BE481236A - - Google Patents

Info

Publication number

BE481236A

BE481236A BE481236DA BE481236A BE 481236 A BE481236 A BE 481236A BE 481236D A BE481236D A BE 481236DA BE 481236 A BE481236 A BE 481236A

Authority

BE

Belgium

Prior art keywords

fractionation column

esterification

azeotrope

sep

alcohol

Prior art date

Links

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• 238000005886 esterification reaction Methods 0.000 claims description 29
• 230000032050 esterification Effects 0.000 claims description 23
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
• 238000006243 chemical reaction Methods 0.000 claims description 18
• 238000005194 fractionation Methods 0.000 claims description 18
• 150000002148 esters Chemical class 0.000 claims description 17
• 239000012071 phase Substances 0.000 claims description 17
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
• ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 9
• 239000003795 chemical substances by application Substances 0.000 claims description 9
• 239000002253 acid Substances 0.000 claims description 7
• QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims description 7
• 239000007788 liquid Substances 0.000 claims description 7
• 239000004641 Diallyl-phthalate Substances 0.000 claims description 6
• 150000001298 alcohols Chemical class 0.000 claims description 5
• 239000003153 chemical reaction reagent Substances 0.000 claims description 5
• 238000000034 method Methods 0.000 claims description 5
• 150000008064 anhydrides Chemical class 0.000 claims description 4
• 238000002360 preparation method Methods 0.000 claims description 4
• UIYHUUARNKRKGV-UHFFFAOYSA-N 2-prop-2-enoxycarbonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OCC=C UIYHUUARNKRKGV-UHFFFAOYSA-N 0.000 claims description 3
• -1 allyl anhydride Chemical class 0.000 claims description 3
• 239000007791 liquid phase Substances 0.000 claims description 3
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
• XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 24
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
• XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 4
• JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• 238000009835 boiling Methods 0.000 description 3
• 239000000919 ceramic Substances 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 3
• 239000000203 mixture Substances 0.000 description 3
• 230000005587 bubbling Effects 0.000 description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
• 239000000376 reactant Substances 0.000 description 2
• 238000010992 reflux Methods 0.000 description 2
• 230000002441 reversible effect Effects 0.000 description 2
• DUKJZYZDOKKAMU-UHFFFAOYSA-N 1-chloronaphthalene-2-carbaldehyde Chemical compound C1=CC=C2C(Cl)=C(C=O)C=CC2=C1 DUKJZYZDOKKAMU-UHFFFAOYSA-N 0.000 description 1
• 230000001174 ascending effect Effects 0.000 description 1
• 125000004432 carbon atom Chemical group C* 0.000 description 1
• 239000003054 catalyst Substances 0.000 description 1
• 150000001875 compounds Chemical class 0.000 description 1
• 230000008021 deposition Effects 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• 230000029142 excretion Effects 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 238000009434 installation Methods 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 150000002689 maleic acids Chemical class 0.000 description 1
• 150000002691 malonic acids Chemical class 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 238000012856 packing Methods 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000002994 raw material Substances 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 235000011149 sulphuric acid Nutrition 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 239000008096 xylene Substances 0.000 description 1
• 150000003738 xylenes Chemical class 0.000 description 1