EP0500660A1 - VERFAHREN ZUR HYDROLYSE VON $g(a)-NAPHTHALINSULFONSÄURE IN EINEM NAPHTHALIN-SULFONIERGEMISCH - Google Patents
VERFAHREN ZUR HYDROLYSE VON $g(a)-NAPHTHALINSULFONSÄURE IN EINEM NAPHTHALIN-SULFONIERGEMISCHInfo
- 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- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 44
- 230000007062 hydrolysis Effects 0.000 title claims abstract description 18
- 238000006460 hydrolysis reaction Methods 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 18
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 title claims description 10
- 238000006277 sulfonation reaction Methods 0.000 claims abstract description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000009835 boiling Methods 0.000 claims description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract description 27
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract description 4
- 238000005406 washing Methods 0.000 abstract 3
- 238000004821 distillation Methods 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- VMSLCPKYRPDHLN-UHFFFAOYSA-N (R)-Humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-UHFFFAOYSA-N 0.000 description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 238000009931 pascalization Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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)
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 (de) | 1992-09-02 |
Family
ID=6393442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19900916743 Withdrawn EP0500660A1 (de) | 1989-11-14 | 1990-11-06 | VERFAHREN ZUR HYDROLYSE VON $g(a)-NAPHTHALINSULFONSÄURE IN EINEM NAPHTHALIN-SULFONIERGEMISCH |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0500660A1 (cs) |
| JP (1) | JPH05501412A (cs) |
| CN (1) | CN1052476A (cs) |
| CS (1) | CS560390A2 (cs) |
| DE (1) | DE3937748A1 (cs) |
| WO (1) | WO1991007383A1 (cs) |
Families Citing this family (2)
| 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)
| 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 |
-
1989
- 1989-11-14 DE DE19893937748 patent/DE3937748A1/de not_active Withdrawn
-
1990
- 1990-11-06 EP EP19900916743 patent/EP0500660A1/de not_active Withdrawn
- 1990-11-06 WO PCT/EP1990/001849 patent/WO1991007383A1/de not_active Ceased
- 1990-11-06 JP JP2515328A patent/JPH05501412A/ja active Pending
- 1990-11-13 CN CN 90109857 patent/CN1052476A/zh active Pending
- 1990-11-13 CS CS905603A patent/CS560390A2/cs unknown
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9107383A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1991007383A1 (de) | 1991-05-30 |
| CN1052476A (zh) | 1991-06-26 |
| DE3937748A1 (de) | 1991-05-16 |
| JPH05501412A (ja) | 1993-03-18 |
| CS560390A2 (en) | 1991-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 19920509 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL SE |
|
| 18W | Application withdrawn |
Withdrawal date: 19930204 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
|
| R18W | Application withdrawn (corrected) |
Effective date: 19930204 |