DE349727C - Process for the preparation of condensation products from aromatic sulphonic acids - Google Patents
Process for the preparation of condensation products from aromatic sulphonic acidsInfo
- Publication number
- DE349727C DE349727C DE1913349727D DE349727DD DE349727C DE 349727 C DE349727 C DE 349727C DE 1913349727 D DE1913349727 D DE 1913349727D DE 349727D D DE349727D D DE 349727DD DE 349727 C DE349727 C DE 349727C
- Authority
- DE
- Germany
- Prior art keywords
- condensation products
- water
- preparation
- sulphonic acids
- aromatic sulphonic
- 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 6
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 title 1
- 150000007513 acids Chemical class 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 4
- 150000003460 sulfonic acids Chemical class 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- -1 aromatic sulfonic acids Chemical class 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001447 alkali salts Chemical class 0.000 description 4
- 239000003929 acidic solution Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 235000017343 Quebracho blanco Nutrition 0.000 description 1
- 244000007853 Sarothamnus scoparius Species 0.000 description 1
- 241000065615 Schinopsis balansae Species 0.000 description 1
- JROURLWMOZCGJV-UHFFFAOYSA-N alizarin blue Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C1=CC=CN=C1C(O)=C2O JROURLWMOZCGJV-UHFFFAOYSA-N 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000010985 leather Substances 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
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C3/00—Tanning; Compositions for tanning
- C14C3/02—Chemical tanning
- C14C3/08—Chemical tanning by organic agents
- C14C3/18—Chemical tanning by organic agents using polycondensation products or precursors thereof
- C14C3/20—Chemical tanning by organic agents using polycondensation products or precursors thereof sulfonated
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Kondensationsprodukten aus aromatischen Sulfosäuren. Es ist bekannt, daß man durch Erhitzen von Sulfosäuren aromatischer Kohlenwasserstoffe Sulfone oder sulfonartige Stoffe erhält.Process for the preparation of condensation products from aromatic Sulfonic acids. It is known that by heating sulfonic acids one more aromatic Hydrocarbons, sulfones or sulfone-like substances.
Es wurde nun gefunden, daß bei weiter fortgesetztem Erhitzen diese erst gebildeten, in Wasser unlöslichen Stoffe wieder verschwinden und die Masse wieder vollkommen üi Wasser löslich wird. Man erhält so neue Produkte von technisch sehr wertvollen Eigenschaften. Die Produkte und ebenso ihre Alkalisalze sind. sehr leicht in Wasser löslich, viel leichter als die ursprünglichen Sulfosäuren. Die Lösungen sind bei vorsichtig durchgeführter Kondensation hell. Die sauren Lösungen geben mit Gelatine starke Fällung.It has now been found that with continued heating this Substances which are only formed and which are insoluble in water disappear again and the mass again becomes completely soluble in water. So you get new products from technically very valuable properties. The products and likewise their alkali salts are. very Easily soluble in water, much more easily than the original sulfonic acids. the Solutions are pale if condensation is carried out carefully. The acidic solutions give strong precipitation with gelatin.
Die Kondensationsprodukte eignen sich vorzüglich zum Gerben. Tierische Häute werden in der stets schwach sauer gehaltenen Lösung der Alkalisalze in Leder von sehr guter Qualität verwandelt.The condensation products are ideal for tanning. Animal Hides become in the always slightly acidic solution of the alkali salts in leather transformed of very good quality.
Die Kondensationsprodukte haben ferner ein sehr großes Lösungsvermögen für die verschiedensten Stoffe. Durch Zusatz ihrer Alkalisalze werden in Wasser schwer lösliche natürliche Gerbstoffe, z. B. Quebracho, leicht und klar in Wasser löslich. Ebenso werden viele Farbstoffe, z. B. Alizarin, Alizarinblau, Martiusgelb hierdurch wasserlöslich.The condensation products also have a very high dissolving power for a wide variety of fabrics. By adding their alkali salts are in water poorly soluble natural tannins, e.g. B. Quebracho, light and clear in water soluble. Likewise, many dyes, e.g. B. Alizarin, Alizarin Blue, Martius Yellow this makes it water-soluble.
Die Bildung der Produkte kann durch Vakuum oder durch Durchblasen von Luft, wodurch das abgespaltene Wasser rascher fortgeführt wird, beschleunigt werden.The formation of the products can be done by vacuum or by blowing accelerated by air, whereby the separated water is carried away more quickly will.
Ferner wirkt Anwesenheit von manchen Besen, in erster Linie von Tonerde, beschleunigend.Furthermore, the presence of some brooms, primarily clay, has an effect accelerating.
Beispiele. i. ioo Teile Naphtalin werden mit ioo Teilen konzentrierter Schwefelsäure etwa 8 Stunden auf 13o° erhitzt, dann wird die Temperatur bis auf 17o bis 18o° erhöht und Luft durchgeblasen. Herausgenommene Proben zeigen zunächst beim Lösen in Wasser steigende Mengen von Unlöslichem, die bei weiterem Erhitzen vollkommen wieder verschwinden. Die Kondensation ist beendet, wenn eine Probe leicht und klar in Wasser löslich ist.Examples. i. 100 parts of naphthalene become more concentrated with 100 parts Sulfuric acid heated to 130 ° for about 8 hours, then the temperature is up to Elevated 17o to 18o ° and air blown through. Samples taken out initially show when dissolving in water, increasing amounts of insolubles, those with further heating disappear again completely. The condensation is over when a sample is light and is clearly soluble in water.
Das Produkt ist in der Kälte glasartig fest. Es löst sich in jedem Verhältnis in Wasser. Ebenso sind die Alkalisalze sehr leicht löslich, ferner auch die Salze der Erdalkalien. Die saure Lösung fällt Gelatine und wirkt gerbend auf tierische Haut.The product is glass-like in the cold. It dissolves in everyone Ratio in water. The alkali salts are also very easily soluble, as well the salts of the alkaline earths. The acidic solution precipitates gelatine and has a tanning effect animal skin.
a. ioo Teile Naphtalin werden bei i8o° in ioo Teile konzentrierter Schwefelsäure eingetragen und weiter etwa q. Stunden bei 18o° gehalten. Dann wird bei 18o bis igo° Luft durchgeblasen, bis die zunächst auftretenden unlöslichen Produkte wieder verschwunden sind und die Masse vollständig und klar wasserlöslich geworden ist. -Eigenschaften der Masse wie Beispiel i.a. 100 parts of naphthalene become more concentrated in 100 parts at 180 ° Sulfuric acid entered and further about q. Held at 180 ° for hours. Then it will be Air blown through at 18o to igo ° until the insoluble products appear have disappeared again and the mass has become completely and clearly water-soluble is. -Properties of the mass as in example i.
3. In 15o Teile Schwefelsäure werden bei 13o bis 14o° zooTeile Toluol eintropfen lassen und am Rückflußkühler bis zur völligen Lösung des Toluols weiter erhitzt, dann nach Entfernung des Kühlers bei i3o ° weiter bei steigender Temperatur bis 179 ' Luft durchgeleitet, bis die zunächst auftretenden unlöslichen Produkte wieder verschwunden sind und die Masse ganz wasserlöslich ist. Die Masse ist zähflüssig, Eigenschaften wie Probe i.3. In 150 parts of sulfuric acid, zoo parts of toluene are added at 130 to 14o ° drop in and continue on the reflux condenser until the toluene has completely dissolved heated, then after removal of the cooler at i3o ° further at increasing temperature to 179 'air passed through until the first occurring insoluble products have disappeared again and the mass is completely water-soluble. The mass is viscous, properties like sample i.
q.. ioo Teile Naphtalinsulfosäure, erhalten durch Sulfieren von 6o Teilen Naphtalin mit 5o Teilen konzentrierter Schwefelsäure bei i8o °, werden mit io Teilen Tonerde versetzt und zunächst wenig über ioo°, dann bei steigender Temperatur bis zu Zoo ° erhitzt. Das Reaktionsprodukt wird mit Natriumkarbonatlösung aus- i gekocht und von der Tonerde abfiltriert. Das Filtrat ist das Natriumsalz des Kondensationsprodukts. Eigenschaften und Verhalten wie oben.q .. 100 parts of naphthalene sulfonic acid, obtained by sulfating 6o Parts of naphthalene with 50 parts of concentrated sulfuric acid at 180 ° are with 10 parts of clay added and initially a little over 100 °, then with increasing temperature heated up to Zoo °. The reaction product is aus- i with sodium carbonate solution cooked and filtered from the clay. The filtrate is the sodium salt of the condensation product. Properties and behavior as above.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE349727T | 1913-12-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE349727C true DE349727C (en) | 1922-03-07 |
Family
ID=6258863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1913349727D Expired DE349727C (en) | 1913-12-09 | 1913-12-09 | Process for the preparation of condensation products from aromatic sulphonic acids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE349727C (en) |
-
1913
- 1913-12-09 DE DE1913349727D patent/DE349727C/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0214543A2 (en) | Process for the preparation of 1-aminonaphthalene-2,4,7-trisulfonic acid and 1-aminonaphthalene-7-sulfonic acid | |
| DE349727C (en) | Process for the preparation of condensation products from aromatic sulphonic acids | |
| DE676854C (en) | Process for the production of tanning agents from lignosulfonic acids | |
| CH232280A (en) | Process for the preparation of a water-soluble, higher molecular weight acyl biguanide. | |
| DE2003112B2 (en) | Aromatic carboxylic acids and anhydrides thereof | |
| DE609477C (en) | Process for the production of condensation products | |
| DE927331C (en) | Process for the production of synthetic tanning agents | |
| US1707506A (en) | Process for manufacture of oil-soluble sulphonates | |
| US1414045A (en) | Tanning | |
| US646772A (en) | Process of making sulfonates. | |
| DE408871C (en) | Process for the preparation of sulfobenzyla ethers from resinous condensation products derived from phenols | |
| DE696777C (en) | Process for the production of water-soluble condensation products from lignosulfonic acids | |
| DE663996C (en) | Process for the production of condensation products with a tanning effect | |
| DE561423C (en) | Process for the preparation of nitrogen-containing sulfonation products of higher paraffinic hydrocarbons | |
| US1421722A (en) | Tanning | |
| DE2104655A1 (en) | 3,3'-disulpho-diphenyl sulphone 4,4'-dicarboxylic acid - dianhydride - useful as an intermediate for eg polyesters and polyami | |
| DE397405C (en) | Process for the production of artificial tanning agents | |
| AT85469B (en) | Process for the production of artificial tanning agents. | |
| DE685961C (en) | Process for the preparation of substituted aromatic sulfonic acids | |
| DE683318C (en) | Process for the production of condensation products with a tanning effect | |
| DE435668C (en) | Process for the preparation of metal compounds of the aromatic biguanides | |
| US1089797A (en) | Tanning material. | |
| DE530823C (en) | Process for the preparation of arylsulfonarylamines | |
| DE961351C (en) | Process for the production of water-soluble, tanning condensation products | |
| DE517498C (en) | Process for the production of condensation products |