CA1045124A - Continuous process for aminoazobenzene - Google Patents
Continuous process for aminoazobenzeneInfo
- Publication number
- CA1045124A CA1045124A CA248,484A CA248484A CA1045124A CA 1045124 A CA1045124 A CA 1045124A CA 248484 A CA248484 A CA 248484A CA 1045124 A CA1045124 A CA 1045124A
- Authority
- CA
- Canada
- Prior art keywords
- aromatic
- alkali metal
- aminoazo
- reactor
- compound
- 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
- 238000010924 continuous production Methods 0.000 title claims abstract description 8
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 title description 9
- -1 aromatic aminoazo compounds Chemical class 0.000 claims abstract description 40
- 239000002253 acid Substances 0.000 claims abstract description 20
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 11
- 239000011707 mineral Substances 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000000376 reactant Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical group [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 235000010288 sodium nitrite Nutrition 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 150000003142 primary aromatic amines Chemical class 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 229910001960 metal nitrate Inorganic materials 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- ALIFPGGMJDWMJH-UHFFFAOYSA-N n-phenyldiazenylaniline Chemical compound C=1C=CC=CC=1NN=NC1=CC=CC=C1 ALIFPGGMJDWMJH-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- PFRYFZZSECNQOL-UHFFFAOYSA-N 2-methyl-4-[(2-methylphenyl)diazenyl]aniline Chemical compound C1=C(N)C(C)=CC(N=NC=2C(=CC=CC=2)C)=C1 PFRYFZZSECNQOL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000003841 chloride salts Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical compound CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-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
- WKURVXXDGMYSDP-UHFFFAOYSA-N 2-propyl-aniline Chemical compound CCCC1=CC=CC=C1N WKURVXXDGMYSDP-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 101150034533 ATIC gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 241001163743 Perlodes Species 0.000 description 1
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- CLRSZXHOSMKUIB-UHFFFAOYSA-M benzenediazonium chloride Chemical compound [Cl-].N#[N+]C1=CC=CC=C1 CLRSZXHOSMKUIB-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- IDNHOWMYUQKKTI-UHFFFAOYSA-M lithium nitrite Chemical compound [Li+].[O-]N=O IDNHOWMYUQKKTI-UHFFFAOYSA-M 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000992 solvent dye Substances 0.000 description 1
- 239000007858 starting material Substances 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S534/00—Organic compounds -- part of the class 532-570 series
- Y10S534/07—Automatic and/or continuous temperature control in the preparation of azo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/566,594 US4018751A (en) | 1975-04-09 | 1975-04-09 | Continuous process for aminoazobenzene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1045124A true CA1045124A (en) | 1978-12-26 |
Family
ID=24263544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA248,484A Expired CA1045124A (en) | 1975-04-09 | 1976-03-22 | Continuous process for aminoazobenzene |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4018751A (enExample) |
| JP (1) | JPS51142021A (enExample) |
| BR (1) | BR7602097A (enExample) |
| CA (1) | CA1045124A (enExample) |
| DE (1) | DE2615705A1 (enExample) |
| FR (1) | FR2306977A1 (enExample) |
| GB (1) | GB1543260A (enExample) |
| IT (1) | IT1058054B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2380253A1 (fr) * | 1977-02-11 | 1978-09-08 | Rhone Poulenc Ind | Procede d'obtention de composes aminoazo aromatiques a partir d'amines aromatiques via les reactions de diazotation, copulation et rearrangement |
| DE2903717A1 (de) * | 1978-02-14 | 1979-08-16 | Ici Ltd | Verfahren zur herstellung einer waessrigen aufschlaemmung einer wasserunloeslichen azoverbindung |
| FR2419279A1 (fr) * | 1978-03-06 | 1979-10-05 | Rhone Poulenc Ind | Procede d'obtention de sels d'aryl diazonium a partir de vapeurs nitreuses riches en oxyde azotique |
| US4279815A (en) * | 1979-01-09 | 1981-07-21 | Herkes Frank E | Production of high-quality aromatic amino azo compounds by the rearrangement of 1,3-diaryl triazenes |
| US4376730A (en) * | 1981-03-13 | 1983-03-15 | Akzo N.V. | Preparation of p-aminoazo-benzene from aniline |
| GB2129434B (en) * | 1982-10-08 | 1986-04-16 | Ciba Geigy Ag | Production of azo compounds |
| US4918168A (en) * | 1987-11-24 | 1990-04-17 | Mallinckrodt Inc. | Process for the continuous diazotization of amines in a multi-stage reactor |
| CN103305898A (zh) * | 2012-03-08 | 2013-09-18 | 鸿富锦精密工业（深圳）有限公司 | 去毛刺方法及使用该去毛刺方法的去毛刺系统 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA580083A (en) * | 1959-07-21 | The B. F. Goodrich Company | Method of preparing amino azo compounds | |
| US2538431A (en) * | 1949-01-06 | 1951-01-16 | Pfister Chemical Works Inc | Preparation of aminoazobenzenes |
| US2809964A (en) * | 1953-07-02 | 1957-10-15 | Gen Aniline & Film Corp | Process of preparing lower alkyl substituted aminoazoanilines |
| DE1231251B (de) * | 1963-11-28 | 1966-12-29 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Diazoverbindungen |
| DE1215724B (de) * | 1964-04-10 | 1966-05-05 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Diazoniumloesungen |
-
1975
- 1975-04-09 US US05/566,594 patent/US4018751A/en not_active Expired - Lifetime
-
1976
- 1976-03-22 CA CA248,484A patent/CA1045124A/en not_active Expired
- 1976-03-24 GB GB11920/76A patent/GB1543260A/en not_active Expired
- 1976-04-01 IT IT48829/76A patent/IT1058054B/it active
- 1976-04-07 BR BR7602097A patent/BR7602097A/pt unknown
- 1976-04-09 DE DE19762615705 patent/DE2615705A1/de active Pending
- 1976-04-09 FR FR7610548A patent/FR2306977A1/fr active Granted
- 1976-04-09 JP JP51039439A patent/JPS51142021A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US4018751A (en) | 1977-04-19 |
| DE2615705A1 (de) | 1976-10-21 |
| FR2306977B1 (enExample) | 1979-08-31 |
| GB1543260A (en) | 1979-03-28 |
| BR7602097A (pt) | 1976-10-05 |
| JPS51142021A (en) | 1976-12-07 |
| FR2306977A1 (fr) | 1976-11-05 |
| IT1058054B (it) | 1982-04-10 |
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