US2013180A - Process of preparing diazonium compounds from 4-aminodiarylamines - Google Patents
Process of preparing diazonium compounds from 4-aminodiarylamines Download PDFInfo
- Publication number
- US2013180A US2013180A US714205A US71420534A US2013180A US 2013180 A US2013180 A US 2013180A US 714205 A US714205 A US 714205A US 71420534 A US71420534 A US 71420534A US 2013180 A US2013180 A US 2013180A
- Authority
- US
- United States
- Prior art keywords
- parts
- solution
- water
- amino
- diazotization
- 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 - Lifetime
Links
- 150000001989 diazonium salts Chemical class 0.000 title description 8
- 238000000034 method Methods 0.000 title description 7
- 239000000243 solution Substances 0.000 description 29
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 18
- 238000006193 diazotization reaction Methods 0.000 description 14
- 239000011592 zinc chloride Substances 0.000 description 14
- 235000005074 zinc chloride Nutrition 0.000 description 13
- 239000007787 solid Substances 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 235000010288 sodium nitrite Nutrition 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000003776 cleavage reaction Methods 0.000 description 8
- 239000012954 diazonium Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 230000007017 scission Effects 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 239000011790 ferrous sulphate Substances 0.000 description 3
- 235000003891 ferrous sulphate Nutrition 0.000 description 3
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 3
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- VWYGTDAUKWEPCZ-UHFFFAOYSA-L dichlorocopper;hydrate Chemical compound O.Cl[Cu]Cl VWYGTDAUKWEPCZ-UHFFFAOYSA-L 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- -1 4-aminophenyl- (ethoxynaphthyl) -amine Chemical compound 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229910000329 aluminium sulfate Inorganic materials 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 235000011128 aluminium sulphate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- VNNIBQJAWHQNPA-UHFFFAOYSA-N aniline;1,1'-biphenyl Chemical class NC1=CC=CC=C1.C1=CC=CC=C1C1=CC=CC=C1 VNNIBQJAWHQNPA-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- ZRSIBBDUMGMJMK-UHFFFAOYSA-J copper dichlorocopper sulfate Chemical compound S(=O)(=O)([O-])[O-].[Cu+2].[Cu](Cl)Cl ZRSIBBDUMGMJMK-UHFFFAOYSA-J 0.000 description 1
- CYKLGTUKGYURDP-UHFFFAOYSA-L copper;hydrogen sulfate;hydroxide Chemical compound O.[Cu+2].[O-]S([O-])(=O)=O CYKLGTUKGYURDP-UHFFFAOYSA-L 0.000 description 1
- 239000011928 denatured alcohol Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- HHIMNFJHTNVXBJ-UHFFFAOYSA-L zinc;dinitrite Chemical compound [Zn+2].[O-]N=O.[O-]N=O HHIMNFJHTNVXBJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
Definitions
- the present invention relates to a process of preparing diazonium compounds from fi-aminodiarylamines;"more particularly it relates to ⁇ a process which comprises diazotizing a li-aminodiarylamine in a Georgianitride, the pH-value of which is between 1 and 4.
- Probst describes a series of complications which are liable tooccur in the diazotization'of-aminodiphenylamine and the derivatives thereof and which he proposes toavoid by a particular kind of diazotization. He states on page 15 of his publication that simultaneously withthe diazotizationanother process takesplace the nal result of which is Ythat part of the Ll-arninodiarylamine is split with formation of a para- Vquinone from the aryl radical carrying the amino-group and of a diazonium compound from thesecond aryl radical.
- This invention is based on the observation that Vthe coursebffthe diazotization of the aminodiarylamines depends on the acidity of the reaction medium and that no cleavage by oxidation occurs if. the diazotization iscarried outl in a medium thepI-I-value of which is between l ande.
- reaction media there may be used aqueous solutions of salts, for instance, of zinc chloride,
- the base may be ground, if desired, with the addition of a suitable'suspending or dispersing agent; or it maybe dissolved previously in a solvent miscible with water, Vsuch as Vacetone or alcohol, so that ⁇ if such a solution is mined with the aqueous reaction liquid the-baseis obtained in a iinely divided form.
- a suitable'suspending or dispersing agent or it maybe dissolved previously in a solvent miscible with water, Vsuch as Vacetone or alcohol, so that ⁇ if such a solution is mined with the aqueous reaction liquid the-baseis obtained in a iinely divided form.
- the base for instance, in a zinc chloride solution with sodiumA nitrite'or Zinc nitrite, the zinc chloride double salts of the diarylamino- Ll-diazcniumchlorides are directly obtained.
- diphenylamines or-naphthylphenylamines or biphenyl-phenylamines and ani thracylphenylamines in which an amino group -portance for the production of ice colors of the 2.3-hydroxynaphthoic ⁇ acid arylaxnide seriesi
- the process of this ⁇ invention has a high technical value. It allows of producing the diazonium salts of the bases without secondary reactions in a pure form. Furthermore, itis only by employingthis invention that the technical utilization of a number ofjbases of this kind for dyestui u manufacturing purposes ble.
- ferrous sulfate there may also be used solutions of, for instance, 360 parts of copper chloride hydrate in 5000 parts of Water or of 3300 parts of copper sulfate hydrate in 5000 parts of water or of 530 parts of aluminium sulfate of the formula Alz(SO4)3.l2I-I2O in 6000 parts of Water, or the like.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Paper (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE434725X | 1933-03-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2013180A true US2013180A (en) | 1935-09-03 |
Family
ID=6506667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US714205A Expired - Lifetime US2013180A (en) | 1933-03-07 | 1934-03-05 | Process of preparing diazonium compounds from 4-aminodiarylamines |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2013180A (fr) |
| FR (1) | FR769810A (fr) |
| GB (1) | GB434725A (fr) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2691649A (en) * | 1951-12-14 | 1954-10-12 | Nat Distillers Prod Corp | Diazotizing of glycine esters |
| US2691650A (en) * | 1951-12-14 | 1954-10-12 | Nat Distillers Prod Corp | Diazotizing of glycine esters |
| US2825724A (en) * | 1958-03-04 | Diazotizing aryl amines | ||
| US2827449A (en) * | 1958-03-18 | Process of diazotization of aromatic | ||
| US3423391A (en) * | 1963-11-28 | 1969-01-21 | Basf Ag | Continuous diazotization process |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL69026C (fr) * | 1948-02-14 |
-
1934
- 1934-03-05 US US714205A patent/US2013180A/en not_active Expired - Lifetime
- 1934-03-07 FR FR769810D patent/FR769810A/fr not_active Expired
- 1934-03-07 GB GB7280/34A patent/GB434725A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2825724A (en) * | 1958-03-04 | Diazotizing aryl amines | ||
| US2827449A (en) * | 1958-03-18 | Process of diazotization of aromatic | ||
| US2691649A (en) * | 1951-12-14 | 1954-10-12 | Nat Distillers Prod Corp | Diazotizing of glycine esters |
| US2691650A (en) * | 1951-12-14 | 1954-10-12 | Nat Distillers Prod Corp | Diazotizing of glycine esters |
| US3423391A (en) * | 1963-11-28 | 1969-01-21 | Basf Ag | Continuous diazotization process |
Also Published As
| Publication number | Publication date |
|---|---|
| GB434725A (en) | 1935-09-09 |
| FR769810A (fr) | 1934-09-03 |
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