DE406153C - Process for the preparation of condensation products from phenols and aldehydes - Google Patents
Process for the preparation of condensation products from phenols and aldehydesInfo
- Publication number
- DE406153C DE406153C DEF51979D DEF0051979D DE406153C DE 406153 C DE406153 C DE 406153C DE F51979 D DEF51979 D DE F51979D DE F0051979 D DEF0051979 D DE F0051979D DE 406153 C DE406153 C DE 406153C
- Authority
- DE
- Germany
- Prior art keywords
- phenols
- parts
- preparation
- aldehydes
- condensation products
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000007859 condensation product Substances 0.000 title claims description 6
- 150000002989 phenols Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001299 aldehydes Chemical class 0.000 title claims description 3
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 4
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- 238000007792 addition Methods 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000000025 natural resin Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 2
- WHRZCXAVMTUTDD-UHFFFAOYSA-N 1h-furo[2,3-d]pyrimidin-2-one Chemical compound N1C(=O)N=C2OC=CC2=C1 WHRZCXAVMTUTDD-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 240000000731 Fagus sylvatica Species 0.000 description 1
- 235000010099 Fagus sylvatica Nutrition 0.000 description 1
- 235000006173 Larrea tridentata Nutrition 0.000 description 1
- 244000073231 Larrea tridentata Species 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960002126 creosote Drugs 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Classifications
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Kondensationsprodukten aus Phenolen und Aldehyden. Durch Patent 36¢0q.1 sowie dessen Zusätze 364043, 388795 und 38879,1 sind Verfahren zur Darstellung von harzartigen, Kondensationsprodukten aus Phenolen aller Art und Aldol bzw. Crotonaldehyd geschützt.Process for the preparation of condensation products from phenols and aldehydes. By patent 36 [0q.1] and its additions 364043, 388795 and 38879.1 are processes for the preparation of resinous, condensation products from phenols of all types and aldol or crotonaldehyde protected.
In weiterer Ausarbeitung dieser Verfahren wurde jefunden, daß man die Kondensation von Phenolen mit Aldol bzw. Crotonaldehyd besonders vorteilhaft in. Gegenwart von Wasser ausführt, das man bei der Reaktion zweckmäßig erwärmt und als Reaktionsbescbleuniger Mineralsäure hinzugibt. Die auf diese Weise erhältlichen Produkte besitzen den besonderen Vorteil, bei der Erhitzung auf höhere Temperatur, z. B. zoo bis z50`, wie es manche Verwendungszwecke der Lacktechnik erfordern, außerordentlich beständig zu sein, d. h. keinerlei Zersetzung zu erleiden, während die in anderer Weise gewonnenen Produkte `beim Erhitzen auf höhere Temperatur unter Entwicklung übelriechender Dämpfe eine teilweise Zersetzung erfahren können, wodurch deren Verwendung in manchen Zweigen der Technik unmöglich gemacht oder mindestens stark beeinträchtigt wird. Die nach dem vorliegenden Verfahren entstehenden harzartigen Kondensationsprodukte sind in organischen Lösungsmitteln, wie Alkohol und Benzol, leichtlöslich, mit fetten Ölen gut verkochbar und lassen sich längere Zeit auf Temperaturen von aoo" erhitzen und mit Füllstoffen aller Art mischen, ohne Zersetzungserscheinungen zu zeigen. Infolgedessen können diese Produkte besonders für Öllack und für die Herstellung von Preßmaterial für die verschiedensten Zwecke Verwendung finden. Beispiele. i. 216 Teile Kresol, zoo Teile Wasser und 116 Teile konzentrierte Salzsäure werden unter gutem Rühren allmählich mit einer Mischung von 97 Teilen Aldol und ioo Teilen Wasser versetzt. Nach kurzem Rühren erhitzt man zum Sieden, bis die Reaktion beendet ist, d. h. bis eine herausgenommene Probe des öligen Kondensationsproduktes beim Abkühlen springhart erstarrt. Darauf wird mit Wasser gewaschen, etwa unverändertes Kresol mit Dampf abgetrieben und das Reaktionsprodukt durch Erhitzen auf 15o bis 20o'" vom Wasser befreit. Die Menge des angewandten Reaktionsbeschleunigers kann in weiten Grenzen schwanken.In further elaboration of this procedure it was found that one the condensation of phenols with aldol or crotonaldehyde is particularly advantageous Executes in the presence of water, which is expediently heated during the reaction and is added as a mineral acid that bleaches the reaction. The ones obtainable in this way Products have the particular advantage that when heated to a higher temperature, z. B. zoo to z50`, as some uses of paint technology require, extraordinary to be consistent, d. H. not to suffer any decomposition while that in others Wise obtained products `when heated to higher temperature with development foul-smelling vapors can undergo partial decomposition, thereby reducing their use in some branches of technology made impossible or at least severely impaired will. The resinous condensation products formed by the present process are easily soluble in organic solvents such as alcohol and benzene, with fats Oils can be boiled well and can be heated to temperatures of aoo "for a long time and mix with fillers of all kinds without showing signs of decomposition. As a result, these products can especially be used for oil varnish and for manufacturing of pressing material for a wide variety of purposes are used. Examples. i. 216 parts of cresol, zoo parts of water and 116 parts of concentrated hydrochloric acid are used with good stirring gradually with a mixture of 97 parts of aldol and 100 parts Water added. After brief stirring, the mixture is heated to the boil until the reaction has ended is, d. H. until a taken sample of the oily condensation product at Cooling solidified as hard as a spring. It is then washed with water, something unchanged Cresol is driven off with steam and the reaction product by heating to 15o until 20o '"freed from water. The amount of reaction accelerator used can fluctuate within wide limits.
2. 65o Teile Kreosot aus Buchenholzteer, 60o Teile Wasser, Zoo Teile konzentrierte Salzsäure werden unter Rühren auf etwa 5o bis 6o' erwärmt und mit einer Mischung von Zoo Teilen Crotonaldehyd und ioo Teilen Wasser versetzt. Die weitere Behandlung erfolgt nach Beispiel i.2. 65o parts creosote from beech tar, 60o parts water, zoo parts concentrated hydrochloric acid are heated to about 5o to 6o 'with stirring and with a mixture of zoo parts crotonaldehyde and 100 parts water. the further treatment takes place according to example i.
3. Zoo Teile Kolophonium werden in 216 Teilen Kresol gelöst und mit etwa 30o Teilen Wasser und i20 Teilen konzentrierter Salzsäure unter Rühren zum Sieden erhitzt. Darauf läßt man eine Lösung von i05 Teilen Aldol in i oo Teilen Wasser langsam zutropfen und beendigt die Umsetzung nach dem in Beispiel i angegebenen Verfahren.3. Zoo parts of rosin are dissolved in 216 parts of cresol and mixed with about 30o parts of water and i20 parts of concentrated hydrochloric acid with stirring Boiling heated. A solution of 10 5 parts of aldol in 10 parts is then left Slowly add dropwise water and terminate the reaction according to that given in Example i Procedure.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF51979D DE406153C (en) | 1922-06-10 | 1922-06-10 | Process for the preparation of condensation products from phenols and aldehydes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF51979D DE406153C (en) | 1922-06-10 | 1922-06-10 | Process for the preparation of condensation products from phenols and aldehydes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE406153C true DE406153C (en) | 1924-11-14 |
Family
ID=7105074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF51979D Expired DE406153C (en) | 1922-06-10 | 1922-06-10 | Process for the preparation of condensation products from phenols and aldehydes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE406153C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2885385A (en) * | 1953-07-16 | 1959-05-05 | Union Carbide Corp | Polyphenylol derivatives of olefinic aldehydes |
-
1922
- 1922-06-10 DE DEF51979D patent/DE406153C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2885385A (en) * | 1953-07-16 | 1959-05-05 | Union Carbide Corp | Polyphenylol derivatives of olefinic aldehydes |
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