DE1255660B - Process for the preparation of acetal peroxides containing glycol ether groups - Google Patents
Process for the preparation of acetal peroxides containing glycol ether groupsInfo
- Publication number
- DE1255660B DE1255660B DEG40792A DEG0040792A DE1255660B DE 1255660 B DE1255660 B DE 1255660B DE G40792 A DEG40792 A DE G40792A DE G0040792 A DEG0040792 A DE G0040792A DE 1255660 B DE1255660 B DE 1255660B
- Authority
- DE
- Germany
- Prior art keywords
- glycol ether
- ether groups
- acetal
- ozone
- groups
- 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
- -1 acetal peroxides Chemical class 0.000 title claims description 16
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 title claims description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 10
- 229920000151 polyglycol Polymers 0.000 claims description 8
- 239000010695 polyglycol Substances 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 7
- 238000006385 ozonation reaction Methods 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229940116411 terpineol Drugs 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000036186 satiety Effects 0.000 description 1
- 235000019627 satiety Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Glykoläthergruppen enthaltenden Acetalperoxiden Die Erfindung betrifft ein Verfahren zur Herstellung von Glykoläthergruppen enthaltenden Acetalperoxiden.Process for the preparation of acetal peroxides containing glycol ether groups The invention relates to a process for the preparation of glycol ether groups containing Acetal peroxides.
Nach den Verfahren der deutschen Patentschriften 1 075 801 und 1 166 975 können Acetalperoxide der allgemeinen Formel in der R und R' einen beliebigen organischen Rest einer Karbonsäure, eines Aldehyds, eines Ketons eines Alkohols oder eines Kohlenwasserstoffs bedeuten und Alk für einen Alkoholrest (Cl~6) steht, durch Ozonisieren der entsprechenden Äthylenverbindungen in Gegenwart von einwertigen Alkoholen hergestellt werden.Acetal peroxides of the general formula can be prepared using the processes described in German patents 1,075,801 and 1,166,975 in which R and R 'mean any organic radical of a carboxylic acid, an aldehyde, a ketone, an alcohol or a hydrocarbon and Alk stands for an alcohol radical (Cl ~ 6), can be prepared by ozonizing the corresponding ethylene compounds in the presence of monohydric alcohols.
Diese Acetalperoxide sind gegen Wasser als weitgehend stabil zu bezeichnen und können zu therapeutischen und hygienischen Zwecken eingesetzt werden. These acetal peroxides can be described as largely stable to water and can be used for therapeutic and hygienic purposes.
In der Praxis zeigte sich jedoch der Nachteil, daß diese Acetalperoxide bei der Lagerung bei Zimmertemperatur einem langsamen Zerfall unterliegen, der mit der Bildung gasförmiger Bestandteile verbunden ist. Der Zerfall der Acetalperoxide war bisher unbekannt. Es zeigte sich, daß die hier auftretenden Gase zu über 900/o aus reinem Wasserstoff bestehen und kein Methan enthalten. Aus 1 1 einer Lösung von Olivenöl -Acetalperoxid in Äthanol (1:1) werden anfangs monatlich 1,5 1 Gas abgespalten. Diese Menge verringert sich im Laufe mehrerer Jahre immer mehr und erlischt nach etwa 5 Jahren. Der Peroxidgehalt der verbleibenden Rückstände ist jedoch immer noch mehr als 50O/o. Es liegt also die merkwürdige Tatsache vor, daß trotz Gegenwart von Peroxiden der naszierende Wasserstoff diese nicht weiter angreift und als Wasserstoffgas aus der Lösung entweicht.In practice, however, there was a disadvantage that these acetal peroxides are subject to slow disintegration when stored at room temperature, with the formation of gaseous components is connected. The breakdown of acetal peroxides was previously unknown. It was found that over 900 per cent of the gases occurring here consist of pure hydrogen and contain no methane. From 1 1 of a solution of olive oil acetal peroxide in ethanol (1: 1) are initially 1.5 1 gas per month cleaved. This amount decreases more and more over the course of several years expires after about 5 years. The peroxide content of the remaining residue is but still more than 50%. So there is the curious fact that despite the presence of peroxides, the nascent hydrogen does not attack them any further and escapes from the solution as hydrogen gas.
Es ist nun gefunden worden, daß diese Abspaltung von Wasserstoffgas dadurch verringert bzw. unterbunden werden kann, daß in die ungesättigten Verbindungen vor ihrer Ozonisierung Polyglykoläthergruppen eingebaut werden. It has now been found that this elimination of hydrogen gas can thereby be reduced or prevented that in the unsaturated compounds polyglycol ether groups are incorporated before ozonization.
Die Herstellung der polyglykoläthergruppenhaltigen äthylenisch ungesättigten Ausgangsverbindungen ist bekannt und stellt keinen Gegenstand des Patentbegehrens dar. Die Herstellung des Ausgangsmaterials kann durch Äthoxylierung von Säuren, Aldehyden oder Alkoholen, aber auch durch Veresterung von vorgebildeten Polyglykolen mit ungesättigten Säuren erfolgen. The production of ethylenically unsaturated polyglycol ether groups Starting compounds are known and are not part of the patent application The production of the starting material can be done by ethoxylation of acids, Aldehydes or alcohols, but also by esterification of preformed polyglycols done with unsaturated acids.
Gegenstand der Erfindung ist daher ein Verfahren zur Herstellung von Glykoläthergruppen enthaltenden Acetalperoxiden, das dadurch gekennzeichnet ist, daß man äthylenisch ungesättigte organische Polyglykoläther-Verbindungen, die eine oder mehrere äthylenisch ungesättigte Gruppen enthalten, in an sich bekannter Weise mit Ozon oder ozonhaltigen Gasen behandelt. The invention therefore relates to a method for production of acetal peroxides containing glycol ether groups, characterized in that is that one ethylenically unsaturated organic polyglycol ether compounds that contain one or more ethylenically unsaturated groups, in per se known Way treated with ozone or ozone-containing gases.
Die Durchführung der Ozonisation dieser Polyglykol-Ausgangsverbindungen kann sowohl in inerten Lösungsmitteln, wie Alkylhalogeniden, oder als auch in Lösungsmitteln mit alkoholischen Gruppen, also kurzen oder langkettigen Alkoholen, erfolgen. In jedem Fall befinden sich also während der Ozonisation freie alkoholische Hydroxylgruppen im Reaktionsgemisch, so daß es also zur Ausbildung der »echten« Ozonide im Reaktionsgemisch nicht kommen kann. Carrying out the ozonization of these polyglycol starting compounds can be used both in inert solvents, such as alkyl halides, or in solvents with alcoholic groups, i.e. short or long-chain alcohols. In In any case, there are free alcoholic hydroxyl groups during ozonization in the reaction mixture, so that the "real" ozonides are formed in the reaction mixture can't come.
Unter Beteiligung dieser alkoholischen Gruppen bilden sich also auch hier Acetalperoxide. Nur die in inerten Lösungsmitteln hergestellten Acetalperoxide weisen eine höhere Viskosität auf, da hierbei die Ausgangsmaterialien mit sich selbst in Reaktion treten.With the participation of these alcoholic groups, too, are formed here acetal peroxides. Only the acetal peroxides made in inert solvents have a higher viscosity because the starting materials with themselves react.
Die in wasserlöslichen Alkoholen ozonisierten Polyglykolverbindungen sind in Wasser völlig löslich. Die in wasserunlöslichen Alkoholen oder in inerten Lösungsmitteln hergestellten Polyglykoläther-acetalperoxide können schon durch Zugabe von geringen Mengen von Lösungsvermittlern, wie Alkylsulfonaten, in Wasser emulgiert werden.The polyglycol compounds ozonated in water-soluble alcohols are completely soluble in water. Those in water-insoluble alcohols or in inert ones Polyglycol ether acetal peroxides produced by solvents can already be added by adding by small amounts of solubilizers, such as alkyl sulfonates, emulsified in water will.
Die nach dem vorliegenden Verfahren herstellbaren, Glykoläthergruppen enthaltenen Acetalperoxide können zur Polymerisation von Kunststoffen in wässerigen Lösungen Verwendung finden wie auch zur Körperhygiene zur Bindung von Fäulnisgiften und in der Therapie zur Versorgung des Gewebes mit aktivem Sauerstoff. The glycol ether groups which can be produced by the present process Acetal peroxides contained can be used to polymerize plastics in aqueous Solutions are used as well as for personal hygiene to bind putrefactive toxins and in therapy to supply the tissue with active oxygen.
Beispiel 1 10 g Oleyltriglykoläther (aus Oleylalkohol und Äthylenoxid hergestellt) werden in 100 ccm Methylenchlorid gelöst und bis zur Sättigung mit Ozon oder ozonhaltigen Gasen behandelt. Das Lösungsmittel wird dann durch Destillation entfernt und gegen Schluß dieses Arbeitsganges 100 ccm Wasser zugesetzt. Nun kann auch der Rest des Methylenchlorids im Vakuum entfernt werden. Es verbleibt eine farblose viskose Masse, die in Alkoholen und Aceton löslich ist. Example 1 10 g of oleyl triglycol ether (from oleyl alcohol and ethylene oxide prepared) are dissolved in 100 cc of methylene chloride and until saturation with Treated with ozone or gases containing ozone. The solvent is then removed by distillation removed and 100 cc of water added towards the end of this operation. Well can the remainder of the methylene chloride can also be removed in vacuo. There remains one colorless viscous mass soluble in alcohols and acetone.
Beispiel 2 10 g Ölsäure-polyglykolester (mit etwa acht Glykoläthergruppen) werden in 100 ccm Isopropylalkohol gelöst und mit Ozon oder ozonhaltigen Gasen bis zur Sättigung behandelt. Nachdem der Isopropylalkohol im schwachen Vakuum entfernt wurde, verbleibt ein farbloses Öl, das in Wasser völlig löslich ist. Example 2 10 g oleic acid polyglycol ester (with about eight glycol ether groups) are dissolved in 100 cc of isopropyl alcohol and with ozone or ozone-containing gases up to treated to satiety. After the isopropyl alcohol is removed in a weak vacuum what remains is a colorless oil that is completely soluble in water.
Beispiel 3 10 g Terpineol-diglykoläther werden in 10 g Tridecylalkohol gelöst und bis zur Sättigung mit Ozon oder ozonhaltigen Gasen behandelt. Das Reaktionsprodukt ist nur teilweise in Wasser löslich. Das eingesetzte Terpineol stellt ein Gemisch mehrerer Isomerer dar, wie es in technischen Handelsprodukten vorliegt. Zersetzungspunkt des Acetalperoxids: oberhalb 83"C. Example 3 10 g of terpineol diglycol ether are dissolved in 10 g of tridecyl alcohol dissolved and treated to saturation with ozone or ozone-containing gases. The reaction product is only partially soluble in water. The used Terpineol is a mixture several isomers, as is found in technical commercial products. Decomposition point of acetal peroxide: above 83 "C.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEG40792A DE1255660B (en) | 1964-06-08 | 1964-06-08 | Process for the preparation of acetal peroxides containing glycol ether groups |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEG40792A DE1255660B (en) | 1964-06-08 | 1964-06-08 | Process for the preparation of acetal peroxides containing glycol ether groups |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1255660B true DE1255660B (en) | 1967-12-07 |
Family
ID=7126518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG40792A Pending DE1255660B (en) | 1964-06-08 | 1964-06-08 | Process for the preparation of acetal peroxides containing glycol ether groups |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1255660B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001037829A1 (en) * | 1999-11-25 | 2001-05-31 | Gomez Moraleda Manuel Antonio | Composition comprising ozonized oils and/or other ozonized natural and/or synthetic products and their use in pharmaceutical, cosmetic, dietetic or food supplement compositions in human and veterinary medicine |
| WO2012120454A1 (en) | 2011-03-07 | 2012-09-13 | Neovalis S.R.L. | Composition for topical use based on ozonized oil |
| IT201800009679A1 (en) | 2018-10-22 | 2020-04-22 | Giorgio Mezzoli | METHOD FOR CHANGING THE ODOR OF OZONIZED OIL |
-
1964
- 1964-06-08 DE DEG40792A patent/DE1255660B/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001037829A1 (en) * | 1999-11-25 | 2001-05-31 | Gomez Moraleda Manuel Antonio | Composition comprising ozonized oils and/or other ozonized natural and/or synthetic products and their use in pharmaceutical, cosmetic, dietetic or food supplement compositions in human and veterinary medicine |
| ES2162586A1 (en) * | 1999-11-25 | 2001-12-16 | Moraleda Manuel Gomez | Composition comprising ozonized oils and/or other natural and/or synthetic ozonized products and use thereof in pharmaceutical, cosmetic, dietetic or food supplement compositions, in the human and veterinary fields |
| WO2012120454A1 (en) | 2011-03-07 | 2012-09-13 | Neovalis S.R.L. | Composition for topical use based on ozonized oil |
| IT201800009679A1 (en) | 2018-10-22 | 2020-04-22 | Giorgio Mezzoli | METHOD FOR CHANGING THE ODOR OF OZONIZED OIL |
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