DE1138755B - Process for the preparation of 3-chloro-butanone- (2) in addition to butanone - Google Patents
Process for the preparation of 3-chloro-butanone- (2) in addition to butanoneInfo
- Publication number
- DE1138755B DE1138755B DEC19308A DEC0019308A DE1138755B DE 1138755 B DE1138755 B DE 1138755B DE C19308 A DEC19308 A DE C19308A DE C0019308 A DEC0019308 A DE C0019308A DE 1138755 B DE1138755 B DE 1138755B
- Authority
- DE
- Germany
- Prior art keywords
- butanone
- chloro
- solution
- addition
- preparation
- 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 3
- 239000000243 solution Substances 0.000 claims description 12
- 239000010949 copper Substances 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 5
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 229940075397 calomel Drugs 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical compound Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 5
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- AALRHBLMAVGWRR-UHFFFAOYSA-N 1-chlorobutan-2-one Chemical class CCC(=O)CCl AALRHBLMAVGWRR-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OIMRLHCSLQUXLL-UHFFFAOYSA-N 3-chlorobutan-2-one Chemical compound CC(Cl)C(C)=O OIMRLHCSLQUXLL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- -1 Butyl alcohols Chemical class 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- 229910021120 PdC12 Inorganic materials 0.000 description 1
- 229910002666 PdCl2 Inorganic materials 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- LPRSRULGRPUBTD-UHFFFAOYSA-N butan-2-one;hydrate Chemical compound O.CCC(C)=O LPRSRULGRPUBTD-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 3-Chlor-Butanon-(2) neben Butanon Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von 3-Chlor-Butanon-(2) neben Butanon durch Oxydation von n-Butylenen mit Sauerstoff und Verwendung von wäßrigen Katalysatorlösungen, welche Palladiumchlorid und Kupferchlorid enthalten. Process for the preparation of 3-chloro-butanone- (2) in addition to butanone Die The present invention relates to a process for the preparation of 3-chloro-butanone- (2) in addition to butanone through the oxidation of n-butylenes with oxygen and the use of aqueous catalyst solutions which contain palladium chloride and copper chloride.
Es ist bekannt, daß man durch Umsetzung von n-Butylenen mit wäßrigen Katalysatorlösungen, welche Palladiumchlorid und Kupferchlorid enthalten, Butanon in hohen Ausbeuten herstellen kann (vgl. Angewandte Chemie, 71, 1959, S. 176 bis 182). It is known that by reacting n-butylenes with aqueous Catalyst solutions containing palladium chloride and copper chloride, butanone Can produce in high yields (see. Angewandte Chemie, 71, 1959, p. 176 bis 182).
Bei diesem Verfahren fallen Chlorbutanone als Nebenprodukte in geringen Mengen an. Diese Chlorbutanone bestehen zu etwa 900/0 aus 3-Chlor-Butanon-(2). 3-Chlor-Butanon-(2) ist ein sehr reaktionsfähiges Chlorketon, das für eine Reihe von organischen Synthesen als wertvolles Ausgangsprodukt verwendet werden kann. In this process, chlorobutanones fall in small amounts as by-products Amounts of. About 900/0 of these chlorobutanones consist of 3-chloro-butanone- (2). 3-chloro-butanone- (2) is a very reactive chloroketone that is used in a number of organic syntheses can be used as a valuable starting product.
Die vorliegende Erfindung betrifft Maßnahmen, die es gestatten, den Anteil an 3-Chlor-Butanon bei der Oxydation von n-Butylenen zu erhöhen. The present invention relates to measures which allow the Increase the proportion of 3-chloro-butanone in the oxidation of n-butylenes.
Es wurde nun gefunden, daß man 3-Chlor-Butanon-(2) neben Butanon herstellen kann, wenn man n-Butylen mit einer wäßrigen Lösung von Kupferchlorid und Palladiumchlorid, die im Liter mehr als 0,8 Mol Kupfer enthält, bei Temperaturen über 95"C umsetzt, wobei das Oxydationspotential der Lösung durch Oxydation mit Sauerstoff auf einem Wert über 330 Millivolt (gemessen bei 80°C gegen die Normalkalomelelektrode) gehalten wird. It has now been found that 3-chloro-butanone- (2) in addition to butanone can be produced if you n-butylene with an aqueous solution of copper chloride and palladium chloride, which contains more than 0.8 mol of copper per liter, at temperatures above 95 "C, whereby the oxidation potential of the solution through oxidation with Oxygen at a value above 330 millivolts (measured at 80 ° C against the standard calomel electrode) is held.
1-Buten ist ein besonders reaktionsfähiges Ausgangsmaterial, man kann aber auch 2-Buten oder Mischungen dieser Isomeren verwenden. In der Technik anfallende, n-Butylene enthaltende Gemische sind gleichfalls als Rohstoffe geeignet. 1-butene is a particularly reactive starting material, man but can also use 2-butene or mixtures of these isomers. In technology Accruing mixtures containing n-butylenes are also suitable as raw materials.
Die Umsetzung der n-Butylene mit der wäßrigen Katalysatorlösung wird in Blasensäulen oder Füllkörpertürmen durchgeführt. The reaction of the n-butylenes with the aqueous catalyst solution is carried out in bubble columns or packed towers.
Die Umsetzung wird zweckmäßig bei erhöhtem Druck durchgeführt. The reaction is expediently carried out at elevated pressure.
Ein weiterer Umstand, der für das Ausmaß der Bildung von 3-Chlorbutanon von Bedeutung ist, ist der Reduktionszustand der Lösung, d. h. das Verhältnis Cu(II) zu Cu(I). Ein praktisches Maß für dieses Verhältnis ist das Redoxpotential der Lösung, das z. B. mit einer Pt-Elektrode gegen die Normalkalomelelektrode gemessen werden kann. Je höher das Potential ist, desto mehr 3-Chlor-Butanon-(2) wird gebildet. Potential und Löslichkeit von CuCl sind von der Zusammensetzung der Lösung abhängig. Another factor that determines the extent to which 3-chlorobutanone is formed What matters is the state of reduction of the solution, i. H. the ratio Cu (II) to Cu (I). A practical measure of this ratio is the redox potential of the solution, the Z. B. measured with a Pt electrode against the normal calomel electrode can. The higher the potential, the more 3-chloro-butanone- (2) is formed. The potential and solubility of CuCl depend on the composition of the solution.
Als Anhaltspunkt ist ein unteres Potential von 330 Millivolt (gemessen bei 80"C gegen die Normal- kalomelelektrode) und eine untere Grenze der Löslichkeit von CuCI bei einem Verhältnis Cu(II) zu Cu(I) gleich 1:1 anzusehen.As a guide, a lower potential of 330 millivolts (measured at 80 "C against the normal calomel electrode) and a lower limit of solubility of CuCI at a ratio of Cu (II) to Cu (I) equal to 1: 1.
Die verschiedenen Maßnahmen, wie Erhöhung der Verweilzeit, Temperatur, Redoxpotential und Gesamt-Kupfer-Konzentration, begünstigen die Bildung von 3-Chlor-Butanon-(2) verschieden stark und entfalten ihren maximalen Einfluß in unterschiedlichen Variationsbereichen. Bei gleichzeitiger Änderung mehrerer Maßnahmen kann es daher zu Überschneidungen der technischen Effekte kommen. The various measures, such as increasing the residence time, temperature, Redox potential and total copper concentration, favor the formation of 3-chloro-butanone- (2) different strengths and develop their maximum influence in different areas of variation. If several measures are changed at the same time, there may be overlaps the technical effects come.
So kann z. B. eine Steigerung der Gesamt-Kupfer-Konzentration durch eine gleichzeitig erfolgende Temperatursenkung überkompensiert werden. Die angegebenen unteren Grenzweiten für die einzelr.en Maßnahmen müssen jedoch in jedem Fall überschritten werden, wenn 3-Chlor-Butanon-(2) in Anteilen von mehr als 10°/o gebildet werden soll.So z. B. by increasing the total copper concentration a simultaneous drop in temperature can be overcompensated. The specified However, the lower limit widths for the individual measures must be exceeded in any case if 3-chloro-butanone- (2) are formed in proportions of more than 10% target.
Die Abtrennung der gebildeten Reaktionsprodukte aus der Katalysatorlösung erfolgt durch Destillation. The separation of the reaction products formed from the catalyst solution takes place by distillation.
Die Katalysatorlösung wird entspannt, zweckmäßig auf Normaldruck oder geringen Unterdruck. Eine vollständige Abtrennung des Butanons ist nicht erforderlich.The catalyst solution is let down, expediently to normal pressure or low negative pressure. Complete separation of the butanone is not necessary.
Die von der Katalysatorlösung abgetrennten Rohketone enthalten noch Nebenprodukte, wie Acetaldehyd, Aceton, Propionaldehyd, Diacetyl, Crotonaldehyd, Butylalkohole, Butyraldehyd und Chlorierungsprodukte; Butyraldehyd fällt in Mengen von einigen Prozenten an, während die übrigen Nebenprodukte im allgemeinen nur in sehr geringen Mengen auftreten. The crude ketones separated from the catalyst solution still contain By-products such as acetaldehyde, acetone, propionaldehyde, diacetyl, crotonaldehyde, Butyl alcohols, butyraldehyde and chlorination products; Butyraldehyde falls in amounts of a few percent, while the other by-products in general occur only in very small quantities.
Die Rohketone werden gegebenenfalls nach Vorheizung und unter vermindertem Druck dampfförmig in eine Kolonne eingeführt. Ein Butanon-Wasserazeotrop wird zusammen mit den niedrigsiedenden Nebenprodukten über Kopf abgezogen, während am unteren Ende der Kolonne ein Gemisch von Chlorbutanon, Wasser und höhersiedenden Nebenprodukten erhalten wird. Chlorbutanon wird in einem Abscheider vom Wasser getrennt und durch weitere Destillation gereinigt. The crude ketones are optionally after preheating and under reduced Pressure introduced in vapor form into a column. A butanone water azeotrope is made together withdrawn with the low-boiling by-products overhead, while at the bottom At the end of the column, a mixture of chlorobutanone, water and higher-boiling by-products is obtained. Chlorobutanone is separated from the water in a separator and through purified further distillation.
In den nachstehenden Beispielen wird als Butylen ein technisches Gemisch von 1-Buten und 2-Buten verwendet. In the examples below, the butylene is a technical one Mixture of 1-butene and 2-butene used.
Beispiel 1 Ein Butylen-Sauerstoff-Gemisch mit 33 Volumprozent O2 wird bei 6 atü und 96 bis 102"C mit einer wäßrigen Lösung umgesetzt, die im Liter 150 g CuC12 und 4,5 g PdCl2 enthält. Redoxpotential 375 bis 390 mV. Example 1 A butylene-oxygen mixture with 33 percent by volume O2 is reacted at 6 atm and 96 to 102 "C with an aqueous solution, which per liter Contains 150 g CuC12 and 4.5 g PdCl2. Redox potential 375 to 390 mV.
Die Rohketone enthalten 20 Gewichtsprozent 3-Chlor-Butanon-(2). The crude ketones contain 20 percent by weight of 3-chloro-butanone- (2).
Beispiel 2 Butylen wird bei 115"C unter einem Druck von 17 atü in einem Reaktionsturm mit einer wäßrigen Lösung umgesetzt, die im Liter 142 g CuCI2 und 3 g PdC12 enthält. Die Verweilzeit der Lösung im Reaktionsturm beträgt 320 Sekunden. Redoxpotential nach Reduktion: 375 bis 385 mV. Die Salzlösung wird in eine Destillationskolonne entspannt, in der die Rohketone bis auf einen Restgehalt von 1,2 g/l entfernt werden. Die ablaufende Salzlösung wird nach Ergänzung des verdampften Wassers und der verbrauchten Salzsäure oxydiert und wieder dem Reaktionsturm zugeführt. Die Rohketone enthalten 70 Gewichtsprozent 3-Chlor-Butanon-(2). Example 2 Butylene is at 115 "C under a pressure of 17 atmospheres reacted in a reaction tower with an aqueous solution containing 142 g of CuCl2 per liter and contains 3 g of PdC12. The residence time of the solution in the reaction tower is 320 seconds. Redox potential after reduction: 375 to 385 mV. The salt solution is placed in a distillation column relaxed, in which the crude ketones are removed to a residual content of 1.2 g / l. The draining saline solution is consumed after replenishing the evaporated water and the Hydrochloric acid is oxidized and fed back to the reaction tower. The raw ketones contain 70 percent by weight 3-chloro-butanone- (2).
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC19308A DE1138755B (en) | 1959-06-29 | 1959-06-29 | Process for the preparation of 3-chloro-butanone- (2) in addition to butanone |
| GB2283960A GB920455A (en) | 1959-06-29 | 1960-06-29 | Process for the manufacture of 3-chlorobutanone-2 and butanone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC19308A DE1138755B (en) | 1959-06-29 | 1959-06-29 | Process for the preparation of 3-chloro-butanone- (2) in addition to butanone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1138755B true DE1138755B (en) | 1962-10-31 |
Family
ID=7016601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC19308A Pending DE1138755B (en) | 1959-06-29 | 1959-06-29 | Process for the preparation of 3-chloro-butanone- (2) in addition to butanone |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1138755B (en) |
| GB (1) | GB920455A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1202263B (en) | 1961-09-27 | 1965-10-07 | Hoechst Ag | Process for the production of chlorinated aldehydes or ketones |
-
1959
- 1959-06-29 DE DEC19308A patent/DE1138755B/en active Pending
-
1960
- 1960-06-29 GB GB2283960A patent/GB920455A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1202263B (en) | 1961-09-27 | 1965-10-07 | Hoechst Ag | Process for the production of chlorinated aldehydes or ketones |
Also Published As
| Publication number | Publication date |
|---|---|
| GB920455A (en) | 1963-03-06 |
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