US725890A - Process of making camphene. - Google Patents

Process of making camphene. Download PDF

Info

Publication number
US725890A
US725890A US11022602A US1902110226A US725890A US 725890 A US725890 A US 725890A US 11022602 A US11022602 A US 11022602A US 1902110226 A US1902110226 A US 1902110226A US 725890 A US725890 A US 725890A
Authority
US
United States
Prior art keywords
camphene
pinene
soap
hydrochlorid
kilograms
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 - Lifetime
Application number
US11022602A
Inventor
Karl Stephan
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.)
CHEM FAB VORM E SCHERING
Original Assignee
CHEM FAB VORM E SCHERING
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 CHEM FAB VORM E SCHERING filed Critical CHEM FAB VORM E SCHERING
Priority to US11022602A priority Critical patent/US725890A/en
Application granted granted Critical
Publication of US725890A publication Critical patent/US725890A/en
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

Definitions

  • camphene 5 of soaps be used not as a reagent, but as a free from chlorin which consists in heating solvent for pinene hydrochlorid, and the hypinene hydrochlorid with a base in watery sodrochloric acid be split off by means of bases, lution in the presence of soap as a solvent the reaction proceeds quite smoothly, and for said pinene hydrochlorid, and isolating camphene free from chlorin is obtained in the camphene so formed, substantially as set 40 good yield without using an excess of soap. forth.
  • drochlorid are heated in an autoclave for 45 twenty hours to from 210 to 220 Celsius, to- KARL STEPHAN' gether with ten kilograms of soap-for in- witnesseses: stance, sodium or potash soap, or a mixture HENRY HASPER, of both-four kilograms of sodium hydrate, WOLDEMAR HAUPT.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Sampling And Sample Adjustment (AREA)

Description

UNITED STATES PATENT @EFTQE.
KARL STEPHAN, OF BERLIN, GERMANY, ASSIGNOR TO' CHEMISCI-IE FABRIK AUF ACTIEN VORM. E. SOHERING, OF BERLIN, GERMANY.
PROCESS OF MAKING CAMPHENE.
SPECIFICATION forming part of Letters Patent N0. 725,890, dated April 21, 1903.
' Application filed June 4, 1902. Serial No. 110,226. T Specimens.)
To all whom it may concern.- and five kilograms of water. After cooling Beitknown thatI, KARL STEPHAN, chemist, the product of reaction is acidified and the 0 doctor of philosophy, a subject of the Emcamphene produced driven over with steam. peror of Germany, residing at Berlin, King- Example 2: Ten kilograms of pinene hy- 5 dom of Prussia, German Empire, have indrochlorid are heated for twenty hours to 210 ventedanewandusefulImprovementin Pr oc- Celsius, together with 5.3 kilograms ammoesses of Manufacturing Camphene free from nia-soap (ammonia stearate) and five kilo- 5 5 Ohlorin, of which the following is a specificagrams vof watery ammonia, whereupon the tion. product of reaction is purified in the same The invention relates to the manufacture manner as indicated in the foregoing exof camphene free from chlorin by reacting ample. with bases upon pinene hydrochlorid (bornyl- It is still more preferable not to use the chiorid) in watery solution and using the already-made ammonia-soap, but to combine kaline salts of the higher fatty acids, es-. an excess of watery ammonia with stearic 15 pecially all kinds of soap, as a solvent. In the acid.for example, six kilograms of watery presence of such substances the actionof the ammonia (specific weight 0.9l0)and five bases upon pinene hydrochlorid is performed kilograms of stearic acid, whereby ammonia in a perfect manner even in watery solution. stearate is formed and an excess'of ammonia The manufacture of camphene by heating remains for the action upon the pinene hy- 2o pinene hydrochlorid with dry powdered soap drochlorid.
is known, (Berthelot, Annalen cler Ohemt'e By usingother bases the production of cam- 110, page 367, and O'omptes Rendus 47, page phone takes place in an analogous manner. 266.) In this reaction the alkali is withdrawn In all cases the camphene is obtained free from the alkaline salt of a fatty acid with the from chlorin.
25 formation of free fatty acid, the alkali being I claim as my inventionutilized for splitting the hydrochloric acid off 1. The process of manufacturing camphene from the pinene hydrochlorid. Under the free from chlorin which consists in heating a conditions given (heating to from 240 to 250 hydrogen-haloid compound of pinene with a Celsius for forty hours) the reaction only sucbase in watery solution in the presence of an 0 ceeds when a very large excess of powdered alkali salt of the higher fatty acids as a solsoap is used, according to Berthelot eight vent for said pinene compound, and isolating times the theoretical amount. If, however, the camphene so formed, substantially as set according to my invention an alkaline salt forth. of the higher fatty acids, especially all kinds 2. The process of manufacturing camphene 5 of soaps, be used not as a reagent, but as a free from chlorin which consists in heating solvent for pinene hydrochlorid, and the hypinene hydrochlorid with a base in watery sodrochloric acid be split off by means of bases, lution in the presence of soap as a solvent the reaction proceeds quite smoothly, and for said pinene hydrochlorid, and isolating camphene free from chlorin is obtained in the camphene so formed, substantially as set 40 good yield without using an excess of soap. forth.
It is even sufficient to use half a molecule of In testimony whereof I have signed my soap referred to as pinene hydrochlorid. name to this specification in the presence of Example 1: Ten kilograms of pinene hytwo subscribing witnesses.
drochlorid are heated in an autoclave for 45 twenty hours to from 210 to 220 Celsius, to- KARL STEPHAN' gether with ten kilograms of soap-for in- Witnesses: stance, sodium or potash soap, or a mixture HENRY HASPER, of both-four kilograms of sodium hydrate, WOLDEMAR HAUPT.
US11022602A 1902-06-04 1902-06-04 Process of making camphene. Expired - Lifetime US725890A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US11022602A US725890A (en) 1902-06-04 1902-06-04 Process of making camphene.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US11022602A US725890A (en) 1902-06-04 1902-06-04 Process of making camphene.

Publications (1)

Publication Number Publication Date
US725890A true US725890A (en) 1903-04-21

Family

ID=2794400

Family Applications (1)

Application Number Title Priority Date Filing Date
US11022602A Expired - Lifetime US725890A (en) 1902-06-04 1902-06-04 Process of making camphene.

Country Status (1)

Country Link
US (1) US725890A (en)

Similar Documents

Publication Publication Date Title
US1841768A (en) Chlorinated and brominated ethine carbinols
US725890A (en) Process of making camphene.
US812554A (en) Alkamin esters of para-aminobenzoic acid.
JPS5821906B2 (en) trans-4-aminomethylcyclohexacarbonate
US3377374A (en) 4-(aminomethyl)cyclohexane-carbonitrile
US2574150A (en) Acenaphthenyl amino alcohols
US1889678A (en) Aromatic esters of amino alcohols and process of manufacture
US1887396A (en) Aromatic halogen-methyl compound and alpha process of preparing it
KR101613065B1 (en) Synthetic method of dihydroquinoline derivatives
US2541747A (en) Production of hydroxyl compounds by hydrolysis of tetrahydropyryl ethers
US2177547A (en) Diaryldithiocarbamyl derivative and method of making the same
US2457226A (en) Preparation of choline chloride
US2837529A (en) Substituted thiazolidones and their preparation
US996096A (en) Derivative of phenylalkylacetic acid.
JPS59101437A (en) Manufacture of fluorene-9-carboxylic acid
Berlin et al. Condensation of Catechol with Phenylphosphonous Dichloride. A Novel Ring-Cleavage Reaction1
US696020A (en) Amidoöxybenzyl compound and process of making same.
US922766A (en) Anhydrid of acyl salicylic acid.
US2845431A (en) Alkyl-piperidiones and process for the manufacture thereof
US707271A (en) Process of making camphene.
US828070A (en) Alkamin ester.
US839100A (en) Carbamic-acid ester and process of making same.
US1030239A (en) Process of producing aliphatic hydrocarbons with more than one double bond.
US994445A (en) Methoxymethylmenthol.
US1069296A (en) Derivatives of phenylcinchoninic acid.