DE852690C - Process for the preparation of sulfonation products of tetrahydronaphthalene and its homologues - Google Patents
Process for the preparation of sulfonation products of tetrahydronaphthalene and its homologuesInfo
- Publication number
- DE852690C DE852690C DED4534D DED0004534D DE852690C DE 852690 C DE852690 C DE 852690C DE D4534 D DED4534 D DE D4534D DE D0004534 D DED0004534 D DE D0004534D DE 852690 C DE852690 C DE 852690C
- Authority
- DE
- Germany
- Prior art keywords
- tetrahydronaphthalene
- homologues
- sulfonation
- preparation
- sulfonation 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
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 Herstellung von Sulfonierungsprodukten des Tetrahydronaphthalins und seiner Homologen Die Sulfonierung aromatischer Kohlenwasserstoffe ist bisher stets mit überschüssigen Mengen Sulfonierungsmitteln oder unter Zuhilfenahme von mit Wasser ein niedrig siedendes Flüssigkeitsgemisch bildenden Stoffen durchgeführt worden. Demgegenüber war es überraschend, daß sich, wie gefunden wurde, Tetrahydronaphthalin und seine Homologen mit äquimolekularen oder nahezu äquimolekularen, d. h. die Theorie nur um wenige Prozente über- oder unterschreitenden Mengen Sulfonierungsmittel durch Erhitzen im Vakuum praktisch vollkommen sulfonieren lassen, wenn man dafür Sorge trägt, daß der während der Sulfonierung abdestillierende Kohlenwasserstoff stetig oder absatzweise in das Sulfonierungsgefäß zurückgeleitet wird. Als Sulfonierungsmittel eignen sich Schwefelsäuremonohydrat, technische Schwefelsäuren mit z oder mehr Prozent Wasser, saure Sulfate oder andere Sulfonierungsmittel. In gleicher Weise wie Tetrahydronaphthalin lassen sich auch Methyltetrahydronaphthalin, Athyltetrahydronaphthalin, Dimethyltetrahydronaphthalin und andere Substitutionsprodukte sulfonieren. Die Höhe des anzuwenden Vakuums kann innerhalb weiter Grenzen schwanken, und sie ist im allgemeinen von der Sulfonierungstemperatur abhängig bzw. dieser anzul)assen.Process for the preparation of sulfonation products of tetrahydronaphthalene and its homologues The sulfonation of aromatic hydrocarbons is so far always with excess amounts of sulfonating agents or with the aid of with water, a low-boiling liquid mixture-forming substances carried out been. In contrast, it was surprising that it was found to be tetrahydronaphthalene and its homologues with equimolecular or nearly equimolecular, i.e. H. theory only a few percent over or under amounts of sulfonating agent through Heat in vacuum practically completely sulfonate if you take care of it contributes to the fact that the hydrocarbon distilling off during the sulfonation is constant or returned batchwise to the sulfonation vessel. As a sulfonating agent sulfuric acid monohydrate, technical sulfuric acids with z or more percent are suitable Water, acid sulphates or other sulphonating agents. In the same way as tetrahydronaphthalene methyl tetrahydronaphthalene, ethyl tetrahydronaphthalene and dimethyl tetrahydronaphthalene can also be used and sulfonate other substitution products. The amount of vacuum to be applied can be vary within wide limits, and it is generally of the sulfonation temperature depending on or to eat this.
Beispiel In einem mit Rührwerk ausgestatteten Sulfoniergefäß «erden zu 5oo kg Tetrahydronaphthalin, die auf ioo bis 12o° erhitzt sind, allmählich 38o kg konzentrierte Schwefelsäure (98%ig) laufen gelassen und ein Vakuum von ioo bis i 5o mm Hg-Druck erzeugt. Dabei destilliert ein Gemisch von Tetrahydronaphthalin und Wasser über, das durch einen Kühler kondensiert und in einer Vorlage aufgefangen wird, die einen ständigen Rücklauf des überdestilliertenTetrahydronaphthalins gestattet. Sobald kein Destillat mehr entsteht, was nach 2 bis 3 Stunden der Fall ist, wird das Sulfonierungserzeugnis unter Rühren in die berechnete Menge Natronlauge (33o/oig) einlaufen gelassen. Das mit Wasser auf eine 2o%ige Lösung von tetrahydronaphthalinsulfonsaurem Natrium eingestellte Neutralisat wird dann einem Walzentrockner zugeführt und liefert ein Sulfonat, das nur etwa 2% Glaubersalz enthält.Example Earth in a sulphonation vessel equipped with a stirrer to 500 kg of tetrahydronaphthalene, the are heated to 100 to 12o °, gradually run 380 kg of concentrated sulfuric acid (98%) and a vacuum from 100 to 50 mm Hg pressure generated. A mixture of tetrahydronaphthalene distills and water, which condenses through a cooler and is collected in a receiver which allows constant reflux of the tetrahydronaphthalene distilled over. As soon as no more distillate is produced, which is the case after 2 to 3 hours add the sulphonation product to the calculated amount of sodium hydroxide solution (33%) while stirring let in. That with water to a 20% solution of tetrahydronaphthalenesulfonic acid Neutralisate adjusted to sodium is then fed to a drum dryer and delivered a sulfonate that contains only about 2% Glauber's salt.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DED4534D DE852690C (en) | 1944-08-12 | 1944-08-12 | Process for the preparation of sulfonation products of tetrahydronaphthalene and its homologues |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DED4534D DE852690C (en) | 1944-08-12 | 1944-08-12 | Process for the preparation of sulfonation products of tetrahydronaphthalene and its homologues |
Publications (1)
Publication Number | Publication Date |
---|---|
DE852690C true DE852690C (en) | 1952-10-16 |
Family
ID=7031049
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DED4534D Expired DE852690C (en) | 1944-08-12 | 1944-08-12 | Process for the preparation of sulfonation products of tetrahydronaphthalene and its homologues |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE852690C (en) |
-
1944
- 1944-08-12 DE DED4534D patent/DE852690C/en not_active Expired
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