DE1023771B - Verfahren zur Diazotierung aromatischer Amine, die in Wasser schwer loeslich sind deren Salze in Wasser leicht hydrolysiert werden - Google Patents
Verfahren zur Diazotierung aromatischer Amine, die in Wasser schwer loeslich sind deren Salze in Wasser leicht hydrolysiert werdenInfo
- Publication number
- DE1023771B DE1023771B DEF19749A DEF0019749A DE1023771B DE 1023771 B DE1023771 B DE 1023771B DE F19749 A DEF19749 A DE F19749A DE F0019749 A DEF0019749 A DE F0019749A DE 1023771 B DE1023771 B DE 1023771B
- Authority
- DE
- Germany
- Prior art keywords
- water
- diazotization
- weight
- parts
- salts
- 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.)
- Pending
Links
- 238000006193 diazotization reaction Methods 0.000 title claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 12
- 150000003839 salts Chemical class 0.000 title claims description 12
- 150000004982 aromatic amines Chemical class 0.000 title claims description 4
- 239000002270 dispersing agent Substances 0.000 claims description 10
- 239000002245 particle Substances 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 6
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 3
- 239000007900 aqueous suspension Substances 0.000 claims 1
- 150000003142 primary aromatic amines Chemical class 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 14
- -1 polyhaloanilines Chemical class 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- 239000000080 wetting agent Substances 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- KBJGBAOGDZOYIZ-UHFFFAOYSA-N 2,5-dimethoxy-4-[(4-nitrophenyl)diazenyl]aniline Chemical compound C1=C(N)C(OC)=CC(N=NC=2C=CC(=CC=2)[N+]([O-])=O)=C1OC KBJGBAOGDZOYIZ-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- JBCUKQQIWSWEOK-UHFFFAOYSA-N 2-(benzenesulfonyl)aniline Chemical compound NC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1 JBCUKQQIWSWEOK-UHFFFAOYSA-N 0.000 description 2
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- BMRVLXHIZWDOOK-UHFFFAOYSA-N 2-butylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCC)=CC=C21 BMRVLXHIZWDOOK-UHFFFAOYSA-N 0.000 description 1
- KQZBSZUGKSCFBL-UHFFFAOYSA-N 2-phenyldiazenylaniline Chemical class NC1=CC=CC=C1N=NC1=CC=CC=C1 KQZBSZUGKSCFBL-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 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
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- BSUFVRGLMWXUDX-UHFFFAOYSA-N n,n-dichloro-2-nitroaniline Chemical class [O-][N+](=O)C1=CC=CC=C1N(Cl)Cl BSUFVRGLMWXUDX-UHFFFAOYSA-N 0.000 description 1
- LHHIALSOMNPUOW-UHFFFAOYSA-N n-chloro-n-phenylnitramide Chemical class [O-][N+](=O)N(Cl)C1=CC=CC=C1 LHHIALSOMNPUOW-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/20—Diazonium compounds
-
- 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
- C09B41/00—Special methods of performing the coupling reaction
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
- Coloring (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE555654D BE555654A (cs) | 1956-03-09 | ||
| DEF19749A DE1023771B (de) | 1956-03-09 | 1956-03-09 | Verfahren zur Diazotierung aromatischer Amine, die in Wasser schwer loeslich sind deren Salze in Wasser leicht hydrolysiert werden |
| CH356779D CH356779A (de) | 1956-03-09 | 1957-02-18 | Verfahren zur Diazotierung aromatischer Amine |
| FR1169206D FR1169206A (fr) | 1956-03-09 | 1957-03-08 | Procédé de diazotation d'amines aromatiques |
| GB783257A GB809350A (en) | 1956-03-09 | 1957-03-08 | Process for diazotising aromatic amines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF19749A DE1023771B (de) | 1956-03-09 | 1956-03-09 | Verfahren zur Diazotierung aromatischer Amine, die in Wasser schwer loeslich sind deren Salze in Wasser leicht hydrolysiert werden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1023771B true DE1023771B (de) | 1958-02-06 |
Family
ID=7089429
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF19749A Pending DE1023771B (de) | 1956-03-09 | 1956-03-09 | Verfahren zur Diazotierung aromatischer Amine, die in Wasser schwer loeslich sind deren Salze in Wasser leicht hydrolysiert werden |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE555654A (cs) |
| CH (1) | CH356779A (cs) |
| DE (1) | DE1023771B (cs) |
| FR (1) | FR1169206A (cs) |
| GB (1) | GB809350A (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0016388A1 (de) * | 1979-03-15 | 1980-10-01 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Diazoniumsalzlösungen |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3511752A1 (de) * | 1985-03-30 | 1986-10-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung aromatischer diazoniumsalze, azofarbstoffe und konzentrierter loesungen von azofarbstoffen |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE615744C (de) * | 1933-03-09 | 1935-07-11 | Chem Ind Basel | Diazotierungsverfahren |
-
0
- BE BE555654D patent/BE555654A/xx unknown
-
1956
- 1956-03-09 DE DEF19749A patent/DE1023771B/de active Pending
-
1957
- 1957-02-18 CH CH356779D patent/CH356779A/de unknown
- 1957-03-08 FR FR1169206D patent/FR1169206A/fr not_active Expired
- 1957-03-08 GB GB783257A patent/GB809350A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE615744C (de) * | 1933-03-09 | 1935-07-11 | Chem Ind Basel | Diazotierungsverfahren |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0016388A1 (de) * | 1979-03-15 | 1980-10-01 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Diazoniumsalzlösungen |
Also Published As
| Publication number | Publication date |
|---|---|
| GB809350A (en) | 1959-02-25 |
| CH356779A (de) | 1961-09-15 |
| BE555654A (cs) | |
| FR1169206A (fr) | 1958-12-24 |
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