SE445551B - Forfarande for framstellning av aromatiska aminoazoforeningar - Google Patents
Forfarande for framstellning av aromatiska aminoazoforeningarInfo
- Publication number
- SE445551B SE445551B SE7801601A SE7801601A SE445551B SE 445551 B SE445551 B SE 445551B SE 7801601 A SE7801601 A SE 7801601A SE 7801601 A SE7801601 A SE 7801601A SE 445551 B SE445551 B SE 445551B
- Authority
- SE
- Sweden
- Prior art keywords
- aromatic amine
- salt
- aniline
- aromatic
- reaction
- Prior art date
Links
- -1 AMINOAZO COMPOUNDS Chemical class 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 28
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 62
- 150000004982 aromatic amines Chemical class 0.000 claims description 36
- 239000007789 gas Substances 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 230000008569 process Effects 0.000 claims description 22
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims description 21
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical group Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 239000000376 reactant Substances 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 2
- GUQAPPPKAMUNSP-UHFFFAOYSA-N aniline;nitric acid Chemical group O[N+]([O-])=O.NC1=CC=CC=C1 GUQAPPPKAMUNSP-UHFFFAOYSA-N 0.000 claims 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 28
- 239000000203 mixture Substances 0.000 description 20
- QPQKUYVSJWQSDY-CCEZHUSRSA-N 4-(phenylazo)aniline Chemical compound C1=CC(N)=CC=C1\N=N\C1=CC=CC=C1 QPQKUYVSJWQSDY-CCEZHUSRSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000002609 medium Substances 0.000 description 11
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 9
- 239000012429 reaction media Substances 0.000 description 9
- 238000010586 diagram Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 6
- 238000006462 rearrangement reaction Methods 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CYGKLLHTPPFPHH-UHFFFAOYSA-N aniline;hydrate Chemical compound O.NC1=CC=CC=C1 CYGKLLHTPPFPHH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- ALIFPGGMJDWMJH-UHFFFAOYSA-N n-phenyldiazenylaniline Chemical compound C=1C=CC=CC=1NN=NC1=CC=CC=C1 ALIFPGGMJDWMJH-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-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
- 241000428352 Amma Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000208202 Linaceae Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 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
- 230000008859 change Effects 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012485 toluene extract 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
- C09B37/00—Azo dyes prepared by coupling the diazotised amine with itself
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7704638A FR2380253A1 (fr) | 1977-02-11 | 1977-02-11 | Procede d'obtention de composes aminoazo aromatiques a partir d'amines aromatiques via les reactions de diazotation, copulation et rearrangement |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7801601L SE7801601L (sv) | 1978-08-12 |
| SE445551B true SE445551B (sv) | 1986-06-30 |
Family
ID=9186894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7801601A SE445551B (sv) | 1977-02-11 | 1978-02-10 | Forfarande for framstellning av aromatiska aminoazoforeningar |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4275003A (it) |
| JP (1) | JPS6013029B2 (it) |
| BE (1) | BE863882A (it) |
| BR (1) | BR7800782A (it) |
| CA (1) | CA1097623A (it) |
| CH (1) | CH629753A5 (it) |
| DE (1) | DE2805477C3 (it) |
| ES (1) | ES466864A1 (it) |
| FR (1) | FR2380253A1 (it) |
| GB (1) | GB1564685A (it) |
| IT (1) | IT1093701B (it) |
| LU (1) | LU79048A1 (it) |
| MX (1) | MX5185E (it) |
| NL (1) | NL7801600A (it) |
| SE (1) | SE445551B (it) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US9051098B2 (en) * | 2009-10-19 | 2015-06-09 | Inoflate, Llc | Method for pressurizing containers with nitrogen |
| KR101897210B1 (ko) | 2016-11-29 | 2018-09-10 | 휴켐스주식회사 | 질소 산화물로 포화된 보조 물질을 이용한 방향족 아민의 디아조화 연속 재순환 공정 |
| KR101882936B1 (ko) | 2016-11-29 | 2018-07-30 | 휴켐스주식회사 | 질소 산화물이 용해된 보조 물질을 이용한 아미노아조 화합물을 제조하는 방법 |
| WO2018101752A1 (ko) * | 2016-11-29 | 2018-06-07 | 휴켐스주식회사 | 질소 산화물이 용해된 보조 물질을 이용한 아미노아조 화합물을 제조하는 방법 |
| CN113003552B (zh) * | 2021-03-09 | 2023-06-16 | 扬州大学 | 一种亚硝酸的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA580083A (en) * | 1959-07-21 | The B. F. Goodrich Company | Method of preparing amino azo compounds | |
| NL69026C (it) * | 1948-02-14 | |||
| 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 |
| NL128603C (it) * | 1963-10-15 | |||
| DE1231251B (de) * | 1963-11-28 | 1966-12-29 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Diazoverbindungen |
| US4018751A (en) * | 1975-04-09 | 1977-04-19 | American Cyanamid Company | Continuous process for aminoazobenzene |
| US4020051A (en) * | 1975-11-25 | 1977-04-26 | E. I. Du Pont De Nemours And Company | Control of nitrogen oxide reactions in off-gases from the diazotization/coupling of aromatic amines |
| US4020052A (en) * | 1975-11-25 | 1977-04-26 | E. I. Du Pont De Nemours And Company | Treatment of aromatic amines with gas mixtures derived from the oxidation of ammonia to effect diazotization/coupling |
| NL174346C (nl) * | 1975-11-25 | 1984-06-01 | Du Pont | Werkwijze voor het bereiden van een 1,3-diaryltriazeen. |
-
1977
- 1977-02-11 FR FR7704638A patent/FR2380253A1/fr active Granted
-
1978
- 1978-02-09 BR BR7800782A patent/BR7800782A/pt unknown
- 1978-02-09 DE DE2805477A patent/DE2805477C3/de not_active Expired
- 1978-02-09 MX MX786833U patent/MX5185E/es unknown
- 1978-02-09 US US05/876,504 patent/US4275003A/en not_active Expired - Lifetime
- 1978-02-10 SE SE7801601A patent/SE445551B/sv not_active IP Right Cessation
- 1978-02-10 CH CH152278A patent/CH629753A5/fr not_active IP Right Cessation
- 1978-02-10 IT IT20189/78A patent/IT1093701B/it active
- 1978-02-10 LU LU79048A patent/LU79048A1/xx unknown
- 1978-02-10 BE BE185099A patent/BE863882A/xx not_active IP Right Cessation
- 1978-02-10 CA CA296,770A patent/CA1097623A/fr not_active Expired
- 1978-02-10 GB GB5541/78A patent/GB1564685A/en not_active Expired
- 1978-02-10 JP JP53014810A patent/JPS6013029B2/ja not_active Expired
- 1978-02-10 NL NL7801600A patent/NL7801600A/xx not_active Application Discontinuation
- 1978-02-10 ES ES466864A patent/ES466864A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6013029B2 (ja) | 1985-04-04 |
| FR2380253B1 (it) | 1980-11-28 |
| MX5185E (es) | 1983-04-21 |
| FR2380253A1 (fr) | 1978-09-08 |
| CH629753A5 (fr) | 1982-05-14 |
| IT1093701B (it) | 1985-07-26 |
| CA1097623A (fr) | 1981-03-17 |
| DE2805477C3 (de) | 1980-12-11 |
| DE2805477B2 (de) | 1980-04-24 |
| LU79048A1 (fr) | 1979-05-25 |
| BR7800782A (pt) | 1979-01-02 |
| IT7820189A0 (it) | 1978-02-10 |
| NL7801600A (nl) | 1978-08-15 |
| ES466864A1 (es) | 1979-06-01 |
| JPS53101316A (en) | 1978-09-04 |
| BE863882A (fr) | 1978-08-10 |
| SE7801601L (sv) | 1978-08-12 |
| GB1564685A (en) | 1980-04-10 |
| US4275003A (en) | 1981-06-23 |
| DE2805477A1 (de) | 1978-08-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SE445551B (sv) | Forfarande for framstellning av aromatiska aminoazoforeningar | |
| EP0077501B1 (de) | Verfahren zur Herstellung von in o-Stellung substituierten Fluoraromaten | |
| US4018751A (en) | Continuous process for aminoazobenzene | |
| JPS5829296B2 (ja) | モノメチルヒドラジンの製造方法 | |
| US4026955A (en) | Preparation of pentachloronitrobenzene | |
| DE2653641C3 (de) | Verfahren zur Herstellung von 1,3- Diaryltriazenen | |
| US3151166A (en) | Method for preparing color stable ethanolamines | |
| EP0415595A1 (en) | Fluorobenzene derivatives | |
| US2621205A (en) | Nitration of olefins | |
| DE3885823T2 (de) | Verfahren zur herstellung von 3-chlor-4-fluornitrobenzol. | |
| DE2211341A1 (de) | Verfahren zur herstellung von 4nitroso-diphenylamin | |
| DE3107700A1 (de) | Verfahren zur herstellung von aromatischen sulfohalogeniden | |
| GB2032427A (en) | Preparing p-aminophenyl | |
| US2524054A (en) | Preparation of guanidine salts | |
| US1599493A (en) | Production of tetrazoles | |
| US3037055A (en) | Preparation of oxamide | |
| US3320241A (en) | Continuous two-stage process for the production of epsilon-caprolactam | |
| JPS6338020B2 (it) | ||
| US4083871A (en) | Preparation of 2-sec.-alkylaminobenzophenones | |
| HU202808B (en) | Process for producing fluorobenzene and fluoropyridine compounds | |
| DE1114193B (de) | Verfahren zur Herstellung polyzyklischer Arylnatriumverbindungen | |
| EP0983982B1 (de) | Verfahren zur Herstellung von aromatischen oder heteroaromatischen Sulfonsäurechloriden | |
| KR810001030B1 (ko) | 질소 증기를 사용하는 디아조화반응, 커플링반응 및 전위반응에 의한 방향족 아민류로부터의 방향족 아미노아조 화합물의 제조방법 | |
| US2483852A (en) | Production of acrolein diacetate | |
| JPH01160952A (ja) | モノーまたはビス−ジチオカルバミン酸ないしは該酸の塩の製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
Ref document number: 7801601-1 Effective date: 19910117 Format of ref document f/p: F |