DE466361C - Process for the preparation of water-soluble condensation products - Google Patents
Process for the preparation of water-soluble condensation productsInfo
- Publication number
- DE466361C DE466361C DEF56545D DEF0056545D DE466361C DE 466361 C DE466361 C DE 466361C DE F56545 D DEF56545 D DE F56545D DE F0056545 D DEF0056545 D DE F0056545D DE 466361 C DE466361 C DE 466361C
- Authority
- DE
- Germany
- Prior art keywords
- water
- condensation products
- preparation
- oleum
- soluble condensation
- 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
- 239000007859 condensation product Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 7
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- -1 arylalkyl halides Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 14
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229940073608 benzyl chloride Drugs 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- KTHUKEZOIFYPEH-UHFFFAOYSA-N 1-benzylnaphthalene Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=CC=CC=C1 KTHUKEZOIFYPEH-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- GJKIRZMMCLLZOJ-UHFFFAOYSA-N 1,1-dichloro-2h-naphthalene Chemical compound C1=CC=C2C(Cl)(Cl)CC=CC2=C1 GJKIRZMMCLLZOJ-UHFFFAOYSA-N 0.000 description 1
- NVLHGZIXTRYOKT-UHFFFAOYSA-N 1-chloro-2,3-dimethylbenzene Chemical compound CC1=CC=CC(Cl)=C1C NVLHGZIXTRYOKT-UHFFFAOYSA-N 0.000 description 1
- QXISTPDUYKNPLU-UHFFFAOYSA-N 2-bromo-1,4-dimethylbenzene Chemical compound CC1=CC=C(C)C(Br)=C1 QXISTPDUYKNPLU-UHFFFAOYSA-N 0.000 description 1
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- BVJSGOYEEDZAGW-UHFFFAOYSA-N [chloro(nitro)methyl]benzene Chemical compound [O-][N+](=O)C(Cl)C1=CC=CC=C1 BVJSGOYEEDZAGW-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung wasserlöslicher Kondensationsprodukte Das aus Naphthalin und Benzvlchlorid -beispielsweise nach den Verfahren der Patente 4169o4 oder 417442 - erhältliche harzige 01 läßt sich auf übliche Weise nicht sulfieren. Bei der Behandlung des Oles mit konzentrierter Schwefelsäure oder Monohydrat in der Wärme tritt nämlich so rasch eine weitere Kondensation des Harzöles zu harten Harzen ein, daß das Reaktionsgut selbst bei hoher Temperatur zähflüssig und unrührbar wird und völlige Wasserlöslichkeit auf keine Weise zu erreichen ist. Die sulfierten Produkte wurden deshalb bisher so dargestellt (s. Patent d36881), daß man von sulfiertem Naphthalin ausging und die N aplitlialinsulfosäure mit Benzylchlorid behandelte.The products of naphthalene and Benzvlchlorid -beispielsweise accordance with the procedures of the patents or 4169o4 417 442 processes for preparing water-soluble condensation products - available resinous 01 can not be sulphonating a conventional manner. When the oil is treated with concentrated sulfuric acid or monohydrate at high temperature, further condensation of the resin oil to hard resins occurs so quickly that the reaction mixture becomes viscous and immovable even at high temperatures and complete solubility in water cannot be achieved in any way. The sulfated products have therefore hitherto been presented in such a way (see Patent 36881) that sulfated naphthalene was used as the starting point and the naphthalene sulfonic acid was treated with benzyl chloride.
Überraschenderweise wurde nun gefunden, daß bei Anwendung stärkerer Sulfierungsmittel, z. B. von Oleum oder Gemischen von Oleum und Chlorsulfonsäure, die weitere Verharzung des Harzöles aus Naphthalin und Benzylchlorid stark zurücktritt und eine Sulfierung der glatt rührbar bleibenden Masse stattfindet, welche rasch und leicht zu einem völlig wasserlöslichen Produkt führt. Dieses Verhalten war nicht vorauszusehen, da bekanntlichOleum undChlorsulfonsäure wesentlich stärkere Kondensationswirkung besitzen als konzentrierte Schwefelsäure, mithin bei ihrer Verwendung in noch stärkerem Maße ein vorzeitiges Verharzen und Erhärten des Oles zu erwarten war.Surprisingly, it has now been found that stronger when used Sulfonating agents, e.g. B. of oleum or mixtures of oleum and chlorosulfonic acid, the further resinification of the resin oil from naphthalene and benzyl chloride is greatly reduced and a sulphonation of the smoothly stirrable mass takes place, which rapidly and easily leads to a completely water-soluble product. This behavior was not to be expected, as it is known that oleum and chlorosulfonic acid have a much stronger condensation effect have as concentrated sulfuric acid, therefore when used in even stronger Premature gumming and hardening of the oil was to be expected.
Weiter wurde gefunden, daß man dasselbe Endprodukt erhält, `nenn man an Stelle des fertigen Benzylnaphthalinharzes direkt Naphthalin und Benzylchlörid mit starken Sulfierungsmitteln behandelt.It was also found that one obtains the same end product, called one instead of the finished benzylnaphthalene resin, naphthalene and benzylchloride are used directly treated with strong sulphonating agents.
Die so erhältliche Benzylnaphthalinharzsulfosäure sowie ihre Salze stellen Produkte dar, die für die verschiedenartigsten chemischtechnischen, färbereitechnischen und pharmazeutischen Verwendungen ausgezeichnete Dienste tun.The benzylnaphthalene resin sulfonic acid obtainable in this way and its salts represent products that are used for the most diverse chemical-technical, dyeing-technical and pharmaceutical uses do excellent services.
An Stelle von Benzylchlorid lassen sich beliebige andere Arylalkylhalogenide verwenden, wie z. B. Benzylbromid, Xylylchlorid, Xylylbromid, Nitrobenzylchlorid, Chlorbenzylchlorid sowie auch solche Arylalkylhalogenide, die Alkylgruppen von ringförmiger Struktur enthalten, wie z. B. das im hydrierten Kerne chlorierte Dichloridhydronaphthalin der Brutto-Formel C1oH1oC1., hergestellt durch Chlorierung von Tetrahydronaphthalin im hydrierten Kern. Entsprechend verwendbar sind die Kondensationsprodukte dieser Halogenide mit Naphthalin. An die Stelle des Naphthalins können ähnliche mehrkernige Kohlenwasserstoffe, z. B. Methylnaphthalin, Tetrahydronaphthalin, Anthracen u. dgl., treten.Any other arylalkyl halides can be used in place of benzyl chloride use, such as B. benzyl bromide, xylyl chloride, xylyl bromide, nitrobenzyl chloride, Chlorobenzyl chloride as well as those arylalkyl halides, the alkyl groups of ring-shaped Structure included, such as B. in the hydrogenated nuclei chlorinated dichloride hydronaphthalene the gross formula C1oH1oC1., produced by chlorination of tetrahydronaphthalene in the hydrogenated core. The condensation products of these can be used accordingly Halides with naphthalene. Instead of naphthalene can similar polynuclear hydrocarbons, e.g. B. methylnaphthalene, tetrahydronaphthalene, Anthracene and the like.
Beispiele 1. Zu Zoo Teilen Öl, hergestellt aus Naphthalin und Benzylchlorid gemäß Patent 416 904, läuft bei 8o bis 9o° in kurzerZeit die Mischung von 25 Teilen 2oprozentigem Oleum und 7o Teilen Chlorsulfonsäure. Nach kurzem Nachrühren ist die Masse völlig wasserlöslich. Nach Zugabe von 143 Teilen Natronlauge von 40° B6 wird der erhaltene Syrup zur Trockne gebracht und pulverisiert. Das gelblichweiße Pulver ist glatt wasserlöslich und färbt Wolle und Baumwolle praktisch nicht an. Die angesäuerte Lösung fällt Gelatine.Examples 1. To Zoo Parts Oil made from naphthalene and benzyl chloride according to patent 416 904, at 8o to 9o ° the mixture of 25 parts runs in a short time 2 percent oleum and 70 parts chlorosulfonic acid. After briefly stirring the Completely soluble in water. After adding 143 parts of sodium hydroxide solution at 40 ° B6 the obtained syrup brought to dryness and pulverized. The yellowish white powder is completely soluble in water and practically does not stain wool and cotton. The acidified Solution falls gelatin.
2. In der Seitenkette monochloriertes Toluol (i Mol.) läßt man bei roo° auf 1 Mol. a-Methylnaphthalin in Gegenwart von Salzsäuregas fließen, wobei unter Chlorwasserstoffabspaltung ein Öl erhalten wird. Dieses Öl wird unter Verwendung von 2 Mol. Chlorsulfonsäure bei 8o bis 9o° sulfiert, worauf man mit Natronlauge neutralisiert und trocknet. Es resultiert ein schwach bräunliches Pulver, welches sich in Wasser klar löst.2. Toluene monochlorinated in the side chain (1 mole) is allowed to flow at roo ° to 1 mole of a-methylnaphthalene in the presence of hydrochloric acid gas, an oil being obtained with elimination of hydrogen chloride. This oil is sulfated using 2 moles of chlorosulfonic acid at 8o to 9o °, whereupon it is neutralized with sodium hydroxide solution and dried. The result is a slightly brownish powder which dissolves clearly in water.
3. 1 Mol. Dichlordihydronaphthalin und 2 Mol. Tetrahydronaphthalin werden in Gegenwart von Stangenchlorzink zu einem Öl kondensiert, worauf man vom Chlorzink abgießt und mit 1 Mol. Oleum 2oprozentig und 1@2 Mol. Chlorsulfonsäure die Sulfierung bewerkstelligt. Nach der Überführung - in Natronsalz wird getrocknet. Man erhält ein mit gelblicher Farbe in Wasser lösliches hellgelbbraunes Produkt.3. 1 mole of dichlorodihydronaphthalene and 2 moles of tetrahydronaphthalene are condensed to an oil in the presence of rod zinc, whereupon from Pour off zinc chloride and add 1 mol. 2% oleum and 1 @ 2 mol. Chlorosulfonic acid the sulfation accomplished. After transfer - in sodium salt is dried. A light yellow-brown product which is soluble in water and has a yellowish color is obtained.
Zu 5o Teilen Naphtbalin und 6o Teilen Benzylchlorid läßt man bei 8o bis 9o° C die Mischung von 25 Teilen Oleum 2oprozentig und 75 Teilen Chlorsulfonsäure langsam zulaufen und rührt nach, bis die Masse klar wasserlöslich ist. Nach dem Neutralisieren und Trocknen erhält man ein Pulver, welches dem nach Beispiel 1 (erhaltenen weitgehend gleicht.To 50 parts of naphthalene and 60 parts of benzyl chloride is allowed to go at 8o up to 90 ° C, the mixture of 25 parts of 2 percent oleum and 75 parts of chlorosulfonic acid run in slowly and stir until the mass is clearly soluble in water. After this Neutralization and drying gives a powder which is similar to that obtained in Example 1 ( largely the same.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF56545D DE466361C (en) | 1924-07-24 | 1924-07-24 | Process for the preparation of water-soluble condensation products |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF56545D DE466361C (en) | 1924-07-24 | 1924-07-24 | Process for the preparation of water-soluble condensation products |
Publications (1)
Publication Number | Publication Date |
---|---|
DE466361C true DE466361C (en) | 1928-10-05 |
Family
ID=7108007
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF56545D Expired DE466361C (en) | 1924-07-24 | 1924-07-24 | Process for the preparation of water-soluble condensation products |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE466361C (en) |
-
1924
- 1924-07-24 DE DEF56545D patent/DE466361C/en not_active Expired
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