JPH0576942B2 - - Google Patents
Info
- Publication number
- JPH0576942B2 JPH0576942B2 JP86227459A JP22745986A JPH0576942B2 JP H0576942 B2 JPH0576942 B2 JP H0576942B2 JP 86227459 A JP86227459 A JP 86227459A JP 22745986 A JP22745986 A JP 22745986A JP H0576942 B2 JPH0576942 B2 JP H0576942B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- ethanolamine
- diketene
- solution
- purity
- 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 - Lifetime
Links
- 238000006243 chemical reaction Methods 0.000 claims description 39
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 38
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 238000000034 method Methods 0.000 description 12
- 239000013067 intermediate product Substances 0.000 description 10
- OKEAMBAZBICIFP-UHFFFAOYSA-N 3-oxido-2,1,3-benzoxadiazol-3-ium Chemical compound C1=CC=CC2=[N+]([O-])ON=C21 OKEAMBAZBICIFP-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- TURHTASYUMWZCC-UHFFFAOYSA-N Olaquindox [BAN:INN] Chemical compound C1=CC=C2N([O-])C(C)=C(C(=O)NCCO)[N+](=O)C2=C1 TURHTASYUMWZCC-UHFFFAOYSA-N 0.000 description 4
- GLLHZHAFSZJULJ-UHFFFAOYSA-N 1-oxido-4-oxoquinoxalin-4-ium-2-carboxamide Chemical compound C1=CC=CC2=[N+]([O-])C(C(=O)N)=C[N+]([O-])=C21 GLLHZHAFSZJULJ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000273 veterinary drug Substances 0.000 description 2
- -1 (hydroxyethyl)-3-methyl-2-quinoxalinecarboxamide-1,4-dioxide Chemical compound 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007886 mutagenicity Effects 0.000 description 1
- 231100000299 mutagenicity Toxicity 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T10/00—Road transport of goods or passengers
- Y02T10/10—Internal combustion engine [ICE] based vehicles
- Y02T10/12—Improving ICE efficiencies
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60-241344 | 1985-10-30 | ||
| JP24134485 | 1985-10-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62174061A JPS62174061A (ja) | 1987-07-30 |
| JPH0576942B2 true JPH0576942B2 (de) | 1993-10-25 |
Family
ID=17072903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61227459A Granted JPS62174061A (ja) | 1985-10-30 | 1986-09-26 | Ｎ−（２−ヒドロキシエチル）−３−メチル−２−キノキサリンカルボキシアミド−１，４−ジオキシドの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62174061A (de) |
-
1986
- 1986-09-26 JP JP61227459A patent/JPS62174061A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62174061A (ja) | 1987-07-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2074854C1 (ru) | Способ получения производных амидоксима о-(2-гидрокси-3-пиперидино-1-пропил)-никотиновой кислоты и их солей (варианты), чистое кристаллическое основание амидоксима о-(2-гидрокси-3-пиперидино-1-пропил)-никотиновой кислоты | |
| DK175838B1 (da) | Fremgangsmåde til fremstilling af 2,6-dichlordiphenylamineddikesyrederivater | |
| IL116384A (en) | Iliden assemblies and their preparation | |
| JP4097291B2 (ja) | 置換バリンアミド誘導体の製造方法 | |
| JPH0136462B2 (de) | ||
| JPH0576942B2 (de) | ||
| KR100502041B1 (ko) | 3-아미노-1,2,4-벤조트리아진디옥사이드의제조방법 | |
| CN104093718B (zh) | 用于2-苯基-[1,2,4]三唑并[1,5-a]吡啶衍生物的制备的方法 | |
| US4264500A (en) | Process of making 6-chloro-α-methyl-carbazole-2-acetic acid | |
| CN112272665A (zh) | 制备立他司特的方法 | |
| JPH0641135A (ja) | イミダゾプテリジン誘導体及びその製造方法 | |
| JP2717995B2 (ja) | １，２，３−トリアゾールの製法 | |
| EP0047674A1 (de) | Verfahren für die Herstellung von Isoindolinderivaten | |
| US4087437A (en) | 2-Phenyl-5-benzoxazolylalkanoic acid purification process | |
| JPH061776A (ja) | 置換ピラジンカルボニトリルの製造方法 | |
| US6011177A (en) | Process for 4-sulfonamidolphenyl hydrazines | |
| JPH072726B2 (ja) | ベンゾグアナミン誘導体の製法 | |
| JPH072742A (ja) | ４−アミノ−３−メチル−Ｎ−エチル−Ｎ−（β−ヒドロキシエチル）アニリン硫酸塩の新規製造法 | |
| JP3592747B2 (ja) | Ｎ−ｔｅｒｔ−ブチル−２，３−ピラジンジカルボキサミド及びその製造法 | |
| JPS62267267A (ja) | ピラゾ−ル誘導体およびその製造法 | |
| JPH05286932A (ja) | インドール類の製造方法 | |
| JPS62273949A (ja) | Ｎ，ｎ−ジアルキルアミノチオアセトアミド類の製造法 | |
| JPS6183168A (ja) | ２−メルカプト−４−アミノ−５−ホルミルピリミジンおよびその製法 | |
| US6333414B1 (en) | Process for the synthesis of trisubstituted oxazoles | |
| CN118324683A (zh) | 一种3-氯-2-氧代-[1,3']双吡咯烷基-1'-羧酸烯丙基酯的制备方法 |