DE1279679B - Process for the preparation of olefinically unsaturated compounds - Google Patents

Process for the preparation of olefinically unsaturated compounds

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Publication number
DE1279679B
DE1279679B DEF50559A DEF0050559A DE1279679B DE 1279679 B DE1279679 B DE 1279679B DE F50559 A DEF50559 A DE F50559A DE F0050559 A DEF0050559 A DE F0050559A DE 1279679 B DE1279679 B DE 1279679B
Authority
DE
Germany
Prior art keywords
parts
weight
unsaturated compounds
olefinically unsaturated
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
Application number
DEF50559A
Other languages
German (de)
Inventor
Dr Friedrich Moeller
Dr Hermann Oediger
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 AG
Original Assignee
Bayer 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 AG filed Critical Bayer AG
Priority to DEF50559A priority Critical patent/DE1279679B/en
Priority to CH1301267A priority patent/CH533068A/en
Priority to AT864567A priority patent/AT276318B/en
Priority to GB48686/67A priority patent/GB1142718A/en
Priority to FR126243A priority patent/FR1543088A/en
Publication of DE1279679B publication Critical patent/DE1279679B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
    • C07C1/30—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms by splitting-off the elements of hydrogen halide from a single molecule
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Description

BUNDESREPUBLIK DEUTSCHLAND DEUTSCHES 4B7VW PATENTAMT FEDERAL REPUBLIC OF GERMANY GERMAN 4B7VW PATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Int. CL:Int. CL:

Deutsche Kl.:German class:

Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:

C07cC07c

C07dC07d

12O-27
19/01,25;
12 ρ-10/10 12O-27
19/01.25;
12 ρ-10/10

P 12 79 679.1-42 (F 50559)P 12 79 679.1-42 (F 50559)

28. Oktober 1966October 28, 1966

10. Oktober 1968October 10, 1968

Gegenstand des Patentes 1 186 063 ist ein Verfahren zur Herstellung von olefinisch ungesättigten Verbindungen durch Dehydrohalogenierung von organischen Halogenverbindungen, deren Halogenatom sich in «- oder /i-Stellung zu einer Carbonyl-, Carboxy-, Nitril-, Äthylen- oder Acetylengruppe befindet, mit tertiären organischen Basen als Dehydrohalogenierungsmitteln, gegebenenfalls in Gegenwart eines Lösungsmittels, welches dadurch gekennzeichnet ist, daß man als Dehydrohalogenierungsmittel eine heterocyclische Base der allgemeinen FormelThe subject of patent 1,186,063 is a process for the production of olefinically unsaturated Compounds by dehydrohalogenation of organic halogen compounds, their halogen atom in «- or / i-position to a carbonyl, Carboxy, nitrile, ethylene or acetylene group, with tertiary organic bases as dehydrohalogenating agents, optionally in the presence of a solvent, which is characterized is that the dehydrohalogenating agent is a heterocyclic base of the general formula

verwendet, in welcher Ri, R>, Rs und Ri Wasserstoffatome oder niedermolekulare Alkylgruppen mit 1 bis 5 Kohlenstoffatomen, η die Zahlen von 2 bis 7 und m die Zahlen von 2 bis 4 bedeuten.used, in which Ri, R>, Rs and Ri are hydrogen atoms or low molecular weight alkyl groups with 1 to 5 carbon atoms, η the numbers from 2 to 7 and m the numbers from 2 to 4.

Bei der weiteren Ausbildung des Verfahrens des deutschen Patentes 1 186 063 wurde nun gefunden, daß sich überraschenderweise auch sekundäre oder tertiäre Halogenverbindungen, deren Halogenatome sich nicht in «- oder /i-Stellung zu einer aktivierenden Gruppe, wie einer Carbonyl-, Carboxy-. Nitril-, Äthylen- oder Acetylengruppe, befinden, in die entsprechenden ungesättigten Verbindungen mit Hilfe der genannten heterocyclischen Basen überführen lassen.In the further development of the method of the German patent 1 186 063 it has now been found that, surprisingly, there are also secondary or tertiary halogen compounds, their halogen atoms not in «- or / i-position to an activating Group, such as a carbonyl, carboxy. Nitrile, ethylene or acetylene group, are in the corresponding convert unsaturated compounds with the aid of the heterocyclic bases mentioned permit.

Als Halogenverbindungen können geradkettige oder verzweigte sekundäre oder tertiäre aliphatische Halogenverbindungen oder auch cycloaliphatische Halogenverbindungen verwendet werden. Die genannten Verbindungstypen können darüber hinaus in ·-. Λ- oder f-Stellung andere funktioneile Gruppen, die keinen aktivierenden Einfluß mehr auf das Halogenatom ausüben, besitzen, wie Nitril-. Carboxy-, Carbonyl-, Äthylen- oder Acetylengruppen.Straight-chain or branched secondary or tertiary aliphatic compounds can be used as halogen compounds Halogen compounds or cycloaliphatic halogen compounds can be used. The mentioned Connection types can also be in · -. Λ- or f-position other functional groups, which no longer exert an activating influence on the halogen atom, such as nitrile. Carboxy, Carbonyl, ethylene or acetylene groups.

Die Halogenatome in den oben angeführten Halogenverbindungen können Chlor, Brom oder auch Jod sein.The halogen atoms in the halogen compounds listed above can be chlorine, bromine or also be iodine.

Verfahren zur Herstellung von olefinisch
ungesättigten VerbindungenProcess for the production of olefinic
unsaturated compounds

Zusatz zum Patent: 1186 063Addendum to the patent: 1186 063

Anmelder:Applicant:

Farbenfabriken Bayer Aktiengesellschaft,Paint factories Bayer Aktiengesellschaft,

5090 Leverkusen5090 Leverkusen

Als Erfinder benannt:Named as inventor:

Dr. Hermann Oediger, 5000 Köln-Flittard;Dr. Hermann Oediger, 5000 Cologne-Flittard;

Dr. Friedrich Möller, 5090 LeverkusenDr. Friedrich Möller, 5090 Leverkusen

Als Dehydrohalogenierungsmittel der obigen allgemeinen Formel eignen sich z. B. 1,5-Diazabicyclo - (4,3,0) - nonen - (5) oder 1,5 - Diaza - bicyclo-(4,5,0)-undecen-(5). Im übrigen verfährt man nach den Angaben des Patentes 1 186 063.Suitable dehydrohalogenating agents of the above general formula are, for. B. 1,5-diazabicyclo - (4,3,0) - nonene - (5) or 1,5 - diaza - bicyclo- (4,5,0) -undecen- (5). The rest of the procedure is as described in patent 1,186,063.

Beispiel 1example 1

Man erwärmt 82 Gewichtsteile Cyclohexylbromid, 40 Volumteile Dimethylsulfoxyd und 83 Gewichtsteile l,5-Diaza-bicyclo-(4,5,0)-undecen-(5) auf 95 C, wobei eine heftige Reaktion eintritt, und destilliert das entstandene Reaktionsprodukt ab. Ausbeute: 38,8 Gewichtsteile (950Ai der Theorie) Cyclohexen vom Siedepunkt 82 C.82 parts by weight of cyclohexyl bromide, 40 parts by volume of dimethyl sulfoxide and 83 parts by weight of 1,5-diaza-bicyclo- (4,5,0) -undecene (5) are heated to 95 ° C., a vigorous reaction occurs, and the resulting reaction product is distilled off. Yield: 38.8 parts by weight (95 0 of theory Ai) cyclohexene of boiling point 82 C.

Beispiel 2Example 2

Man verfährt wie im Beispiel 1 beschrieben, ,ersetzt jedoch die Base durch 70 Gewichtsteile l,5-Diaza-bicyclo-(4.3,0)-nonen-(5) und erhält 38 Gewichtsteile (93"/o der Theorie) Cyclohexen vom Siedepunkt 82 C.The procedure described in Example 1 is followed, but the base is replaced by 70 parts by weight l, 5-diaza-bicyclo- (4.3,0) -nonen- (5) and receives 38 parts by weight (93 "/ o of theory) cyclohexene from Boiling point 82 C.

Beispiel 3Example 3

Man erwärmt 36 Gewichtsteile 4-Bromheptan. 45 Gewichtsteile l,5-Diaza-bicyclo-(4.5,0)~undecen-(5) und 3 5 Volumteile Dimethylsulfoxyd auf 95 C, wobei das Reaktionsprodukt entsteht und aus dem Ansatz destilliert wird. Ausbeute: 17,9 Gewichtsteile (91 °,o der Theorie) Hepten-(3) vom Siedepunkt % bis 97 "C.36 parts by weight of 4-bromoheptane are heated. 45 parts by weight 1,5-diaza-bicyclo- (4.5,0) ~ undecen- (5) and 3 5 parts by volume of dimethyl sulfoxide at 95 C, the reaction product being formed and from the Approach is distilled. Yield: 17.9 parts by weight (91 °, o of theory) Hepten- (3) from the boiling point% to 97 "C.

809 620/592809 620/592

Beispiel 4Example 4

Man erwärmt 36 Gewichtsteile 2-Bromheptan und 33,4 Gewichtsteile l,5-Diaza-bicyclo-(4,5,0)-undecen-(5) bis zur Reaktionstemperatur von 800C und destilliert das Reaktionsprodukt ab. Ausbeute: 15,3 Gewichtsteile (78% der Theorie) Heptene vom Siedepunkt 96° C mit einem Gehalt von 79% Hepten-(2) und 19% Hepten-(l).The mixture is heated 36 parts by weight of 2-bromoheptane and 33.4 parts by weight of l, 5-diaza-bicyclo (4,5,0) -undecen- (5) up to the reaction temperature of 80 0 C and the reaction product is distilled off. Yield: 15.3 parts by weight (78% of theory) of heptene with a boiling point of 96 ° C. with a content of 79% heptene (2) and 19% heptene (1).

Beispiel5Example5

Man verfahrt wie im Beispiel 4 beschrieben, setzt jedoch als Halogenverbindung 2-Bromoctan ein. Man erhält 18,9 Gewichtsteile (84% der Theorie) Octene vom Siedepunkt 122° C mit einem Gehalt von 78% Octen-(2) und 21% Octen-(l).The procedure is as described in Example 4, but 2-bromooctane is used as the halogen compound. 18.9 parts by weight (84% of theory) of octenes with a boiling point of 122 ° C. and a content are obtained of 78% octene (2) and 21% octene (1).

Claims (1)

Patentanspruch:Claim: Weitere Ausbildung des Verfahrens zur Herstellung von olefinisch ungesättigten Verbindungen nach Patent 1 186 063, dadurch gekennzeichnet, daß man als organische Ausgangshalogenverbindungen sekundäre oder tertiäre organische Halogenverbindungen verwendet, deren Halogenatome sich nicht in α- oder /S-Stellung zu einer Carbonyl-, Carboxy-, Nitril-, Äthylen- oder Acetylengruppe befinden.Further development of the process for the production of olefinically unsaturated compounds according to patent 1,186,063, thereby characterized in that the organic starting halogen compounds are secondary or tertiary organic halogen compounds used whose halogen atoms are not in the α- or / S-position to a carbonyl, carboxy, Nitrile, ethylene or acetylene group. S09 620/592 9.68 O Bundesdruckerei BerlinS09 620/592 9.68 O Bundesdruckerei Berlin
DEF50559A 1962-05-15 1966-10-28 Process for the preparation of olefinically unsaturated compounds Pending DE1279679B (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
DEF50559A DE1279679B (en) 1966-10-28 1966-10-28 Process for the preparation of olefinically unsaturated compounds
CH1301267A CH533068A (en) 1962-05-15 1967-09-18 Preparation of olefins from heterocyclic bases and
AT864567A AT276318B (en) 1966-10-28 1967-09-22 Process for the preparation of olefinically unsaturated compounds
GB48686/67A GB1142718A (en) 1966-10-28 1967-10-26 Process for the production of olefinically unsaturated compounds
FR126243A FR1543088A (en) 1966-10-28 1967-10-27 Manufacturing process of olefinically unsaturated compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF50559A DE1279679B (en) 1966-10-28 1966-10-28 Process for the preparation of olefinically unsaturated compounds

Publications (1)

Publication Number Publication Date
DE1279679B true DE1279679B (en) 1968-10-10

Family

ID=7103889

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF50559A Pending DE1279679B (en) 1962-05-15 1966-10-28 Process for the preparation of olefinically unsaturated compounds

Country Status (3)

Country Link
AT (1) AT276318B (en)
DE (1) DE1279679B (en)
GB (1) GB1142718A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3898248A (en) * 1972-02-10 1975-08-05 Ciba Geigy Corp Dioxatricyclodecenes
US3900500A (en) * 1972-02-10 1975-08-19 Ciba Geigy Corp Esters of hydroxymethyl-dioxabicyclononene

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3707903A1 (en) * 1987-03-12 1988-09-22 Basf Ag PRODUCTION OF OLEFINS FROM TERTIA ALKYL HALOGENIDES

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3898248A (en) * 1972-02-10 1975-08-05 Ciba Geigy Corp Dioxatricyclodecenes
US3900500A (en) * 1972-02-10 1975-08-19 Ciba Geigy Corp Esters of hydroxymethyl-dioxabicyclononene

Also Published As

Publication number Publication date
GB1142718A (en) 1969-02-12
AT276318B (en) 1969-11-25

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