable.
  • POCl 3 is hydrolyzed in the air by moisture immediately, so it has no persistence and no
  • POCl 3 is a low-cost industrial chemical and can easily be recovered by distillation.
  • reaction temperatures can be varied within a substantial range when carrying out the first step of the process according to the invention. In general is carried out at tempera- tures of from -10 0 C to +150 0 C, preferably in the range from 0 0 C to 80 0 C.
  • reaction temperatures can be varied within a relatively wide range when carrying out the second step of the process according to the invention. In general, one works at temperatures of -10 0 C to +150 0 C, preferably in the range of 50 0 C to 85 ° C. ⁇ ⁇

Landscapes

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

Abstract

La présente invention concerne un procédé de production de 3,3,4,4-tétrachlortétrahydro-thiophendioxyde. On utilise avantageusement comme solvant dans la réaction de chloration un chlorure de phosphoryle dépourvu d'action nuisible sur la couche d'ozone mondiale.
EP06723124A 2005-03-11 2006-02-27 Procede de representation de 3,3,4,4-tetrachlortetrahydrothiophen-1,1-dioxyde Withdrawn EP1863786A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005011229A DE102005011229A1 (de) 2005-03-11 2005-03-11 Verfahren zur Darstellung von 3,3,4,4-Tetrachlortetrahydrothiophen-1,1-dioxid
PCT/EP2006/001763 WO2006094667A1 (fr) 2005-03-11 2006-02-27 Procede de representation de 3,3,4,4-tetrachlortetrahydrothiophen-1,1-dioxyde

Publications (1)

Publication Number Publication Date
EP1863786A1 true EP1863786A1 (fr) 2007-12-12

Family

ID=36218437

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06723124A Withdrawn EP1863786A1 (fr) 2005-03-11 2006-02-27 Procede de representation de 3,3,4,4-tetrachlortetrahydrothiophen-1,1-dioxyde

Country Status (6)

Country Link
EP (1) EP1863786A1 (fr)
JP (1) JP2008532960A (fr)
CN (1) CN101137640A (fr)
DE (1) DE102005011229A1 (fr)
IL (1) IL185858A0 (fr)
WO (1) WO2006094667A1 (fr)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3963751A (en) * 1975-07-14 1976-06-15 Diamond Shamrock Corporation Chlorination of butadiene sulfone to 3,3,4,4-tetrachlorotetrahydrothiophene-1,1-dioxide
ES2008765A6 (es) * 1987-11-12 1989-08-01 Miret Lab Mejoras introducidas en el objeto de la patente principal numero 549.317 por proceso de fabricaciondel 3,3,4,4-tetrahalotetrahidro-tiofeno-1,1-dioxido.
JP3436568B2 (ja) * 1993-08-04 2003-08-11 武田薬品工業株式会社 チオフェン誘導体の製造方法
JP4002314B2 (ja) * 1996-09-25 2007-10-31 日本エンバイロケミカルズ株式会社 ３，３，４，４−テトラクロロテトラヒドロチオフェン −１，１−ジオキサイドの製造方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006094667A1 *

Also Published As

Publication number Publication date
WO2006094667A1 (fr) 2006-09-14
CN101137640A (zh) 2008-03-05
DE102005011229A1 (de) 2006-09-14
IL185858A0 (en) 2008-01-06
JP2008532960A (ja) 2008-08-21

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