DE125308C - - Google Patents
Info
- Publication number
- DE125308C DE125308C DENDAT125308D DE125308DA DE125308C DE 125308 C DE125308 C DE 125308C DE NDAT125308 D DENDAT125308 D DE NDAT125308D DE 125308D A DE125308D A DE 125308DA DE 125308 C DE125308 C DE 125308C
- Authority
- DE
- Germany
- Prior art keywords
- anthranilic acid
- methyl ester
- acid methyl
- oil
- artificial
- 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
- GVOWHGSUZUUUDR-UHFFFAOYSA-N methyl 2-methylaminobenzoate Chemical compound CNC1=CC=CC=C1C(=O)OC GVOWHGSUZUUUDR-UHFFFAOYSA-N 0.000 claims description 8
- 230000035943 smell Effects 0.000 claims description 3
- 239000003205 fragrance Substances 0.000 claims description 2
- 239000001071 citrus reticulata blanco var. mandarin Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VAMXMNNIEUEQDV-UHFFFAOYSA-N Methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 235000019645 odor Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-(4R)-Limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 2
- WVMBPWMAQDVZCM-UHFFFAOYSA-N N-methylanthranilic acid Chemical compound CNC1=CC=CC=C1C(O)=O WVMBPWMAQDVZCM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000001524 citrus aurantium oil Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N (+-)-(RS)-limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- KSMVZQYAVGTKIV-UHFFFAOYSA-N Decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 1
- GYHFUZHODSMOHU-UHFFFAOYSA-N Nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N Terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 229940116411 Terpineol Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229930007650 limonene Natural products 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
Description
PATENTAMTPATENT OFFICE
M 125308 KLASSE 23«. M 125308 CLASS 23 «.
anthranilsäuremethylester.anthranilic acid methyl ester.
Wie durch wissenschaftliche Untersuchungen, die darauf hinzielten, den für das Mandarinenöl charakteristischen Geruchsträger aufzufinden, ermittelt wurde, ist dieser wesentliche Bestandtheil der Methylester der Methylanthranilsäure. Dieser bisher noch nicht dargestellte Körper wurde nicht allein aus dem Mandarinenöl, sondern auch auf synthetischem Wege gewonnen. As through scientific research aimed at making the mandarin oil to find characteristic odor carriers, is this essential component the methyl ester of methyl anthranilic acid. This body not yet shown was not only obtained from mandarin oil, but also synthetically.
Auf Grund dieser Feststellung gelingt es, unter Verwendung von Methylanthranilsäuremethylester künstliches Mandarinenöl wie überhaupt künstliche Blumengerüche herzustellen. Es ist bisher kein Körper bekannt geworden, der den Methylanthranilsäuremethylester ersetzen könnte. Beispielsweise gelingt es ebensowenig, mit Hülfe von Anthranilsäuremethylester künstliches Mandarinenöl zu erzeugen, wie es unmöglich ist, mit Hülfe von Methylanthranilsäuremethylester künstliches Neroliöl darzustellen, denn wie für das Neroliöl der Anthranilsäuremethylester der charakteristische Geruchsträger ist, so ist es der Methylanthranilsäuremethylester für das Mandarinenöl.Based on this finding, it is possible to use methyl anthranilic acid methyl ester to make artificial mandarin oil like any artificial flower scents. So far, no body has become known which can replace methyl anthranilic acid methyl ester could. For example, it is just as unsuccessful with the aid of anthranilic acid methyl ester To produce artificial mandarin oil as it is impossible with the aid of methyl anthranilic acid methyl ester To represent artificial neroli oil, because as for the neroli oil the anthranilic acid methyl ester the characteristic odor carrier is, it is the methyl anthranilic acid methyl ester for the mandarin oil.
Der reine Ester ist ein bei 12 mm Druck und 1300C. siedendes OeI, das in der Kälte erstarrt und bei 20° C schmilzt; das spec. Gew. beträgt 1,120 bei 150C. Es besitzt in Verdünnung einen milden Blumengeruch, der namentlich im Gemisch mit anderen Riechstoffen angenehm hervortritt und diesen Gemischen einen besonderen Charakter verleiht. In dem Mandarinenöl ist der Körper dadurch nachzuweisen, dafs man das OeI mit 25 proc. Schwefelsäure ausschüttelt, die Säure mit Soda übersättigt und den sich ausscheidenden Ester mit Aether aufnimmt. Nach dem Verdunsten des Aethers bleibt die Verbindung als OeI zurück. Durch Verseifen desselben mit alkoholischem Kali läfst sich daraus leicht die bei 1790 C. schmelzende Methylanthranilsäure gewinnen.The pure ester is a 12 mm pressure and 130 0 C. boiling, melting oil solidifies in the cold and at 20 ° C; the spec. Weight is. 1,120 at 15 0 C. Dilution It has a mild floral scent, which notably pleasant emerges as a mixture with other fragrances and these mixtures gives a special character. In the mandarin oil, the body can be demonstrated by adding 25 per cent to the oil. Sulfuric acid is shaken out, the acid is supersaturated with soda and the ester which is precipitated is absorbed with ether. After the ether has evaporated, the compound remains as an OeI. By hydrolysis thereof with alcoholic potash läfst therefrom easily, the melting at 179 0 C. methylanthranilic gain.
Die Darstellung des Methylanthranilsäuremethylesters erfolgt nach den Angaben der Patentschrift 122568.The methyl anthranilic acid methyl ester is represented in accordance with the information provided by Patent 122568.
Die Herstellung der künstlichen Blumengerüche kann entweder in der Weise geschehen, dafs die verschiedenen Substanzen mit Methylanthranilsäuremethylester direct vermischt werden, oder dafs man erst eine Lösung der Stoffe herstellt und diese Lösungen vermischt.The production of artificial flower scents can be done either in the way that the various substances are mixed directly with methyl anthranilic acid, or that one first prepares a solution of the substances and mixes these solutions.
Die Natur der weiteren Substanzen aufser Methylanthranilsäuremethy!ester, die zur Herstellung der künstlichen BlumengerUche benutzt werden sollen, richtet sich nach dem besonderen, im Einzelfalle gewünschten Gerüche.The nature of the other substances other than methyl anthranilic acid methyl ester, which are used for the production the artificial flower smells are to be used, depends on the special, odors desired in individual cases.
Als Beispiel· für die Darstellung synthethischer Blumengerüche wird im Folgenden das tür die Herstellung von künstlichem Mandarinenöl vortheilhaft innegehaltene Mischungsverhällnifs angegeben:As an example for the representation of synthetic floral smells, the door will be used below Manufacture of artificial mandarin oil advantageously maintained mixing ratios specified:
800 g d-Limonen,800 g d-limonene,
250 g Dipenten,250 g dipentene,
ι g Decylaldehyd,ι g decylaldehyde,
2 g Nonylaldehyd,
4 g Linalool,2 g nonyl aldehyde,
4 g linalool,
3 g Terpineol,3 g terpineol,
40 g Methylanthranilsäuremethylester.40 g of methyl anthranilic acid methyl ester.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE125308C true DE125308C (en) |
Family
ID=394044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT125308D Active DE125308C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE125308C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2865806A (en) * | 1955-08-05 | 1958-12-23 | Interstate Sanitation Company | Solidified air odor control liquids |
| US2871526A (en) * | 1955-10-04 | 1959-02-03 | Interstate Sanitation Company | Porous containers for thickened air odor control liquids |
| US2905591A (en) * | 1955-08-05 | 1959-09-22 | Interstate Sanitation Company | Air odor control liquids |
| FR2584926A1 (en) * | 1985-07-22 | 1987-01-23 | Robertet Cie P | Novel application of 2-aminobenzaldehyde and perfumes or aromatic compositions containing this synthetic substance |
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0
- DE DENDAT125308D patent/DE125308C/de active Active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2865806A (en) * | 1955-08-05 | 1958-12-23 | Interstate Sanitation Company | Solidified air odor control liquids |
| US2905591A (en) * | 1955-08-05 | 1959-09-22 | Interstate Sanitation Company | Air odor control liquids |
| US2871526A (en) * | 1955-10-04 | 1959-02-03 | Interstate Sanitation Company | Porous containers for thickened air odor control liquids |
| FR2584926A1 (en) * | 1985-07-22 | 1987-01-23 | Robertet Cie P | Novel application of 2-aminobenzaldehyde and perfumes or aromatic compositions containing this synthetic substance |
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