EP0500660A1 - PROCEDE D'HYDROLYSE D'ACIDE SULFONIQUE DE NAPTHALINE $g(a) DANS UN MELANGE DE SULFONATION DE NAPTHALINE - Google Patents

PROCEDE D'HYDROLYSE D'ACIDE SULFONIQUE DE NAPTHALINE $g(a) DANS UN MELANGE DE SULFONATION DE NAPTHALINE

Info

Publication number
EP0500660A1
EP0500660A1 EP19900916743 EP90916743A EP0500660A1 EP 0500660 A1 EP0500660 A1 EP 0500660A1 EP 19900916743 EP19900916743 EP 19900916743 EP 90916743 A EP90916743 A EP 90916743A EP 0500660 A1 EP0500660 A1 EP 0500660A1
Authority
EP
European Patent Office
Prior art keywords
column
mixture
naphthalene
hydrolysis
steam
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.)
Withdrawn
Application number
EP19900916743
Other languages
German (de)
English (en)
Inventor
Siegfried Bildstein
Joachim Heck
Dieter Schmid
Klaus Schmiedel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of EP0500660A1 publication Critical patent/EP0500660A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/42—Separation; Purification; Stabilisation; Use of additives
    • C07C303/44—Separation; Purification

Definitions

  • ß-naphthol In the large-scale production of. ß-naphthol is first reacted with naphthalene with sulfuric acid and the resulting ß-aphthalinsulfonic acid is subsequently converted into ß-naphthol by alkali melt (Ullmann, Enzyklopadie der techn. Chemie, 4th edition, vol. 17 (1979), pp. 115-120);
  • the mixture formed in the sulfonation of naphthalene contains, in addition to the desired ⁇ -naphthalenesulfonic acid, the most important by-product also ⁇ -aphthalinsulfonic acid.
  • ⁇ -aphthaline sulfonic acid the most important by-product also ⁇ -aphthalinsulfonic acid.
  • This hydrolysis process can be improved by introducing steam into the sulfonation mixture.
  • the naphthalene formed during hydrolysis becomes constantly removed and achieved a corresponding shift in the hydrolysis balance.
  • This "steam hydrolysis” can reduce the ⁇ -acid content from approx. 5% by weight to less than 0.3% by weight. Based on the content of naphthalene monosulfonic acids, this means that the ⁇ -acid content is less than 0.5% by weight.
  • steam has generally been introduced into the molten sulfonation mixture, which is either still in the sulfonation vessel or in a special hydrolysis vessel. Temperatures between 140 ° C. and 160 ° C. and steam introduction times of up to 8 hours are customary (DE-Auslegeschrift 1,080,566 and 1,167,333 and US Pat. No. 1,922,813).
  • trickle column can be used successfully if the sulfonation mixture is circulated from a receiver vessel over the column and treated with steam in countercurrent.
  • the invention therefore relates to a process for the hydrolysis of ⁇ -naphthalenesulfonic acid in a naphthalene-sulfonation mixture by treatment with steam, characterized in that the
  • the "total amount of sulfonation mixture introduced at the top of the column” is composed of the sulfonation mixture which has not yet been treated with water vapor and which is introduced for the first time at the top of the column and the bottom effluent from the column which has already been treated with water vapor and then again added to the top.
  • This total amount added at the top of the column can be easily measured, for example using a flow meter or calibrated accordingly
  • the total residence time of the sulfonation mixture in the column is preferably at least 30 minutes, in particular 30 to 180 minutes.
  • the total residence time can be increased by lengthening the column or by increasing the total amount of sulfonation mixture charged at the top of the column (i.e. roughly speaking, by the number of passes through the column).
  • FIG. 1 The principle of the method is illustrated in FIG. 1.
  • the molten sulfonation mixture is poured into the container (1) equipped with a stirrer and heating jacket and fed via line (2) to the top of the heated packed column (4) with the aid of the pump (3).
  • the melt trickles down on the packing in a thin film and comes into contact with the rising water vapor, which is fed in via line (5) at the bottom of the column.
  • the water vapor containing naphthalene leaves the column via line (6) and is fed to a condenser where it is condensed.
  • the naphthalene is separated from the condensate water and thus recovered.
  • the steam treatment in the trickle column is continued until the proportion of ⁇ -naphthalenesulfonic acid in the total content of the monosulfonic acids in the sulfonation mixture has reached the desired value, e.g. 0.4% by weight.
  • the steam hydrolysis should not be continued for an unnecessarily long time, since there is always a small but undesirable hydrolysis of ⁇ -aphthaline sulfonic acid.
  • An apparatus made of glass components corresponding to FIG. 1 was used for the experiment.
  • a 20 liter round bottom flask served as the storage container.
  • a glass tube of 80 mm diameter with packed bed was used as the trickle column; the filling height of the packing was 1 m.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pinball Game Machines (AREA)

Abstract

L'invention concerne un procédé d'hydrolyse d'acide sulfonique de napthaline alpha dans un mélange de sulfonation de naphtaline par traitement à la vapeur d'eau. Le mélange de sulfonation est appliqué à la tête d'une colonne de lavage, mis en contact en contre-courant avec la vapeur d'eau et l'écoulement de distillation est reconduit vers la tête de la colonne de lavage jusqu'à ce que la quantité de mélange de sulfonation appliquée totalement à la tête de la colonne de lavage soit au moins deux fois plus grande que la quantité à nettoyer et que la durée de séjour du mélange de sulfonation dans la colonne soit au moins de 15 minutes.
EP19900916743 1989-11-14 1990-11-06 PROCEDE D'HYDROLYSE D'ACIDE SULFONIQUE DE NAPTHALINE $g(a) DANS UN MELANGE DE SULFONATION DE NAPTHALINE Withdrawn EP0500660A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3937748 1989-11-14
DE19893937748 DE3937748A1 (de) 1989-11-14 1989-11-14 Verfahren zur hydrolyse von (alpha)-naphtalinsulfonsaeure in einem nahptalin-sulfoniergemisch

Publications (1)

Publication Number Publication Date
EP0500660A1 true EP0500660A1 (fr) 1992-09-02

Family

ID=6393442

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19900916743 Withdrawn EP0500660A1 (fr) 1989-11-14 1990-11-06 PROCEDE D'HYDROLYSE D'ACIDE SULFONIQUE DE NAPTHALINE $g(a) DANS UN MELANGE DE SULFONATION DE NAPTHALINE

Country Status (6)

Country Link
EP (1) EP0500660A1 (fr)
JP (1) JPH05501412A (fr)
CN (1) CN1052476A (fr)
CS (1) CS560390A2 (fr)
DE (1) DE3937748A1 (fr)
WO (1) WO1991007383A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102746195A (zh) * 2011-04-27 2012-10-24 江苏尼高科技有限公司 一种改进萘系减水剂磺化工艺的方法
CN104628607B (zh) * 2015-02-16 2016-05-25 曲靖众一合成化工有限公司 一种α-萘磺酸连续加压水解方法及其装置

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1332203A (en) * 1917-07-06 1920-03-02 Louis M Dennis Method of sulfonation of hydrocarbons of the aromatic series
US1922813A (en) * 1932-09-15 1933-08-15 Nat Aniline & Chem Co Inc 2-naphthalenemonosulphonic acid
CH502424A (de) * 1968-05-17 1971-01-31 Ciba Geigy Ag Verfahren zur Herstellung von Monoazofarbstoffen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9107383A1 *

Also Published As

Publication number Publication date
JPH05501412A (ja) 1993-03-18
WO1991007383A1 (fr) 1991-05-30
CN1052476A (zh) 1991-06-26
CS560390A2 (en) 1991-09-15
DE3937748A1 (de) 1991-05-16

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