DE1125915B - Process for the preparation of 1, 2, 2, 2-Tetrahalogenaethylsulfenylhalogeniden - Google Patents
Process for the preparation of 1, 2, 2, 2-TetrahalogenaethylsulfenylhalogenidenInfo
- Publication number
- DE1125915B DE1125915B DEH38971A DEH0038971A DE1125915B DE 1125915 B DE1125915 B DE 1125915B DE H38971 A DEH38971 A DE H38971A DE H0038971 A DEH0038971 A DE H0038971A DE 1125915 B DE1125915 B DE 1125915B
- Authority
- DE
- Germany
- Prior art keywords
- chlorine
- bis
- disulfide
- journal
- preparation
- 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
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- -1 1,2,2,2-tetrachloroethyl Chemical group 0.000 claims description 3
- SUFFXMSAHQIUJA-UHFFFAOYSA-N 1,1,1,2-tetrabromo-2-(1,2,2,2-tetrabromoethyldisulfanyl)ethane Chemical compound BrC(Br)(Br)C(Br)SSC(Br)C(Br)(Br)Br SUFFXMSAHQIUJA-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 5
- SAPVRZJHCTUGIW-UHFFFAOYSA-N 1,1,1,2-tetrachloro-2-(1,2,2,2-tetrachloroethyldisulfanyl)ethane Chemical compound ClC(Cl)(Cl)C(Cl)SSC(Cl)C(Cl)(Cl)Cl SAPVRZJHCTUGIW-UHFFFAOYSA-N 0.000 description 3
- RUFAFKWLURMVKG-UHFFFAOYSA-N 1,2,2,2-tetrachloroethyl thiohypochlorite Chemical compound ClSC(Cl)C(Cl)(Cl)Cl RUFAFKWLURMVKG-UHFFFAOYSA-N 0.000 description 2
- GCGSLMNJWBLLAH-UHFFFAOYSA-N 2-chloroethyl thiohypochlorite Chemical compound ClCCSCl GCGSLMNJWBLLAH-UHFFFAOYSA-N 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/08—Sulfenic acids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Die Erfindung bezieht sich auf ein Verfahren zur Herstellung von 1,2,2,2-Tetrahalogenäthylsulfenylhalogeniden der allgemeinen Formel C2HX4SX, in der X ein Chlor- oder Bromatom bedeutet, welches dadurch gekennzeichnet ist, daß Bis-(l,2,2,2-tetrachloräthyl)-disulfid oder Bis-(l,2,2,2-tetrabromäthyl)-disulfid mit Chlor oder Brom umgesetzt wird. Vorzugsweise wird im Rahmen des erfindungsgemäßen Verfahrens das 1,2,2,2-Tetrachloräthylsulfenylchlorid durch Chlorierung von Bis-(l,2,2,2-tetrachloräthyl)-disulfid hergestellt. Die beim erfindungsgemäßen Verfahren als Ausgangsverbindungen verwendeten Bis-(tetrahalogenäthyl)-disulfide können nach dem Verfahren der Patentanmeldung H 38970 IVb / 12 ο hergestellt werden.The invention relates to a process for the preparation of 1,2,2,2-Tetrahalogenäthylsulfenylhalogeniden of the general formula C2HX4SX, in which X is a chlorine or bromine atom, which characterized in that bis (1,2,2,2-tetrachloroethyl) disulfide or bis (1,2,2,2-tetrabromoethyl) disulfide is reacted with chlorine or bromine. Preferably, within the scope of the invention Process the 1,2,2,2-tetrachloroethylsulfenyl chloride produced by chlorination of bis (1,2,2,2-tetrachloroethyl) disulfide. The in the invention Process used as starting compounds bis (tetrahalogenoethyl) disulfides can after Procedure of the patent application H 38970 IVb / 12 ο getting produced.
Die erfindungsgemäß erhältlichen Verbindungen sind als Zwischenprodukte und als insbesondere gegen Nematoden wirksame biologische Gifte verwendbar. The compounds obtainable according to the invention are as intermediates and as particular Biological poisons effective against nematodes can be used.
Für die Verwendbarkeit der nach dem erfindungsgemäßen Verfahren hergestellten 1,2,2,2-Tetrahalogenäthylsulfenylhalogenide ist vor allem deren unerwartete Beständigkeit maßgebend. Die Stabilität dieser Verbindungen ist so groß, daß sie bei den üblichen Temperaturen ohne weiteres transportfähig sind und mindestens 6 Monate ohne wesentliche Zersetzung lagern können. Diese Beständigkeit ist ausreichend, um diese neuen, nach dem erfindungsgemäßen Verfahren hergestellten Verbindungen als Mittel zur Bekämpfung von Nematoden zu verwenden. In dieser Hinsicht zeichnen sich die 1,2,2,2 - Tetrahalogenäthylsulfenylhalogenide besonders aus gegenüber anderen bekannten ähnlichen Verbindungen, nämlich dem Trichloräthylsulfenylchlorid und dem 2-Chloräthylsulfenylchlorid, von welchen beiden Verbindungen insbesondere das 2-Chloräthylsulfenylchlorid besonders instabil ist.For the usability of the 1,2,2,2-Tetrahalogenäthylsulfenylhalogenide prepared by the process according to the invention Above all, their unexpected resistance is decisive. The stability of these compounds is so great that they are in the normal temperatures are easily transportable and at least 6 months without significant Can store decomposition. This resistance is sufficient to make this new, according to the invention Processes to use compounds prepared as agents for controlling nematodes. The 1,2,2,2-tetrahaloethylsulfenyl halides are particularly notable in this regard from other known similar compounds, namely Trichloräthylsulfenylchlorid and the 2-chloroethylsulfenyl chloride, from which two compounds in particular the 2-chloroethylsulfenyl chloride is particularly unstable.
Das folgende Ausführungsbeispiel soll das erfindungsgemäße Verfahren erläutern:The following exemplary embodiment is intended to explain the method according to the invention:
398 Gewichtsteile Bis-(l,2,2,2-Tetrachloräthyl)-disulfid werden auf — 20° C gekühlt und mit gasförmigem Chlor unter Rühren und Kühlung zur Aufrechterhaltung der Temperatur behandelt. Sobald das Gewicht der Reaktionsmischung auf 469 Gewichtsteile angestiegen war, wurde die Mischung langsam auf Raumtemperatur erwärmt. Hierauf wurde die Mischung unter Verwendung einer Kolonne von etwa drei theoretischen Böden fraktioniert destilliert. Die bei einem Druck von 0,5 mm Quecksilbersäule zwischen 53 und 57° C übergehende Fraktion ist398 parts by weight of bis (1,2,2,2-tetrachloroethyl) disulfide are cooled to - 20 ° C and with gaseous Treated chlorine with stirring and cooling to maintain the temperature. As soon When the weight of the reaction mixture increased to 469 parts by weight, the mixture became slow warmed to room temperature. The mixture was then made using a column of about three theoretical plates fractionally distilled. The one at a pressure of 0.5 mm of mercury between 53 and 57 ° C passing fraction is
Verfahren zur HerstellungMethod of manufacture
von 1,2,2,2-Tetrahalogenäthyl-of 1,2,2,2-tetrahaloethyl
sulfenylhalogenidensulfenyl halides
Anmelder:Applicant:
Hooker Chemical Corporation,
Niagara Falls, N. Y. (V. St. A.)Hooker Chemical Corporation,
Niagara Falls, NY (V. St. A.)
Vertreter: Dr.-Ing. E. HoffmannRepresentative: Dr.-Ing. E. Hoffmann
und Dipl.-Ing. W. Eitle, Patentanwälte,and Dipl.-Ing. W. Eitle, patent attorneys,
München 22, Widenmayerstr. 34Munich 22, Widenmayerstr. 34
Beanspruchte Priorität:
V. St. v. Amerika vom 23. März 1959 (Nr. 800 981)Claimed priority:
V. St. v. America, March 23, 1959 (No. 800 981)
Edward David Weil, Lewiston, N. Y.,Edward David Weil, Lewiston, N.Y.,
Emil John Geering, Grand Island, N. Y..Emil John Geering, Grand Island, N.Y ..
und Keith Jacob Smith, Lockport, N. Y. (V. St. A.),and Keith Jacob Smith, Lockport, N.Y. (V. St. A.),
sind als Erfinder genannt wordenhave been named as inventors
eine übelriechende gelbe Flüssigkeit mit einem spezifischen Gewicht von 1,760 bei 23° C, deren Analyse dem Tetrachloräthylsulfenylchlorid entspricht.a malodorous yellow liquid with a specific gravity of 1.760 at 23 ° C, the analysis of which corresponds to the tetrachloroethylsulfenyl chloride.
Analyse bei C2HCI5S:Analysis with C2HCI5S:
Berechnet Cl 75,7<>/0, S 13,6%;Calculated Cl 75.7 <> / 0 , S 13.6%;
gefunden Cl 76,2%, S 13,5%.found Cl 76.2%, S 13.5%.
Die oben beschriebene Arbeitsweise kann durch Anwendung höherer oder niedriger Temperaturen, welche vorzugsweise zwischen — 40 und +400C liegen, durch Anwendung eines größeren oder kleineren Druckes als Atmosphärendruck abgeändert werden, wobei wie in obigem Beispiel ohne Katalysator oder mit einem Katalysator, wie beispielsweise Ferrichlorid, gearbeitet werden kann. Obwohl, wie bekannt ist, die Umsetzung anderer Alkyldisulfide mit Chlor von störenden Nebenreaktionen, wie beispielsweise Überchlorierung, begleitet wird, treten derartige Schwierigkeiten im vorliegenden Falle überraschenderweise nicht auf, und es werden auch dann gute Ausbeuten erzielt, wenn eine Chlormenge zugeführt wird, welche die theoretische Chlormenge übersteigt.The procedure described above can be modified by using higher or lower temperatures, which are preferably between -40 and +40 0 C, by using a higher or lower pressure than atmospheric pressure, as in the above example without a catalyst or with a catalyst, such as Ferric chloride, can be worked. Although, as is known, the reaction of other alkyl disulfides with chlorine is accompanied by troublesome side reactions, such as, for example, overchlorination, such difficulties surprisingly do not occur in the present case, and good yields are achieved even if an amount of chlorine is added which exceeds the the theoretical amount of chlorine exceeds.
209 520/452209 520/452
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80098159A | 1959-03-23 | 1959-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1125915B true DE1125915B (en) | 1962-03-22 |
Family
ID=25179876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH38971A Pending DE1125915B (en) | 1959-03-23 | 1960-03-21 | Process for the preparation of 1, 2, 2, 2-Tetrahalogenaethylsulfenylhalogeniden |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE588647A (en) |
| DE (1) | DE1125915B (en) |
| GB (1) | GB949375A (en) |
| NL (1) | NL249640A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1197877B (en) | 1959-09-26 | 1965-08-05 | Bayer Ag | Process for the preparation of polyhaloalkanesulfene acid halides |
| US3234272A (en) * | 1963-06-07 | 1966-02-08 | Chevron Res | Polyhaloalkylthiosulfenyl halides and process of preparation |
| DE1220852B (en) * | 1962-10-29 | 1966-07-14 | Hooker Chemical Corp | Process for the preparation of 1, 1, 2, 2-tetrachloroethylsulfenyl chloride |
| EP0485856A1 (en) * | 1990-11-16 | 1992-05-20 | Bayer Ag | Process for the preparation of 1,1-difluoralkansulfenyl chlorides |
-
0
- NL NL249640D patent/NL249640A/xx unknown
-
1960
- 1960-03-15 BE BE588647A patent/BE588647A/en unknown
- 1960-03-18 GB GB971860A patent/GB949375A/en not_active Expired
- 1960-03-21 DE DEH38971A patent/DE1125915B/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1197877B (en) | 1959-09-26 | 1965-08-05 | Bayer Ag | Process for the preparation of polyhaloalkanesulfene acid halides |
| DE1220852B (en) * | 1962-10-29 | 1966-07-14 | Hooker Chemical Corp | Process for the preparation of 1, 1, 2, 2-tetrachloroethylsulfenyl chloride |
| US3234272A (en) * | 1963-06-07 | 1966-02-08 | Chevron Res | Polyhaloalkylthiosulfenyl halides and process of preparation |
| EP0485856A1 (en) * | 1990-11-16 | 1992-05-20 | Bayer Ag | Process for the preparation of 1,1-difluoralkansulfenyl chlorides |
Also Published As
| Publication number | Publication date |
|---|---|
| NL249640A (en) | |
| BE588647A (en) | 1960-07-01 |
| GB949375A (en) | 1964-02-12 |
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