BE491986A - - Google Patents

Info

Publication number

BE491986A

BE491986A BE491986DA BE491986A BE 491986 A BE491986 A BE 491986A BE 491986D A BE491986D A BE 491986DA BE 491986 A BE491986 A BE 491986A

Authority

BE

Belgium

Prior art keywords

water

temperature

acid

ester

mixture

Prior art date

Links

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• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 57
• MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 claims description 23
• 239000000178 monomer Substances 0.000 claims description 22
• 230000032050 esterification Effects 0.000 claims description 20
• 238000005886 esterification reaction Methods 0.000 claims description 20
• 238000006243 chemical reaction Methods 0.000 claims description 19
• FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 18
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
• 239000004327 boric acid Substances 0.000 claims description 16
• 239000000203 mixture Substances 0.000 claims description 16
• 150000002148 esters Chemical class 0.000 claims description 14
• 238000000034 method Methods 0.000 claims description 14
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
• -1 boric acid ester Chemical class 0.000 claims description 12
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
• 239000002253 acid Substances 0.000 claims description 10
• 238000004821 distillation Methods 0.000 claims description 9
• 238000010992 reflux Methods 0.000 claims description 9
• XDVOLDOITVSJGL-UHFFFAOYSA-N 3,7-dihydroxy-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound O1B(O)OB2OB(O)OB1O2 XDVOLDOITVSJGL-UHFFFAOYSA-N 0.000 claims description 8
• 239000013078 crystal Substances 0.000 claims description 8
• 238000000926 separation method Methods 0.000 claims description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
• KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 7
• JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims description 7
• 239000002609 medium Substances 0.000 claims description 5
• 238000002360 preparation method Methods 0.000 claims description 5
• 239000000126 substance Substances 0.000 claims description 5
• 238000005406 washing Methods 0.000 claims description 5
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
• 238000010438 heat treatment Methods 0.000 claims description 4
• 239000002002 slurry Substances 0.000 claims description 4
• 238000001256 steam distillation Methods 0.000 claims description 4
• 150000001408 amides Chemical class 0.000 claims description 3
• 238000001816 cooling Methods 0.000 claims description 3
• 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
• 150000008064 anhydrides Chemical class 0.000 claims description 2
• 239000012736 aqueous medium Substances 0.000 claims description 2
• 238000001914 filtration Methods 0.000 claims description 2
• 238000005194 fractionation Methods 0.000 claims description 2
• 238000007710 freezing Methods 0.000 claims description 2
• 230000008014 freezing Effects 0.000 claims description 2
• 125000002560 nitrile group Chemical group 0.000 claims description 2
• 230000001476 alcoholic effect Effects 0.000 claims 1
• 150000001298 alcohols Chemical class 0.000 claims 1
• 239000007795 chemical reaction product Substances 0.000 claims 1
• 230000007062 hydrolysis Effects 0.000 claims 1
• 238000006460 hydrolysis reaction Methods 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
• 239000000047 product Substances 0.000 description 23
• VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 17
• 230000015572 biosynthetic process Effects 0.000 description 8
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
• 239000012452 mother liquor Substances 0.000 description 5
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
• 150000001875 compounds Chemical class 0.000 description 4
• 238000000354 decomposition reaction Methods 0.000 description 4
• 230000009466 transformation Effects 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
• 239000002994 raw material Substances 0.000 description 3
• 239000011541 reaction mixture Substances 0.000 description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
• CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• 229910052802 copper Inorganic materials 0.000 description 2
• 239000010949 copper Substances 0.000 description 2
• LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
• 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
• 238000011403 purification operation Methods 0.000 description 2
• 238000007086 side reaction Methods 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 1
• 239000005997 Calcium carbide Substances 0.000 description 1
• 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 238000010533 azeotropic distillation Methods 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• 238000003763 carbonization Methods 0.000 description 1
• 238000005119 centrifugation Methods 0.000 description 1
• 230000001010 compromised effect Effects 0.000 description 1
• 239000013505 freshwater Substances 0.000 description 1
• 239000011521 glass Substances 0.000 description 1
• 239000011872 intimate mixture Substances 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 150000004702 methyl esters Chemical class 0.000 description 1
• 239000004926 polymethyl methacrylate Substances 0.000 description 1
• 229910052938 sodium sulfate Inorganic materials 0.000 description 1
• 235000011152 sodium sulphate Nutrition 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• CLZWAWBPWVRRGI-UHFFFAOYSA-N tert-butyl 2-[2-[2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-5-bromophenoxy]ethoxy]-4-methyl-n-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]anilino]acetate Chemical compound CC1=CC=C(N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)C(OCCOC=2C(=CC=C(Br)C=2)N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)=C1 CLZWAWBPWVRRGI-UHFFFAOYSA-N 0.000 description 1
• 238000005292 vacuum distillation Methods 0.000 description 1