DE1163315B - Process for the preparation of Trihalogenessigsaeureimidchloriden - Google Patents
Process for the preparation of TrihalogenessigsaeureimidchloridenInfo
- Publication number
- DE1163315B DE1163315B DEF38509A DEF0038509A DE1163315B DE 1163315 B DE1163315 B DE 1163315B DE F38509 A DEF38509 A DE F38509A DE F0038509 A DEF0038509 A DE F0038509A DE 1163315 B DE1163315 B DE 1163315B
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- DE
- Germany
- Prior art keywords
- preparation
- chloride
- chlorides
- general formula
- trihalogenessigsaeureimidchloriden
- 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
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
Internat. Kl.: C 07 cBoarding school Class: C 07 c
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Deutsche Kl.: 12 ο-22German class: 12 ο-22
F 38509 IVb/12 ο
10. Dezember 1962
20. Februar 1964F 38509 IVb / 12 ο
December 10, 1962
February 20, 1964
Die Erfindung betrifft ein Verfahren zur Herstellung von Trihalogenessigsäureimidchloriden. Es ist bereits bekannt, daß sich Trichlormethansulfochlorid in einer Radikalreaktion unter Abspaltung von Schwefeldioxyd an Olefine anlagert, wie z. B.The invention relates to a process for the preparation of trihaloacetic acid imide chlorides. It it is already known that trichloromethanesulfonyl chloride is split off in a radical reaction of sulfur dioxide attached to olefins, such as. B.
ClSO2CCl3 ClSO 2 CCl 3
SO2 SO 2
CCl3 CCl 3
Es wurde nun gefunden, daß sich Trihalogenmethansulfochloride unter Abspaltung von Schwefeldioxyd an Isonitrile anlagern lassen. Hierbei erhält man entsprechend folgendem Reaktionsschema Imidchloride der Trihalogenessigsäure:It has now been found that trihalomethanesulfonyl chlorides are formed with elimination of sulfur dioxide add to isonitrile. Imide chlorides are obtained in accordance with the following reaction scheme of trihaloacetic acid:
R-N => C + ClSO2CX3
-SO2 RN => C + ClSO 2 CX 3
-SO 2
ClCl
R-N = CR-N = C
CX3 CX 3
In dem obigen Formelbild bedeutet R einen beliebigen aliphatischen, cycloaliphatischen oder aromatischen Rest. X steht für Chlor, Brom und/oder Fluor.In the above formula, R means any aliphatic, cycloaliphatic or aromatic radical. X stands for chlorine, bromine and / or fluorine.
Geeignete Isonitrile sind beispielsweise Butyl-, Dodecyl-, Heptadecyl-, Cyclopentyl-, 4-Methylcyclohexyl-, Phenyl-, 5-Chlor-2,4-dimethoxy-phenyl-, 3-Nitrophenyl-, 1-Naphthyl-, 2-Methoxyphenylisonitril, 1,3 - Phenylendiisonitril und 4,4' - Diphenylmethan-diisonitril. Suitable isonitriles are, for example, butyl, dodecyl, heptadecyl, cyclopentyl, 4-methylcyclohexyl, Phenyl, 5-chloro-2,4-dimethoxyphenyl, 3-nitrophenyl, 1-naphthyl, 2-methoxyphenylisonitrile, 1,3-phenylenediisonitrile and 4,4'-diphenylmethane-diisonitrile.
Als Trihalogenmethansulfochloride können Trichlormethansulfochlorid und Dichlorfluormethansulfochlorid eingesetzt werden. Ihre Herstellung erfolgt zweckmäßigerweise durch Oxydation der zugehörigen Sulfensäurechloride, z. B. mit Wasserstoffsuperoxyd. Trichloromethanesulfonyl chloride can be used as trihalomethanesulfonyl chloride and dichlorofluoromethanesulfonyl chloride can be used. Your manufacture is expediently carried out by oxidation of the associated sulfenic acid chlorides, e.g. B. with hydrogen peroxide.
Die erfindungsgemäße Reaktion erfolgt bei erhöhter Temperatur zwischen 50 und 15O0C (bevorzugt bei 100 bis 1200C), durch Erhitzen der beiden Reaktionskomponenten, zweckmäßig in einem inerten Lösungsmittel, wie Benzol, Toluol, Dioxan oder Xylol.The reaction of the invention takes place at elevated temperature between 50 and 15O 0 C (preferably at 100 to 120 0 C), by heating the two reactants, preferably in an inert solvent such as benzene, toluene, dioxane or xylene.
Verfahren zur Herstellung von
TrihalogenessigsäureimidchloridenProcess for the production of
Trihaloacetic acid imide chlorides
Anmelder:Applicant:
Farbenfabriken Bayer Aktiengesellschaft,Paint factories Bayer Aktiengesellschaft,
LeverkusenLeverkusen
Als Erfinder benannt:Named as inventor:
Dr. Engelbert Kühle, Köln-StammheimDr. Engelbert Kühle, Cologne-Stammheim
Die Imidchloride dienen als Zwischenprodukte fiir weitere organische Synthesen, besonders zur Herstellung von Pflanzenschutzmitteln.The imide chlorides serve as intermediates for further organic syntheses, especially for Manufacture of plant protection products.
32 g Fluordichlormethansulfochlorid und 17 g Cyclohexylisonitril werden in 100 ml Toluol 2 Stunden lang zum Sieden erhitzt. Hierbei spaltet sich fortlaufend Schwefeldioxyd ab. Nach Abdampfen des Lösungsmittels erhält man 12 g Fluordichloressigsäure-cyclohexylimidchlorid vom Kp.n = 98 bis 990C.32 g of fluorodichloromethanesulfochloride and 17 g of cyclohexylisonitrile are heated to the boil in 100 ml of toluene for 2 hours. Sulfur dioxide is continuously split off. After evaporation of the solvent Fluordichloressigsäure-cyclohexylimidchlorid obtained 12 g of Kp.n = 98 to 99 0 C.
24 g n-Butylisonitril und 65 g Fluordichlormethansulfochlorid werden 8 Stunden lang in 150 ml Benzol erhitzt. Durch nachfolgende Destillation erhält man 11 g Fluordichloressigsäurebutylimidchlorid vom Kp.i4 = 68 bis 72°C.24 g n-butyl isonitrile and 65 g fluorodichloromethanesulphochloride are heated in 150 ml of benzene for 8 hours. Subsequent distillation gives 11 g of fluorodichloroacetic acid butylimide chloride with a b.p.i4 = 68 to 72 ° C.
37 g 2,6-Dimethylphenylisonitril und 70 g Fluordichlormethansulfochlorid werden 3 Stunden lang in 200 ml Toluol erhitzt. Durch Vakuumdestillation gewinnt man 22 g Fluordichloressigsäure-(2,6-dimethylphenyl)-imidchlorid vom Kp.10 = 135 bis 138°C.37 g of 2,6-dimethylphenyl isonitrile and 70 g of fluorodichloromethanesulfochloride are heated for 3 hours in 200 ml of toluene. By vacuum distillation 22 g of fluorodichloroacetic acid (2,6-dimethylphenyl) imide chloride are obtained from bp 10 = 135 to 138 ° C.
CH3 CH 3
FCl2CFCl 2 C
CH3 CH 3
CFCI2CFCI2
4095QJ/45B4095QJ / 45B
25 g 3,5,3',5'-Tetramethyl-diphenylmethan-4,4'-diisonitril und 120 g Fluordichlormethansulfochlorid werden 8 Stunden lang in 100 ml Xylol zum Sieden erhitzt. Hierbei entwickelt sich fortlaufend SO2. Anschließend destilliert man das Lösungsmittel 5 sowie das überschüssige Fluordichlormethansulfochlorid im Vakuum ab und erhält als Rückstand 38 g des Bisimidchlorids in Form eines zähflüssigen Öles.25 g of 3,5,3 ', 5'-tetramethyl-diphenylmethane-4,4'-diisonitrile and 120 g of fluorodichloromethane sulfochloride are heated to boiling in 100 ml of xylene for 8 hours. During this process, SO2 is continuously developing. The solvent 5 and the excess fluorodichloromethanesulfonyl chloride are then distilled off in vacuo and receives 38 g of the bisimide chloride in the form of a viscous residue as a residue Oil.
Claims (2)
an Isonitrile der allgemeinen FormelCl-SO2 -CX 3
of isonitriles of the general formula
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF38509A DE1163315B (en) | 1962-12-10 | 1962-12-10 | Process for the preparation of Trihalogenessigsaeureimidchloriden |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF38509A DE1163315B (en) | 1962-12-10 | 1962-12-10 | Process for the preparation of Trihalogenessigsaeureimidchloriden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1163315B true DE1163315B (en) | 1964-02-20 |
Family
ID=7097376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF38509A Pending DE1163315B (en) | 1962-12-10 | 1962-12-10 | Process for the preparation of Trihalogenessigsaeureimidchloriden |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1163315B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006104528A1 (en) * | 2005-03-28 | 2006-10-05 | Albemarle Corporation | Diimines and secondary diamines |
| US7964695B2 (en) | 2005-03-28 | 2011-06-21 | Albemarle Corporation | Chain extenders |
| US8076518B2 (en) | 2005-03-28 | 2011-12-13 | Albemarle Corporation | Chain extenders |
-
1962
- 1962-12-10 DE DEF38509A patent/DE1163315B/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006104528A1 (en) * | 2005-03-28 | 2006-10-05 | Albemarle Corporation | Diimines and secondary diamines |
| US7288677B2 (en) | 2005-03-28 | 2007-10-30 | Albemarle Corporation | Diimines and secondary diamines |
| US7767858B2 (en) | 2005-03-28 | 2010-08-03 | Albemarle Corporation | Diimines and secondary diamines |
| US7964695B2 (en) | 2005-03-28 | 2011-06-21 | Albemarle Corporation | Chain extenders |
| US8076518B2 (en) | 2005-03-28 | 2011-12-13 | Albemarle Corporation | Chain extenders |
| US8080626B2 (en) | 2005-03-28 | 2011-12-20 | Albemarle Corporation | Chain extenders |
| US8212078B2 (en) | 2005-03-28 | 2012-07-03 | Albemarle Corporation | Diimines and secondary diamines |
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