DE1128855B - Process for the production of phenol ethers or esters suitable as vulcanization or crosslinking agents for organic polymers - Google Patents
Process for the production of phenol ethers or esters suitable as vulcanization or crosslinking agents for organic polymersInfo
- Publication number
- DE1128855B DE1128855B DEH35981A DEH0035981A DE1128855B DE 1128855 B DE1128855 B DE 1128855B DE H35981 A DEH35981 A DE H35981A DE H0035981 A DEH0035981 A DE H0035981A DE 1128855 B DE1128855 B DE 1128855B
- Authority
- DE
- Germany
- Prior art keywords
- group
- vulcanization
- general formula
- carboxylic acid
- production
- 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 9
- 238000000034 method Methods 0.000 title claims description 5
- 229920000620 organic polymer Polymers 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 238000004073 vulcanization Methods 0.000 title claims 2
- 150000008379 phenol ethers Chemical class 0.000 title description 5
- 239000003431 cross linking reagent Substances 0.000 title description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- -1 phenolic ethers Chemical class 0.000 claims description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000003172 aldehyde group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000007860 aryl ester derivatives Chemical group 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims description 2
- 229940031826 phenolate Drugs 0.000 claims description 2
- 229940067157 phenylhydrazine Drugs 0.000 claims description 2
- 150000001348 alkyl chlorides Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- ZPDCCOTYWBACPZ-UHFFFAOYSA-N [K].OC1=CC=C(C=O)C=C1 Chemical compound [K].OC1=CC=C(C=O)C=C1 ZPDCCOTYWBACPZ-UHFFFAOYSA-N 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- NBKFKDJHUNQQKY-UHFFFAOYSA-N (4-formylphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(C=O)C=C1 NBKFKDJHUNQQKY-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- JJTTWBQZKLOHOA-UHFFFAOYSA-N N-(6-benzylidenecyclohexa-2,4-dien-1-yl)hydroxylamine Chemical compound C(C1=CC=CC=C1)=C1C(NO)C=CC=C1 JJTTWBQZKLOHOA-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/28—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von als Vulkanisations- oder Vernetzungsmittel für organische Polymere geeigneten Phenoläthern oder -estern Es wurde gefunden, daß eine Reihe von neuen ungesättigten Phenoläthern oder -estern mit reaktionsfähigen Gruppen der allgemeinen Formel CH2 = C(R)-R1-O-C6H4-X in welcher R ein Wasserstoffatom oder eine Alkylgruppe, R1 eine Methylen- oder eine Carbonylgruppe und X eine Aldehydgruppe, eine durch den Anilin-, Hydroxylamin- oder Phenylhydrazinrest substituierte Aldehydgruppe, eine Hydroxylgruppe, eine Carbonsäuregruppe, eine Carbonsäurealkyl- oder -arylestergruppe, eine Aminogruppe oder eine durch den Benzaldehydrest substituierte Aminogruppe bedeutet, durch Umsetzung eines o;-ungesättigten Alkylchlorids oder eines oc-ungesättigten Carbonsäurechlorids der allgemeinen Formel CH2 = C(R)-R1-Cl in welcher R und R1 die obige Bedeutung haben, mit einem Phenol in Gegenwart eines säurebindenden Mittels, gegebenenfalls einem Phenolat, der allgemeinen Formel HO-C6H4-X worin X die obige Bedeutung hat, hergestellt werden können. Die azomethingruppenhaltigen Phenoläther oder -ester lassen sich auch durch nachträgliche Umsetzung der aldehyd- oder aminogruppenhaltigen ungesättigten Phenoläther oder -ester mit den entsprechenden Verbindungen, wie z. B. Anilin oder Benzaldehyd, herstellen. Process for the preparation of as a vulcanizing or crosslinking agent Phenolic ethers or esters suitable for organic polymers It has been found that a number of new unsaturated phenolic ethers or esters with reactive Groups of the general formula CH2 = C (R) -R1-O-C6H4-X in which R is a hydrogen atom or an alkyl group, R1 a methylene or a carbonyl group and X an aldehyde group, an aldehyde group substituted by the aniline, hydroxylamine or phenylhydrazine radical, a hydroxyl group, a carboxylic acid group, a carboxylic acid alkyl or aryl ester group, denotes an amino group or an amino group substituted by the benzaldehyde radical, by reacting an o; -unsaturated alkyl chloride or an oc-unsaturated one Carboxylic acid chloride of the general formula CH2 = C (R) -R1-Cl in which R and R1 have the above meaning, with a phenol in the presence of an acid-binding agent, optionally a phenolate, of the general formula HO-C6H4-X in which X has the above Has meaning, can be produced. The phenol ethers containing azomethine groups or esters can also be obtained by subsequent reaction of the aldehyde or amino groups unsaturated phenol ethers or esters with the appropriate compounds, such as. B. aniline or benzaldehyde.
Die verfahrensmäßig hergestellten Phenoläther- oder -ester sind als Vernetzungsmittel verwendbar, denn sie ermöglichen auf Grund ihrer reaktionsfähigen Gruppen die Aufpfropfung der ungesättigten Phenoläther- oder -esterreste auf Polymere, welche geeignete funktionelle Gruppen tragen. Über diese ungesättigten Gruppen erfolgt dann beim Erhitzen eine Vernetzung der ursprünglichen Makromoleküle. Diese monomeren Phenoläther oder -ester können außerdem auch homo-und copolymerisiert werden, wobei die reaktionsfähigen Gruppen der so erhaltenen Polymerisate Pfropf- und Vernetzungsreaktionen ermöglichen. The phenolic ethers or esters produced by the process are as Crosslinking agents can be used because they allow due to their reactive Groups the grafting of unsaturated phenol ether or ester residues onto polymers, which carry suitable functional groups. Takes place through these unsaturated groups then, when heated, a crosslinking of the original macromolecules. These monomers Phenol ethers or esters can also be homo- and copolymerized, with the reactive groups of the polymers thus obtained, grafting and crosslinking reactions enable.
Beispiel 1 a) 24 g 4-Hydroxybenzaldehydkalium wurden in 200 ccm trockenem Äther aufgeschlämmt. Unter heftigem Rühren wurden bei Zimmertemperatur 14,1 g Methacrylsäurechlorid eingetropft. Die Reaktion verlief, obwohl sie heterogen ist, sehr rasch und unter schwacher Erwärmung. Nach der Säurechloridzugabe wurde noch 1/2 Stunde nachgerührt, von dem ausgeschiedenen Kaliumchlorid abfiltriert und die ätherische Lösung über Natriumsulfat getrocknet. Beim Abdestillieren des Äthers fiel das Rohprodukt als schwach gelbes Ö1 an. Als günstigstes Reinigungsverfahren erwies sich sie chromatographische Reinigung an Aluminiumoxyd. Die Ausbeute betrug 23 g, das sind etwa 900/o der Theorie. F. = 27 bis 28° C, Kpzoßol = 84 bis 85" C. Example 1 a) 24 g of 4-hydroxybenzaldehyde potassium were in 200 ccm of dry Ether slurried. With vigorous stirring, 14.1 g of methacrylic acid chloride were obtained at room temperature dripped in. The reaction, although heterogeneous, was very rapid and subtle weak heating. After the acid chloride had been added, the mixture was stirred for a further 1/2 hour, filtered off from the precipitated potassium chloride and the ethereal solution over Dried sodium sulfate. When distilling off the ether, the crude product fell as pale yellow Ö1. Chromatographic proved to be the most favorable purification method Cleaning with aluminum oxide. The yield was 23 g, which is about 900 / o of theory. F. = 27 to 28 ° C, Kpzoßol = 84 to 85 "C.
Analyse für CllHl003: Berechnet .. . C 69,45, H 5,31; gefunden .. ........ C 69,50, H 5,31, 69,70, 5,30. b) 85 ccm der ätherischen Lösung des 4-Methacryloxybenzaldehyd, wie sie oben erhalten wurde und die etwa 9,5 g Aldehyd enthielt, wurden mit 4,65 g Anilin versetzt und 1/2 Stunde am Rückfluß gekocht. Beim Einengen kristallisierte die Schiffsche Base aus. Sie wurde abgesaugt und aus Methanol umkristallisiert.Analysis for CllHl003: Calculated ... C 69.45, H 5.31; found .. ........ C 69.50, H 5.31, 69.70, 5.30. b) 85 cc of the ethereal solution of 4-methacryloxybenzaldehyde, as obtained above and which contained about 9.5 g of aldehyde, were 4.65 g of aniline are added and the mixture is refluxed for 1/2 hour. Crystallized on concentration the Schiff's base. It was filtered off with suction and recrystallized from methanol.
Es wurden farblose Kristallplättchen vom F. = 83 bis 84° C in einer Ausbeute von 12,5 g, das sind etwa 93 der Theorie, erhalten, die löslich in Benzol, Styrol, Methanol und Äther waren. Diese Verbindung polymerisiert und copolymerisiert radikalisch.There were colorless crystal flakes with a melting point of 83 to 84 ° C in one Yield of 12.5 g, that is about 93 of theory, obtained, which is soluble in benzene, Styrene, methanol and ether were. This compound polymerizes and copolymerizes radical.
Analyse für Cl7HlsNO2 Berechnet . . C 76,96, H 5,70, N 5,28; gefunden . C 76,77, H 5,79, N 5,51.Analysis calculated for Cl7HlsNO2. . C 76.96, H 5.70, N 5.28; found . C 76.77, H 5.79, N 5.51.
Beispiel 2 70,6 g 4-Hydroxybenzaldehydkalium wurden analog der Vorschrift im Beispiel 1 mit Acrylsäurechlorid umgesetzt. Das Rohprodukt ist ein schwach gelbes, nicht kristallisierendes Öl. Die Ausbeute betrug 18,5 g, das sind etwa 830/o der Theorie. Die Reinigung erfolgte ebenfalls durch chromatographische Adsorption der Verunreinigung an Aluminiumoxyd. Example 2 70.6 g of 4-hydroxybenzaldehyde potassium were obtained analogously to the instructions in example 1 with acrylic acid chloride implemented. The raw product is a pale yellow, non-crystallizing oil. The yield was 18.5 g that are about 830 / o of theory. The purification was also carried out by chromatography Adsorption of the impurity on aluminum oxide.
Hierbei fällt der Aldehyd in kristalliner Form an und kann bei 0°C ohne Stabilisator aufbewahrt werden.The aldehyde is obtained in crystalline form and can be used at 0 ° C stored without stabilizer.
F. = 29 bis 30°C, Kp. 126 bis 127°C.M.p. = 29 to 30 ° C, b.p. 126 to 127 ° C.
Analyse für CloH803 Berechnet , C 68,17,C68,17, H4,58; gefunden ................. C 68,55, H 5,02, 68,54, 5,05. Analysis for CloH803 Calculated, C 68.17, C68.17, H4.58; found ................. C 68.55, H 5.02, 68.54, 5.05.
Beispiel 3 21,7 g Benzyliden-Phydroxyanilin wurden mit 5,7 g KO H in 150 ccm Methanol umgesetzt, und danach wurden bei Siedetemperatur 14,5 g Allylbromid in das Gemisch eingetropft. Die sofort einsetzende KBr-Ausscheidung war nach etwa 3 Stunden beendet. Example 3 21.7 g of benzylidene-hydroxyaniline were mixed with 5.7 g of KO H reacted in 150 cc of methanol, and then 14.5 g of allyl bromide were added at the boiling point dripped into the mixture. The KBr excretion, which started immediately, was about Finished 3 hours.
Die filtrierte Lösung wurde eingeengt und die ausfallende Verbindung abgesaugt und aus Äthanol umkristallisiert. Es wurden farblose Kristalle vom F. = 72 bis 73°C in einer Ausbeute von 15,2 g, das sind etwa 64°/o der Theorie, erhalten, die löslich in Methanol und Benzol sind.The filtered solution was concentrated and the compound which precipitated was concentrated suctioned off and recrystallized from ethanol. Colorless crystals of F. = 72 to 73 ° C in a yield of 15.2 g, that is about 64% of theory, which are soluble in methanol and benzene.
Analyse für Cl6Hl5NO: Berechnet ............ C 80,98, H 6,37, N 5,90; gefunden ............ C 81,15, H 6,13, N 5,97, 81,17, 6,19.Analysis for Cl6Hl5NO: Calculated ............ C 80.98, H 6.37, N 5.90; Found ............ C 81.15, H 6.13, N 5.97, 81.17, 6.19.
Beispiel 4 12 g 4-Aminophenol wurden mit 5,7 g KO H in 100 ccm Methanol umgesetzt. In das Gemisch wurden bei Siedetemperatur 14,5 g Allylbromid eingetropft. Example 4 12 g of 4-aminophenol were mixed with 5.7 g of KO H in 100 cc of methanol implemented. 14.5 g of allyl bromide were added dropwise to the mixture at the boiling point.
Die KBr-Ausscheidung setzt sofort ein. Nach 3 Stunden wird die Lösung filtriert und das Methanol abdestilliert. Das Rohprodukt wird durch Destillation gereinigt. Die Ausbeute betrug etwa 51 0/o der Theorie, Kp. 103 bis 105° C. Das Produkt ist löslich in Methanol, Chloroform und Styrol.KBr excretion starts immediately. After 3 hours the solution will filtered and the methanol was distilled off. The crude product is made by distillation cleaned. The yield was about 51% of theory, Bp 103 to 105 ° C. The product is soluble in methanol, chloroform and styrene.
Analyse für CSHllON: Berechnet ...................... N 9,46, - ; gefunden ....................... N 9,62, 9,27.Analysis for CSHIION: Calculated ...................... N 9.46, -; found ....................... N 9.62, 9.27.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH35981A DE1128855B (en) | 1957-12-23 | 1957-12-23 | Process for the production of phenol ethers or esters suitable as vulcanization or crosslinking agents for organic polymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH35981A DE1128855B (en) | 1957-12-23 | 1957-12-23 | Process for the production of phenol ethers or esters suitable as vulcanization or crosslinking agents for organic polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1128855B true DE1128855B (en) | 1962-05-03 |
Family
ID=7152877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH35981A Pending DE1128855B (en) | 1957-12-23 | 1957-12-23 | Process for the production of phenol ethers or esters suitable as vulcanization or crosslinking agents for organic polymers |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1128855B (en) |
-
1957
- 1957-12-23 DE DEH35981A patent/DE1128855B/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
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