US536324A - Chimiques de thann et mulhouse - Google Patents
Chimiques de thann et mulhouse Download PDFInfo
- Publication number
- US536324A US536324A US536324DA US536324A US 536324 A US536324 A US 536324A US 536324D A US536324D A US 536324DA US 536324 A US536324 A US 536324A
- Authority
- US
- United States
- Prior art keywords
- musk
- thann
- mulhouse
- chimiques
- hydrindene
- 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
Links
- 150000002430 hydrocarbons Chemical class 0.000 description 12
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N Indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- 238000006396 nitration reaction Methods 0.000 description 10
- JHGWQSGWUPCKNT-UHFFFAOYSA-N 2-tert-butyl-4-methyl-1,3,5-trinitrobenzene Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(C(C)(C)C)=C1[N+]([O-])=O JHGWQSGWUPCKNT-UHFFFAOYSA-N 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- -1 ethol aromatic hydrocarbons Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 4
- YFRGOBSBDSYRNN-UHFFFAOYSA-N 1-butyl-2,3-dimethylbenzene Chemical group CCCCC1=CC=CC(C)=C1C YFRGOBSBDSYRNN-UHFFFAOYSA-N 0.000 description 2
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 241001676573 Minium Species 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000001145 hydrido group Chemical group *[H] 0.000 description 2
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 230000000802 nitrating Effects 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
Definitions
- I may also effect the butylation of hydrindone by introducing the same mixed with butylic alcohol in concentrated sulfuric acid. I obtain in this way a mixture of the hydrocarbon and of its sulfuric acid. The latter by nitration yields also a musk but the formerly described process is much better.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
Description
U TED STATES PATENT Orricm.
ALBERT BAUR, or GERNRODE, ASSIGNOR' TO THE FABRIQUES nus PRODUITS CH IMIQUES DE THANN- ET MULHOUSE, OF TIIANN, GERMANY.
.ARTlFlClAL M USK.
SPECIFICATION forming part of letters Patent No. 536,324, dated March 26, 1895.
Application filed NovemberBO,
To aZZ whom it may concern:
Be it known that I, ALBERT BAUR, a resident of Gernrode, in the dukedom of Anhalt, Germany, have invented certain new'and useful Improvements in the Manufacture of Artificial Musk, which are fully described in the following specification, and for which I have obtained Patents in France June 30, 1894, (certificate of addition to Patent No.195,360,)
to and in England July 4, 1894, No. 12,980.
In previous patents, Nos. 416,710, dated December 10, 1889, 451,847, dated May 5, 1891, and 481,685, dated August 30, 1892, I have describedand claimed the preparation of artificial musk by nitration of aromatic hydrocarbons containing two or three lateral chains, one of which-mustbe a butylic, amylic or propylic one, while the others are methyle or ethyle. Hydrocarbons of this family are bu- 2o tyl-toluen e, butyl-xylene and many others. I have found that not only the hydrocarbons of .the said series are able to yield musk by nitration, but ethol aromatic hydrocarbons minium, ten parts of chlorid of tertiary butyl 0 until no more evolution of hydrochloric acid takes place. I pour in water, distill the hydro; carbon with steam and purify .thebutyl-hy drindene by fractional distillation. This butyl-hydrindene is itself a new body. The boiling point of the pure hydrocarbon is 237? to 240 centigrade.
In order to transform the butyl-hydrindene into its musk-smelling trinitro derivative, it
with lateral chains for instance hydrindene 1 4:- Serial No. 580,382. (Specimens) Patented in France June 30, 1894, No. 196,360,:uu1 in England July 4, 1894, No. 12,980-
is more convenient to prepare first the dinitro compound in a state of purity and to submit it afterward to a further nitration. For this purpose I introduce ten parts of butyl: hydrindene into a well cooled mixture of'forty; parts of fuming nitric acid (specific gravity 1.48 about) and eighty parts of fuming sulfuric acid, containing about fifteen per cent. of S0,, and allow the solutionto stand a few hours. I then pour in water, filter the nitro compound, wash it with soda and afterward with water and crystallize it out of alcohol. I thus obtain white crystals melting at 121 centigrade and possessing no musky odor. I
In order to transform the dinitro into trinitro derivative I introduce ten parts of the dinitro compound into a strong nitration mixture containing forty parts of fuming nitric acid and eighty parts of fuming sulfuric acid containing from thirty to forty per cent. of S0 and heat at a temperature not exceeding 50 or 55". After a few hours I pour in water, filter and crystallize the new compound from alcohol.
The trinitrobutylhydrindene comes outin the form of white needles, sparingly soluble in cold alcohol, melting at 139 to 140 centigrade and musk odor.
I may also effect the butylation of hydrindone by introducing the same mixed with butylic alcohol in concentrated sulfuric acid. I obtain in this way a mixture of the hydrocarbon and of its sulfuric acid. The latter by nitration yields also a musk but the formerly described process is much better.
By using chlorid of propyle or anlyle instead of chlorid of butyle, I obtain derivatives 90 analogous to the butylic but presenting no advantage. It will be understood therefore that where mention is made of the butylic chlorid, the propylic and amylicchlorids are included as equivalents. It will also be im- 5 derstood that theamylic and propylio derivapossessing a very stron g Having nowparticularly described my in- I q vention and the manner in which thesaine is 0- be carried out; what I claim isli The described process of obtaining an ertificial iuskgby heating an ethoi-aromatie hydrocarbon, such 4 as hydrindene, with a chlorid such as butylie c'hlorid in presence of l a metalliechiorid, and nitrating the product 9f this reaction,
(Terivetifire bf the hydrocarbon orth. v
:5 7 2.111 the menuf ac ture of artificial musk,
the-improvement consisting in'heacing hythereby obtaining a trinitroi treated, as set drindene with butyl'ie chlerid and a metallic chlerid, thereby-producing bntyi hydrindene,
asset forth. 4 v
3. The artificial musk herein described, the
same being the trinitroderivativeof bnty1-' hydrindene in'th'eform of white needles,
sparingly soluble in alcohoi, and characterized by a strong 0301' of musk, as set forth,
In itness whereof I have hereunto signer my name in the presence-of two subscribing witnesses; r
I ALBERT BAUR.
\Vitnesses: V
'EDUARD M'i'JAzLL, .EMIL NORT.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US536324A true US536324A (en) | 1895-03-26 |
Family
ID=2605085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US536324D Expired - Lifetime US536324A (en) | Chimiques de thann et mulhouse |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US536324A (en) |
-
0
- US US536324D patent/US536324A/en not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2182242A (en) | Process for hydrogenating aromatic hydrocarbons | |
| US536324A (en) | Chimiques de thann et mulhouse | |
| US1878950A (en) | Reduction of organic nitro compounds | |
| US2121183A (en) | Process for the manufacture of condensation products of dicarboxylic acid anhydrides | |
| US1961397A (en) | Preparing of a new condensation product from meta-cresol and acetone | |
| Perkin et al. | CCCLXXXIV.—Dihydropentindole and its derivatives. Part I | |
| JPS5821906B2 (en) | trans-4-aminomethylcyclohexacarbonate | |
| US2890248A (en) | Preparation of alpha-chlorocyclooctanone oxime | |
| US2047946A (en) | Process for the chlorination of phthalide and further treatment of the chlorination product | |
| US3318956A (en) | Process for producing dihydroxy-diphenyl sulfone | |
| Ekeley et al. | The nitration of piperonal | |
| US1806564A (en) | Process of producing x-stjbstittttion products of the quinoline series | |
| US560771A (en) | Albert baur | |
| US546086A (en) | August bischleb | |
| US1887396A (en) | Aromatic halogen-methyl compound and alpha process of preparing it | |
| US692656A (en) | Acidyl derivative of unsymmetrical acetonalkamins and process of making same. | |
| US1892128A (en) | Nitroderivative of butylcymene and the process of preparing the same | |
| US2256195A (en) | Manufacture of dinitro-orthocresol | |
| US800442A (en) | Alkyl salicylglycollate and process of making same. | |
| Esselen et al. | THE SPLITTING OF BENZHYDROLS BY THE ACTION OF BROMINE. | |
| US2569423A (en) | Process fob preparing phenoxtalktl | |
| US2396282A (en) | Unsaturated dinitro compounds and method of preparation thereof | |
| US715680A (en) | Aromatic derivative of amido compounds of the fatty series and process of producing same. | |
| US3347918A (en) | Production of cyclododecylamine | |
| US2599432A (en) | Tetrachlorothiolane and method for preparing the same |