PL55011B1 - - Google Patents
Download PDFInfo
- Publication number
- PL55011B1 PL55011B1 PL113556A PL11355666A PL55011B1 PL 55011 B1 PL55011 B1 PL 55011B1 PL 113556 A PL113556 A PL 113556A PL 11355666 A PL11355666 A PL 11355666A PL 55011 B1 PL55011 B1 PL 55011B1
- Authority
- PL
- Poland
- Prior art keywords
- reaction
- aldehyde
- catalyst
- ammonia
- catalyst solution
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 claims description 30
- 150000001299 aldehydes Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 19
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 8
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 4
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 15
- 239000002585 base Substances 0.000 description 13
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
- -1 aluminum alkoxides Chemical class 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 6
- 238000007086 side reaction Methods 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 238000006423 Tishchenko reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229960004011 methenamine Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 150000002843 nonmetals Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL55011B1 true PL55011B1 (https=) | 1968-02-26 |
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102110117B1 (ko) | 네오펜틸 글리콜의 제조 방법 | |
| KR102110115B1 (ko) | 네오펜틸 글리콜의 연속 제조 방법 | |
| CN105418394A (zh) | 一种烯烃氢甲酰化制备醛类化合物的方法 | |
| Lerman et al. | Acetyl hypofluorite, a new moderating carrier of elemental fluorine and its use in fluorination of 1, 3-dicarbonyl derivatives | |
| JPS63107949A (ja) | アルコキシル化エステルの接触製造法 | |
| PL55011B1 (https=) | ||
| JP3437207B2 (ja) | 有機カーボネート製造のための接触法 | |
| Cokley et al. | The solvent promoted addition of tetraallyltin to aldehydes: A convenient and chemoselective allylation procedure | |
| US12257563B2 (en) | Aldol condensation reaction apparatus | |
| JPS62255456A (ja) | ジエチルホルムアミドの製造方法 | |
| EP4306514A1 (en) | Method for preparing intermediate for synthesis of sphingosine-1-phosphate receptor agonist | |
| KR102418587B1 (ko) | 이산화탄소 고정화 반응용 촉매 조성물 | |
| JPS5843936A (ja) | グリコ−ルアルデヒドの製法 | |
| CN110545912B (zh) | 用于由d2o制备氘代乙醇的方法 | |
| CN105435791B (zh) | 一种用于丙二酸二烷基酯加氢制备1，3-丙二醇的催化剂及其制备方法和应用 | |
| JP2002539216A (ja) | ホスファベンゾール化合物および該化合物のヒドロホルミル化触媒のための配位子としての使用 | |
| EP0675129A1 (de) | Verfahren zur Herstellung von heterosubstituierten Acetalen | |
| RU2249478C2 (ru) | Катализатор для получения 2,3-диалкил-1,10-фенантролинов | |
| CN101094826B (zh) | 使用催化剂从烯烃制备羟醛衍生物的方法 | |
| RU2249477C2 (ru) | Катализатор для получения 2,3-диалкил-7,8-бензо-1,6-нафтиридинов | |
| Yoneda et al. | Superacid catalyzed oxygenation of aliphatic ethers with ozone | |
| EP0108332B1 (en) | Preparation of acetone dicarboxylic acid diester | |
| Yeritsyan et al. | New Nitrogen Containing Derivatives of Glycol and Compounds on Their Basis | |
| JPS58109446A (ja) | 蓚酸エステルの製法 | |
| KR20010021550A (ko) | 로듐-트리-폴리에틸렌 글리콜레이트를 사용한 알칸알의제조 방법 |