DE2134519C3 - Verfahren zur Diazotierung von Aminen - Google Patents
Verfahren zur Diazotierung von AminenInfo
- Publication number
- DE2134519C3 DE2134519C3 DE2134519A DE2134519A DE2134519C3 DE 2134519 C3 DE2134519 C3 DE 2134519C3 DE 2134519 A DE2134519 A DE 2134519A DE 2134519 A DE2134519 A DE 2134519A DE 2134519 C3 DE2134519 C3 DE 2134519C3
- Authority
- DE
- Germany
- Prior art keywords
- diazotization
- amines
- acid
- base
- reaction
- 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
- 150000001412 amines Chemical class 0.000 title claims description 12
- 238000006193 diazotization reaction Methods 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 8
- 239000002585 base Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- -1 nitrosyl group Chemical group 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical group O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000004157 Nitrosyl chloride Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- ZVAKTWSQIIRIIH-UHFFFAOYSA-N [K].[I] Chemical compound [K].[I] ZVAKTWSQIIRIIH-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229960003116 amyl nitrite Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE786093D BE786093A (fr) | 1971-07-10 | Procede de diazotation d'amines | |
| DE2134519A DE2134519C3 (de) | 1971-07-10 | 1971-07-10 | Verfahren zur Diazotierung von Aminen |
| NL7208191A NL7208191A (enExample) | 1971-07-10 | 1972-06-15 | |
| CH1015472A CH566968A5 (enExample) | 1971-07-10 | 1972-07-06 | |
| CA146,583A CA983483A (en) | 1971-07-10 | 1972-07-07 | Process for diazotizing amines |
| JP47067638A JPS5747180B1 (enExample) | 1971-07-10 | 1972-07-07 | |
| BR4506/72A BR7204506D0 (pt) | 1971-07-10 | 1972-07-07 | Processo para diazotacao de aminas |
| IT26802/72A IT962667B (it) | 1971-07-10 | 1972-07-08 | Processo per la diazotazione di amine |
| AU44333/72A AU468730B2 (en) | 1971-07-10 | 1972-07-09 | Process for diazotizing amines |
| US270256A US3888841A (en) | 1971-07-10 | 1972-07-10 | Process for diazotizing aromatic amines |
| FR7224905A FR2145993A5 (enExample) | 1971-07-10 | 1972-07-10 | |
| GB3212372A GB1396534A (en) | 1971-07-10 | 1972-07-10 | Process for diazotizing aromatic amines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2134519A DE2134519C3 (de) | 1971-07-10 | 1971-07-10 | Verfahren zur Diazotierung von Aminen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2134519A1 DE2134519A1 (de) | 1973-01-25 |
| DE2134519B2 DE2134519B2 (de) | 1973-09-20 |
| DE2134519C3 true DE2134519C3 (de) | 1974-04-25 |
Family
ID=5813283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2134519A Expired DE2134519C3 (de) | 1971-07-10 | 1971-07-10 | Verfahren zur Diazotierung von Aminen |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3888841A (enExample) |
| JP (1) | JPS5747180B1 (enExample) |
| AU (1) | AU468730B2 (enExample) |
| BE (1) | BE786093A (enExample) |
| BR (1) | BR7204506D0 (enExample) |
| CA (1) | CA983483A (enExample) |
| CH (1) | CH566968A5 (enExample) |
| DE (1) | DE2134519C3 (enExample) |
| FR (1) | FR2145993A5 (enExample) |
| GB (1) | GB1396534A (enExample) |
| IT (1) | IT962667B (enExample) |
| NL (1) | NL7208191A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2516031A1 (de) * | 1975-04-12 | 1976-10-28 | Bayer Ag | Verfahren zur herstellung von azofarbstoffen |
| DE2516032C2 (de) * | 1975-04-12 | 1984-10-04 | Bayer Ag, 5090 Leverkusen | Verfahren zum Diazotieren aromatischer Amine |
| JPS60176530A (ja) * | 1984-02-21 | 1985-09-10 | 三井東圧化学株式会社 | 殺虫成分の揮散装置 |
| US6233989B1 (en) | 2000-10-13 | 2001-05-22 | Changing Paradigms, Llc | Method and apparatus for stamping a metal sheet with an apertured design having rolled edges |
| GB2575010A (en) * | 2018-05-15 | 2020-01-01 | Syso Products Ltd | A garden bag |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH318195A (de) * | 1953-07-20 | 1956-12-31 | Geigy Ag J R | Verfahren zur Herstellung von aromatischen o-Oxydiazoverbindungen |
| NL135513C (enExample) * | 1967-06-19 |
-
0
- BE BE786093D patent/BE786093A/xx unknown
-
1971
- 1971-07-10 DE DE2134519A patent/DE2134519C3/de not_active Expired
-
1972
- 1972-06-15 NL NL7208191A patent/NL7208191A/xx unknown
- 1972-07-06 CH CH1015472A patent/CH566968A5/xx not_active IP Right Cessation
- 1972-07-07 JP JP47067638A patent/JPS5747180B1/ja active Pending
- 1972-07-07 CA CA146,583A patent/CA983483A/en not_active Expired
- 1972-07-07 BR BR4506/72A patent/BR7204506D0/pt unknown
- 1972-07-08 IT IT26802/72A patent/IT962667B/it active
- 1972-07-09 AU AU44333/72A patent/AU468730B2/en not_active Expired
- 1972-07-10 US US270256A patent/US3888841A/en not_active Expired - Lifetime
- 1972-07-10 FR FR7224905A patent/FR2145993A5/fr not_active Expired
- 1972-07-10 GB GB3212372A patent/GB1396534A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7208191A (enExample) | 1973-01-12 |
| CH566968A5 (enExample) | 1975-09-30 |
| AU468730B2 (en) | 1976-01-22 |
| JPS5747180B1 (enExample) | 1982-10-07 |
| GB1396534A (en) | 1975-06-04 |
| DE2134519A1 (de) | 1973-01-25 |
| FR2145993A5 (enExample) | 1973-02-23 |
| BR7204506D0 (pt) | 1973-05-31 |
| US3888841A (en) | 1975-06-10 |
| IT962667B (it) | 1973-12-31 |
| BE786093A (fr) | 1973-01-10 |
| CA983483A (en) | 1976-02-10 |
| AU4433372A (en) | 1974-01-10 |
| DE2134519B2 (de) | 1973-09-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |