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The synthesis of the insecticides Aldrin and Dieldrin labelled with carbon-14 at high specific activity; Synthese des insecticides aldrine et dieldrine marques au carbone-14 de haute activite specifique; Sintez insektitsidnogo aldrina i dildrina, mechennykh uglerodom-14 pri vysokoj udel'noj aktivnosti; Sintesis de los insecticidas aldrin y dieldrin de elevada actividad especifica marcados con carbono-14

Conference:

Abstract

Aldrin is the trade name given by Shell Chemicals to 1, 2, 3, 4, 10, 10-hexachloro-1, 4, 4a, 5, 8, 8a-hexahydro-exo-1, 4-endo-5, 8-dimethanonapthalene. Acetylene-1, 2-C{sup 14} is converted successively to tetrachloroethane and trichloroethylene, and this is condensed with carbon tetrachloride by the Prins reaction in the presence of aluminium chloride to octachlorocyclopentene. Dechlorination gives hexachlorocyclopentadiene which undergoes a Diels-Alder addition to bicyclo(2, 2, 1) hepta-2,5-diene to give aldrin-C{sup 14} in 12% yield from barium carbonate. Oxidation of Aldrin gives the 6,7 epoxide, Dieldrin, in 87% yield. The paper includes an account of the separation of octachlorocyclopentene from the crude product of the Prins reaction by gas-liquid chromatography and of the separation of Aldrin and Dieldrin on a small preparative scale by reversed-phase paper chromatography. (author) [French] Aldrine est la denomination commerciale par laquelle la Shell Chemicals designe l'hexachloro-1, 2, 3, 4, 10, 10-hexahydro-1, 4, 4a, 5, 8, 8a-exo-endo-1,4- dimethano-5, 8-naphtalene. L'acetylene-1,2-C{sup 14} est successivement transforme en terachloroethane et en trichloroethylene, lequel se condense avec le tetrachlorure de carbone, par la reaction de Prins, en presence de chlorure d'aluminium, pour donner de l'octachlorocyclopentene. La dechloruration fournit de l'hexachlorocyclopentadiene, lequel, par une synthese de Diels-Alder, se transforme en bicyclohepta(2, 2, 1)-diene-2, 5  More>>
Authors:
Thomas, Daniel J; Kilner, A Edward [1] 
  1. Radiochemical Centre, UKAEA, Amersham, Bucks (United Kingdom)
Publication Date:
Mar 15, 1962
Product Type:
Conference
Resource Relation:
Conference: Conference on the Use of Radioisotopes in the Physical Sciences and Industry, Copenhagen (Denmark), 6-17 Sep 1960; Other Information: 6 figs, 7 refs; Related Information: In: Radioisotopes in the Physical Sciences and Industry. Proceedings of the Conference on the Use of Radioisotopes in the Physical Sciences and Industry. V. III| 652 p.
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; ACETYLENE; ALDRIN; ALUMINIUM CHLORIDES; BARIUM CARBONATES; CARBON 14; CARBON TETRACHLORIDE; DECHLORINATION; DIELDRIN; EPOXIDES; LIQUID COLUMN CHROMATOGRAPHY; OXIDATION; SYNTHESIS
OSTI ID:
22025711
Research Organizations:
International Atomic Energy Agency, Vienna (Austria); United Nations Educational, Scientific and Cultural Organization, Paris (France)
Country of Origin:
IAEA
Language:
English
Other Identifying Numbers:
Other: ISSN 0074-1884; TRN: XA12N1727113004
Submitting Site:
INIS
Size:
page(s) 83-90
Announcement Date:
Jan 16, 2013

Conference:

Citation Formats

Thomas, Daniel J, and Kilner, A Edward. The synthesis of the insecticides Aldrin and Dieldrin labelled with carbon-14 at high specific activity; Synthese des insecticides aldrine et dieldrine marques au carbone-14 de haute activite specifique; Sintez insektitsidnogo aldrina i dildrina, mechennykh uglerodom-14 pri vysokoj udel'noj aktivnosti; Sintesis de los insecticidas aldrin y dieldrin de elevada actividad especifica marcados con carbono-14. IAEA: N. p., 1962. Web.
Thomas, Daniel J, & Kilner, A Edward. The synthesis of the insecticides Aldrin and Dieldrin labelled with carbon-14 at high specific activity; Synthese des insecticides aldrine et dieldrine marques au carbone-14 de haute activite specifique; Sintez insektitsidnogo aldrina i dildrina, mechennykh uglerodom-14 pri vysokoj udel'noj aktivnosti; Sintesis de los insecticidas aldrin y dieldrin de elevada actividad especifica marcados con carbono-14. IAEA.
Thomas, Daniel J, and Kilner, A Edward. 1962. "The synthesis of the insecticides Aldrin and Dieldrin labelled with carbon-14 at high specific activity; Synthese des insecticides aldrine et dieldrine marques au carbone-14 de haute activite specifique; Sintez insektitsidnogo aldrina i dildrina, mechennykh uglerodom-14 pri vysokoj udel'noj aktivnosti; Sintesis de los insecticidas aldrin y dieldrin de elevada actividad especifica marcados con carbono-14." IAEA.
@misc{etde_22025711,
title = {The synthesis of the insecticides Aldrin and Dieldrin labelled with carbon-14 at high specific activity; Synthese des insecticides aldrine et dieldrine marques au carbone-14 de haute activite specifique; Sintez insektitsidnogo aldrina i dildrina, mechennykh uglerodom-14 pri vysokoj udel'noj aktivnosti; Sintesis de los insecticidas aldrin y dieldrin de elevada actividad especifica marcados con carbono-14}
author = {Thomas, Daniel J, and Kilner, A Edward}
abstractNote = {Aldrin is the trade name given by Shell Chemicals to 1, 2, 3, 4, 10, 10-hexachloro-1, 4, 4a, 5, 8, 8a-hexahydro-exo-1, 4-endo-5, 8-dimethanonapthalene. Acetylene-1, 2-C{sup 14} is converted successively to tetrachloroethane and trichloroethylene, and this is condensed with carbon tetrachloride by the Prins reaction in the presence of aluminium chloride to octachlorocyclopentene. Dechlorination gives hexachlorocyclopentadiene which undergoes a Diels-Alder addition to bicyclo(2, 2, 1) hepta-2,5-diene to give aldrin-C{sup 14} in 12% yield from barium carbonate. Oxidation of Aldrin gives the 6,7 epoxide, Dieldrin, in 87% yield. The paper includes an account of the separation of octachlorocyclopentene from the crude product of the Prins reaction by gas-liquid chromatography and of the separation of Aldrin and Dieldrin on a small preparative scale by reversed-phase paper chromatography. (author) [French] Aldrine est la denomination commerciale par laquelle la Shell Chemicals designe l'hexachloro-1, 2, 3, 4, 10, 10-hexahydro-1, 4, 4a, 5, 8, 8a-exo-endo-1,4- dimethano-5, 8-naphtalene. L'acetylene-1,2-C{sup 14} est successivement transforme en terachloroethane et en trichloroethylene, lequel se condense avec le tetrachlorure de carbone, par la reaction de Prins, en presence de chlorure d'aluminium, pour donner de l'octachlorocyclopentene. La dechloruration fournit de l'hexachlorocyclopentadiene, lequel, par une synthese de Diels-Alder, se transforme en bicyclohepta(2, 2, 1)-diene-2, 5 pour donner de l'aldrine-C{sup 14}, avec un rendement de 12% par rapport au carbonate de baryum. L'oxydation de l'aldrine donne l'epoxyde-6 7-(dieldrine), avec un rendement de 87%. Les auteurs decrivent, en outre, la separation de l'octachlorocyclopentene par chromatographie gaz-liquide, a partir du produit brut de la reaction de Prins, ainsi que la separation de l'aldrine et de la dieldrine, en petite quantite, par chromatographie sur papier a phase renversee. (author) [Spanish] Aldrin es el nombre comercial que la compania Shell Chemicals dio al 1, 2, 3, 4, 10, 10-hexacloro-1, 4, 4a, 5, 8, 8a-hexabidro-exo-1, 4-endo-5, 8-dimetanonaftaleno. El acetileno-1, 2-{sup 14}C se convierte primero en tetracloroetano y despues en tricloroetileno, y este se condensa con tetracloruro de carbono, por la reaccion de Prins, en presencia de cloruro de aluminio, para dar octaclorociclopenteno. Por decloracion se obtiene hexaclorociclopentadieno que, por una sintesis de Diels-Alder, da biciclo (2, 2, 1) hepta-2, 5-dieno para llegar al aldrin-{sup 14}C con un rendimiento del 12% referido al carbonato de bario. La oxidacion del aldrin da el 6, 7-epoxido, denominado dieldrin, con un rendimiento del 87%. Los autores describen la separacion del octaclorociclopenteno del producto bruto de la reaccion de Prins por cromatografia gas-liquido, y la separacion del aldrin y del dieldrin en pequena escala, por cromatografia sobre el papel, de fase invertida. (author) [Russian] Aldrin - kommercheskoe nazvanie, dannoe SHellom Kemikalom dlya 1 ,2, 3, 4, 10, 10-geksakhloro-1, 4, 4a, 5, 8, 8a-geksagidro ehkso-1,4-ehndo-5,8-dimetanonaftalina. Atsetilen-1,2-C{sup 14} uspeshno prevrashchaetsya v tetrakhloroehtilen i trikhloroehtilen i kondensiruetsya s uglerodistym tetrakhloridom v reaktsii Prinsa v prisutstvii alyuminievogo khlorida v oktakhlorotsiklopentan. Dekhlorizatsiya privodit k geksakhlorotsiklopentadinu, kotoryj dobavlyaetsya v vide Dils-Aldera k bitsiklo (2, 2, 1) gepta-2,5-dinu dlya polucheniya iz barievogo karbonata 12% aldrina-C{sup 14}. Okislenie aldrina privodit k obrazovaniyu ehloksida 6,7 i dildrina v razmere 87%. V dokumente soderzhitsya otchet ob otdelenii oktokhlorotsiklopentana ot syrogo produkta reaktsii Prinsa putem gazozhidkoj khromatografii i ob otdelenii aldrina i dildrina v nebol'shom kolichestve putem obratnoj fazy bumazhnoj khromatografii. (author)}
place = {IAEA}
year = {1962}
month = {Mar}
}