DE1028557B - Process for the preparation of ª ‰ -alkoxy-ª ‡ -chloropropionic esters - Google Patents
Process for the preparation of ª ‰ -alkoxy-ª ‡ -chloropropionic estersInfo
- Publication number
- DE1028557B DE1028557B DEB43789A DEB0043789A DE1028557B DE 1028557 B DE1028557 B DE 1028557B DE B43789 A DEB43789 A DE B43789A DE B0043789 A DEB0043789 A DE B0043789A DE 1028557 B DE1028557 B DE 1028557B
- Authority
- DE
- Germany
- Prior art keywords
- alkoxy
- acid esters
- preparation
- alcohols
- parts
- 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
- 150000002148 esters Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- -1 saturated aliphatic alcohols Chemical class 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical class OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 125000005396 acrylic acid ester group Chemical group 0.000 description 3
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 3
- AWJZTPWDQYFQPQ-UHFFFAOYSA-N methyl 2-chloroprop-2-enoate Chemical compound COC(=O)C(Cl)=C AWJZTPWDQYFQPQ-UHFFFAOYSA-N 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical class CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- UCKZQZDVQVFOHP-UHFFFAOYSA-N bromo propanoate Chemical compound CCC(=O)OBr UCKZQZDVQVFOHP-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
- NGYIMTKLQULBOO-UHFFFAOYSA-L mercury dibromide Chemical compound Br[Hg]Br NGYIMTKLQULBOO-UHFFFAOYSA-L 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/12—Oxygen-containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
Es ist bekannt, daß man /?-Methoxy-a~brompropionsäuremethylester erhält, wenn man Acrylsäuremethylester mit Methanol in Gegenwart von Mercuriacetat behandelt, das erhaltene Gemisch mit Kaliumbromid umsetzt und auf die organische Quecksilberbromidadditionsverbindung Brom einwirken läßt (vgl. »Organic Syntheses«, Coll. Vol. Ill [1955], S. 774). Ferner ist aus »Chemical Abstracts«, Bd. 49 [1955], Spalte 850d, bekannt, daß α-Chlor-^-methoxypropionsäureester als Nebenprodukt in einer Menge bis zu 20% bei der Chlorierung von Methylacrylat in Methanollösung entsteht.It is known that methyl methoxy-a ~ bromopropionate is used obtained when methyl acrylate is obtained with methanol in the presence of mercuric acetate treated, the mixture obtained is reacted with potassium bromide and the organic mercury bromide addition compound Allows bromine to act (cf. "Organic Syntheses", Coll. Vol. Ill [1955], p. 774). It is also known from Chemical Abstracts, Vol. 49 [1955], column 850d, that α-chloro - ^ - methoxypropionic acid ester as a by-product in an amount up to 20% in the chlorination of methyl acrylate in methanol solution arises.
Es wurde nun gefunden, daß man in einfacher Weise /?-Alkoxy~a-chlorpropionsäureester einwertiger Alkohole erhält, wenn man die entsprechenden α-Chloracrylsäureester mit gesättigten einwertigen aliphatischen Alkoholen in Gegenwart von Alkalialkoholaten umsetzt.It has now been found that /? - Alkoxy ~ α-chloropropionic acid esters can be obtained in a simple manner Alcohols are obtained when the corresponding α-chloroacrylic acid esters are used with saturated monohydric aliphatic alcohols in the presence of alkali alcoholates implements.
Als einwertige aliphatische Alkohole sind insbesondere die niedermolekularen Alkohole, wie Methanol und Äthanol sowie die isomeren Propanole und Butanole, geeignet.Monohydric aliphatic alcohols are in particular the low molecular weight alcohols, such as methanol and ethanol and the isomeric propanols and butanols, are suitable.
Zur Umsetzung, die mit a-Chloracrylsäureestern beliebiger einwertiger Alkohole durchgeführt werden kann, werden bevorzugt diejenigen Ester verwendet, die sich von Alkoholen der aliphatischen Reihe, insbesondere den unteren Gliedern dieser Reihe, ableiten. Besonders geeignet sind a-Chloracrylsäureester, die als Alkoholkomponente den zur Anlagerung verwendeten Alkohol enthalten.To implement that with α-chloroacrylic acid esters any monohydric alcohols can be carried out, those esters are preferably used which are derived from alcohols of the aliphatic series, especially the lower members of this series. Α-Chloroacrylic acid esters, the alcohol component used for the addition, are particularly suitable Contain alcohol.
Als Alkalialkoholate kommen vor allem die Natrium- und Kaliumalkoholate der Alkohole in Betracht, die bei dieser Reaktion zur Umsetzung gelangen. Besonders geeignet sind z. B. Natriummethylat, Kaliummethylat sowie die entsprechenden Äthylate, Projjylate und Butylate. Zur Umsetzung werden sie nur in geringen Mengen, z. B. etwa 0,3 bis 5 Gewichtsprozent, bezogen auf eingesetzten Chloracrylsäureester, verwendet.The most suitable alkali alcoholates are the sodium and potassium alcoholates of the alcohols, which are implemented in this reaction. Particularly suitable are, for. B. sodium methylate, potassium methylate as well as the corresponding ethylates, projectylates and butylates. To implement they are only used in small amounts, e.g. B. about 0.3 to 5 percent by weight, based on the chloroacrylic acid ester used.
Die Umsetzung erfolgt bei einer Temperatur zwischen etwa 0° C und dem Siedepunkt des verwendeten Alkohols, vorteilhaft bei etwa 20 bis 60° C. Die Umsetzung läßt sich beispielsweise in der Weise durchführen, daß man zu dem Chloracrylsäureester den zur Addition benötigten Alkohol in der berechneten Menge oder im Überschuß zufügt und das Alkalialkoholat einträgt. Das Alkoholat kann sowohl in fester Form als auch zweckmäßig in einer alkoholischen Lösung zugegeben werden.The reaction takes place at a temperature between about 0 ° C and the boiling point of the used Alcohol, advantageously at about 20 to 60 ° C. The reaction can be carried out, for example, in the manner that the alcohol required for addition to the chloroacrylic acid ester in the calculated Adds amount or in excess and introduces the alkali alcoholate. The alcoholate can be used in solid form as well as expediently in an alcoholic solution.
Es hat sich ferner als zweckmäßig erwiesen, geringe Mengen eines Stabilisators, z. B. Hydrochinon oder
Phenthiazin, bei der Umsetzung mitzuverwenden, um um Selbstpolymerisation des Chloracrylsäureesters zu
vermeiden. Aus dem Umsetzungsgemisch kann der Verfahren zur Herstellung
von ß-Alkoxy-a-chlorpropionsäureesternIt has also proven to be useful to use small amounts of a stabilizer, e.g. B. hydroquinone or phenthiazine, to be used in the reaction in order to avoid self-polymerization of the chloroacrylic acid ester. From the reaction mixture, the process for the preparation
of ß- alkoxy-a-chloropropionic acid esters
Anmelder:Applicant:
ίο Badische Anilin- & Soda-Fabrikίο Badische Anilin- & Soda-Fabrik
Aktiengesellschaft, Ludwigshafen/RheinAktiengesellschaft, Ludwigshafen / Rhein
Dr. Manfred Minsinger, Ludwigshafen/Rhein,Dr. Manfred Minsinger, Ludwigshafen / Rhine,
und Dr. Herbert Friederich, Worms,and Dr. Herbert Friederich, Worms,
sind als Erfinder genannt wordenhave been named as inventors
/9-Alkoxy-a-chlorpropionsäureester nach an sich bekannten Methoden, z. B. durch fraktionierte Destillation, gewonnen werden./ 9-Alkoxy-α-chloropropionic acid esters according to known ones Methods, e.g. B. by fractional distillation can be obtained.
Es ist zwar bekannt, daß man /J-Alkoxypropionsäureester oder deren a-methylsubstituierte Derivate erhält, wenn man Acrylsäureester bzw. Methacrylsäureester mit Alkoholen in Gegenwart von Alkalialkoholaten behandelt (vgl. »Journal of American Chemical Society«, Bd. 68 [1946], S. 544, und »Comptes Rendus«, Bd. 234 [1952], S. 1783. Die Ausbeuten sinken jedoch bei Verwendung von Methacrylsäureestern infolge sterischer Hinderung durch die in α-Stellung befindliche Methylgruppe im Vergleich zur Umsetzung der nicht substituierten Acrylsäureester erheblich ab, auch erfolgt die Umsetzung der Methacrylsäureester erheblich langsamer als die der Acrylsäureester. Es war daher unerwartet, daß bei Verwendung von a-Chloracrylsäureestern trotz der sterischen Hinderung durch das in α-Stellung befindliche Chloratom die Umsetzung schnell und glatt gelingt und in guten Ausbeuten zu den /J-Alkoxy-a-chlorpropionsäureestern führt. Dieser Befund war um so überraschender, als man hätte erwarten sollen, daß sich die für die Umsetzung verwendeten Katalysatormengen mit dem Chloratom der a-Chloracrylsäureester unter Bildung von katalytisch inaktiven Alkalichloriden und von in α-Stellung durch Alkoxygruppen substituierten Estern umsetzen und hierdurch die Anlagerungsreaktion der Alkohole unterbunden wird.It is known that one / I-alkoxypropionic acid ester or their α-methyl-substituted derivatives are obtained when acrylic acid esters or methacrylic acid esters are used treated with alcohols in the presence of alkali alcoholates (cf. »Journal of American Chemical Society ", Vol. 68 [1946], p. 544, and" Comptes Rendus ", Vol. 234 [1952], p. 1783. The yields however, decrease when methacrylic acid esters are used due to steric hindrance caused by the in α-position methyl group compared to the implementation of the unsubstituted acrylic acid ester The conversion of the methacrylic acid esters also takes place considerably more slowly than that of the acrylic acid esters. It was therefore unexpected that when using a-chloroacrylic acid esters, despite the steric Hindrance by the chlorine atom in the α-position, the reaction succeeds quickly and smoothly and in good yields to the / J-alkoxy-α-chloropropionic acid esters leads. This finding was all the more surprising as one should have expected that it would the amounts of catalyst used for the reaction with the chlorine atom of the α-chloroacrylic acid ester with the formation of catalytically inactive alkali chlorides and of in the α-position by alkoxy groups React substituted esters and thereby the addition reaction of the alcohols is suppressed.
Die erhaltenen ^-Alkoxy-a-chlorpropionsäureesterThe obtained ^ -alkoxy-α-chloropropionic acid ester
sind gute Lösungsmittel für organische Verbindungen.are good solvents for organic compounds.
S09 507/414S09 507/414
Ferner eignen sie sich als Sparbeizmittel und können zur Herstellung von Aminosäuren verwendet werden. Die in dem Beispiel angegebenen Teile sind Ge wichtsteile.They are also suitable as a seed dressing agent and can be used for the production of amino acids. The parts given in the example are parts by weight.
In eine Lösung, bestehend aus 1000 Teilen a-Chloracrylsäuremethylester, 500 Teilen Methanol und 4 Teilen Phenthiazin, läßt man bei 40° C unter Rühren eine Lösung von 20 Teilen Natriummethylat in 100 Teilen Methanol langsam einfließen. Nachdem das Eintragen beendet ist, erwärmt man das Umsetzungsgemisch auf die Siedetemperatur des Methanols und destilliert dann das nicht umgesetzte Methanol und den nicht umgesetzten crChloracrylsäuremethylester (Kp. 760 = 128° C) bei Normaldruck ab. Man erhält so 366 Teile Methanol und 92 Teile a-Chloracrvlsäuremethylester zurück. Durch Vakuumdestillation des verbleibenden Rückstandes erhält man bei 77° C und Torr 1056 Teile /f-Methoxy-a-chlorpropionsäuremethylester. 92 Teile bleiben als Rückstand zurück. Die Ausbeute an /J-Methoxy-a-chlorpropionsäuremethylester beträgt bei 91 %iger Umsetzung des ct-Chloracrylsäuremethylesters 92% der Theorie.A solution of 20 parts of sodium methylate in 100 parts of methanol is slowly run into a solution consisting of 1000 parts of methyl α-chloroacrylate, 500 parts of methanol and 4 parts of phenthiazine at 40 ° C. with stirring. After the introduction has ended, the reaction mixture is heated to the boiling temperature of the methanol and the unconverted methanol and the unconverted methyl chloroacrylate (boiling point 760 = 128 ° C.) are then distilled off at atmospheric pressure. In this way, 366 parts of methanol and 92 parts of methyl α-chloroacrylate are obtained. Vacuum distillation of the remaining residue gives 1056 parts / f-methoxy-α-chloropropionic acid methyl ester at 77 ° C. and torr. 92 parts remain as residue. The yield of / J-methoxy-α-chloropropionic acid methyl ester is 92% of theory with 91% conversion of the ct-chloroacrylic acid methyl ester.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB43789A DE1028557B (en) | 1957-03-06 | 1957-03-06 | Process for the preparation of ª ‰ -alkoxy-ª ‡ -chloropropionic esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB43789A DE1028557B (en) | 1957-03-06 | 1957-03-06 | Process for the preparation of ª ‰ -alkoxy-ª ‡ -chloropropionic esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1028557B true DE1028557B (en) | 1958-04-24 |
Family
ID=6967152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB43789A Pending DE1028557B (en) | 1957-03-06 | 1957-03-06 | Process for the preparation of ª ‰ -alkoxy-ª ‡ -chloropropionic esters |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1028557B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9771317B2 (en) | 2012-11-01 | 2017-09-26 | Cambrex Karlskoga Ab | Process for preparing lacosamide and related compounds |
-
1957
- 1957-03-06 DE DEB43789A patent/DE1028557B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9771317B2 (en) | 2012-11-01 | 2017-09-26 | Cambrex Karlskoga Ab | Process for preparing lacosamide and related compounds |
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