DE1276041B - Process for the preparation of 2, 2, 4, 4, 6-penta-methyl-2, 3, 4, 5-tetrahydropyrimidine - Google Patents
Process for the preparation of 2, 2, 4, 4, 6-penta-methyl-2, 3, 4, 5-tetrahydropyrimidineInfo
- Publication number
- DE1276041B DE1276041B DESCH36798A DESC036798A DE1276041B DE 1276041 B DE1276041 B DE 1276041B DE SCH36798 A DESCH36798 A DE SCH36798A DE SC036798 A DESC036798 A DE SC036798A DE 1276041 B DE1276041 B DE 1276041B
- Authority
- DE
- Germany
- Prior art keywords
- ammonia
- tetrahydropyrimidine
- acetone
- preparation
- reaction
- 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
- PIFBMJMXJMZZRG-UHFFFAOYSA-N 2,2,4,6,6-pentamethyl-1,5-dihydropyrimidine Chemical compound CC1=NC(C)(C)NC(C)(C)C1 PIFBMJMXJMZZRG-UHFFFAOYSA-N 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 13
- 229910021529 ammonia Inorganic materials 0.000 claims description 11
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
- PCXAQLMRLMZKRL-UHFFFAOYSA-N 2-methylpentane-2,4-diamine Chemical compound CC(N)CC(C)(C)N PCXAQLMRLMZKRL-UHFFFAOYSA-N 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- VNSBYDPZHCQWNB-UHFFFAOYSA-N calcium;aluminum;dioxido(oxo)silane;sodium;hydrate Chemical compound O.[Na].[Al].[Ca+2].[O-][Si]([O-])=O VNSBYDPZHCQWNB-UHFFFAOYSA-N 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229910000271 hectorite Inorganic materials 0.000 description 1
- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 229910000273 nontronite Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 229910000275 saponite Inorganic materials 0.000 description 1
- 229910000276 sauconite Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/5073—Amines heterocyclic containing only nitrogen as a heteroatom having two nitrogen atoms in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Herstellung von 2,2,4,4,6-Pentamethyl-2,3,4,5-tetrahydropyrimidin Die Erfindung betrifft ein Verfahren zur kontinuierlichen Herstellung von 2,2,4,4,6-Pentamethyl-2,3,4,5-tetrahydropyrimidin, im folgenden Acetonin genannt, durch Umsetzung von Aceton mit Ammoniak in Gegenwart von bestimmten sauren, fest angeordneten Katalysatoren bei gegebenenfalls erhöhtem Druck und erhöhten Temperaturen.Process for the preparation of 2,2,4,4,6-pentamethyl-2,3,4,5-tetrahydropyrimidine The invention relates to a process for the continuous production of 2,2,4,4,6-pentamethyl-2,3,4,5-tetrahydropyrimidine, hereinafter referred to as acetonin, by reacting acetone with ammonia in the presence of certain acidic, permanently arranged catalysts with possibly increased Pressure and elevated temperatures.
Es ist bekannt, Acetonin aus Aceton und Ammoniak in Gegenwart saurer Katalysatoren zu synthetisieren. So wird beispielsweise nach einem Verfahren in eine Suspension von gemahlenem Calciumchlorid in Aceton bei 250 C Ammoniak so eingeleitet, daß ständig ein Überdruck von 20 cm Wassersäule aufrechterhalten bleibt. Es bilden sich zwei Schichten im Reaktionsgefäß, von denen die organische Schicht nach Beendigung des Versuchs abgetrennt und destillativ aufgearbeitet wird. Der Katalysator löst sich im Laufe der Reaktion in dem entstandenen Wasser. Die Ausbeute beträgt etwa 80 O/o der Theorie. It is known to acidic acetonin from acetone and ammonia in the presence Synthesize catalysts. For example, according to a method in a suspension of ground calcium chloride in acetone at 250 C ammonia is introduced in such a way that that an overpressure of 20 cm of water column is maintained at all times. Make it up two layers in the reaction vessel, of which the organic layer after completion of the experiment is separated and worked up by distillation. The catalyst dissolves in the course of the reaction in the resulting water. The yield is about 80 o / o of theory.
Nach einer weiteren bekannten Arbeitsweise werden über die Verwendung von Calciumchlorid als Katalysator hinausgehend alle sauer reagierenden Salze bzw. die ihnen zugrunde liegenden Säuren mit einbezogen. Auch in diesem Fall wird Aceton mit Ammoniak bei Raum- oder erhöhter Temperatur, unter Normal- oder erhöhtem Druck chargenweise zur Reaktion gebracht, wobei als wesentliche Aufarbeitungsstufe eine Entwässerung des Reaktionsgemisches durch Zugabe von Atzkali oder Benzol und eine Neutralisation der abgezogenen organischen Phase angegeben wird, bevor man sie destillativ reinigt. Die Ausbeute beträgt etwa 50010. Another known way of working is to use In addition to calcium chloride as a catalyst, all acidic salts or the acids on which they are based are included. Also in this case is acetone with ammonia at room or elevated temperature, under normal or elevated pressure brought to reaction in batches, with an essential work-up stage Dehydration of the reaction mixture by adding caustic potash or benzene and a Neutralization of the withdrawn organic phase is indicated before they are distilled cleans. The yield is about 50,010.
Im Gegensatz zu den obengenannten Verfahren werden erfindungsgemäß als saure Katalysatoren solche verwendet, die montmorillonitartige Mineralien in einem hohen Anteil enthalten, fest angeordnet sind und weder in den Einsatzprodukten noch in der wasserhaltigen Reaktionsmischung löslich sind. Dieser Umstand ist Voraussetzung für eine einfache kontinuierliche Verfahrensweise, da der Zusatz von Säuren oder sauren Salzen immer eine Phasentrennung, zumindest aber eine Neutralisation und Abtrennung des zugesetzten Katalysators und damit einen zusätzlichen Verfahrensschritt vor der destillativen Aufarbeitung notwendig macht. In contrast to the above-mentioned methods are according to the invention as acidic catalysts those used, the montmorillonite-like minerals in contain a high proportion, are firmly arranged and neither in the input products are still soluble in the water-containing reaction mixture. This fact is a prerequisite for a simple continuous procedure, since the addition of acids or acid salts always phase separation, but at least neutralization and Separation of the added catalyst and thus an additional process step makes necessary before the work-up by distillation.
Bei den obengenannten unlöslichen Katalysatoren, die sich selbstverständlich auch für einen Chargenbetrieb eignen, handelt es sich insbesondere um solche, die Bentonit enthalten. Die erfindungsgemäß zu verwendenden Katalysatoren können neben einem hohen Anteil an montmorillonitartigen Mineralien gegebenenfalls noch Beidellit, Nontronit, Hectorit, Saponit und Sauconit enthalten. Gut geeignet ist beispielsweise der unter der Bezeichnung K 306 handelsübliche Katalysator der Südchemie, München, bei dem es sich um ein aus Montmorillonit gewonnenes Aluminiumhydrosilikat handelt. Die Azidität der Kontakte muß ausreichen, um die Reaktion zwischen Aceton und Ammoniak zu katalysieren. Je nach den übrigen Reaktionsbedingungen ist eine Raumgeschwindigkeit von etwa 0,2 bis 1,0 pro Stunde erforderlich. Die optimalen Reaktionstemperaturen liegen bei 20 bis 1300 C, insbesondere bei 50 bis 1000 C, jedoch können auch Temperaturen außerhalb dieser Grenzen noch durchaus zulässig sein. In the case of the above-mentioned insoluble catalysts, of course are also suitable for batch operation, these are in particular those that Contains bentonite. The catalysts to be used according to the invention can in addition to a high proportion of montmorillonite-like minerals, possibly also beidellite, Nontronite, hectorite, Contains saponite and sauconite. For example, it is well suited the commercially available catalyst from Südchemie, Munich, under the name K 306, which is an aluminum hydrosilicate obtained from montmorillonite. The acidity of the contacts must be sufficient to prevent the reaction between acetone and ammonia to catalyze. A space velocity depends on the other reaction conditions from about 0.2 to 1.0 per hour is required. The optimal reaction temperatures are from 20 to 1300 ° C., in particular from 50 to 1000 ° C., but temperatures can also be used outside these limits still be entirely permissible.
Der Katalysator kann in beliebiger Form eingesetzt werden. Bevorzugt werden Katalysatorkörper in Form von Kugeln, Zylindern oder Tabletten. The catalyst can be used in any form. Preferred are catalyst bodies in the form of spheres, cylinders or tablets.
Um bei den angegebenen Reaktionstemperaturen ein Vergasen des Ammoniaks und damit eine Turbulenz vor allem in den Reaktionsräumen möglichst zu vermeiden, empfiehlt es sich, unter erhöhtem Druck zu arbeiten. Es kommen Drücke von 10 bis 100 atü in Frage. In order to gasify the ammonia at the specified reaction temperatures and thus to avoid turbulence, especially in the reaction spaces, as far as possible, it is advisable to work under increased pressure. There are pressures from 10 to 100 atü in question.
Das Verhältnis Aceton zu Ammoniak sollte mindestens stöchiometrisch, d. h. 3 : 2 sein. Bessere Ausbeuten erhält man jedoch mit einem großen Ammoniaküberschuß. The ratio of acetone to ammonia should be at least stoichiometric, d. H. Be 3: 2. However, better yields are obtained with a large excess of ammonia.
Das aus dem Reaktor austretende Produkt stellt, da es keine gelösten Salze enthält, ein homogenes Gemisch dar, das direkt der destillativen Aufarbeitung zugeführt werden kann. The product emerging from the reactor represents, as there is no dissolved product Contains salts, a homogeneous mixture, which directly the distillative work-up can be fed.
Das Verfahrensprodukt Acetonin hat neben seiner Eignung als Härter für Epoxyharze und als Fungizid wertvolle Eigenschaften als Zwischenprodukt, insbesondere zur Herstellung von 2,4-Diamino-2-methylpentan. In addition to its suitability as a hardener, the process product acetonine for epoxy resins and as a fungicide valuable properties as an intermediate product, in particular for the production of 2,4-diamino-2-methylpentane.
Beispiel In einem Druckreaktor von 101 Inhalt, der mit 8 1 des oben definierten sauren Kontakts mit der Handelsbezeichnung K 306 (kugelförmig, etwa 5 mm Durchmesser) gefüllt ist, werden pro Stunde 4 1 einer Mischung aus 17,4kg Aceton und 34,0 kg Ammoniak von unten eingepumpt. Die Temperatur im Reaktor beträgt 850 C. Durch Aufdrücken eines Inertgases wird ein Druck von 50 atü eingestellt. Example In a pressure reactor of 101 contents, the one with 8 1 of the above defined acidic contact with the trade name K 306 (spherical, approx 5 mm diameter) is filled, 4 liters of a mixture of 17.4 kg of acetone per hour and 34.0 kg of ammonia are pumped in from below. The temperature in the reactor is 850 C. A pressure of 50 atm is set by forcing in an inert gas.
Das am Kopf des Reaktionsofens austretende Produkt wird über ein Vorlagegefäß einer Reihe von Destillationskolonnen zugeführt, in denen zunächst überschüssiges Ammoniak und nicht umgesetztes Aceton abgetrennt und in die Reaktion zurückgeführt werden. Eine dritte Kolonne liefert über Kopf ein teilweise azeotropes Gemisch aus Reaktionswasser, Diacetonalkohol, Mesityloxid und anderen Nebenprodukten, während am Kopf der vierten Kolonne reines Acetonin abgezogen werden kann. Siedepunkt bei 50 Torr 850 C; n25 = 1,4560. Man gewinnt pro Stunde durchschnittlich 157 g Aceton zurück, entsprechend einem Umsatz von 82,5°/o. Bezogen auf diesen Umsatz beträgt die durchschnittliche Acetoninausbeute 600 g/Std., entsprechend 91,7 O/o der Theorie. The product emerging at the top of the reaction furnace is via a Receiving vessel fed to a number of distillation columns, in which initially Excess ammonia and unreacted acetone separated and put into the reaction to be led back. A third column delivers a partially azeotropic overhead Mixture of reaction water, diacetone alcohol, mesityl oxide and other by-products, while pure acetonine can be drawn off at the top of the fourth column. boiling point at 50 torr 850 C; n25 = 1.4560. An average of 157 g of acetone is obtained per hour back, corresponding to a conversion of 82.5%. Based on this conversion is the average acetonin yield 600 g / h, corresponding to 91.7 o / o of theory.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH36798A DE1276041B (en) | 1965-03-27 | 1965-03-27 | Process for the preparation of 2, 2, 4, 4, 6-penta-methyl-2, 3, 4, 5-tetrahydropyrimidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH36798A DE1276041B (en) | 1965-03-27 | 1965-03-27 | Process for the preparation of 2, 2, 4, 4, 6-penta-methyl-2, 3, 4, 5-tetrahydropyrimidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1276041B true DE1276041B (en) | 1968-08-29 |
Family
ID=7434010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DESCH36798A Pending DE1276041B (en) | 1965-03-27 | 1965-03-27 | Process for the preparation of 2, 2, 4, 4, 6-penta-methyl-2, 3, 4, 5-tetrahydropyrimidine |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1276041B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0839797A1 (en) * | 1996-11-05 | 1998-05-06 | Bayer Ag | Process for the preparation of 2-methyl-2,4-diaminopentane |
| WO2022029154A1 (en) | 2020-08-04 | 2022-02-10 | Basf Se | Heterogeneous catalyzed process for the production of 2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydro-pyrimidine |
-
1965
- 1965-03-27 DE DESCH36798A patent/DE1276041B/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0839797A1 (en) * | 1996-11-05 | 1998-05-06 | Bayer Ag | Process for the preparation of 2-methyl-2,4-diaminopentane |
| US5801285A (en) * | 1996-11-05 | 1998-09-01 | Bayer Aktiengesellschaft | Process for the preparation of 2-methyl-2,4-diaminopentane |
| WO2022029154A1 (en) | 2020-08-04 | 2022-02-10 | Basf Se | Heterogeneous catalyzed process for the production of 2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydro-pyrimidine |
| CN116057012A (en) * | 2020-08-04 | 2023-05-02 | 巴斯夫欧洲公司 | A Heterogeneous Catalytic Method for the Preparation of 2,2,4,6,6-Pentamethyl-1,2,5,6-tetrahydropyrimidine |
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