CS236279B1 - Method of 2-naphtol-6-sulphonic acid,2-naphtol-3,6-disulphonic acid and 2-naphtol-6,8-disulphonic acid mixture's production - Google Patents
Method of 2-naphtol-6-sulphonic acid,2-naphtol-3,6-disulphonic acid and 2-naphtol-6,8-disulphonic acid mixture's production Download PDFInfo
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- CS236279B1 CS236279B1 CS912283A CS912283A CS236279B1 CS 236279 B1 CS236279 B1 CS 236279B1 CS 912283 A CS912283 A CS 912283A CS 912283 A CS912283 A CS 912283A CS 236279 B1 CS236279 B1 CS 236279B1
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- Czechoslovakia
- Prior art keywords
- acid
- naphthol
- naphtol
- mixture
- production
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- 239000000203 mixture Substances 0.000 title claims abstract description 14
- 239000002253 acid Substances 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000006277 sulfonation reaction Methods 0.000 claims abstract description 7
- VVPHSMHEYVOVLH-UHFFFAOYSA-N 6-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(O)=CC=C21 VVPHSMHEYVOVLH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229950011260 betanaphthol Drugs 0.000 claims abstract description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- DOBIZWYVJFIYOV-UHFFFAOYSA-N 7-hydroxynaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(O)=CC=C21 DOBIZWYVJFIYOV-UHFFFAOYSA-N 0.000 claims description 8
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 2
- -1 2-naphthol sulfonates Chemical class 0.000 claims 1
- USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 abstract description 4
- 238000004904 shortening Methods 0.000 abstract 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- GFPQSWFFPRQEHH-UHFFFAOYSA-N 7-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1S(O)(=O)=O GFPQSWFFPRQEHH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 229910001018 Cast iron Inorganic materials 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- VNEBWJSWMVTSHK-UHFFFAOYSA-L disodium;3-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=CC2=C1 VNEBWJSWMVTSHK-UHFFFAOYSA-L 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Vynález se týká způsobu sulfonace 2-naftolu za vzniku směsi mono- a disulfokyselin. Podstatou vynálezu je zkrácení doby sulfonace 2-naftolu za vzniku směsi sulfokyselin o obsahu 10 až 30 % kyseliny 2-naftol-6-sulfonové, 60 až 80 % kyseliny 2-naftol-6,8-disulfonové a 0,1 až 10 % kyseliny 2-naftol-3,6-disulfonové. Tato směs -se získá ve vysokém výtěžku a je možno ji zpracovat po předchozí ami ngci na kyselinu 2-naftylamin -3,6,8-trisulfonovou.The present invention relates to a sulfonation process 2-naphthol to form a mixture of mono- and disulfoacids. The essence of the invention is shortening sulfonation time of 2-naphthol to form a mixture sulfoacids containing 10 to 30% acid 2-naphthol-6-sulfonic acid, 60-80% acid 2-naphthol-6,8-disulfonic and 0.1 to 10% of 2-naphthol-3,6-disulfonic acid. This mixture is obtained in high yield and it can be processed after previous ami ngci to 2-naphthylamino-3,6,8-trisulfonic acid.
Description
Vynález ee týká způsobu výroby směsi kyeel^nsítel-6,8-disulfonové, 2-naftol-6-sulfonové a 2-naftol-3,6-disulfonové sulfonacíjL-naftolu.The invention relates to a process for the preparation of a mixture of 6,6-disulfonic acid, 2-naphthol-6-sulfonic acid and 2-naphthol-3,6-disulfone sulfonation of 1-naphthol.
Dosud známé a popsané způsoby sulfonace Λ-naftolu kysličníkem sírovým τ prostředí kyseliny sírově jsou vedeny tak, aby vznikala pokud možno jednotná látka, a to buá naftolsulfokyselina, anebo naftoldisulfokyselina, které pak slouží jako polotovary k připraví dalších sloučenin, obsahujících sulfoskupiny. Tak např. při přípravě kyseliny 2-naftol ^,^-disulfonové (G-kyselina), ze které se po aminaci další sulionací vyrábí kyselina 2-naftylamin-3,6,8-trisulfonová, se provádí sulfonaoe <&-naftolu při teplotě 60 °C po dobu osmi hodin, pak se teplota zvýší na 80 °C a sulfonuje se dalších osm hodin. Reakce je vedena tak, aby vznikala v co nejvyšším výtěžku G-kyselina, jako vedlejší produkt vzniká kyselina 2-naftol-3,6-disulfonová (R-kyselina)·The known and described methods of sulfonation of Λ-naphthol with sulfur trioxide τ of sulfuric acid are conducted so as to produce as uniform a substance as possible, either naphtholsulfoacid or naphtholdisulfoacid, which then serve as blanks to prepare other sulfo-containing compounds. For example, in the preparation of 2-naphthol-4-disulfonic acid (G-acid) from which 2-naphthylamine-3,6,8-trisulfonic acid is produced after amination by further sulionation, sulfonation of naphthol is carried out at a temperature of 60 ° C for eight hours, then raise the temperature to 80 ° C and sulfonate for an additional eight hours. The reaction is conducted in such a way that G-acid is produced in the highest possible yield.
Při izolaci ve formě draselné soli však odchází R-sůl nevyužita do matečných louhů, výtěžek G-kyseliny je poměrně nízký - cca 60 teorie. Tento postup je nevýhodný, neboí výtěžnost je nízkáIn the isolation in the form of the potassium salt, however, the R-salt leaves unused to the mother liquors, the yield of G-acid being relatively low - about 60 theory. This process is disadvantageous because the yield is low
V f a to nepříznivě ovlivňuje ekonomiku dalšího zpracovatelského řetězce pro výrobu kyseliny 2-naftylamin-3,6,8-trisulfonové.In this, it adversely affects the economy of another processing chain for the production of 2-naphthylamine-3,6,8-trisulfonic acid.
Nyní bylo zjištěno, že výše uvedenou nevýhodu lze odstranit způsobem výroby směsi kyselin-2-naftol-6,8-disulfonové, 2-naftol-6-sulfonové a 2-naftol-3,6-disulfonové sulfonací Λ-naftolu podle tohoto vynálezu^ jehož podstata spočívá v tom, že se 2-naftol sulfonuje po rozpuštění v kyselině sirové působením kysličníku sírového o koncentraci 25 % hmotnostních V molárním poměru 3 až 7 molů kysličníku sírového na jeden mol sulfonované látky nejprve při teplotě 45 °C po dobu 3 hodinIt has now been found that the above disadvantage can be overcome by a process for preparing a mixture of 2-naphthol-6,8-disulfonic acid, 2-naphthol-6-sulfonic acid and 2-naphthol-3,6-disulfonic acid by sulfonating the Λ-naphthol of the present invention. characterized in that, after dissolution in sulfuric acid, 2-naphthol is sulfonated with 25% by weight sulfuric trioxide in a molar ratio of 3 to 7 moles of sulfur trioxide per mole of sulfonated substance first at 45 ° C for 3 hours
- 2 236 279 a dále při teplotě 60 až 70 °C po dobu 1 až 5 hodin, načež se suli onace ukončí a isoluj e se směs sulfokyselin o složení 10 až 30 % kyseliny 2-naftol-6-sulfonové, 60 až 80 % kyseliny 2-naftol-6,8-disulíonové a 0,1 až 10 % kyseliny 2-naftol-3»6-disulfonovó.- 2 236 279 and thereafter at a temperature of 60 to 70 ° C for 1 to 5 hours, after which time the salification is terminated and a mixture of sulfo acids of 10 to 30% 2-naphthol-6-sulfonic acid, 60 to 80% of 2-naphthol-6,8-disulfonic acid and 0.1 to 10% of 2-naphthol-3,6-disulfonic acid.
Výhodou postupupdle vynálezu je získání směsi sulf 0-¾ disulfokyselin ve vysokém výtěžku při zkrácené době sulfonace.^’An advantage of the process of the invention is to obtain a mixture of sulfo-¾ disulfoacids in high yield with reduced sulfonation time.
Tato směs je vhodná pro přípravu kyseliny 2-naftylamin-3,6,8-trisul· fonové.This mixture is suitable for the preparation of 2-naphthylamine-3,6,8-trisulfonic acid.
Pro bližší objasnění podstaty vynálezu je dále uveden pří&lad provedení:In order to further elucidate the nature of the invention, the following example is given:
PříkladExample
Do litinového sulf oné toru 3 000 1, opatře&elio mícháním a chlazením se předložíInto a cast iron sulphonator of 3000 L, provided with stirring and cooling, is introduced
367 kg kyseliny sírové 100^%ní a připustí kg vody· Směs se ochladí na 25 °C a během jednéhoifay z«p.ese367 kg of sulfuric acid 100% and allow for kg of water · The mixture is cooled to 25 ° C and during one day of the process.
030 kg šupinkového 2-naítolu· Po zanesení se obsah sulfonátoru promíchá, přičemž teplota v kotli vystoupí na 35 až 40 °C· Ihned se začne připouštět první dávka030 kg of scale 2-naphthol · After clogging, the sulphonator content is mixed and the temperature in the boiler rises to 35 to 40 ° C · The first batch is started immediately
496 kg kys ličníku sírového 25_%ního tak, aby dávkování trvale 6 hodin· Teplota se udržuje do 45 0G. Přestane se chladit sjpřipustí se druhá dávka496 kg of sulfuric oxide 25% so that the dosage is continuous for 6 hours · The temperature is maintained at 45 0 G. The cooling stops and a second charge is allowed
236 kg kysličníku sírového 25_%ního» Teplota se zvýší během 3 hodin na 60 °0 a udržuje 3 hodiny·236 kg of sulfur dioxide »The temperature is raised to 60 ° 0 within 3 hours and maintained for 3 hours ·
Obsah sulfonátoru se pak přetlačí doThe contents of the sulfonator are then forced into
672 1 vody, Vyhřeje na 90 <xž 100 °C a připustí během 2 hodin672 liters of water, heated to 90 <x to 100 ° C and allowed in 2 hours
835 kg 10€L%ního hydroxidu draselného ve formě roztoku o koncentraci 37 až 55 $>· Obsah kádě se nechá volně bez míchání chladnout na 55 °C a potom za přerušovaného míchání se ochladí na 20 °C· Filtruje se na vakuových nučích a vykrývá835 kg of 10% L% potassium hydroxide in the form of a solution with a concentration of 37 to 55 $> · The contents of the vat are allowed to cool freely to 55 ° C without stirring and then cooled to 20 ° C with intermittent stirring. he covers
300 až 500 1 chladné vody ke zbavení kyseliny, ulpělé na krystalech produktu·300 to 500 liters of cold water to remove acid adhering to product crystals
Průměrné molámí složení získané směsi je 73 % dikaliové soli G-kyseliny, 25 % kaliové soli kyseliny 2-naftol-6-sulfonové a 2 % dikaliové soli R-kyseliny·The average molar composition of the mixture obtained is 73% of dicalcium salt of G-acid, 25% of dicalcium salt of 2-naphthol-6-sulfonic acid and 2% of dicalcium salt of R-acid ·
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS912283A CS236279B1 (en) | 1983-12-06 | 1983-12-06 | Method of 2-naphtol-6-sulphonic acid,2-naphtol-3,6-disulphonic acid and 2-naphtol-6,8-disulphonic acid mixture's production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS912283A CS236279B1 (en) | 1983-12-06 | 1983-12-06 | Method of 2-naphtol-6-sulphonic acid,2-naphtol-3,6-disulphonic acid and 2-naphtol-6,8-disulphonic acid mixture's production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS236279B1 true CS236279B1 (en) | 1985-05-15 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS912283A CS236279B1 (en) | 1983-12-06 | 1983-12-06 | Method of 2-naphtol-6-sulphonic acid,2-naphtol-3,6-disulphonic acid and 2-naphtol-6,8-disulphonic acid mixture's production |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS236279B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110229083A (en) * | 2019-06-27 | 2019-09-13 | 九江学院 | A kind of preparation method of G salt |
-
1983
- 1983-12-06 CS CS912283A patent/CS236279B1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110229083A (en) * | 2019-06-27 | 2019-09-13 | 九江学院 | A kind of preparation method of G salt |
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