DEF0014527MA - - Google Patents
Info
- Publication number
- DEF0014527MA DEF0014527MA DEF0014527MA DE F0014527M A DEF0014527M A DE F0014527MA DE F0014527M A DEF0014527M A DE F0014527MA
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- trimethylene oxide
- trimethylolpropane
- reaction
- 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.)
- Active
Links
- 238000006243 chemical reaction Methods 0.000 claims description 8
- AHHWIHXENZJRFG-UHFFFAOYSA-N Oxetane Chemical class C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000004651 carbonic acid esters Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- -1 methylol groups Chemical group 0.000 claims description 2
- 125000004429 atoms Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 230000000875 corresponding Effects 0.000 description 8
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 239000001569 carbon dioxide Substances 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- GDCVWNMIFDZYRE-UHFFFAOYSA-N (2-ethyloxetan-2-yl)methanol Chemical compound CCC1(CO)CCO1 GDCVWNMIFDZYRE-UHFFFAOYSA-N 0.000 description 4
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- HPXRVTGHNJAIIH-UHFFFAOYSA-N Cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000001184 potassium carbonate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VVQDPBBEEQETOE-UHFFFAOYSA-N 2-ethyl-2-methyloxane Chemical compound CCC1(C)CCCCO1 VVQDPBBEEQETOE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N Diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 101700077614 URAD Proteins 0.000 description 1
- POXJOYYCYMCJGY-UHFFFAOYSA-N [2-(hydroxymethyl)oxetan-2-yl]methanol Chemical compound OCC1(CO)CCO1 POXJOYYCYMCJGY-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- FYIBPWZEZWVDQB-UHFFFAOYSA-N dicyclohexyl carbonate Chemical compound C1CCCCC1OC(=O)OC1CCCCC1 FYIBPWZEZWVDQB-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl N-phenylcarbamate Chemical compound CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- HIFJOEJCXUJQBO-UHFFFAOYSA-N sodium;cyclohexanolate Chemical compound [Na+].[O-]C1CCCCC1 HIFJOEJCXUJQBO-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0876316B1 (fr) | Procede de preparation de polyalcools | |
| DE2507461C3 (de) | Verfahren zur Herstellung von 2,2- Dimethylolalkanalen | |
| DE2523838A1 (de) | Verfahren zur herstellung von gemischen aus butandiol-(1,4) und 2-methylpropandiol-(1,3) | |
| DE1183899B (de) | Verfahren zur kontinuierlichen Herstellung von Glykolmonoestern | |
| EP0289921B1 (fr) | Procédé d'obtention de trialkylamines et du formiate de méthyle lors de la préparation de triméthylolalcanes | |
| WO2001051438A1 (fr) | Procede de preparation de trimethylolalcanes | |
| EP0897380A1 (fr) | PROCEDE DE PRODUCTION DE CETONES $g(g), $g(d)-INSATUREES PAR REACTION D'ALCOOLS ALLYLIQUES TERTIAIRES AVEC DES ETHERS D'ALCENYLALKYLE | |
| AT391691B (de) | Verfahren zur herstellung von kohlensaeureestern, die sich von ungesaettigten alkoholen und mehrwertigen alkoholen ableiten | |
| DE2928944A1 (de) | Verbessertes verfahren zur herstellung von hoeheren ungesaettigten ketonen | |
| EP0266690B1 (fr) | Procédé pour la fabrication d'esters de l'acide 3-chlorpropionique 2,2-disubstitué | |
| DEF0014527MA (fr) | ||
| EP0131860A2 (fr) | Procédé de production de monoesters purs de l'acide adipinique | |
| EP1216979A1 (fr) | Procédé de préparation de triméthylolalcanes et de l'acide formique | |
| EP0919532B1 (fr) | Procédé pour la préparation d'alcools saturés | |
| DE950850C (de) | Verfahren zur Herstellung von hydroxylgruppenhaltigen Trimethylenoxydverbindungen | |
| DE3422412A1 (de) | Verfahren zur herstellung eines gemisches aus einem gegebenenfalls substituierten zimtsaeureester und einem gegenbenenfalls substituierten ss-alkoxy-ss-phenyl-propionsaeureester sowie verfahren zur herstellung von gegebenenfalls substituierter zimtsaeure | |
| DE2523839A1 (de) | Cyclische acetalaldehyde und deren verwendung zur herstellung von diolen | |
| DE69806957T2 (de) | Vinylether derivate | |
| DE102019209233A1 (de) | Verfahren zur Herstellung eines β-Hydroxyketons | |
| DE69530229T2 (de) | Verfahren zur herstellung von 1,5-pentandiol-derivaten | |
| EP0182168B1 (fr) | Procédé de préparation d'esters de l'acide hydroxyméthylène-alcoxyacétique | |
| DE2818150C3 (de) | Verfahren zur Herstellung von terpenoiden Alkoholen bzw. deren Ameisensäureestern | |
| DE964044C (de) | Verfahren zur Herstellung von Alkenolen | |
| EP0866064A1 (fr) | Procédé amélioré de préparation de trifluorométhyloxirane | |
| EP0912544B1 (fr) | Procede de preparation de but-2-ene-1,4-dial-4-acetals 2-substitues et nouveaux hemi-acetals de glyoxalmonoacetals |