US583720A - Helm ferdinand - Google Patents
Helm ferdinand Download PDFInfo
- Publication number
- US583720A US583720A US583720DA US583720A US 583720 A US583720 A US 583720A US 583720D A US583720D A US 583720DA US 583720 A US583720 A US 583720A
- Authority
- US
- United States
- Prior art keywords
- ferdinand
- helm
- september
- ionone
- dated
- 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
- 241000380131 Ammophila arenaria Species 0.000 title description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 3
- 229940043350 citral Drugs 0.000 description 3
- 229930003633 citronellal Natural products 0.000 description 3
- 235000000983 citronellal Nutrition 0.000 description 3
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 3
- 229930002839 ionone Natural products 0.000 description 3
- 150000002499 ionone derivatives Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- HNZUNIKWNYHEJJ-FMIVXFBMSA-N geranyl acetone Chemical compound CC(C)=CCC\C(C)=C\CCC(C)=O HNZUNIKWNYHEJJ-FMIVXFBMSA-N 0.000 description 2
- YJRODKCOICMRBO-BQYQJAHWSA-N (e)-4-(2,2,6-trimethylcyclohexyl)but-3-en-2-one Chemical compound CC1CCCC(C)(C)C1\C=C\C(C)=O YJRODKCOICMRBO-BQYQJAHWSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000001046 cacaotero Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 238000006467 substitution reaction Methods 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
Definitions
- citronellone (citronellal) may be used.
- Oitronellone is an aldehyde containing two atoms more of hydrogen than citral. The properties of the final products of the process, as far as their industrial application is concerned, are not essentially altered by this substitution.
- the process is carried out in the following manner: Equal parts of citronellone and acetone are shaken together with dilute alkaline lye for several days.
- the product of reaction is extracted by means of ether, and the ether residue of the distillation is subjected to a strong steam-current.
- the oil passed over is collected.
- a repeated fractional distillation in cacao a fraction boiling under a pressure of twenty-one millimeters at a temperature of from 153 to 156 centigrade is obtained. This represents the product of condensation of citronellone (citronellal) with acetone, which I term dihydro-pseudo-ionone.
- the hydrated ionone thus obtained, as well as the ionone itself, are intended to be used as odoriferous substances in perfumery and as aromatics for food.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
UNITED STATES PATENT OFFICE.
J OHANN CARL \VILHELM FERDINAND TIEMANN, OF BERLIN, GERMANY, ASSIGNOR TO HAARMANN & REIMER, OF HOLZMINDEN, GERMANY.
FRAGRANT KETONE.
SPECIFICATION forming part of Letters Patent No. 583,720, dated June 1, 1897.
Application filed April 21, 1896. Serial No. 588,505-
(No specimens.) Patented in France April 27, 1893, No. 229,683,- in
England May 1, 1893, No. 8,736, and September 18, 1893, No.17,539, in Germany September 8, 1893,11'0. 75,120, anclin Belgium September 23,1893, No. 106,520.
To all whom, it may concern.-
Be it known that I, J OHANN CARL VIL- HELM FERDINAND TIEMANN, (coproprietor of the firm of Haarmann & Reimer, of Holzminden,) a subject of the King of Prussia, residing at Berlin, in the Kingdom of Prussia, Germany, have invented new and useful Improvements in Processes of Making Odoriferous Substances from (Jitral and its Homologues, (for which I have obtained Letters Patent in Germany, N 0. 75,120, dated September 8, 1893; in Belgium, No. 106,520, dated September 23, 1893; in England, No. 8,736, dated May 1, 1893, and No. 17,539, dated September 18, 1893, and in France, No. 229,683, dated April 27, 1893, and patent of addition in France, dated September 18, 1893,) of which the following is a specification.
In my prior application for Letters Patent, Serial No. 488,321, I have described a process for manufacturing perfumes or odoriferous substances from citral and the homologues of acetone, which process constitutes a further perfecting of the process for manufacturing ionone described in United States Letters Patent No. 556,943, granted to me March 24;, 1896.
Hereinafter another mode for carrying out this process will be described.
In place ofthe citral in the first-men tioned process citronellone (citronellal) may be used. Oitronellone is an aldehyde containing two atoms more of hydrogen than citral. The properties of the final products of the process, as far as their industrial application is concerned, are not essentially altered by this substitution.
The process is carried out in the following manner: Equal parts of citronellone and acetone are shaken together with dilute alkaline lye for several days. The product of reaction is extracted by means of ether, and the ether residue of the distillation is subjected to a strong steam-current. The oil passed over is collected. By a repeated fractional distillation in cacao a fraction boiling under a pressure of twenty-one millimeters at a temperature of from 153 to 156 centigrade is obtained. This represents the product of condensation of citronellone (citronellal) with acetone, which I term dihydro-pseudo-ionone. By digesting with dilute sulfuric (about three per cent.) acid at a temperature of at least 102 centigrade the dihydro-pseudoionone passes over into the dihydro-ionone, boiling under apressure of 23. 5 millimeters at a temperature of about 136 Centigrade and having an odor of fresh flowers. Considerable quantities of by-products are formed during this operation. Also, in this process acetone may be substituted by its homologues.
The hydrated ionone thus obtained, as well as the ionone itself, are intended to be used as odoriferous substances in perfumery and as aromatics for food.
I claim The herein-described process for the manufacture of fragrant ketones consisting in treating citronellone (citronellal) and acetone or its h omologues with an alkaline condensing agent to form new ketones and then converting said ketones by means of acids into ketones isomeric with said ketones first formed.
In testimony whereof I have signed my name to 'this specification in the presence of two subscribing witnesses.
JOHANN CARL WILHELM FERDINAND TIEMANN.
Witnesses:
OTTO HERING, GUSTAV HULSMANN.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US583720A true US583720A (en) | 1897-06-01 |
Family
ID=2652392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US583720D Expired - Lifetime US583720A (en) | Helm ferdinand |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US583720A (en) |
-
0
- US US583720D patent/US583720A/en not_active Expired - Lifetime
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