DD247669A1 - PROCESS FOR THE PREPARATION OF ALPHA, BETA-UNSATURATED ETHERS - Google Patents
PROCESS FOR THE PREPARATION OF ALPHA, BETA-UNSATURATED ETHERS Download PDFInfo
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- DD247669A1 DD247669A1 DD28786786A DD28786786A DD247669A1 DD 247669 A1 DD247669 A1 DD 247669A1 DD 28786786 A DD28786786 A DD 28786786A DD 28786786 A DD28786786 A DD 28786786A DD 247669 A1 DD247669 A1 DD 247669A1
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- ethers
- elimination
- reaction
- unsaturated ethers
- preparation
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 12
- 150000002170 ethers Chemical class 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000003379 elimination reaction Methods 0.000 claims abstract description 12
- 230000008030 elimination Effects 0.000 claims abstract description 11
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 10
- 239000011541 reaction mixture Substances 0.000 claims abstract description 5
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims abstract description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims abstract description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 5
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical class O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 claims abstract 2
- LNTHITQWFMADLM-UHFFFAOYSA-N anhydrous gallic acid Natural products OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims abstract 2
- 229940074391 gallic acid Drugs 0.000 claims abstract 2
- 235000004515 gallic acid Nutrition 0.000 claims abstract 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 150000002084 enol ethers Chemical class 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 3
- -1 vinyl halides Chemical class 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- MZKUGCOENXBMFR-UHFFFAOYSA-N pyridin-1-ium;phosphate Chemical compound [O-]P([O-])([O-])=O.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1 MZKUGCOENXBMFR-UHFFFAOYSA-N 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 238000007086 side reaction Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 229950000244 sulfanilic acid Drugs 0.000 claims description 2
- 230000001960 triggered effect Effects 0.000 claims description 2
- 150000001241 acetals Chemical class 0.000 claims 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000010538 cationic polymerization reaction Methods 0.000 claims 1
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- 238000009776 industrial production Methods 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 abstract description 2
- 229950000688 phenothiazine Drugs 0.000 abstract description 2
- 239000000654 additive Substances 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- BRKIPAWFUDCCOO-UHFFFAOYSA-N 1,1-diethoxyoctane Chemical compound CCCCCCCC(OCC)OCC BRKIPAWFUDCCOO-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- ZMHXVWJGPYCKMF-UHFFFAOYSA-N 1-ethoxyoct-1-ene Chemical group CCCCCCC=COCC ZMHXVWJGPYCKMF-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Die Erfindung betrifft ein Verfahren zur Herstellung von a,b-ungesaettigten Ethern der allgemeinen Formel I RCHCHOCnH2n1 in der R:m0-10 und n1-4 bedeuten, welche u. a. zur Produktion substituierter Acroleine und Malonaldehyde verwendet werden. Ziel der Erfindung ist die Herstellung von a,b-ungesaettigten Ethern auch im technischen Massstab mit hohen Ausbeuten. Erfindungsgemaess werden dem Reaktionsgemisch bei der thermischen Alkanolabspaltung gemaess Gleichung 1 Antioxidantien zugesetzt, geeignet sind z. B. Phenothiazin, p-Methoxyphenol, Di-tert.-butylkresol, Gallussaeure-alkylester und p-tert.-Butyl-phenol. Durch diese Additive ist es moeglich, die fuer kleine Laboransaetze beschriebenen hohen Ausbeuten auch im technischen Massstab zu erreichen.The invention relates to a process for the preparation of a, b ungesaettigten ethers of the general formula I RCHCHOCnH2n1 in the R: m0-10 and n1-4 mean, which u. a. used for the production of substituted acroleins and malonaldehydes. The aim of the invention is the preparation of a, b ungesaettigten ethers on an industrial scale with high yields. According to the invention, antioxidants are added to the reaction mixture in the thermal alkanol elimination according to equation 1; As phenothiazine, p-methoxyphenol, di-tert-butylcresol, gallic acid alkyl ester and p-tert-butyl-phenol. These additives make it possible to achieve the high yields described for small laboratory purposes also on an industrial scale.
Description
Erfindungsgemäß werden dem Reaktionsgemisch bei der thermischen Alkanolabspaltung gemäß Gleichung 1:According to the reaction mixture in the thermal alkanol cleavage according to equation 1:
GH^ n 2n+1 > R-CHGH ^ n 2n + 1 > R-CH
Antioxidantien zugesetzt, geeignet sind z. B. Phenothiazin, p-Methoxyphenol, Di-tert.-butylkresol, Gallussäurealkylester und p-tert.-Butylphenol. Durch diese Addition ist es möglich, die für kleine Laboransätze beschriebenen hohen Ausbeuten auch im technischen Maßstab zu erreichen. Der Effekt von Antioxidantien bei diesem Verfahren ist überraschend, da bekannt ist, daß Enolether gegenüber Luftsauerstoff recht stabil sind und Oxidationsprozesse erst von starken Oxidationsmitteln, wie Ozon oder Perbenzoesäure, ausgelöst werden.Antioxidants added, are suitable for. As phenothiazine, p-methoxyphenol, di-tert-butylcresol, Gallussäurealkylester and p-tert-butylphenol. This addition makes it possible to achieve the high yields described for small laboratory approaches on an industrial scale. The effect of antioxidants in this process is surprising, since it is known that enol ethers are quite stable to atmospheric oxygen and oxidation processes are triggered only by strong oxidants, such as ozone or perbenzoic acid.
Das erfindungsgemäße Verfahren wird durchgeführt, indem zum Reaktionsgemisch, bestehend aus einem 1-Subst.-2,2-dialkyloxy-ethan Il und bekannten, meist schwach sauren Katalysatoren, wie z. B. p-Toluensulfonsäure, Alkalimetallhydrogensulfat, Borsäure, Sulfanilsäure oder Pyridiniumphosphat, vor oder während der termischen Alkanolabspaltung, Antioxidantien, vorzugsweise in Mengen von 10~2bis 10~4Mol-%, zugegeben werden. Der Reaktionsansatz wird nun in einer Destillationsanlage, die mit einer wirksamen Kolonne versehen ist, erhitzt, bis die Alkanolabspaltung einsetzt. Es wird möglichst der reine Alkohol CnH2n+ lOH abdestilliert, wobei die Temperatur im Reaktionskolben langsam erhöht wird, bis die Eliminierung beendet ist. Der im Kolben verbleibende Sumpf wird in bekannter Weise ausgearbeitet, indem der gebildete a,j8-ungesättigte Ether I im Vakuum überdestilliert und nochmals rektifiziert wird. Zur Vermeidung von Nebenreaktionen können die oben erwähnten säurebindenden Substanzen und Hydrochinon in die Vorlage gegeben werden.The inventive method is carried out by the reaction mixture, consisting of a 1-Subst.-2,2-dialkyloxy-ethane II and known, usually weakly acidic catalysts such. For example, p-toluenesulfonic acid, alkali metal hydrogen sulfate, boric acid, sulfanilic acid or pyridinium phosphate, before or during the thermal alkanol elimination, antioxidants, preferably in amounts of 10 ~ 2 to 10 ~ 4 mol%, are added. The reaction mixture is then heated in a distillation plant, which is provided with an effective column, until the Alkanolabspaltung begins. If possible, the pure alcohol C n H 2n + lOH is distilled off, the temperature in the reaction flask being slowly increased until the elimination has ended. The sump remaining in the flask is worked up in a known manner by distilling off the a, j8-unsaturated ether I formed in vacuo and rectifying again. To avoid side reactions, the above-mentioned acid-binding substances and hydroquinone can be added to the template.
Die Wirkung der erfindungsgemäß zugegebenen Antioxidantien kann durch die Kontrolle der Ausbeuten verfolgt werden, wie beim Vergleich der Beispiele 1 und 2 zu sehen ist. Bei Anwendung des erfindungsgemäßen Verfahrens sind die Ausbeuten nahezu unabhängig von der Ansatzgröße und liegen für I bei 76-93%. Entsprechend dem erfindungsgemäßen Verfahren wurden u.a. die in Tab. 1 genannten α,/3-ungesättigten Ether I hergestellt.The effect of the antioxidants added according to the invention can be monitored by controlling the yields, as can be seen in the comparison of Examples 1 and 2. When using the method according to the invention, the yields are almost independent of the batch size and are for I at 76-93%. According to the method of the invention, i.a. Tab. 1 mentioned α, / 3-unsaturated ether I prepared.
Tabelle 1 R-CH=CH-OC2H5 Table 1 R-CH = CH-OC 2 H 5
R Ausbeute (%) KpC/KPaR Yield (%) KpC / KPa
C5H11- 88 59-65/1,9C 5 H 11 - 88 59-65 / 1.9
C6Hi3- 84 78-B3/1.6C 6 Hi 3 - 84 78-B3 / 1.6
C7H15- 85 110-115/3,1C 7 H 15 - 85 110-115 / 3,1
C4H9 -/ L_| \_ 79 1 128-134/1,1C 4 H 9 - / L_ | \ _ 79 1 128-134 / 1,1
84 70-82/0,2684 70-82 / 0.26
Herstellung von 1-n-Hexyl-2-ethoxy-ethylen ohne erfindungsgemäßen Zusatz eines Antioxidants bei der thermischen EliminierungPreparation of 1-n-hexyl-2-ethoxy-ethylene without inventive addition of an antioxidant in the thermal elimination
In einem 2-l-Zweihalskolben, versehen mit Kolonne, Destillationsaufsatz und Innenthermometer, werden 1010g (5 Mol) n-Octanal-diethylacetal mit 5g 85%iger Phosphorsäure und 10g Pyridin langsam auf 1800C erhitzt.In a 2-liter two-necked flask equipped with a column, distillation head and internal thermometer, 1010 g (5 mol) of n-octanal diethyl acetal are slowly heated to 180 0 C with 5 g of 85% phosphoric acid and 10 g of pyridine.
Es destilliert Ethanol ab, wobei die Innentemperatur langsam auf 2300C erhöht wird. Steigt die Kopftemperatur über79°C an, so läßt man abkühlen und destilliert den Rückstand im Vakuum in eine Vorlage, die mit 2g Natriumcarbonat und 0,5g Hydrochinon versehen wurde. Das Destillat wird nochmals unter Zusatz von 0,5g Hydrochinon rektifiziert.It distills off ethanol, the internal temperature is slowly increased to 230 0 C. If the head temperature rises above 79 ° C., the mixture is allowed to cool and the residue is distilled under reduced pressure into a vessel which has been provided with 2 g of sodium carbonate and 0.5 g of hydroquinone. The distillate is rectified again with the addition of 0.5 g of hydroquinone.
Kp= 78-83°C Ausbeute 37%Kp = 78-83 ° C Yield 37%
1,6KPa1,6KPa
Herstellung von i-n-Hexyl-2-ethoxy-ethylenPreparation of i-n-hexyl-2-ethoxy-ethylene
unter erfindungsgemäßem Zusatz eines Antioxidants bei der thermischen Eliminierung In einem 2-l-Zweihalskolben, versehen mit Kolonne, Destillationsaufsatz und Innenthermometer, werden 1010g (5MoI) n-Octanal-diethylacetal mit5g Phosphorsäure (85%ig), 10g Pyridin sowie7,25g (0,008 Mol-%) p-tert.-Butylphenol langsam auf 180°C erhitzt. Es destilliert Ethanol ab, wobei die Innentemperatur langsam auf 230°C erhöht wird. Steigt die Kopftemperatur über79°Can, so läßt man abkühlen und destilliert den Rückstand im Vakuum in eine Vorlage, die mit 2 g Natriumcarbonat und 0,5g Hydrochinon versehen wurde. Das Destillat wird nochmals unter Zusatz von 0,5g Hydrochinon rektifiziert.with inventive addition of an antioxidant in the thermal elimination In a 2-liter two-necked flask equipped with column, distillation head and internal thermometer, 1010g (5MoI) n-octanal diethyl acetal with 5g phosphoric acid (85%), 10g pyridine and 7,25g (0.008 Mol%) p-tert-butylphenol slowly heated to 180 ° C. It distills off ethanol, the internal temperature is slowly increased to 230 ° C. If the head temperature rises above 79 ° C., it is allowed to cool and the residue is distilled off under reduced pressure into a vessel which has been provided with 2 g of sodium carbonate and 0.5 g of hydroquinone. The distillate is rectified again with the addition of 0.5 g of hydroquinone.
Kp= 78-83°C Ausbeute 84%Kp = 78-83 ° C Yield 84%
1,6KPa1,6KPa
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD28786786A DD247669B1 (en) | 1986-03-14 | 1986-03-14 | PROCESS FOR THE PREPARATION OF ALPHA, BETA-UNSATURATED ETHERS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD28786786A DD247669B1 (en) | 1986-03-14 | 1986-03-14 | PROCESS FOR THE PREPARATION OF ALPHA, BETA-UNSATURATED ETHERS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DD247669A1 true DD247669A1 (en) | 1987-07-15 |
| DD247669B1 DD247669B1 (en) | 1988-07-20 |
Family
ID=5577165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD28786786A DD247669B1 (en) | 1986-03-14 | 1986-03-14 | PROCESS FOR THE PREPARATION OF ALPHA, BETA-UNSATURATED ETHERS |
Country Status (1)
| Country | Link |
|---|---|
| DD (1) | DD247669B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0490221A3 (en) * | 1990-12-14 | 1993-03-24 | Hoechst Aktiengesellschaft | Method for the production of unsaturated ethers |
-
1986
- 1986-03-14 DD DD28786786A patent/DD247669B1/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0490221A3 (en) * | 1990-12-14 | 1993-03-24 | Hoechst Aktiengesellschaft | Method for the production of unsaturated ethers |
| US5354911A (en) * | 1990-12-14 | 1994-10-11 | Hoechst Aktiengesellschaft | Process for the preparation of unsaturated ethers |
Also Published As
| Publication number | Publication date |
|---|---|
| DD247669B1 (en) | 1988-07-20 |
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