DE1269115B - Process for the preparation of 2, 3, 4-trichlorobenzotrichloride - Google Patents

Process for the preparation of 2, 3, 4-trichlorobenzotrichloride

Info

Publication number
DE1269115B
DE1269115B DEP1269A DE1269115A DE1269115B DE 1269115 B DE1269115 B DE 1269115B DE P1269 A DEP1269 A DE P1269A DE 1269115 A DE1269115 A DE 1269115A DE 1269115 B DE1269115 B DE 1269115B
Authority
DE
Germany
Prior art keywords
trichlorobenzotrichloride
hexachlorocyclopentadiene
preparation
acetylene
reaction
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
DEP1269A
Other languages
German (de)
Inventor
Dr Heinz Frensch
Dr Helmut Goebel
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 DEP1269A priority Critical patent/DE1269115B/en
Publication of DE1269115B publication Critical patent/DE1269115B/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/02—Halogenated hydrocarbons
    • C08K5/03—Halogenated hydrocarbons aromatic, e.g. C6H5-CH2-Cl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
    • C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von 2,3,4-Trichlorbenzotrichlorid Die Verwendung von Hexahalocyclopentadien bei der von D i e 1 s und A 1 d e r gefundenen Reaktion zwischen einer Verbindung mit konjugierter Doppelbindung und einer ungesättigten Substanz, dem sogenannten Dienophil, ist bekannt. In der britischen Patentschrift 614931 wird die Umsetzung mit einer dreifach ungesättigten Verbindung, nämlich dem Phenylacetylen, angeführt.Process for the preparation of 2,3,4-trichlorobenzotrichloride The use of hexahalocyclopentadiene in the reaction found by D i e 1 s and A 1 d e r between a compound with a conjugated double bond and an unsaturated one Substance, the so-called dienophile, is known. In British patent specification 614931 is the implementation with a triunsaturated compound, namely the Phenylacetylene.

Die Darstellung des 2,3,4-Trichlorbenzotrichlorid aus Hexachlorcyclopentadien und Acetylen ist bisher nicht beschrieben. The preparation of 2,3,4-trichlorobenzotrichloride from hexachlorocyclopentadiene and acetylene has not yet been described.

Es wurde nun gefunden, daß man in glatter Reaktion und mit guten Ausbeuten zu dem neuen 2,3,4-Trichlorbenzotrichlorid gelangt, wenn man Hexachlorcyclopentadien mit gasförmigem Acetylen bei 100 bis 300° C, gegebenenfalls unter Druck und in Gegenwart eines Verdünnungsmittels, z. B. o-Dichlorbenzol, Nitrobenzol oder 1,2,3-Trichlorbenzol, umsetzt. It has now been found that you can react smoothly and with good Yields of the new 2,3,4-trichlorobenzotrichloride are obtained when using hexachlorocyclopentadiene with gaseous acetylene at 100 to 300 ° C, optionally under pressure and in the presence a diluent, e.g. B. o-dichlorobenzene, nitrobenzene or 1,2,3-trichlorobenzene, implements.

Für die Umsetzung von Hexachlorcyclopentadien mit Acetylen ergibt sich folgendes Schema: Cl Cl CH Cl2 + C1 + CH Cl CH Cl CCl3 180 bis {lCCl2IHH ) C Cl Cl Das intermediär entstandene Hexachlorbicyclo-[2,2,l]-heptadien-(2,5) ist unter den Umsetzungsbedingungen nicht faßbar und lagert sich sogleich zum 2,3,4-Trichlorbenzotrichlorid um.The following scheme results for the reaction of hexachlorocyclopentadiene with acetylene: Cl Cl CH Cl2 + C1 + CH Cl CH Cl CCl3 180 to {lCCl2IHH) C Cl Cl The intermediate hexachlorobicyclo- [2.2, l] -heptadiene- (2.5) cannot be detected under the reaction conditions and is immediately rearranged to form 2,3,4-trichlorobenzotrichloride.

Das neue Verfahrensprodukt 2,3,4-Trichlorbenzotrichlorid eignet sich zur Herstellung von Farbstoffen, Schädlingsbekämpfungsmitteln, als Weichmacher sowie als Lösungsmittel vor allem für chlorierte Verbindungen. The new process product 2,3,4-trichlorobenzotrichloride is suitable for the production of dyes, pesticides, as plasticizers and as a solvent especially for chlorinated compounds.

Beispiel 350 g Hexachlorcyclopentadien werden im DIbad auf 180 bis 200"C erwärmt. Hierzu leitet man durch eine Fritte einen langsamen Acetylenstrom ein. Das Reaktionsgefäß wird zweckmäßig so gewählt, daß das Gas in der Flüssigkeit einen möglichst langen Weg zurücklegen muß. Im günstigsten Fall tritt hierbei vollständige Absorption des Gases ein. Gegebenenfalls kann durch Hintereinanderschalten mehrerer Reaktionsgefäße die Ausnutzung des Acetylens 1000/,in gestaltet werden. Nach etwa 80 Stunden wird das Reaktionsgemisch durch Vakuumdestillation aufgearbeitet. Man erhält folgende Fraktionen: 1. Kr.0*6 70 bis 94"C 20 g 2. Kp.07-o,g 98 bis 128"C 40 g 3. Kp.og 128"C 250 g Im Reaktionsgefäß bleiben 30 g eines dunkelbraunen glasigen Harzes. Fraktion 1 besteht aus Hexachlorcyclopentadien, Fraktion 2 ist eine Mischung aus Hexachlorcyclopentadien und 2,3,4-Trichlorbenzotrichlorid, während Fraktion 3 reines 2,3,4-Trichlorbenzotrichlorid darstellt. Example 350 g of hexachlorocyclopentadiene are increased to 180 in a DI bath 200 "C. For this purpose, a slow stream of acetylene is passed through a frit a. The reaction vessel is expediently chosen so that the gas in the liquid has to travel as long as possible. In the best case this occurs complete Absorption of the gas. If necessary, several can be connected in series Reaction vessels utilizing the acetylene 1000 / can be designed in. After about The reaction mixture is worked up by vacuum distillation for 80 hours. Man receives the following fractions: 1. Kr.0 * 6 70 to 94 "C 20 g 2. Kp.07-o, g 98 to 128" C 40 g 3. Kp.og 128 "C 250 g 30 g of a dark brown glassy remains in the reaction vessel Resin. Fraction 1 consists of hexachlorocyclopentadiene, fraction 2 is a mixture from hexachlorocyclopentadiene and 2,3,4-trichlorobenzotrichloride, while fraction 3 represents pure 2,3,4-trichlorobenzotrichloride.

Bezogen auf verbrauchtes Hexachlorcyclopentadien, beträgt die Ausbeute etwa 85% an 2,3,4-Trichlorbenzotrichlorid. Die neue orangegelbgefärbte Substanz ist unter normalen Bedingungen flüssig und siedet bei Kr.35 151 bis 152"C, n2D0 1,6129. Based on the hexachlorocyclopentadiene consumed, the yield is about 85% of 2,3,4-trichlorobenzotrichloride. The new orange-yellow colored substance is liquid under normal conditions and boils at Kr.35 151 to 152 "C, n2D0 1.6129.

C7H2Cl6: Berechnet C 28,14, H 0,68, C1 71,20%; gefunden C 27,98, H 0,69, C171,16/71,25%.C7H2Cl6: Calculated C 28.14, H 0.68, C1 71.20%; found C 27.98, H 0.69, C171.16 / 71.25%.

Claims (2)

Patentansprüche: 1. Verfahren zur Herstellung von 2,3,4-Trichlorbenzotrichlorid, dadurch gekennzeichn e t, daß man Hexachlorcyclopentadien mit gasförmigem Acetylen bei 100 bis 300"C umsetzt. Claims: 1. Process for the production of 2,3,4-trichlorobenzotrichloride, characterized in that hexachlorocyclopentadiene is combined with gaseous acetylene converts at 100 to 300 "C. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man die Umsetzung unter Druck in Gegenwart eines Verdünnungsmittels durchfuhrt. 2. The method according to claim 1, characterized in that the Reaction carried out under pressure in the presence of a diluent. In Betracht gezogene Druckschriften: Deutsche Patentschrift Nr 709 129; französische Patentschrift Nr.926 593; britische Patentschriften Nr. 578 867, 614931; USA.-Patentschriften Nr. 2 097 854, 2 528 656; Angewandte Chemie, 47 (1934), S. 837; Organic Reactions, Bd. IV, S.8l,9l, 154; W. Foerst, Neuere Methoden der präparativen organischen Chemie, 3.Auflage, 1949, S.303. Documents considered: German Patent No. 709 129; French Patent No. 926 593; British Patent Specification No. 578 867, 614931; U.S. Patent Nos. 2,097,854, 2,528,656; Angewandte Chemie, 47 (1934), P. 837; Organic Reactions, Vol. IV, pp.8l, 91, 154; W. Foerst, Newer Methods of preparative organic chemistry, 3rd edition, 1949, p.303. In Betracht gezogene ältere Patente: Deutsches Patent Nr. 977 582. Older patents considered: German Patent No. 977 582.
DEP1269A 1953-06-17 1953-06-17 Process for the preparation of 2, 3, 4-trichlorobenzotrichloride Pending DE1269115B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEP1269A DE1269115B (en) 1953-06-17 1953-06-17 Process for the preparation of 2, 3, 4-trichlorobenzotrichloride

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEP1269A DE1269115B (en) 1953-06-17 1953-06-17 Process for the preparation of 2, 3, 4-trichlorobenzotrichloride

Publications (1)

Publication Number Publication Date
DE1269115B true DE1269115B (en) 1968-05-30

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DEP1269A Pending DE1269115B (en) 1953-06-17 1953-06-17 Process for the preparation of 2, 3, 4-trichlorobenzotrichloride

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DE (1) DE1269115B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1418334B1 (en) * 1955-08-10 1971-01-07 Shell Oil Co Process for the preparation of 1,2,3,4,7,7-hexachlorobicyclo [2,2,1] -2,5-heptadiene from hexachlorocyclopentadiene and acetylene

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2097854A (en) * 1933-03-25 1937-11-02 Ig Farbenindustrie Ag Cyclopentadienone condensation compounds and process of making them
DE709129C (en) * 1937-12-23 1941-08-07 I G Farbenindustrie Akt Ges Process for the preparation of addition compounds "diene synthesis"
GB578867A (en) * 1944-09-07 1946-07-15 Peter George Carter Cyclopentadiene addition products
FR926593A (en) * 1945-03-05 1947-10-06 Velsicol Corp Improvements relating to a process for manufacturing a new composition and resulting product
GB614931A (en) * 1945-03-05 1948-12-30 Velsicol Corp Improvements in or relating to the production of new diels-alder adducts
US2528656A (en) * 1948-07-22 1950-11-07 Velsicol Corp 1-hydroxy-4, 7-methano-3a, 4, 7, 7a-tetrahydro 4, 5, 6, 7, 8, 8-hexachloroindene andmethod of preparing same
DE977582C (en) * 1948-08-21 1967-05-03 Bataafse Petroleum Mij Process for the preparation of bicyclo [2, 2, 1] -2, 5-heptadiene

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2097854A (en) * 1933-03-25 1937-11-02 Ig Farbenindustrie Ag Cyclopentadienone condensation compounds and process of making them
DE709129C (en) * 1937-12-23 1941-08-07 I G Farbenindustrie Akt Ges Process for the preparation of addition compounds "diene synthesis"
GB578867A (en) * 1944-09-07 1946-07-15 Peter George Carter Cyclopentadiene addition products
FR926593A (en) * 1945-03-05 1947-10-06 Velsicol Corp Improvements relating to a process for manufacturing a new composition and resulting product
GB614931A (en) * 1945-03-05 1948-12-30 Velsicol Corp Improvements in or relating to the production of new diels-alder adducts
US2528656A (en) * 1948-07-22 1950-11-07 Velsicol Corp 1-hydroxy-4, 7-methano-3a, 4, 7, 7a-tetrahydro 4, 5, 6, 7, 8, 8-hexachloroindene andmethod of preparing same
DE977582C (en) * 1948-08-21 1967-05-03 Bataafse Petroleum Mij Process for the preparation of bicyclo [2, 2, 1] -2, 5-heptadiene

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1418334B1 (en) * 1955-08-10 1971-01-07 Shell Oil Co Process for the preparation of 1,2,3,4,7,7-hexachlorobicyclo [2,2,1] -2,5-heptadiene from hexachlorocyclopentadiene and acetylene

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