JP4956428B2 - Ｎ−ヒドロキシアルキル化アミドから（メタ）アクリレートを製造する接触法 - Google Patents

Ｎ−ヒドロキシアルキル化アミドから（メタ）アクリレートを製造する接触法 Download PDF

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Publication number: JP4956428B2
Authority: JP; Japan
Prior art keywords: urea; hydroxypropyl; meth; hydroxyethyl; species
Prior art date: 2004-07-29
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 - Fee Related

Application number

JP2007522958A

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English (en)

Japanese (ja)

Other versions

JP2008508205A (ja

JP2008508205A5 (ko

Inventor

ヘーファーフランク

ヘーリングディートマー

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date 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 date listed.)

2004-07-29

Filing date

2005-07-13

Publication date

2012-06-20

2004-07-29 Priority claimed from DE102004036930A external-priority patent/DE102004036930A1/de

2005-07-13 Application filed by BASF SE filed Critical BASF SE

2008-03-21 Publication of JP2008508205A publication Critical patent/JP2008508205A/ja

2012-03-08 Publication of JP2008508205A5 publication Critical patent/JP2008508205A5/ja

2012-06-20 Application granted granted Critical

2012-06-20 Publication of JP4956428B2 publication Critical patent/JP4956428B2/ja

Status Expired - Fee Related legal-status Critical Current

2025-07-13 Anticipated expiration legal-status Critical

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150000001408 amides Chemical class 0.000 title claims description 16
150000001252 acrylic acid derivatives Chemical class 0.000 title claims description 15
238000000034 method Methods 0.000 title claims description 13
230000008569 process Effects 0.000 title claims description 7
230000003197 catalytic effect Effects 0.000 title description 3
-1 hydroxypropyl Chemical group 0.000 claims description 161
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 27
238000005809 transesterification reaction Methods 0.000 claims description 24
102000004190 Enzymes Human genes 0.000 claims description 17
108090000790 Enzymes Proteins 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 14
239000002638 heterogeneous catalyst Substances 0.000 claims description 11
108090001060 Lipase Proteins 0.000 claims description 10
102000004882 Lipase Human genes 0.000 claims description 9
239000004367 Lipase Substances 0.000 claims description 9
235000019421 lipase Nutrition 0.000 claims description 9
239000012429 reaction media Substances 0.000 claims description 7
241000222120 Candida <Saccharomycetales> Species 0.000 claims description 6
229910017053 inorganic salt Inorganic materials 0.000 claims description 6
108090000371 Esterases Proteins 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
CLAHOZSYMRNIPY-UHFFFAOYSA-N 2-hydroxyethylurea Chemical compound NC(=O)NCCO CLAHOZSYMRNIPY-UHFFFAOYSA-N 0.000 claims description 3
VHEYHMGSWDZXEN-UHFFFAOYSA-N 2-hydroxypropylurea Chemical compound CC(O)CNC(N)=O VHEYHMGSWDZXEN-UHFFFAOYSA-N 0.000 claims description 3
DNPHEDNKXRMPAX-UHFFFAOYSA-N 3-hydroxypropylurea Chemical compound NC(=O)NCCCO DNPHEDNKXRMPAX-UHFFFAOYSA-N 0.000 claims description 3
108091005804 Peptidases Proteins 0.000 claims description 3
239000004365 Protease Substances 0.000 claims description 3
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 3
XOIAIDITJQAORS-UHFFFAOYSA-N 1,1-dibutyl-3-(2-hydroxyethyl)urea Chemical compound CCCCN(CCCC)C(=O)NCCO XOIAIDITJQAORS-UHFFFAOYSA-N 0.000 claims description 2
LGLUBDUVOUGKEI-UHFFFAOYSA-N 1,1-dibutyl-3-(2-hydroxypropyl)urea Chemical compound CCCCN(CCCC)C(=O)NCC(C)O LGLUBDUVOUGKEI-UHFFFAOYSA-N 0.000 claims description 2
KSDUDEOLYZWKPC-UHFFFAOYSA-N 1,1-diethyl-3-(2-hydroxyethyl)urea Chemical compound CCN(CC)C(=O)NCCO KSDUDEOLYZWKPC-UHFFFAOYSA-N 0.000 claims description 2
QJCLKJUKXGZKII-UHFFFAOYSA-N 1,1-diethyl-3-(2-hydroxypropyl)urea Chemical compound CCN(CC)C(=O)NCC(C)O QJCLKJUKXGZKII-UHFFFAOYSA-N 0.000 claims description 2
FUBUFOFJOAOOGC-UHFFFAOYSA-N 1,1-diethyl-3-(3-hydroxypropyl)urea Chemical compound CCN(CC)C(=O)NCCCO FUBUFOFJOAOOGC-UHFFFAOYSA-N 0.000 claims description 2
VVBPOTSWEHWZRG-UHFFFAOYSA-N 1-(2-hydroxyethyl)-1,3-diazinane-2,4-dione Chemical compound OCCN1CCC(=O)NC1=O VVBPOTSWEHWZRG-UHFFFAOYSA-N 0.000 claims description 2
NUBXHOAFDQNYTN-UHFFFAOYSA-N 1-(2-hydroxyethyl)imidazolidine-2,4-dione Chemical compound OCCN1CC(=O)NC1=O NUBXHOAFDQNYTN-UHFFFAOYSA-N 0.000 claims description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
CZLBNWYGPWGFEF-UHFFFAOYSA-N 3-(2-hydroxyethyl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NCCO CZLBNWYGPWGFEF-UHFFFAOYSA-N 0.000 claims description 2
CBBPPTNMRXEOMD-UHFFFAOYSA-N 3-(2-hydroxypropyl)-1,1-dimethylurea Chemical compound CC(O)CNC(=O)N(C)C CBBPPTNMRXEOMD-UHFFFAOYSA-N 0.000 claims description 2
JMYOLCDBCNCJPC-UHFFFAOYSA-N 3-(3-hydroxypropyl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NCCCO JMYOLCDBCNCJPC-UHFFFAOYSA-N 0.000 claims description 2
241000588986 Alcaligenes Species 0.000 claims description 2
241000228212 Aspergillus Species 0.000 claims description 2
241001453380 Burkholderia Species 0.000 claims description 2
241000255925 Diptera Species 0.000 claims description 2
241000159512 Geotrichum Species 0.000 claims description 2
229910018119 Li 3 PO 4 Inorganic materials 0.000 claims description 2
241000235395 Mucor Species 0.000 claims description 2
241000228143 Penicillium Species 0.000 claims description 2
241000589516 Pseudomonas Species 0.000 claims description 2
241000235527 Rhizopus Species 0.000 claims description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
239000004202 carbamide Substances 0.000 claims description 2
150000004677 hydrates Chemical class 0.000 claims description 2
210000000496 pancreas Anatomy 0.000 claims description 2
241000894007 species Species 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 description 47
230000032050 esterification Effects 0.000 description 20
238000005886 esterification reaction Methods 0.000 description 20
239000000047 product Substances 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 14
229910052760 oxygen Inorganic materials 0.000 description 14
239000001301 oxygen Substances 0.000 description 14
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 13
239000003054 catalyst Substances 0.000 description 11
125000000217 alkyl group Chemical group 0.000 description 10
125000004434 sulfur atom Chemical group 0.000 description 10
125000001841 imino group Chemical group [H]N=* 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
150000001875 compounds Chemical class 0.000 description 8
125000000623 heterocyclic group Chemical group 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
238000000926 separation method Methods 0.000 description 8
239000001257 hydrogen Substances 0.000 description 7
229910052739 hydrogen Inorganic materials 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
125000004104 aryloxy group Chemical group 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
238000004821 distillation Methods 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
125000005842 heteroatom Chemical group 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
241001550224 Apha Species 0.000 description 5
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000007789 gas Substances 0.000 description 5
150000002431 hydrogen Chemical class 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
239000000203 mixture Substances 0.000 description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
229910019142 PO4 Inorganic materials 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
239000002585 base Substances 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
235000021317 phosphate Nutrition 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
238000005406 washing Methods 0.000 description 4
238000010626 work up procedure Methods 0.000 description 4
125000005838 1,3-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[*:1] 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
FFYWKOUKJFCBAM-UHFFFAOYSA-N ethenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC=C FFYWKOUKJFCBAM-UHFFFAOYSA-N 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
239000012528 membrane Substances 0.000 description 3
239000002808 molecular sieve Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000002829 nitrogen Chemical class 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
125000005837 1,2-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([*:2])C1([H])[H] 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
HBAIZGPCSAAFSU-UHFFFAOYSA-N 1-(2-hydroxyethyl)imidazolidin-2-one Chemical compound OCCN1CCNC1=O HBAIZGPCSAAFSU-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
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150000001298 alcohols Chemical class 0.000 description 2
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150000001340 alkali metals Chemical class 0.000 description 2
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230000015572 biosynthetic process Effects 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
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150000004649 carbonic acid derivatives Chemical class 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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238000010908 decantation Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
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239000000178 monomer Substances 0.000 description 2
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125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
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238000000746 purification Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
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239000011593 sulfur Substances 0.000 description 2
239000010936 titanium Substances 0.000 description 2
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125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
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CVLZIMQQVZWUSW-UHFFFAOYSA-N 1,1-dibutyl-3-(3-hydroxypropyl)urea Chemical compound CCCCN(CCCC)C(=O)NCCCO CVLZIMQQVZWUSW-UHFFFAOYSA-N 0.000 description 1
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
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125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000006017 1-propenyl group Chemical group 0.000 description 1
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SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
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GZEXHGDBYMTBCP-UHFFFAOYSA-N 2-carbamoyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(N)=O GZEXHGDBYMTBCP-UHFFFAOYSA-N 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
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125000006040 2-hexenyl group Chemical group 0.000 description 1
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AMDLSVKFPKDTIX-UHFFFAOYSA-N 2-methyl-3-[2-(2-oxoimidazolidin-1-yl)ethoxy]propanoic acid Chemical compound OC(=O)C(C)COCCN1CCNC1=O AMDLSVKFPKDTIX-UHFFFAOYSA-N 0.000 description 1
UZXXTFCFLINECE-UHFFFAOYSA-N 2-methyl-3-[3-[2-(2-methylprop-2-enoylamino)ethyl]-2-oxoimidazolidin-1-yl]propanoic acid Chemical compound OC(=O)C(C)CN1CCN(CCNC(=O)C(C)=C)C1=O UZXXTFCFLINECE-UHFFFAOYSA-N 0.000 description 1
LVPNWEZYTJFBTO-UHFFFAOYSA-N 2-methyl-n-[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]prop-2-enamide Chemical compound CC(=C)C(=O)NCCN1CCOC1=O LVPNWEZYTJFBTO-UHFFFAOYSA-N 0.000 description 1
ZKBUDNROQIMUQD-UHFFFAOYSA-N 2-methyl-n-[2-[3-(2-methylprop-2-enoyl)-2-oxoimidazolidin-1-yl]ethyl]prop-2-enamide Chemical compound CC(=C)C(=O)NCCN1CCN(C(=O)C(C)=C)C1=O ZKBUDNROQIMUQD-UHFFFAOYSA-N 0.000 description 1
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
GOXNUYXRIQJIEF-UHFFFAOYSA-N 3-(2-hydroxyethyl)-1,3-oxazolidin-2-one Chemical compound OCCN1CCOC1=O GOXNUYXRIQJIEF-UHFFFAOYSA-N 0.000 description 1
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SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
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QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
229910052684 Cerium Inorganic materials 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
239000004971 Cross linker Substances 0.000 description 1
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102100031375 Endothelial lipase Human genes 0.000 description 1
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FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 1
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ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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230000009471 action Effects 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910000318 alkali metal phosphate Inorganic materials 0.000 description 1
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150000001342 alkaline earth metals Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
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238000010533 azeotropic distillation Methods 0.000 description 1
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238000000576 coating method Methods 0.000 description 1
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NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
239000001177 diphosphate Substances 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical class [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
235000011180 diphosphates Nutrition 0.000 description 1
125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000011043 electrofiltration Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004688 heptahydrates Chemical class 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000004690 nonahydrates Chemical class 0.000 description 1
125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
238000005373 pervaporation Methods 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
229950000688 phenothiazine Drugs 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
150000003017 phosphorus Chemical class 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000001205 polyphosphate Substances 0.000 description 1
235000011176 polyphosphates Nutrition 0.000 description 1
239000011148 porous material Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
125000001725 pyrenyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
230000005855 radiation Effects 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
239000001226 triphosphate Substances 0.000 description 1
235000011178 triphosphate Nutrition 0.000 description 1
125000002264 triphosphate group Chemical class [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 description 1
125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1
125000006839 xylylene group Chemical group 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/02—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of urea, its salts, complexes or addition compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D231/08—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with oxygen or sulfur atoms directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/16—Hydrolases (3) acting on ester bonds (3.1)

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Zoology (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Wood Science & Technology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Microbiology (AREA)
Biotechnology (AREA)
Biomedical Technology (AREA)
Polymers & Plastics (AREA)
Molecular Biology (AREA)
Chemical Kinetics & Catalysis (AREA)
Biochemistry (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

JP2007522958A 2004-07-29 2005-07-13 Ｎ−ヒドロキシアルキル化アミドから（メタ）アクリレートを製造する接触法 Expired - Fee Related JP4956428B2 (ja)

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DE102004036930.5		2004-07-29
DE102004036930A DE102004036930A1 (de)	2004-07-29	2004-07-29	Katalysiertes Verfahren zur Herstellung von(Meth)acrylaten von N-hydroxyalkylierten Amiden
US67966505P	2005-05-11	2005-05-11
US60/679,665		2005-05-11
PCT/EP2005/007576 WO2006012980A1 (de)	2004-07-29	2005-07-13	Katalysiertes verfahren zur herstellung von (meth)acrylaten von n-hydroxyalkylierten amiden

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JP2008508205A JP2008508205A (ja)	2008-03-21
JP2008508205A5 JP2008508205A5 (ko)	2012-03-08
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JP (1)	JP4956428B2 (ko)
KR (1)	KR20070047328A (ko)
BR (1)	BRPI0513778B1 (ko)
RU (1)	RU2415133C2 (ko)
SG (1)	SG155168A1 (ko)
TW (1)	TWI363052B (ko)

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WO2013004767A1 (de) *	2011-07-06	2013-01-10	Basf Se	Verfahren zur herstellung von (meth)acrylsäureestern
RU2515247C1 (ru) *	2013-01-25	2014-05-10	Федеральное государственное бюджетное учреждение науки Институт органической и физической химии им. А.Е. Арбузова Казанского научного центра Российской академии наук	Средство, стимулирующее физическую работоспособность

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US2871223A (en) *	1954-11-01	1959-01-27	Rohm & Haas	Polymers, copolymers, and processes for preparing them
JPH0651663B2 (ja) *	1986-02-10	1994-07-06	三井東圧化学株式会社	アクリル酸またはメタクリル酸のアルキルアミノアルキルエステルの製造方法
US4777265A (en) *	1986-03-11	1988-10-11	Basf Aktiengesellschaft	Preparation of acrylates and methacrylates
JPH0651664B2 (ja) *	1986-04-01	1994-07-06	三井東圧化学株式会社	アクリル酸またはメタクリル酸のアルキルアミノアルキルエステルの製造方法
DE10257094A1 (de) *	2002-12-05	2004-06-24	Basf Ag	Enzymatische Herstellung urethangruppenhaltiger (Meth)acrylsäureester

2005
- 2005-07-13 SG SG200905074-1A patent/SG155168A1/en unknown
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- 2005-07-13 KR KR1020077004632A patent/KR20070047328A/ko active Search and Examination
- 2005-07-13 BR BRPI0513778A patent/BRPI0513778B1/pt not_active IP Right Cessation
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JP2008508205A (ja)	2008-03-21
RU2415133C2 (ru)	2011-03-27
TWI363052B (en)	2012-05-01
BRPI0513778A (pt)	2008-05-13
SG155168A1 (en)	2009-09-30
BRPI0513778B1 (pt)	2015-11-24
RU2007107176A (ru)	2008-09-10
KR20070047328A (ko)	2007-05-04
TW200615380A (en)	2006-05-16

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