DE121975C - - Google Patents
Info
- Publication number
- DE121975C DE121975C DENDAT121975D DE121975DA DE121975C DE 121975 C DE121975 C DE 121975C DE NDAT121975 D DENDAT121975 D DE NDAT121975D DE 121975D A DE121975D A DE 121975DA DE 121975 C DE121975 C DE 121975C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- water
- bases
- hydrobenzylamine
- solution
- 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
- -1 hydrogenated cyclic aldehydes Chemical class 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 150000001299 aldehydes Chemical class 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
- 235000007586 terpenes Nutrition 0.000 description 4
- QUVVWJCCKDPUTC-UHFFFAOYSA-N 1,6,6-trimethylcyclohex-2-ene-1-carbaldehyde Chemical compound CC1(C)CCC=CC1(C)C=O QUVVWJCCKDPUTC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- MMBONBGNSXPWSM-UHFFFAOYSA-N 1,2,2-trimethylcyclohexane-1-carbaldehyde Chemical compound CC1(C)CCCCC1(C)C=O MMBONBGNSXPWSM-UHFFFAOYSA-N 0.000 description 2
- MOQGCGNUWBPGTQ-UHFFFAOYSA-N 2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde Chemical compound CC1=C(C=O)C(C)(C)CCC1 MOQGCGNUWBPGTQ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- WQTVNGHNKXINJE-UHFFFAOYSA-N N-(cyclohexylmethyl)-N,2,3-trimethylaniline Chemical compound CC=1C(=C(N(CC2CCCCC2)C)C=CC1)C WQTVNGHNKXINJE-UHFFFAOYSA-N 0.000 description 2
- BUPPOBQAJKCHHT-UHFFFAOYSA-N N-(cyclohexylmethyl)-N-methyl-2-propan-2-ylaniline Chemical compound C(C)(C)C1=C(N(CC2CCCCC2)C)C=CC=C1 BUPPOBQAJKCHHT-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000035943 smell Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- GWEYIWCYHAXIBE-UHFFFAOYSA-N 3-cyclohexyl-n-methyl-n-propan-2-ylpropan-1-amine Chemical compound CC(C)N(C)CCCC1CCCCC1 GWEYIWCYHAXIBE-UHFFFAOYSA-N 0.000 description 1
- IGBBADDXMAUKGV-UHFFFAOYSA-N C(C)(C)C1=C(N(CC2CCCC=C2)C)C=CC=C1 Chemical compound C(C)(C)C1=C(N(CC2CCCC=C2)C)C=CC=C1 IGBBADDXMAUKGV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000218645 Cedrus Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- LXWDTQVXKREAHM-UHFFFAOYSA-N N-(Cyclohexylmethyl)-N-methylbenzenamine Chemical compound C=1C=CC=CC=1N(C)CC1CCCCC1 LXWDTQVXKREAHM-UHFFFAOYSA-N 0.000 description 1
- GWLOCUSRCDRZKG-UHFFFAOYSA-N N-(cyclohex-2-en-1-ylmethyl)-N,2,3-trimethylaniline Chemical compound CC=1C(=C(N(CC2CCCC=C2)C)C=CC1)C GWLOCUSRCDRZKG-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000012544 Viola sororia Nutrition 0.000 description 1
- 241001106476 Violaceae Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 235000019717 geranium oil Nutrition 0.000 description 1
- 239000010648 geranium oil Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/516—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of nitrogen-containing compounds to >C = O groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE121975C true DE121975C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Family
ID=390938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT121975D Active DE121975C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE121975C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2501200A (en) * | 1946-12-26 | 1950-03-21 | Fmc Corp | Process for production of menthane aldehyde |
| US2519327A (en) * | 1947-01-13 | 1950-08-15 | Fmc Corp | Condensation of beta-(4-methyl-delta3-cyclohexenyl)-butyraldehyde with aldehydes andketones |
-
0
- DE DENDAT121975D patent/DE121975C/de active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2501200A (en) * | 1946-12-26 | 1950-03-21 | Fmc Corp | Process for production of menthane aldehyde |
| US2519327A (en) * | 1947-01-13 | 1950-08-15 | Fmc Corp | Condensation of beta-(4-methyl-delta3-cyclohexenyl)-butyraldehyde with aldehydes andketones |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1174769C2 (de) | Verfahren zur Herstellung von Polyenalkoholen | |
| DE2043366C2 (de) | Mercapto- oder alkylthio-substituierte Terpenoide, deren Herstellung und Geschmack- bzw. Riechstoffkompositionen auf deren Basis | |
| DE121975C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| CH617852A5 (en) | Perfume compositions | |
| CH626805A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2064097A1 (de) | Verfahren zur Herstellung von Brenzcatechin und dessen Monoäthern | |
| EP0010213B1 (de) | Bicyclische Verbindungen, Verfahren zu deren Herstellung und deren Verwendung | |
| DE2333265A1 (de) | Neue nitrile | |
| DE2141309C3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE3851528T2 (de) | Hydrolyse von aktivierten olefinischen aldehyden und ketonen. | |
| DE1170920B (de) | Verfahren zur Synthese von Alkoholen nach dem Oxoverfahren | |
| DE910054C (de) | Verfahren zur kontinuierlichen Herstellung von gesaettigten, Sauerstoff enthaltenden Verbindungen | |
| DE699032C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE1002754B (de) | Verfahren zur Herstellung von zur Adipinsaeureherstellung geeigneten Gemischen aus Cyclohexanon und Cyclohexanol | |
| DE414912C (de) | Verfahren zur Herstellung von p-Cymol und einem Produkt von hohem Schwefelgehalt ausmonocyclischen Terpenen | |
| DE639455C (de) | Verfahren zur Darstellung von Dihydrojasmon und dessen Homologen | |
| DE545398C (de) | Verfahren zur Darstellung von Riechstoffen | |
| EP0149054A2 (de) | Verfahren zur Herstellung von Cyclododecenylacetonitril und seine Verwendung als Riechstoff oder Riechstoffkomponente | |
| DE280226C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE880284C (de) | Verfahren zur Entfernung aldehydischer Verunreinigungen aus waesserigen Loesungen von aus Olefinen hergestellten Alkoholen | |
| DE1065410B (de) | Verfahren zur Herstellung von Cyclohexanol und Cyclohexanon durch Oxydation von Cyclohexan | |
| DE892442C (de) | Verfahren zur Reinigung von o-Methoxyphenylaceton | |
| DE2039818A1 (de) | Verfahren zur kontinuierlichen Herstellung von Bis(-aminocyclohexyl)-alkanen oder -aethern | |
| DE1058047B (de) | Verfahren zur Herstellung von Mesityloxyd oder seiner Homologen | |
| DE223868C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |