DE1768704C - - Google Patents
Info
- Publication number
- DE1768704C DE1768704C DE19681768704 DE1768704 DE1768704C DE 1768704 C DE1768704 C DE 1768704C DE 19681768704 DE19681768704 DE 19681768704 DE 1768704 DE1768704 DE 1768704 DE 1768704 C DE1768704 C DE 1768704C
- Authority
- DE
- Germany
- Prior art keywords
- trans
- phenyl
- cyclohexene
- dimethylamino
- cis
- 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
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000011780 sodium chloride Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- XTEGVFVZDVNBPF-UHFFFAOYSA-N Armstrong's acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000005755 formation reaction Methods 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- VNIQZQGVXVYHSP-UHFFFAOYSA-N N,N-dimethylbuta-1,3-dien-1-amine Chemical compound CN(C)C=CC=C VNIQZQGVXVYHSP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- BOIWYTYYWPXGAT-UHFFFAOYSA-N ethyl 2-phenylprop-2-enoate Chemical compound CCOC(=O)C(=C)C1=CC=CC=C1 BOIWYTYYWPXGAT-UHFFFAOYSA-N 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- HGCIXCUEYOPUTN-UHFFFAOYSA-N Cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000012535 impurity Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- WYVAVFURKHCMTG-UHFFFAOYSA-N ethyl 3-(dimethylamino)-2-phenylpropanoate Chemical compound CCOC(=O)C(CN(C)C)C1=CC=CC=C1 WYVAVFURKHCMTG-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- UQKWCEMNYBVRGY-UHFFFAOYSA-M 3-(dimethylamino)-2-phenylpropanoate Chemical compound CN(C)CC(C([O-])=O)C1=CC=CC=C1 UQKWCEMNYBVRGY-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- -1 atropic acid ester Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001935 cyclohexenes Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010407 vacuum cleaning Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1768704C true DE1768704C (fr) | 1972-06-22 |
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69208120T2 (de) | Verfahren zur Herstellung von Ferulasäure | |
| DE2127851A1 (de) | Verfahren zur Herstellung von Hydrochinon | |
| DE1906401A1 (de) | Verfahren zur Herstellung von 4-Acyloxy-azetidin-2-onen | |
| DE1768704C (fr) | ||
| DE1768704B1 (de) | Verfahren zur Abtrennung von 3-trans-Dimethylamino-4-phenyl-4-trans-carbaethoxy-delta?-cyclohexen | |
| EP1127879B1 (fr) | Procédé pour la préparation de l'acide 1,3-dibenzyle-imidazolidine-2-one- cis-4,5 dicarboxylique et son anhydride | |
| DE3104310A1 (de) | Verfahren zur herstellung von 5-chlor-2-nitroanilin | |
| DE2721265C2 (de) | Verfahren zur Herstellung von Di- n-propylacetonitril | |
| DE2055494A1 (de) | Verfahren zur Herstellung von Thiobisphenolen | |
| DE1618476C (fr) | ||
| DE2339086A1 (de) | Verfahren zur herstellung von terephthaldialdehyd | |
| DE10231496B4 (de) | Verfahren zur Herstellung von hochreinem, kristallinem 4-Amino-5,6-dimethoxypyrimidin | |
| DE1276635B (de) | Verfahren zur Herstellung von Kaliumsorbat | |
| DE4020056A1 (de) | Verfahren zur herstellung sehr reiner 5-aminosalicylsaeure | |
| DE1908883A1 (de) | Verfahren zur Herstellung von Dibutylzinnmaleat | |
| DE850297C (de) | Verfahren zur Herstellung von Amidinsalzen | |
| DE2640123A1 (de) | Maleinsaeuresalz von 2-phenyl-6-(1-hydroxy-2-tert.-butylaminoaethyl)-4h-pyrido- (3,2-d)-1,3-dioxin, ein verfahren zur herstellung desselben sowie ein verfahren zur herstellung von 2-hydroxymethyl-3- hydroxy-6-(1-hydroxy-2-tert.-butylaminoaethyl)-pyridin | |
| DE1468736C (de) | Verfahren zur Herstellung von Benzoesäureestern der Saccharose | |
| DE2359107A1 (de) | Verfahren zur herstellung von 2oder 4-(2-alkylaminoaethyl)-pyridinen | |
| DE929191C (de) | Verfahren zur Herstellung von Aminocarbonsaeuren | |
| DE1618476B1 (de) | Verfahren zur Trennung eines aus 3c-Dimethylamino-4-phenyl-4c-carbäthoxy-Delta1-cyclohexen und 3t-Dimethylamino-4-phenyl-4t-carbäthoxy-Delta1-cyclohexen zusammengesetzten Isomerengemisches in die Einzelverbindungen | |
| DE2355917A1 (de) | Verfahren zur herstellung von hochreinem 1.3-bis-(beta-aethylhexyl)-5-amino- 5-methyl-hexahydropyrimidin | |
| EP0064651A1 (fr) | Procédé pour l'isolation de l'acide H et de l'acide K | |
| EP1284253A2 (fr) | Procédé de préparation d'hydrocarbures monochlorés à haute pureté d'isomères | |
| DE2154437A1 (de) | Verfahren zur Herstellung von substituierten alpha-Naphthoxyacetamiden |