DE426865C - Process for the production of a reactive chloride from pinene or turpentine oil - Google Patents

Process for the production of a reactive chloride from pinene or turpentine oil

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Publication number
DE426865C
DE426865C DEH101354D DEH0101354D DE426865C DE 426865 C DE426865 C DE 426865C DE H101354 D DEH101354 D DE H101354D DE H0101354 D DEH0101354 D DE H0101354D DE 426865 C DE426865 C DE 426865C
Authority
DE
Germany
Prior art keywords
pinene
turpentine oil
production
chloride
reactive chloride
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.)
Expired
Application number
DEH101354D
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German (de)
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.)
FRITZ HOEHN DR
Original Assignee
FRITZ HOEHN DR
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 FRITZ HOEHN DR filed Critical FRITZ HOEHN DR
Priority to DEH101354D priority Critical patent/DE426865C/en
Application granted granted Critical
Publication of DE426865C publication Critical patent/DE426865C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
    • C07C17/08—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated hydrocarbons

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung eines reaktionsfähigen Chlorids aus. Pinen bzw. Terpentinöl. Während Pinen mit trockenem Chlor= Wasserstoff unter Bildung von Pinenchlorhydrat (Bornylchlorid) und dem nicht ein-' heitlichen »flüssigen Pinenchlorhydrat« reagiert, liefert es bei mehrwöchigem Stehen mit konzentrierter wässeriger Salzsäure Dipentendichlorhvdrat und wenig Pinenchlorhydrat (Berthe 1 o t, Ann. de Chimie [3] 37, 22q.). Es wurde nun gefunden, daß die Reaktion zwischen Pinen und HCI einen ganz anderen, nicht vorauszusehenden Verlauf nimmt, wenn man völlig gesättigte wässerige Salzsäure (D. nicht unter i,2) verwendet und die Säure während der Reaktion durch Einleiten von HCl-Gas dauernd gesättigt erhält. Dabei entsteht dann kein Dipentendichlorhydrat, sondern in sehr guter Ausbeute ein kristallisiertes, stechend riechendes, sehr reaktionsfähiges Chlorid C"H" Cl, das im Gegensatz zum Pinenchlorhydrat bei gewöhnlicher Temperatur langsam, beim Erhitzen lebhaft HCl abspaltet unter Bildung von Camphen. Letzteres läßt sich nach bekannten Verfahren in Isobornylderivate oder Kampfer überführen.Process for the production of a reactive chloride from. Pinene or turpentine oil. While pinene with dry chlorine = hydrogen with the formation of Pinene chlorohydrate (bornyl chloride) and the inconsistent »liquid pinene chlorohydrate« reacts, it delivers when standing for several weeks with concentrated aqueous hydrochloric acid Dipentene dichlorohydrate and a little pinene chlorohydrate (Berthe 10, Ann. De Chimie [3] 37, 22q.). It has now been found that the reaction between pinene and HCl is one takes a completely different, unforeseeable course if one is completely saturated with water Hydrochloric acid (D. not under i, 2) is used and the acid is carried out during the reaction Introducing HCl gas is kept continuously saturated. No dipentene dichlorohydrate is then formed, but in very good yield a crystallized, pungent smelling, very reactive one Chloride C "H" Cl, which, in contrast to pinene chlorohydrate, occurs at ordinary temperature slowly, vigorously splitting off HCl on heating with the formation of camphene. The latter can be converted into isobornyl derivatives or camphor by known processes.

Gute Kühlung während derEinwirkung der Salzsäure auf das Pinen erhöht die Ausbeute beträchtlich, doch erhält man auch noch bei etwa + io° das gleiche Chlorid, allerdings bedeutend langsamer (wegen der geringeren HCl-Konzentration der wässerigen Phase) und in geringerer Ausbeute.Good cooling during the action of the hydrochloric acid on the pinene increases the yield is considerable, but the same is still obtained at about + 10 ° Chloride, but much more slowly (because of the lower HCl concentration the aqueous phase) and in lower yield.

B e i s p i e 1. Man sättigt i 1 konzentrierte Salzsäure (D i, ig) unter Kühlung durch Eis-Kochsalz-Mischung mit Chlorwasserstoffgas und läßt dann unter Kühlung und dauerndem weiteren Durchleiten von HCl-Gas 2 kg 1-Pinen bzw. rektifiziertes Terpentinöl, für sich oder mit indifferentem Lösungsmittel, z. B. Petroläther, verdünnt, auf die Salzsäure fließen. Die Reaktion verläuft rasch und glatt und ist % Stunde, nachdem das Pinen eingetragen ist, beendet. Hat man unverdünntes Pinen angewandt, :o stellt das Reaktionsprodukt eine schwach rötlich oder lila gefärbte kampferartige Masse dar, aus der man durch Absaugen und Abpressen das feste weiße Chlorid C",H"C1 in genügender Reinheit erhält. Als Nebenprodukt erhält man ein schwach bräunliches 0I (etwa 30 Prozent der Gesamtausbeute), das bei starker Abkühlung noch weitere Mengen des festen Chlorids ausscheidet und dann beim Erhitzen unter HCl-Entwicklung noch etwas Camphen liefert. -Die gesättigte Salzsäure wird bei dieser Reaktion nur durch geringe Mengen rötlicher harziger Nebenprodukte verunreinigt und ist wiederholt verwendbar.Example 1. One saturates i 1 concentrated hydrochloric acid (D i, ig) while cooling with an ice-common salt mixture with hydrogen chloride gas and then leaving 2 kg of 1-pinene or rectified turpentine oil for themselves or with an inert solvent, e.g. B. petroleum ether, diluted, flow on the hydrochloric acid. The reaction proceeds quickly and smoothly and is completed 1 hour after the pinene has been introduced. If undiluted pinene has been used: o the reaction product is a pale reddish or purple colored camphor-like mass, from which the solid white chloride C ", H" C1 is obtained in sufficient purity by suction and pressing. A slightly brownish oil is obtained as a by-product (about 30 percent of the total yield), which separates out further amounts of solid chloride when cooled down and then yields some camphene when heated with evolution of HCl. -The saturated hydrochloric acid is only contaminated by small amounts of reddish resinous by-products in this reaction and can be used repeatedly.

Claims (1)

PATENT-ANSpRUcH Verfahren zur Herstellung eines reaktionsfähigen Chlorids aus Pinen bzw. Terpentinöl, darin bestehend, daß mangereinigtes Terpentinöl bei einer unter -3- i5° liegenden Temperatur mit gesättigter wässeriger Salzsäure behandelt.PATENT CLAIM Process for the production of a reactive chloride from pinene or turpentine oil, consisting in the fact that unpurified turpentine oil at a temperature below -3- 15 ° treated with saturated aqueous hydrochloric acid.
DEH101354D 1925-04-04 1925-04-04 Process for the production of a reactive chloride from pinene or turpentine oil Expired DE426865C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEH101354D DE426865C (en) 1925-04-04 1925-04-04 Process for the production of a reactive chloride from pinene or turpentine oil

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEH101354D DE426865C (en) 1925-04-04 1925-04-04 Process for the production of a reactive chloride from pinene or turpentine oil

Publications (1)

Publication Number Publication Date
DE426865C true DE426865C (en) 1926-10-25

Family

ID=7168775

Family Applications (1)

Application Number Title Priority Date Filing Date
DEH101354D Expired DE426865C (en) 1925-04-04 1925-04-04 Process for the production of a reactive chloride from pinene or turpentine oil

Country Status (1)

Country Link
DE (1) DE426865C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE752613C (en) * 1939-11-26 1952-07-17 Ig Farbenindustrie Ag Process for the production of terpene alcohols

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE752613C (en) * 1939-11-26 1952-07-17 Ig Farbenindustrie Ag Process for the production of terpene alcohols

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