DE272572C - - Google Patents
Info
- Publication number
- DE272572C DE272572C DENDAT272572D DE272572DA DE272572C DE 272572 C DE272572 C DE 272572C DE NDAT272572 D DENDAT272572 D DE NDAT272572D DE 272572D A DE272572D A DE 272572DA DE 272572 C DE272572 C DE 272572C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- heated
- camphene
- chlorohydrate
- pinene
- 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.)
- Active
Links
- GRWFGVWFFZKLTI-UHFFFAOYSA-N (+-)-2-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- CRPUJAZIXJMDBK-DTWKUNHWSA-N (+)-camphene Chemical compound C1C[C@@H]2C(=C)C(C)(C)[C@H]1C2 CRPUJAZIXJMDBK-DTWKUNHWSA-N 0.000 claims description 7
- 229930006739 camphene Natural products 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 235000007586 terpenes Nutrition 0.000 claims description 6
- -1 Terpene hydrocarbons Chemical class 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- XMGQYMWWDOXHJM-UHFFFAOYSA-N (+-)-(RS)-limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 3
- 229930007650 limonene Natural products 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 150000003505 terpenes Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N Phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 1
- 229910000394 calcium triphosphate Inorganic materials 0.000 claims 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- RFWLACFDYFIVMC-UHFFFAOYSA-D pentacalcium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O.[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O RFWLACFDYFIVMC-UHFFFAOYSA-D 0.000 claims 1
- 239000003610 charcoal Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 5
- 210000004369 Blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L Calcium hydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000006004 Quartz sand Substances 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- PZZYQPZGQPZBDN-UHFFFAOYSA-N Aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M Sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M Sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M methanoate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 150000003097 polyterpenes Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
■- M 272572-KLASSE 12 o. GRUPPE■ - M 272572-CLASS 12 or GROUP
Dr. ALFRED MEYER in MULHAUSEN i. Els.Dr. ALFRED MEYER in MULHAUSEN i. Els.
Zusatz zum Patent 272562.Addendum to patent 272562.
Patentiert im Deutschen Reiche vom 12. Dezember 1911 ab. Längste Dauer: 19.Juni 1926.Patented in the German Empire on December 12, 1911. Longest duration: June 19, 1926.
Wie in dem Patent 272562 beschriebenAs described in patent 272562
wurde, tritt beim Erhitzen der Halogenhydrate der Terpenkohlenwasserstoffe, beispielsweise von Pinen- oder Dipentenchlorhydrat mit Kieselgur, eine lebhafte Salzsäureentwicklung ein unter Bildung von Terpenkohlenwasserstoffen.occurs when the halohydrates of the terpene hydrocarbons are heated, for example of pinene or dipentene chlorohydrate with kieselguhr, a lively development of hydrochloric acid with the formation of terpene hydrocarbons.
Die Reaktion hat ■ auch Geltung für dieThe reaction also applies to the
Halogenhydrate der Hemi- und der Polyterpene. Halohydrates of the hemi- and polyterpenes.
Wird z. B. Pinenmonochlorhydrat mit 1 bis 3 Prozent seines Gewichts Kieselgur während 30 Stunden auf Siedetemperatur erhitzt, so wird die gebundene Salzsäure ganz abgespalten. Man erhält ungefähr 35 Prozent Camphen neben flüssigen Terpenen und harzartigenVerbiridungen. Is z. B. pinene monochlorohydrate with 1 to 3 percent of its weight kieselguhr during When heated to boiling temperature for 30 hours, the bound hydrochloric acid is completely split off. About 35 percent camphene is obtained along with liquid terpenes and resinous compounds.
Es wurde nun gefunden, daß auch andere katalytisch wirkende, im übrigen indifferente Substanzen die gleiche Wirkung wie Kieselgur, teilweise sogar mit besserem Erfolg, ergeben. It has now been found that other catalytically active, otherwise indifferent ones Substances have the same effect as diatomaceous earth, sometimes even with better results.
Versuche haben ergeben, daß die Ausbeute mit der Art des verwendeten Katalysators wechselt; Blut- und Tierkohle liefern die besten Resultate. So erhält man beispielsweise beim Erhitzen von Pinenchlorhydrat mit künstlicher Kohle, z. B. Tierkohle, Camphen in 85 prozentiger Ausbeute. Andere Katalysatoren, wie Quarzsand, Kaolin, Korkmehl, Glaspulver, ergeben weniger gute Resultate.Tests have shown that the yield depends on the type of catalyst used changes; Blood and animal charcoal give the best results. For example, the Heating pinene chlorohydrate with charcoal, e.g. B. animal charcoal, camphene in 85 percent Yield. Other catalysts, such as quartz sand, kaolin, cork flour, glass powder, result less good results.
Verdünnt man das Reaktionsgemisch oder sorgt dafür, daß die entstehende Salzsäure in statu nascendi gebunden wird, was mit verschiedenartigen Zusätzen, wie Amine, Phenolate, Salze der organischen Säuren, Oxyde, Hydroxyde, Metalle u. a. m., geschehen kann, so erhält man in jedem Falle weit bessere Ausbeuten. Es können bei solcher Arbeitsweise außer künstlicher Kohle auch andere Katalysatoren mit zufriedenstellendem Erfolg verwendet werden.If you dilute the reaction mixture or ensure that the hydrochloric acid formed is in statu nascendi is bound, what with various additives, such as amines, phenolates, Salts of organic acids, oxides, hydroxides, metals and others. m., can happen, far better yields are obtained in each case. It can work in such a way in addition to charcoal, other catalysts have also met with satisfactory results be used.
Ausführungsbeispiele..Embodiments ..
100 Teile der bei der Herstellung von Pinenchlorhydrat erhaltenen chlorhaltigen Nebenprodukte und 10 Teile Blutkohle werden auf Siedetemperatur erhitzt, bis keine Salzsäuredämpfe mehr entweichen. Das Reaktionsprodukt wird der Wasserdampfdestillation unterworfen, wobei etwa 70 Teile chlorfreie Kohlenwasserstoffe übergehen, deren Siedepunkte zwischen 155 und 185 ° liegen.100 parts of the amount used in the manufacture of pinene chlorohydrate obtained chlorine-containing by-products and 10 parts of blood charcoal are on Heated to boiling temperature until no more hydrochloric acid vapors escape. The reaction product is subjected to steam distillation, with about 70 parts of chlorine-free hydrocarbons pass over, the boiling points of which are between 155 and 185 °.
52 Teile Pinenchlorhydrat und 4 Teile Tierkohle werden nach Beispiel 1 behandelt. Die Ausbeute an Camphen erreicht 80 bis 85 Prozent.52 parts of pinene chlorohydrate and 4 parts of animal charcoal are treated according to Example 1. the Yield of camphene reaches 80 to 85 percent.
Eine innige Mischung von 52 Teilen Pinenchlorhydrat, 5 bis 10 Teilen Blutkohle, 48 Teilen Natriumbenzoat oder 50 Teilen Bleiformiat oder 35 Teilen Natriumformiat wird währendAn intimate mixture of 52 parts of pinene chlorohydrate, 5 to 10 parts of blood charcoal, 48 parts Sodium benzoate or 50 parts of lead formate or 35 parts of sodium formate is used during
5555
6060
4 bis ίο Stunden auf 115 bis 160° erhitzt. Das mit guter Ausbeute gebildete Camphen wird mittels Wasserdampfdestillation isoliert.Heated to 115 to 160 ° for 4 to ίο hours. The camphene formed in good yield is isolated by means of steam distillation.
Beispiel 4. .Example 4..
52 Teile Pinenchlorhydrat, 4 bis 8 Teile Blut- oder Tierkohle, 8 bis 30 Teile wasserfreies Natriumcarbonat oder 12 Teile Natriumhydrat in Pulver werden etwa 4 Stunden zum Sieden erhitzt. Das gebildete Camphen kann durch direkte Destillation oder mit Wasserdampf gewonnen werden. Die Ausbeute ist eine fast quantitative.52 parts pinene chlorohydrate, 4 to 8 parts blood or animal charcoal, 8 to 30 parts anhydrous Sodium carbonate or 12 parts of sodium hydrate in powder will take about 4 hours Boiling heated. The camphene formed can be produced by direct distillation or with steam be won. The yield is almost quantitative.
Man erhitzt während 5 bis 6 Stunden auf 120° ein Gemisch von 52 Teilen Pinenchlorhydrat, 15 Teilen Tierkohle, 10 bis 40 Teilen Benzoesäure.A mixture of 52 parts of pinene chlorohydrate is heated to 120 ° for 5 to 6 hours, 15 parts of animal charcoal, 10 to 40 parts of benzoic acid.
100 Teile flüssige Nebenprodukte der Pinenchlorhydratdarstellung, 100 Teile Calciumhydroxyd, 10 Teile Glaspulver werden während 3 Stunden auf etwa 160° erhitzt. Man erhält 65 bis 70 Teile flüchtige Kohlenwasserstoffe, zwischen 155 und 185 ° siedend.100 parts of liquid by-products of the pinene chlorohydrate representation, 100 parts of calcium hydroxide, 10 parts of glass powder are used during Heated to about 160 ° for 3 hours. 65 to 70 parts of volatile hydrocarbons are obtained, boiling between 155 and 185 °.
42 Teile Dipentenchlorhydrat, 42 Teile CaI-ciumhydroxyd, 4 Teile Quarzsand werden wäh-42 parts of dipentene chlorohydrate, 42 parts of calcium hydroxide, 4 parts of quartz sand are
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE272572C true DE272572C (en) |
Family
ID=529118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT272572D Active DE272572C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE272572C (en) |
-
0
- DE DENDAT272572D patent/DE272572C/de active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1271115C2 (en) | Process for the purification of reducible, cyclic, organic compounds by distillation | |
| DE272572C (en) | ||
| DE2324390A1 (en) | PROCESS FOR THE PRODUCTION OF DERIVATIVES OF CYCLOPROPANE | |
| DE2416584A1 (en) | HEXAMETHYLTETRACOSANE DIOL DERIVATIVES AND PROCESS FOR THE PREPARATION | |
| AT398969B (en) | 4-TRANS- (N-ISOPROPYLIDEN-AMINO) -CYCLOHEXANOL AND METHOD FOR THE PRODUCTION THEREOF | |
| DE2225443C3 (en) | Process for the preparation of thiophenes | |
| DE2353330C2 (en) | Process for the production of pure 1,1,2-trifluoro-2-chloroethyl difluoromethyl ether | |
| DE576388C (en) | Process for the preparation of camphene | |
| DE2405251A1 (en) | PROCESS FOR REMOVING CARBONYL COMPOUNDS | |
| DE1241430B (en) | Process for the preparation of primary aliphatic alcohols | |
| DE890339C (en) | Process for the production of symm. 1, 2, 4, 5-tetrachlorobenzene from ª € -heptachlorocyclohexane | |
| DE740987C (en) | Process for the preparation of alcohols of the acetylene series | |
| DE854503C (en) | Process for the production of higher molecular conversion products of allyl compounds | |
| DE657069C (en) | Process for the preparation of ª ‡ -oxyisobutyrate methyl ester | |
| DE862016C (en) | Process for the preparation of tetrahydropyran derivatives | |
| DE2051320C3 (en) | Process for the purification of aliphatic dicarboxylic acid mixtures | |
| DE272562C (en) | ||
| DE151880C (en) | ||
| DE498281C (en) | Process for the preparation of thymol | |
| DE511949C (en) | Process for the preparation of thymol (3-oxy-1-methyl-4-isopropylbenzene) | |
| DE445524C (en) | Process for the preparation of ªÏ-chloroacetobrenzcatechol | |
| DE1095267B (en) | Process for the production of ªÏ-halostyrenes and their homologues | |
| DE895898C (en) | Process for the preparation of ª ‡ -alkyl-substituted carboxylic acids | |
| DE696724C (en) | Process for the production of hydrinds and ª ‡ and ª ‰ truxes | |
| DE1518787C (en) |