DE259363C - - Google Patents
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- Publication number
- DE259363C DE259363C DENDAT259363D DE259363DA DE259363C DE 259363 C DE259363 C DE 259363C DE NDAT259363 D DENDAT259363 D DE NDAT259363D DE 259363D A DE259363D A DE 259363DA DE 259363 C DE259363 C DE 259363C
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- DE
- Germany
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- parts
- yield
- theory
- percent
- nitrile
- 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.)
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- 150000002825 nitriles Chemical class 0.000 claims description 15
- 150000003585 thioureas Chemical class 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 20
- 239000005662 Paraffin oil Substances 0.000 description 12
- 229910052742 iron Inorganic materials 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 238000007127 saponification reaction Methods 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000010721 machine oil Substances 0.000 description 3
- -1 p-dimethoxyphenylthiourea Chemical compound 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N Anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N Benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N Thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- SJSYJHLLBBSLIH-SDNWHVSQSA-N (E)-3-(2-methoxyphenyl)-2-phenylprop-2-enoic acid Chemical compound COC1=CC=CC=C1\C=C(\C(O)=O)C1=CC=CC=C1 SJSYJHLLBBSLIH-SDNWHVSQSA-N 0.000 description 1
- LQZPSWMMTICWHD-UHFFFAOYSA-N 1,3-dibenzylthiourea Chemical compound C=1C=CC=CC=1CNC(=S)NCC1=CC=CC=C1 LQZPSWMMTICWHD-UHFFFAOYSA-N 0.000 description 1
- ZVFTWKBRNQSRLB-UHFFFAOYSA-N 1,3-diheptylthiourea Chemical compound CCCCCCCNC(=S)NCCCCCCC ZVFTWKBRNQSRLB-UHFFFAOYSA-N 0.000 description 1
- YXGYUUQULAOVTE-UHFFFAOYSA-N 1,3-dinaphthalen-2-ylthiourea Chemical compound C1=CC=CC2=CC(NC(NC=3C=C4C=CC=CC4=CC=3)=S)=CC=C21 YXGYUUQULAOVTE-UHFFFAOYSA-N 0.000 description 1
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
- BOHCMQZJWOGWTA-UHFFFAOYSA-N 3-methylbenzonitrile Chemical compound CC1=CC=CC(C#N)=C1 BOHCMQZJWOGWTA-UHFFFAOYSA-N 0.000 description 1
- GJNGXPDXRVXSEH-UHFFFAOYSA-N 4-chlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1 GJNGXPDXRVXSEH-UHFFFAOYSA-N 0.000 description 1
- XDJAAZYHCCRJOK-UHFFFAOYSA-N 4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1 XDJAAZYHCCRJOK-UHFFFAOYSA-N 0.000 description 1
- VCZNNAKNUVJVGX-UHFFFAOYSA-N 4-methylbenzonitrile Chemical compound CC1=CC=C(C#N)C=C1 VCZNNAKNUVJVGX-UHFFFAOYSA-N 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N Benzyl cyanide Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N M-Toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N O-Toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N P-Anisic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
- LPNBBFKOUUSUDB-UHFFFAOYSA-N P-Toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N Phenylacetic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- FCSHMCFRCYZTRQ-UHFFFAOYSA-N Thiocarbanilide Chemical compound C=1C=CC=CC=1NC(=S)NC1=CC=CC=C1 FCSHMCFRCYZTRQ-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- YSIMAPNUZAVQER-UHFFFAOYSA-N octanenitrile Chemical compound CCCCCCCC#N YSIMAPNUZAVQER-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMTPATENT OFFICE
Es ist bekannt (W. Weith, B. 6,419), daßIt is known (W. Weith, B. 6,419) that
bei der Behandlung der Thioharnstoffe mit Kupferpulver in der Wärme Nitrile entstehen; die Ausbeute ist jedoch hierbei sehr schlecht.when the thioureas are treated with copper powder in the heat, nitriles are formed; however, the yield here is very poor.
Es wurde nun gefunden, daß die Thioharnstoffe in sehr guter Ausbeute in Nitrile übergeführt werden können, wenn man die Reaktion in Gegenwart geeigneter Verdünnungsmittel, wie z. B. Paraffinöl, Maschinenöl, Anthracen usw., ausführt. Auch wurde gefunden, daß bei dieser Reaktion Kupfer durch andere Metalle, wie. z. B. durch das billigere Eisen, ersetzt werden kann.It has now been found that the thioureas are converted into nitriles in very good yield can be if the reaction in the presence of suitable diluents, such as. B. paraffin oil, machine oil, anthracene etc., executes. It was also found that in this reaction, copper was caused by others Metals like. z. B. can be replaced by the cheaper iron.
Beispiel 1.
o-Tolunitril.Example 1.
o-tolunitrile.
In einem mit Rührwerk und Rücknußkühler versehenen Kessel werden 100 Teile Paraffinöl und 20 Teile Eisen auf etwa 280 ° erhitzt und hierauf 10 Teile o-Ditolylthioharnstoff allmählich eingetragen. Man hält darauf die Reaktionsmasse bis zur völligen Entschweflung des Thioharnstoffes in gelindem Sieden. Dann *5 destilliert man die Reaktionsprodukte (o-Tolunitril und o-Toluidin) ab, extrahiert aus dem Gemenge mit verdünnter Säure das Amin, treibt aus der sauren Lösung die gelösten Anteile des Nitrils mit Wasserdampf ab und vereinigt sie mit der Hauptmenge.100 parts of paraffin oil are placed in a kettle equipped with a stirrer and a re-nut cooler and 20 parts of iron heated to about 280 ° and then 10 parts of o-ditolylthiourea gradually registered. The reaction mixture is then kept at a gentle boil until the thiourea has completely desulfurized. then * 5 the reaction products are distilled (o-tolunitrile and o-toluidine), extracted the amine from the mixture with dilute acid, drives off the dissolved nitrile from the acidic solution with steam and unites them with the bulk.
Das so erhaltene Rohnitril wird durch fraktionierte Destillation gereinigt.
Ausbeute: 64 Prozent der Theorie,The crude nitrile thus obtained is purified by fractional distillation.
Yield: 64 percent of theory,
Durch Verseifung des Nitrils erhält man o-Toluylsäure vom Schmelzpunkt 103 °.Saponification of the nitrile gives o-toluic acid with a melting point of 103 °.
Beispiel 2.
Benzonitril.Example 2.
Benzonitrile.
In einem Rührwerkskessel mit Destillationsaufsatz und Kühler werden 40 Teile Maschinenöl und 20 Teile Eisen auf 280 ° erhitzt und darauf in kleineren Anteilen 10 Teile Diphenylthioharnstoff eingetragen. Die entstandenen Reaktionsprodukte (Nitril und Amin) werden durch Destillation kontinuierlich aus dem Reaktionsgemisch entfernt. Man reinigt das so erhaltene Rohnitril, wie in Beispiel 1 angegeben ist. Ausbeute: 54 Prozent der Theorie.40 parts of machine oil are used in a stirred tank with a distillation attachment and cooler and 20 parts of iron heated to 280 ° and then 10 parts of diphenylthiourea in smaller portions registered. The resulting reaction products (nitrile and amine) are continuously removed from the reaction mixture by distillation removed. The crude nitrile thus obtained is purified as indicated in Example 1. Yield: 54 percent of theory.
Durch Verseifung des Nitrils wird die Benzoesäure vom Schmelzpunkt 1210 erhalten.The benzoic acid is obtained of melting point 121 0 by hydrolysis of the nitrile.
Beispiel 3.
m-Tolunitril.Example 3.
m-tolunitrile.
40 Teile Maschinenöl, 20 Teile Eisen und 10 Teile m-Ditolylthioharnstoff werden wie in Beispiel 2 behandelt.40 parts of machine oil, 20 parts of iron and 10 parts of m-ditolylthiourea are used as in Example 2 treated.
Ausbeute: 62 Prozent der Theorie.
Durch Verseifung des Nitrils wird die m-Toluylsäure vom Schmelzpunkt iio° erhalten.Yield: 62 percent of theory.
By saponifying the nitrile, m-toluic acid is obtained with a melting point of 10 °.
Beispiel 4.
o-Tolunitril.Example 4.
o-tolunitrile.
. 32 Teile Paraffmöl, 8 Teile Kupferpulver und 10 Teile o-Ditolylthioharnstoff werden wie in Beispiel 2 behandelt. Ausbeute: 68 Prozent der Theorie.. 32 parts paraffin oil, 8 parts copper powder and 10 parts of o-ditolylthiourea are treated as in Example 2. Yield: 68 percent of theory.
Beispiel 5.
p-Tolünitril.Example 5.
p-tolunitrile.
ίο Teile Paraffinöl und 12 Teile Eisen werden in einem Rührkessel mit Destillationsaufsatz und Kühler auf etwa 280° erhitzt und darauf 10 Teile p-Ditoly!thioharnstoff, suspendiert in 20 Teile Paraffinöl, allmählich eingetragen. Die weitere Behandlung erfolgt, wie in Beispiel 2 angegeben ist.ίο parts paraffin oil and 12 parts iron will be heated in a stirred tank with a distillation attachment and condenser to about 280 ° and thereupon 10 parts of p-ditoly / thiourea, suspended in 20 parts of paraffin oil, gradually added. Further treatment is carried out as is given in Example 2.
Ausbeute: 75 Prozent der Theorie.Yield: 75 percent of theory.
Durch Verseifung des Nitrils wird die p-Toluylsäure vom Schmelzpunkt 178° erhalten.By saponifying the nitrile, p-toluic acid is obtained with a melting point of 178 °.
Beispiel 6.
ß-Naphtonitril.Example 6.
ß-naphtonitrile.
10 Teile Paraffinöl und 15 Teile Eisen werden auf 280 ° erhitzt und darauf 10 Teile ß-Dinaphtylthioharnstoff, in 35 Teile Paraffinöl aufgeschlämmt, allmählich eingetragen. Die Aufarbeitung erfolgt, wie in Beispiel 2 angegeben ' ist.10 parts of paraffin oil and 15 parts of iron will be heated to 280 ° and then 10 parts of ß-dinaphthylthiourea, slurried in 35 parts of paraffin oil, gradually entered. Working up is carried out as indicated in Example 2.
Ausbeute: 75 Prozent der Theorie.'
Durch Verseifung des Nitrils wird die ß-Naphtoesäure vom Schmelzpunkt 182° erhalten.Yield: 75 percent of theory. '
By saponifying the nitrile, β-naphthoic acid is obtained with a melting point of 182 °.
. ■ ■; . Beispiel 7.. ■ ■; . Example 7.
m-Xylonitril.m-xylonitrile.
55 Teile Anthracen, 25 Teile Eisen und 10 Teile m-Dixylylthioharnstoff werden wie in Beispiel 2 behandelt.55 parts of anthracene, 25 parts of iron and 10 parts of m-dixylylthiourea are used as in Example 2 treated.
Ausbeute: 65,5 Prozent der Theorie.
Durch Verseifung des Nitrils wird die Xylylsäure
vom Schmelzpunkt 126 ° erhalten.Yield: 65.5 percent of theory.
By saponifying the nitrile, xylyl acid is obtained with a melting point of 126 °.
p-Methoxybenzonitril.
500 Teile Paraffinöl, 250 Teile Eisen und Teile p-Dimethoxyphenylthioharnstoff werden
wie in Beispiel 2 behandelt.p-methoxybenzonitrile.
500 parts of paraffin oil, 250 parts of iron and parts of p-dimethoxyphenylthiourea are treated as in Example 2.
Ausbeute: 67 Prozent der Theorie.
Durch Verseifung des Nitrils wird p-Methoxybenzoesäure vom Schmelzpunkt 184 ° erhalten.Yield: 67 percent of theory.
By saponifying the nitrile, p-methoxybenzoic acid with a melting point of 184 ° is obtained.
p-Chlorbenzonitril.
500 Teile Paraffinöl, 200 Teile Eisen, 100 Teile p-Dichlorphenylthioharnstoff werden wie in
Beispiel 2 behandelt.p-chlorobenzonitrile.
500 parts of paraffin oil, 200 parts of iron, 100 parts of p-dichlorophenylthiourea are treated as in Example 2.
Ausbeute: 51 Prozent der Theorie.Yield: 51 percent of theory.
Durch Verseifung des Nitrils wird p-Chlor-By saponification of the nitrile, p-chlorine
benzoesäure vom Schmelzpunkt 236° erhalten. Benzoic acid obtained with a melting point of 236 °.
Beispiel 10. p-Cyanchinolin.Example 10. p -cyanquinoline.
In einem mit Rührwerk und Kühler versehenen Kessel' werden 200 Teile Paraffinöl, 60 Teile Kupferbronze und 20 Teile p-Dichinolylthioharnstoff zur Trockne destilliert. Das Destillat wird mit verdünnter Salzsäure ausgeschüttelt. Durch Fällen mit Alkali erhält man ein Gemisch von p-Cyanchinolin und p-Aminochinolin, die man durch fraktionierte Kristallisation trennen kann.200 parts of paraffin oil, 60 parts of copper bronze and 20 parts of p-dichinolylthiourea are distilled to dryness. The distillate is extracted with dilute hydrochloric acid. Preserved by felling with alkali a mixture of p-cyanoquinoline and p-aminoquinoline, which one fractionated by Can separate crystallization.
Ausbeute: 21 Prozent der Theorie.Yield: 21 percent of theory.
Durch Verseifen wird p-Chinolincarbonsäure vom Schmelzpunkt 290 ° erhalten.Saponification gives p-quinolinecarboxylic acid with a melting point of 290 °.
Beispiel 11. Caprylsäurenitril. 500 Teile Paraffinöl, 40 Teile Kupferpulver und 24 Teile Diheptylthioharnstoff werden wie in Beispiel 2 behandelt.Example 11. Caprylonitrile. 500 parts paraffin oil, 40 parts copper powder and 24 parts of diheptylthiourea are treated as in Example 2.
Ausbevite: 6 τ Prozent der Theorie.Yield: 6 τ percent of theory.
Durch Verseifung wird Caprylsäure vom Siedepunkt 234 ° erhalten.Saponification gives caprylic acid with a boiling point of 234 °.
Beispiel 12. Phenylacetonitril. ■Example 12. Phenylacetonitrile. ■
400 Teile Paraffinöl, 200 Teile Eisen und 100 Teile Dibenzylthioharnstoff werden wie in Beispiel 2 behandelt. .400 parts of paraffin oil, 200 parts of iron and 100 parts of dibenzylthiourea are used as in Example 2 treated. .
Ausbeute: 20 Prozent der Theorie.Yield: 20 percent of theory.
Durch Verseifung wurde Phenylessigsäure vom Schmelzpunkt 76 ° erhalten.Phenylacetic acid with a melting point of 76 ° was obtained by saponification.
Die in oben angeführten Beispielen erwähnten Temperaturen sowie die Mengen der Verdünnungsmittel und Metalle können in weiten Grenzen abgeändert werden.The temperatures mentioned in the above examples and the amounts of the diluents and metals can be varied within wide limits.
Das Verfahren ist nicht auf die angeführten Beispiele beschränkt, sondern läßt sich auf andere, sowohl aliphatische wie aromatische bzw. heterocyklische Thioharnstoffe und deren Substitutionsprodukte anwenden.The method is not limited to the examples given, but can be based on other, both aliphatic and aromatic or heterocyclic thioureas and their Use substitution products.
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Publications (1)
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| DE259363C true DE259363C (en) |
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