JPH0460699B2 - - Google Patents
Info
- Publication number
- JPH0460699B2 JPH0460699B2 JP59032513A JP3251384A JPH0460699B2 JP H0460699 B2 JPH0460699 B2 JP H0460699B2 JP 59032513 A JP59032513 A JP 59032513A JP 3251384 A JP3251384 A JP 3251384A JP H0460699 B2 JPH0460699 B2 JP H0460699B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- catalyst
- glycidate
- mmol
- 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.)
- Expired - Lifetime
Links
- 239000003054 catalyst Substances 0.000 claims description 111
- -1 glycidic acid ester Chemical class 0.000 claims description 82
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 81
- 238000006317 isomerization reaction Methods 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 201
- 238000006243 chemical reaction Methods 0.000 description 125
- 239000002904 solvent Substances 0.000 description 116
- 239000002994 raw material Substances 0.000 description 108
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 103
- 230000035484 reaction time Effects 0.000 description 90
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 87
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
- YKNYRRVISWJDSR-UHFFFAOYSA-N methyl oxirane-2-carboxylate Chemical compound COC(=O)C1CO1 YKNYRRVISWJDSR-UHFFFAOYSA-N 0.000 description 27
- 229910020366 ClO 4 Inorganic materials 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000002253 acid Substances 0.000 description 21
- 229910052763 palladium Inorganic materials 0.000 description 21
- 238000000034 method Methods 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 16
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 15
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000010948 rhodium Substances 0.000 description 12
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 11
- 239000011701 zinc Substances 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical class OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002841 Lewis acid Substances 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 150000007517 lewis acids Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- HAFFKTJSQPQAPC-UHFFFAOYSA-N methyl 3-phenyloxirane-2-carboxylate Chemical compound COC(=O)C1OC1C1=CC=CC=C1 HAFFKTJSQPQAPC-UHFFFAOYSA-N 0.000 description 5
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 3
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000005595 acetylacetonate group Chemical group 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- KAOSFPBSWNREAY-UHFFFAOYSA-N methyl 2-oxo-3-phenylpropanoate Chemical compound COC(=O)C(=O)CC1=CC=CC=C1 KAOSFPBSWNREAY-UHFFFAOYSA-N 0.000 description 3
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- KXXIUSPPIOSKAZ-UHFFFAOYSA-N 2-hydroxy-2,3-dimethylbut-3-enoic acid Chemical compound CC(=C)C(C)(O)C(O)=O KXXIUSPPIOSKAZ-UHFFFAOYSA-N 0.000 description 2
- UWJHQSIQXLYZJB-UHFFFAOYSA-N 3-(8-methoxycycloocten-1-yl)cycloocta-1,5-diene Chemical compound COC1CCCCCC=C1C1CC=CCCC=C1 UWJHQSIQXLYZJB-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- RLTPXEAFDJVHSN-UHFFFAOYSA-N 4-(trifluoromethyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 RLTPXEAFDJVHSN-UHFFFAOYSA-N 0.000 description 2
- 101710134784 Agnoprotein Proteins 0.000 description 2
- ICNJODGWVRXUTM-UHFFFAOYSA-N C1C=C2C=CC=CC2=CC1(C)C1(C(=O)OC)CO1 Chemical compound C1C=C2C=CC=CC2=CC1(C)C1(C(=O)OC)CO1 ICNJODGWVRXUTM-UHFFFAOYSA-N 0.000 description 2
- OUUZMZBGOVTGCJ-UHFFFAOYSA-N C1NC2=CC=CC=C2C1(C)C1(C(=O)OC)CO1 Chemical compound C1NC2=CC=CC=C2C1(C)C1(C(=O)OC)CO1 OUUZMZBGOVTGCJ-UHFFFAOYSA-N 0.000 description 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FYGNJYLXDRROPN-UHFFFAOYSA-N [2-(4-phenylmethoxyphenyl)-1,3-thiazol-4-yl]methanamine Chemical compound NCC1=CSC(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=N1 FYGNJYLXDRROPN-UHFFFAOYSA-N 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BTNMPGBKDVTSJY-UHFFFAOYSA-N keto-phenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-N 0.000 description 2
- 239000005453 ketone based solvent Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- LYNWTSVFQIMZAY-UHFFFAOYSA-N methyl 2-(cyclopenten-1-yl)-2-hydroxyacetate Chemical compound COC(=O)C(O)C1=CCCC1 LYNWTSVFQIMZAY-UHFFFAOYSA-N 0.000 description 2
- BKBOOXDDXOBIBG-UHFFFAOYSA-N methyl 2-hydroxy-3-naphthalen-2-ylbut-3-enoate Chemical compound C1=CC=CC2=CC(C(=C)C(O)C(=O)OC)=CC=C21 BKBOOXDDXOBIBG-UHFFFAOYSA-N 0.000 description 2
- VRHSFVNLFOJOQT-UHFFFAOYSA-N methyl 2-hydroxy-3-phenylbut-3-enoate Chemical compound COC(=O)C(O)C(=C)C1=CC=CC=C1 VRHSFVNLFOJOQT-UHFFFAOYSA-N 0.000 description 2
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- RXBXBWBHKPGHIB-UHFFFAOYSA-L zinc;diperchlorate Chemical compound [Zn+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O RXBXBWBHKPGHIB-UHFFFAOYSA-L 0.000 description 2
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- AKFXQYMORAUSBD-UHFFFAOYSA-N 1-chloro-3-methylpyrido[1,2-a]benzimidazole-4-carbonitrile Chemical compound C12=CC=CC=C2N=C2N1C(Cl)=CC(C)=C2C#N AKFXQYMORAUSBD-UHFFFAOYSA-N 0.000 description 1
- WHQOKFZWSDOTQP-UHFFFAOYSA-N 2,3-dihydroxypropyl 4-aminobenzoate Chemical compound NC1=CC=C(C(=O)OCC(O)CO)C=C1 WHQOKFZWSDOTQP-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- XGTUCPXTUCGASU-UHFFFAOYSA-N 2-hydroxy-3-[4-(2-methylpropyl)phenyl]but-3-enoic acid Chemical compound CC(C)CC1=CC=C(C(=C)C(O)C(O)=O)C=C1 XGTUCPXTUCGASU-UHFFFAOYSA-N 0.000 description 1
- VBWPSWWDYVWZKA-UHFFFAOYSA-N 2-hydroxybut-3-enoic acid Chemical class C=CC(O)C(O)=O VBWPSWWDYVWZKA-UHFFFAOYSA-N 0.000 description 1
- 239000001903 2-oxo-3-phenylpropanoic acid Substances 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- RBWNDBNSJFCLBZ-UHFFFAOYSA-N 7-methyl-5,6,7,8-tetrahydro-3h-[1]benzothiolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CNC(=S)C2=C1SC1=C2CCC(C)C1 RBWNDBNSJFCLBZ-UHFFFAOYSA-N 0.000 description 1
- CPOTUIZHRVJVTN-UHFFFAOYSA-N C1CCCCC1C1(C(=O)OC)CO1 Chemical compound C1CCCCC1C1(C(=O)OC)CO1 CPOTUIZHRVJVTN-UHFFFAOYSA-N 0.000 description 1
- JKWOPESHWSJONJ-UHFFFAOYSA-N CCCCCC(CC)C1(C(=O)OC)CO1 Chemical compound CCCCCC(CC)C1(C(=O)OC)CO1 JKWOPESHWSJONJ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- SCMDKDGVHDAFGO-UHFFFAOYSA-M Cl(=O)(=O)(=O)[O-].C1(C=CC=C1)[Co+]C1C=CC=C1 Chemical compound Cl(=O)(=O)(=O)[O-].C1(C=CC=C1)[Co+]C1C=CC=C1 SCMDKDGVHDAFGO-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- MPCRDALPQLDDFX-UHFFFAOYSA-L Magnesium perchlorate Chemical compound [Mg+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O MPCRDALPQLDDFX-UHFFFAOYSA-L 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- LCTONWCANYUPML-UHFFFAOYSA-N PYRUVIC-ACID Natural products CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- DEDGUGJNLNLJSR-UHFFFAOYSA-N alpha-hydroxycinnamic acid Natural products OC(=O)C(O)=CC1=CC=CC=C1 DEDGUGJNLNLJSR-UHFFFAOYSA-N 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- OOULUYZFLXDWDQ-UHFFFAOYSA-L barium perchlorate Chemical compound [Ba+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O OOULUYZFLXDWDQ-UHFFFAOYSA-L 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- PSIBWKDABMPMJN-UHFFFAOYSA-L cadmium(2+);diperchlorate Chemical compound [Cd+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O PSIBWKDABMPMJN-UHFFFAOYSA-L 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 229910001914 chlorine tetroxide Inorganic materials 0.000 description 1
- CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- QVMDWPVVFYBRQY-UHFFFAOYSA-K cycloocta-1,5-diene;rhodium(3+);trifluoromethanesulfonate Chemical compound [Rh+3].C1CC=CCCC=C1.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F QVMDWPVVFYBRQY-UHFFFAOYSA-K 0.000 description 1
- KDUIUFJBNGTBMD-VXMYFEMYSA-N cyclooctatetraene Chemical compound C1=C\C=C/C=C\C=C1 KDUIUFJBNGTBMD-VXMYFEMYSA-N 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- ACQFOMVLRAEQCK-UHFFFAOYSA-N ethyl 2-hydroxy-3-methylbut-3-enoate Chemical compound CCOC(=O)C(O)C(C)=C ACQFOMVLRAEQCK-UHFFFAOYSA-N 0.000 description 1
- NCAODUGFMUTPCD-UHFFFAOYSA-N ethyl 2-hydroxy-3-methylideneheptanoate Chemical compound CCCCC(=C)C(O)C(=O)OCC NCAODUGFMUTPCD-UHFFFAOYSA-N 0.000 description 1
- CLRHEGMAWYPMJF-UHFFFAOYSA-N ethyl 2-oxo-3-phenylpropanoate Chemical compound CCOC(=O)C(=O)CC1=CC=CC=C1 CLRHEGMAWYPMJF-UHFFFAOYSA-N 0.000 description 1
- SSYWONPQBLHLSL-UHFFFAOYSA-N ethyl 3-(4-chlorophenyl)-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CC1=CC=C(Cl)C=C1 SSYWONPQBLHLSL-UHFFFAOYSA-N 0.000 description 1
- MOTXKEQQXJIDHO-UHFFFAOYSA-N ethyl hept-3-enoate Chemical compound CCCC=CCC(=O)OCC MOTXKEQQXJIDHO-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- LHOWRPZTCLUDOI-UHFFFAOYSA-K iron(3+);triperchlorate Chemical compound [Fe+3].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O LHOWRPZTCLUDOI-UHFFFAOYSA-K 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
- 229910052749 magnesium Inorganic materials 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- BPEHDTJAUHYENC-UHFFFAOYSA-N methyl 1-methyl-7-oxabicyclo[4.1.0]heptane-6-carboxylate Chemical compound C1CCCC2(C)OC21C(=O)OC BPEHDTJAUHYENC-UHFFFAOYSA-N 0.000 description 1
- HNMZJPRASCDUMF-UHFFFAOYSA-N methyl 2-(3-methyloctan-3-yl)oxirane-2-carboxylate Chemical compound CCCCCC(C)(CC)C1(C(=O)OC)CO1 HNMZJPRASCDUMF-UHFFFAOYSA-N 0.000 description 1
- XBRKXWZJLVZFLC-UHFFFAOYSA-N methyl 2-(cyclohexen-1-yl)-2-hydroxypropanoate Chemical compound COC(=O)C(C)(O)C1=CCCCC1 XBRKXWZJLVZFLC-UHFFFAOYSA-N 0.000 description 1
- AHVSUSBOVBQTHO-UHFFFAOYSA-N methyl 2-hydroxy-2-methyl-3-phenylbut-3-enoate Chemical compound COC(=O)C(C)(O)C(=C)C1=CC=CC=C1 AHVSUSBOVBQTHO-UHFFFAOYSA-N 0.000 description 1
- DKZSQWFWHJRSPG-UHFFFAOYSA-N methyl 2-hydroxy-3-(2-phenylphenyl)but-3-enoate Chemical compound COC(=O)C(O)C(=C)C1=CC=CC=C1C1=CC=CC=C1 DKZSQWFWHJRSPG-UHFFFAOYSA-N 0.000 description 1
- LUWZNHVVJBMDIR-UHFFFAOYSA-N methyl 2-hydroxy-3-(4-methoxyphenyl)but-3-enoate Chemical compound COC(=O)C(O)C(=C)C1=CC=C(OC)C=C1 LUWZNHVVJBMDIR-UHFFFAOYSA-N 0.000 description 1
- BBDUQKILRWOXAB-UHFFFAOYSA-N methyl 2-hydroxy-3-[4-(2-methylpropyl)phenyl]but-3-enoate Chemical compound COC(=O)C(O)C(=C)C1=CC=C(CC(C)C)C=C1 BBDUQKILRWOXAB-UHFFFAOYSA-N 0.000 description 1
- CWBNCNKOFGYUKG-UHFFFAOYSA-N methyl 2-oxo-3-phenylbutanoate Chemical compound COC(=O)C(=O)C(C)C1=CC=CC=C1 CWBNCNKOFGYUKG-UHFFFAOYSA-N 0.000 description 1
- NAQGOYHXFOHGHQ-UHFFFAOYSA-N methyl 3,3-dimethyloxirane-2-carboxylate Chemical compound COC(=O)C1OC1(C)C NAQGOYHXFOHGHQ-UHFFFAOYSA-N 0.000 description 1
- KTZQZXHMJMSACN-UHFFFAOYSA-N methyl 3-(4-chlorophenyl)-2-oxopropanoate Chemical compound COC(=O)C(=O)CC1=CC=C(Cl)C=C1 KTZQZXHMJMSACN-UHFFFAOYSA-N 0.000 description 1
- DGVONDNWBZZHGC-UHFFFAOYSA-N methyl 3-(4-cyclohexylphenyl)-2-hydroxybut-3-enoate Chemical compound C1=CC(C(=C)C(O)C(=O)OC)=CC=C1C1CCCCC1 DGVONDNWBZZHGC-UHFFFAOYSA-N 0.000 description 1
- GFWPXDAMKQTSQT-UHFFFAOYSA-N methyl 3-(4-ethylphenyl)-2-oxopropanoate Chemical compound CCC1=CC=C(CC(=O)C(=O)OC)C=C1 GFWPXDAMKQTSQT-UHFFFAOYSA-N 0.000 description 1
- VWQIOSBFCOHUTH-UHFFFAOYSA-N methyl 3-(4-methoxyphenyl)-2-oxobutanoate Chemical compound COC(=O)C(=O)C(C)C1=CC=C(OC)C=C1 VWQIOSBFCOHUTH-UHFFFAOYSA-N 0.000 description 1
- HLXOGWSIWXWMDU-UHFFFAOYSA-N methyl 3-(4-methylphenyl)-2-oxobutanoate Chemical compound COC(=O)C(=O)C(C)C1=CC=C(C)C=C1 HLXOGWSIWXWMDU-UHFFFAOYSA-N 0.000 description 1
- NCBDLVJLYPGXTR-UHFFFAOYSA-N methyl 3-(4-methylphenyl)-2-oxopropanoate Chemical compound COC(=O)C(=O)CC1=CC=C(C)C=C1 NCBDLVJLYPGXTR-UHFFFAOYSA-N 0.000 description 1
- TZIVIEDKXIVYAY-UHFFFAOYSA-N methyl 3-[4-(2-methylpropyl)phenyl]-2-oxobutanoate Chemical compound COC(=O)C(=O)C(C)C1=CC=C(CC(C)C)C=C1 TZIVIEDKXIVYAY-UHFFFAOYSA-N 0.000 description 1
- AJMGIOJRUFPGTD-UHFFFAOYSA-N methyl 7-oxabicyclo[4.1.0]heptane-6-carboxylate Chemical compound C1CCCC2OC21C(=O)OC AJMGIOJRUFPGTD-UHFFFAOYSA-N 0.000 description 1
- GITITJADGZYSRL-UHFFFAOYSA-N methyl but-3-enoate Chemical compound COC(=O)CC=C GITITJADGZYSRL-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000001475 oxazolidinediones Chemical class 0.000 description 1
- HSAJRDKFYZAGLU-UHFFFAOYSA-M perchloryloxymercury Chemical compound [Hg+].[O-]Cl(=O)(=O)=O HSAJRDKFYZAGLU-UHFFFAOYSA-M 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 229960005190 phenylalanine Drugs 0.000 description 1
- YOKQMKAKDHBIID-UHFFFAOYSA-L platinum(2+);trifluoromethanesulfonate Chemical compound [Pt+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F YOKQMKAKDHBIID-UHFFFAOYSA-L 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940076788 pyruvate Drugs 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- HGYUMUDYLWGCJK-UHFFFAOYSA-K rhodium(3+);trifluoromethanesulfonate Chemical compound [Rh+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HGYUMUDYLWGCJK-UHFFFAOYSA-K 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- SLXXHLHFINYNPJ-UHFFFAOYSA-M silver;4-(trifluoromethyl)benzenesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 SLXXHLHFINYNPJ-UHFFFAOYSA-M 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- UZPUXLRDLVOKTB-UHFFFAOYSA-N trifluoromethyl benzenesulfonate Chemical compound FC(F)(F)OS(=O)(=O)C1=CC=CC=C1 UZPUXLRDLVOKTB-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59032513A JPS60179147A (ja) | 1984-02-24 | 1984-02-24 | 異性化用触媒 |
| EP85101842A EP0153692B1 (fr) | 1984-02-24 | 1985-02-20 | Métode pour l'isomérisation d'un glycidate |
| DE8585101842T DE3586403T2 (de) | 1984-02-24 | 1985-02-20 | Methode zum isomerisieren eines glycidats. |
| AT85101842T ATE78722T1 (de) | 1984-02-24 | 1985-02-20 | Methode zum isomerisieren eines glycidats. |
| US06/703,617 US4621150A (en) | 1984-02-24 | 1985-02-21 | Catalyst and method for isomerization |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59032513A JPS60179147A (ja) | 1984-02-24 | 1984-02-24 | 異性化用触媒 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60179147A JPS60179147A (ja) | 1985-09-13 |
| JPH0460699B2 true JPH0460699B2 (fr) | 1992-09-28 |
Family
ID=12361054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59032513A Granted JPS60179147A (ja) | 1984-02-24 | 1984-02-24 | 異性化用触媒 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60179147A (fr) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2434244A1 (de) * | 1973-01-29 | 1975-02-13 | Nisshin Flour Milling Co | 2-hydroxy-3-(4-alkylphenyl)-3-butensaeureester, verfahren zu ihrer herstellung und deren verwendung |
| JPS5116614A (en) * | 1974-07-29 | 1976-02-10 | Nisshin Flour Milling Co | Shinkina pirubinsanjudotaino seiho |
| JPS55164648A (en) * | 1979-06-08 | 1980-12-22 | Texaco Development Corp | Manufacture of unsaturated carboxylic acids and their ester derivatives from aliphatic conjugated diene |
-
1984
- 1984-02-24 JP JP59032513A patent/JPS60179147A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2434244A1 (de) * | 1973-01-29 | 1975-02-13 | Nisshin Flour Milling Co | 2-hydroxy-3-(4-alkylphenyl)-3-butensaeureester, verfahren zu ihrer herstellung und deren verwendung |
| JPS5116614A (en) * | 1974-07-29 | 1976-02-10 | Nisshin Flour Milling Co | Shinkina pirubinsanjudotaino seiho |
| JPS55164648A (en) * | 1979-06-08 | 1980-12-22 | Texaco Development Corp | Manufacture of unsaturated carboxylic acids and their ester derivatives from aliphatic conjugated diene |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60179147A (ja) | 1985-09-13 |
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