DE1038549B - Process for the production of ª € -oxydekaneeurelactone serving as a flavoring agent - Google Patents
Process for the production of ª € -oxydekaneeurelactone serving as a flavoring agentInfo
- Publication number
- DE1038549B DE1038549B DEU3872A DEU0003872A DE1038549B DE 1038549 B DE1038549 B DE 1038549B DE U3872 A DEU3872 A DE U3872A DE U0003872 A DEU0003872 A DE U0003872A DE 1038549 B DE1038549 B DE 1038549B
- Authority
- DE
- Germany
- Prior art keywords
- production
- serving
- acid
- lactone
- oxydekaneeurelactone
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000796 flavoring agent Substances 0.000 title description 2
- 235000013355 food flavoring agent Nutrition 0.000 title description 2
- 150000002596 lactones Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- BMHXYCAVLBMDOD-UHFFFAOYSA-N decane-1,5-diol Chemical compound CCCCCC(O)CCCCO BMHXYCAVLBMDOD-UHFFFAOYSA-N 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 235000021149 fatty food Nutrition 0.000 claims 1
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910001923 silver oxide Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KLTVSWGXIAYTHO-UHFFFAOYSA-N 1-Octen-3-one Chemical compound CCCCCC(=O)C=C KLTVSWGXIAYTHO-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- KOQSVGLEJAKIQO-UHFFFAOYSA-N 6-pentyl-3,4-dihydro-2h-pyran Chemical compound CCCCCC1=CCCCO1 KOQSVGLEJAKIQO-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000005670 ethenylalkyl group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
- A23D7/0056—Spread compositions
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/206—Dairy flavours
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von als Aromatisierungsmittel dienendem b-Oxydekansäurelacton Die Erfindung bezieht sich auf ein Verfahren zur Herstellung des b-Oxydekansäurelactons (= b-Oxycaprinsäurelacton), das zur Aromatisierung von fetthaltigen oder aus Fett bestehenden Nahrungsmitteln dient. Process for the preparation of serving as a flavoring agent b-Oxydekanoic Acid Lactone The invention relates to a process for the preparation of b-Oxydekansäurelactons (= b-Oxycaprinsäurelacton), which is used to aromatize is used for foods containing or consisting of fat.
Gemäß der Erfindung geht man von 1,5-n-Dekandiol oder von 5-Oxy-n-dekanal aus und führt den Ausgangsstoff durch Oxydation in die entsprechende Oxycarbonsäure und diese durch Wasserabspaltung in das Lacton über. Die Oxycarbonsäure kann man auch aus 5-Oxyn-dekanal erhalten, weil dieses ein Zwischenprodukt bei der Bildung der Säure aus dem Diol ist. Die Oxydation des 1,5-n-Dekandiols kann z. B. mit Hilfe von Kupferchromit oder Silberoxyd vorgenommen werden. According to the invention, one starts from 1,5-n-decanediol or from 5-oxy-n-decanal and converts the starting material into the corresponding oxycarboxylic acid by oxidation and this is converted into the lactone by splitting off water. The oxycarboxylic acid can be also obtained from 5-oxyn-decanal, because this is an intermediate product in its formation the acid is from the diol. The oxidation of the 1,5-n-decanediol can, for. B. with help made of copper chromite or silver oxide.
Das nach dem erfindungsgemäßen Verfahren hergestellte Lacton kann beispielsweise verwendet werden, um Margarine einen butterähnlichen Geschmack und Geruch zu erteilen. Die bisher für diesen Zweck benutzten Stoffe, wie z. B. Diacetyl oder Buttersäure, sind oxydationsanfällig und bzw. oder sehr flüchtig. Dagegen zeichnet sich das erfindungsgemäß hergestellte Lacton dadurch aus, daß es praktisch nicht oxydationsanfällig ist und sich weniger leicht verflüchtigt. Darüber hinaus zeichnet es sich auch noch dadurch aus, daß es dem fetthaltigen oder aus Fett bestehenden Nahrungsmittel, dem es zugesetzt wird, von vornherein ein lieblicheres und abgerundeteres Aroma verleiht als die bekannten Stoffe. The lactone produced by the process according to the invention can for example used to give a butter-like taste and margarine Grant smell. The substances previously used for this purpose, such as. B. diacetyl or butyric acid, are susceptible to oxidation and / or very volatile. Against it draws the lactone produced according to the invention is characterized in that it is practically not is susceptible to oxidation and less easily volatilized. It also draws it is also characterized by the fact that it is fatty or consisting of fat Food to which it is added is sweeter and more rounded from the start Aroma confers as the known substances.
Das als Ausgangsmaterial dienende, 1,5-n-Dekandiol kann z. B. durch Hydrolyse und Hydrierung des 2-Alkyläthers von 6-n-Pentyl-2,3-dihydropyran hergestellt werden, der durch Kondensation von Vinyl-n-pentylketon mit einem Vinylalkyläther, z. B. Vinylisobutyläther, erhalten werden kann. Die Herstellung des 1,5-n-Dekandiols ist jedoch nicht Gegenstand der Erfindung. Serving as starting material, 1,5-n-decanediol can, for. B. by Hydrolysis and hydrogenation of the 2-alkyl ether produced by 6-n-pentyl-2,3-dihydropyran be produced by condensation of vinyl n-pentyl ketone with a vinyl alkyl ether, z. B. vinyl isobutyl ether can be obtained. The production of 1,5-n-decanediol however, is not the subject of the invention.
Das Verfahren gemäß der Erfindung wird an Hand der folgenden Beispiele näher erläutert. The method according to the invention is illustrated by the following examples explained in more detail.
Beispiel 1 295 g 1,5-n-Dekandiol werden mit 10 g Kupferchromit bei 200"C all/2 Stunden gerührt. Wenn die Wasserstoffentwicklung beendet ist, wird das Reaktionsgemisch im Vakuum destilliert. Bei 2 mm destilliert das Lacton der b-Oxy-n-dekansäure in einer Ausbeute von etwa 50010 über. Es besitzt die folgenden Kennzahlen Kp.0,5 = 113"C; n2,0 = 1,4577. Example 1 295 g of 1,5-n-decanediol are added with 10 g of copper chromite 200 "C every / 2 hours. When the evolution of hydrogen has ended, the Reaction mixture distilled in vacuo. At 2 mm, the lactone of the b-oxy-n-decanoic acid distills in a yield of about 50,010 over. It has the following key figures Kp 0.5 = 113 "C; n2.0 = 1.4577.
Beispiel 2 175 g 5-Oxy-n-dekanal werden mit 20 g Silberoxyd unter ständigem Durchleiten von Sauerstoff und Rühren lll2 Stunden auf 180"C erhitzt. Nach Abkühlung des Reaktionsgemisches wird dieses mit 50/0iger wäßriger Salzsäure angesäuert. Die erhaltene d-Oxy-n-dekansäure wird durch Destillation bei 2 mm in das entsprechende Lacton übergeführt. Ausbeute 70 g. Example 2 175 g of 5-oxy-n-decanal are mixed with 20 g of silver oxide Continuous passage of oxygen and stirring heated to 180 ° C. for 11.2 hours. After the reaction mixture has cooled, it is treated with 50/0 aqueous hydrochloric acid acidified. The resulting d-oxy-n-decanoic acid is by distillation at 2 mm in the corresponding lactone transferred. Yield 70g.
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1038549X | 1952-08-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1038549B true DE1038549B (en) | 1958-09-11 |
Family
ID=10869662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEU3872A Pending DE1038549B (en) | 1952-08-08 | 1953-08-05 | Process for the production of ª € -oxydekaneeurelactone serving as a flavoring agent |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1038549B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1277836B (en) * | 1962-07-24 | 1968-09-19 | Unilever Nv | cis- and trans-Hepten- (4) -al- (1), as well as processes for the production of cis- or trans-Hepten- (4) -al- (1) suitable for flavoring foods |
| DE1298975B (en) * | 1959-07-01 | 1969-07-10 | Unilever Nv | Process for the production of optically active ª † - or delta-lactones |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR873904A (en) * | 1938-07-15 | 1942-07-23 | Ig Farbenindustrie Ag | Process for preparing oxidative transformation products |
| GB572752A (en) * | 1944-04-14 | 1945-10-22 | John George Mackay Bremner | A process for the preparation of ª€-valerolactone |
| FR916087A (en) * | 1944-10-20 | 1946-11-26 | Ici Ltd | Obtaining lactones |
| US2420250A (en) * | 1944-09-08 | 1947-05-06 | Monsanto Chemicals | Method of preparing gammavalerolactone |
-
1953
- 1953-08-05 DE DEU3872A patent/DE1038549B/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR873904A (en) * | 1938-07-15 | 1942-07-23 | Ig Farbenindustrie Ag | Process for preparing oxidative transformation products |
| GB572752A (en) * | 1944-04-14 | 1945-10-22 | John George Mackay Bremner | A process for the preparation of ª€-valerolactone |
| US2420250A (en) * | 1944-09-08 | 1947-05-06 | Monsanto Chemicals | Method of preparing gammavalerolactone |
| FR916087A (en) * | 1944-10-20 | 1946-11-26 | Ici Ltd | Obtaining lactones |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1298975B (en) * | 1959-07-01 | 1969-07-10 | Unilever Nv | Process for the production of optically active ª † - or delta-lactones |
| DE1277836B (en) * | 1962-07-24 | 1968-09-19 | Unilever Nv | cis- and trans-Hepten- (4) -al- (1), as well as processes for the production of cis- or trans-Hepten- (4) -al- (1) suitable for flavoring foods |
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