DE615744C - Diazotization process - Google Patents
Diazotization processInfo
- Publication number
- DE615744C DE615744C DEG85050D DEG0085050D DE615744C DE 615744 C DE615744 C DE 615744C DE G85050 D DEG85050 D DE G85050D DE G0085050 D DEG0085050 D DE G0085050D DE 615744 C DE615744 C DE 615744C
- Authority
- DE
- Germany
- Prior art keywords
- water
- diazotization
- soluble
- salts
- parts
- 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
- 238000006193 diazotization reaction Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000002585 base Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- -1 oleyl taurine Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N Taurine Natural products NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- ITFGZZGYXVHOOU-UHFFFAOYSA-N n,n-dimethylmethanamine;methyl hydrogen sulfate Chemical compound C[NH+](C)C.COS([O-])(=O)=O ITFGZZGYXVHOOU-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Es wurde gefunden, daß sich primäre aromatische Basen, welche in Wasser schwer löslich, sind oder deren Salze in Wasser leicht der Hydrolyse unterliegen, leicht und glatt diazotieren lassen, wenn man in Gegenwart solcher säure- und salzbeständiger wasserlöslicher kapillaraktiver Stoffe arbeitet,, die keine oder leicht lösliche Diazosalze bilden. Das Verfahren eignet sich also für die Diazotierung solcher Basen, die nach den allgemein gebräuchlichen und geeigneten Diazotierungsverfahren nur schwer diazotierbar sind. Ferner verhindert die Mitverwendung der genanntein Hilfsstoffe die Bildung unerwünschter Nebenprodukte, die infolge Oxydation, Selbstkupplung usw. entstehen können.It has been found that primary aromatic bases, which are heavy in water soluble, or their salts are easily hydrolyzed in water, easily and smoothly Let diazotize if you are water-soluble in the presence of such acid and salt-resistant capillary-active substances, which form no or easily soluble diazo salts. The process is therefore suitable for the diazotization of such bases, which are generally used and suitable Diazotization processes are difficult to diazotize. It also prevents co-use the called one auxiliary substances the formation of undesired by-products, which as a result Oxidation, self-coupling, etc. can occur.
Als Hilfsstoffe eignen sich besonders die wasserlöslichen Kondensationsprodukte, die aus höheren Fettalkoholen und Äthylenoxyd erhalten werden; die mit Hilfe von höheren Fettsäuren acylierten asymmetrischen Dialkyläthylendiamine und deren Ammoniumverbindungen, Polyvinylalkohole, Methylcellulose, Alkalisalze des Oleyltaurins und des Ölsäureisäthionssäureesters usw.Particularly suitable auxiliaries are the water-soluble condensation products made from higher fatty alcohols and ethylene oxide obtained; the asymmetric dialkylethylenediamines acylated with the aid of higher fatty acids and their ammonium compounds, polyvinyl alcohols, methyl cellulose, alkali salts of oleyl taurine and oleic acid ester etc.
Beispiel. S Teile 4-(1'-Methyl)-phenoxyacetylamino -2, 5 - dimethoxy-1 -aminobenzol werden mit 0,3 Teilen Trimethylammoniummethylsulfat * des Monooleyläthylendiamins und 40 Teilen heißem Wasser gut angeteigt. Hierauf setzt man 6 Raumteile 32,10/0ige Salzsäure zu und stellt mit kaltem Wasser auf 200 Raumteile ein. Unter Rühren werden 5,5 Raumteile einer 250/oigen Natriumnitritlösung unter die Oberfläche der Flüssigkeit eingeführt. Nach kurzer Zeit ist die Diazotierung beendet.Example. S parts 4- (1'-methyl) -phenoxyacetylamino -2, 5 - dimethoxy-1-aminobenzene are mixed with 0.3 parts of trimethylammonium methyl sulfate * the Monooleyläthylendiamins and 40 parts of hot water well pasted. On this you place 6 room parts 32,10 / 0ige Add hydrochloric acid and adjust to 200 parts by volume with cold water. Be stirring 5.5 parts by volume of a 250% sodium nitrite solution inserted under the surface of the liquid. The diazotization takes place after a short time completed.
Ähnlich verfährt man mit anderen Basen, wie z. B. !mit dem i-Amino-2, 5-dichlor-4-benzoylaminobenzol, oder tnit dem Anilid des 2-Amino-5, 4'-dichlor-4-carbonsäure-1, i'-diphenyläthers. The procedure is similar with other bases, such as B.! With the i-amino-2, 5-dichloro-4-benzoylaminobenzene, or with the anilide of 2-amino-5, 4'-dichloro-4-carboxylic acid-1, i'-diphenyl ether.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH769591X | 1933-03-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE615744C true DE615744C (en) | 1935-07-11 |
Family
ID=4535291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG85050D Expired DE615744C (en) | 1933-03-09 | 1933-03-12 | Diazotization process |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH165829A (en) |
| DE (1) | DE615744C (en) |
| FR (1) | FR769591A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1023771B (en) * | 1956-03-09 | 1958-02-06 | Bayer Ag | Process for the diazotization of aromatic amines which are sparingly soluble in water, the salts of which are easily hydrolyzed in water |
-
1933
- 1933-03-09 CH CH165829D patent/CH165829A/en unknown
- 1933-03-12 DE DEG85050D patent/DE615744C/en not_active Expired
-
1934
- 1934-03-05 FR FR769591D patent/FR769591A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1023771B (en) * | 1956-03-09 | 1958-02-06 | Bayer Ag | Process for the diazotization of aromatic amines which are sparingly soluble in water, the salts of which are easily hydrolyzed in water |
Also Published As
| Publication number | Publication date |
|---|---|
| CH165829A (en) | 1933-12-15 |
| FR769591A (en) | 1934-08-28 |
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