JPS60116656A - 純粋な３‐アセチルアミノ‐アニリンを製造する方法 - Google Patents
純粋な３‐アセチルアミノ‐アニリンを製造する方法Info
- Publication number
- JPS60116656A JPS60116656A JP59240869A JP24086984A JPS60116656A JP S60116656 A JPS60116656 A JP S60116656A JP 59240869 A JP59240869 A JP 59240869A JP 24086984 A JP24086984 A JP 24086984A JP S60116656 A JPS60116656 A JP S60116656A
- Authority
- JP
- Japan
- Prior art keywords
- acetylamino
- parts
- general formula
- aniline
- alkanol
- 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.)
- Granted
Links
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 238000001556 precipitation Methods 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 15
- 238000001914 filtration Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 6
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 5
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 5
- 239000012433 hydrogen halide Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 29
- 239000000243 solution Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- -1 Cetyl amino Chemical group 0.000 description 10
- 239000012535 impurity Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 230000021736 acetylation Effects 0.000 description 6
- 238000006640 acetylation reaction Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000006193 diazotization reaction Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 230000001476 alcoholic effect Effects 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 239000000395 magnesium oxide Substances 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- ZSBDPRIWBYHIAF-UHFFFAOYSA-N n-acetylacetamide Chemical compound CC(=O)NC(C)=O ZSBDPRIWBYHIAF-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001448 anilines Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 2
- 239000011654 magnesium acetate Substances 0.000 description 2
- 235000011285 magnesium acetate Nutrition 0.000 description 2
- 229940069446 magnesium acetate Drugs 0.000 description 2
- GPIFQTIYGHWALE-UHFFFAOYSA-N n-(3-amino-4-ethoxyphenyl)acetamide;hydrochloride Chemical compound Cl.CCOC1=CC=C(NC(C)=O)C=C1N GPIFQTIYGHWALE-UHFFFAOYSA-N 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000006864 oxidative decomposition reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- NALDFXSDXQXFPL-UHFFFAOYSA-N (3-acetamidophenyl)azanium;chloride Chemical compound [Cl-].CC(=O)NC1=CC=CC([NH3+])=C1 NALDFXSDXQXFPL-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000270708 Testudinidae Species 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000033 alkoxyamino group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 0.000 description 1
- KQJXHDWKWOKWGM-UHFFFAOYSA-N n-(3-acetamido-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1NC(C)=O KQJXHDWKWOKWGM-UHFFFAOYSA-N 0.000 description 1
- XTXFAVHDQCHWCS-UHFFFAOYSA-N n-(3-amino-4-ethoxyphenyl)acetamide Chemical compound CCOC1=CC=C(NC(C)=O)C=C1N XTXFAVHDQCHWCS-UHFFFAOYSA-N 0.000 description 1
- IFGNRGSBGBNVHV-UHFFFAOYSA-N n-[3-amino-4-(2-hydroxyethoxy)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(OCCO)C(N)=C1 IFGNRGSBGBNVHV-UHFFFAOYSA-N 0.000 description 1
- HSOJAZLHMOYNJP-UHFFFAOYSA-N n-[3-amino-4-(2-methoxyethoxy)phenyl]acetamide Chemical compound COCCOC1=CC=C(NC(C)=O)C=C1N HSOJAZLHMOYNJP-UHFFFAOYSA-N 0.000 description 1
- NWBPJGXONLXNMX-UHFFFAOYSA-N n-acetyl-n-(4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(N(C(C)=O)C(C)=O)C=C1 NWBPJGXONLXNMX-UHFFFAOYSA-N 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical class ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3341883.7 | 1983-11-19 | ||
| DE19833341883 DE3341883A1 (de) | 1983-11-19 | 1983-11-19 | Verfahren zur herstellung von reinen 3-acetylaminoanilinen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60116656A true JPS60116656A (ja) | 1985-06-24 |
| JPH0456824B2 JPH0456824B2 (en, 2012) | 1992-09-09 |
Family
ID=6214755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59240869A Granted JPS60116656A (ja) | 1983-11-19 | 1984-11-16 | 純粋な３‐アセチルアミノ‐アニリンを製造する方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4540815A (en, 2012) |
| EP (1) | EP0142788B1 (en, 2012) |
| JP (1) | JPS60116656A (en, 2012) |
| DE (2) | DE3341883A1 (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3874583D1 (de) * | 1987-04-02 | 1992-10-22 | Ciba Geigy Ag | Verfahren zur herstellung von 2-amino-4-acylaminophenylethern. |
| US5344979A (en) * | 1993-04-29 | 1994-09-06 | Hoechst Celanese Corporation | Process for preparing color-stabilized acetaminophen |
| US5663434A (en) * | 1996-01-29 | 1997-09-02 | Eastman Chemical Company | Process for preparing N-(3-amino-4-chlorophenyl) acylamides |
| DE19730168A1 (de) * | 1997-07-15 | 1999-01-28 | Basf Ag | Phenylazoaniline |
| CN110105220B (zh) * | 2019-05-31 | 2022-05-06 | 济南和润化工科技有限公司 | 一种以间位油为原料制备间苯二胺的方法 |
| CN111138311B (zh) * | 2019-12-31 | 2022-04-15 | 烟台安诺其精细化工有限公司 | 一种间氨基乙酰苯胺的生产方法 |
| CN112300022A (zh) * | 2020-11-11 | 2021-02-02 | 杭州吉华江东化工有限公司 | 一种无水间氨基乙酰苯胺的制备方法 |
| CN113387827A (zh) * | 2021-07-09 | 2021-09-14 | 徐圣杰 | 一种二硝基氯苯制备间氨基乙酰苯胺盐酸盐的合成方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3960886A (en) * | 1968-07-03 | 1976-06-01 | Sterling Drug Inc. | Substituted N-arylanilines |
| US3919269A (en) * | 1971-01-28 | 1975-11-11 | Stauffer Chemical Co | Acylated phenylene diamines |
| BE788332A (fr) * | 1971-09-03 | 1973-01-02 | Degussa | Procede pour la fabrication de n-alkyl-formamides |
| JPS5511533A (en) * | 1978-07-10 | 1980-01-26 | Sumitomo Chem Co Ltd | Preparation of 2-amino-4-acylaminophenyl ether |
| EP0011048B1 (en) * | 1978-09-11 | 1982-01-27 | Toms River Chemical Corporation | A process for the manufacture of substantially pure 3-amino-4-alkoxy-acylanilides from 2,4-dinitrochlorobenzene |
-
1983
- 1983-11-19 DE DE19833341883 patent/DE3341883A1/de not_active Withdrawn
-
1984
- 1984-11-09 EP EP84113516A patent/EP0142788B1/de not_active Expired
- 1984-11-09 DE DE8484113516T patent/DE3460828D1/de not_active Expired
- 1984-11-16 US US06/672,400 patent/US4540815A/en not_active Expired - Lifetime
- 1984-11-16 JP JP59240869A patent/JPS60116656A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3460828D1 (en) | 1986-10-30 |
| EP0142788B1 (de) | 1986-09-24 |
| DE3341883A1 (de) | 1985-05-30 |
| US4540815A (en) | 1985-09-10 |
| JPH0456824B2 (en, 2012) | 1992-09-09 |
| EP0142788A1 (de) | 1985-05-29 |
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