CH619700A5 - - Google Patents
Download PDFInfo
- Publication number
- CH619700A5 CH619700A5 CH281776A CH281776A CH619700A5 CH 619700 A5 CH619700 A5 CH 619700A5 CH 281776 A CH281776 A CH 281776A CH 281776 A CH281776 A CH 281776A CH 619700 A5 CH619700 A5 CH 619700A5
- Authority
- CH
- Switzerland
- Prior art keywords
- pyran
- oxo
- hydroxy
- epoxy
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 12
- VEYIMQVTPXPUHA-UHFFFAOYSA-N 3-hydroxypyran-4-one Chemical class OC1=COC=CC1=O VEYIMQVTPXPUHA-UHFFFAOYSA-N 0.000 claims description 10
- KFIDJGBHJNJNFC-UHFFFAOYSA-N 3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical class O=C1COCC2OC12 KFIDJGBHJNJNFC-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 150000002978 peroxides Chemical class 0.000 claims description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000006735 epoxidation reaction Methods 0.000 claims description 6
- 239000003456 ion exchange resin Substances 0.000 claims description 5
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- YIKYNHJUKRTCJL-UHFFFAOYSA-N Ethyl maltol Chemical compound CCC=1OC=CC(=O)C=1O YIKYNHJUKRTCJL-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 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 claims description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 3
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 3
- 238000007796 conventional method Methods 0.000 claims description 3
- 238000003912 environmental pollution Methods 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- YYRYKNXDWXDXSN-UHFFFAOYSA-N 2h-pyran-5-one Chemical class O=C1COCC=C1 YYRYKNXDWXDXSN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 235000013305 food Nutrition 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 150000000530 4H-pyran-4-ones Chemical class 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 238000000855 fermentation Methods 0.000 claims 1
- 230000004151 fermentation Effects 0.000 claims 1
- 229910001385 heavy metal Inorganic materials 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- -1 ortho-formic acid ester Chemical class 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000000921 elemental analysis Methods 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 239000007788 liquid Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- 238000006359 acetalization reaction Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- BOABLGZTHBBHPW-UHFFFAOYSA-N 2-hydroxy-2h-pyran-5-one Chemical class OC1OCC(=O)C=C1 BOABLGZTHBBHPW-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 150000004292 cyclic ethers Chemical class 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 4
- VPOBZOGAFVUGIX-UHFFFAOYSA-N 2-ethoxy-4-methyl-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound CCOC1OC(C)C(=O)C2OC12 VPOBZOGAFVUGIX-UHFFFAOYSA-N 0.000 description 3
- PLYSJDAYJMFETG-UHFFFAOYSA-N 2-hydroxy-6-methyl-2h-pyran-5-one Chemical compound CC1OC(O)C=CC1=O PLYSJDAYJMFETG-UHFFFAOYSA-N 0.000 description 3
- YUTAFCIWIJWQIX-UHFFFAOYSA-N 6-ethyl-2-hydroxy-2h-pyran-5-one Chemical compound CCC1OC(O)C=CC1=O YUTAFCIWIJWQIX-UHFFFAOYSA-N 0.000 description 3
- VYWBYISNYZSJLL-UHFFFAOYSA-N 6-ethyl-2-methoxy-2h-pyran-5-one Chemical compound CCC1OC(OC)C=CC1=O VYWBYISNYZSJLL-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- GMRFAZZMYGJAQO-UHFFFAOYSA-N (6-methyl-5-oxo-2h-pyran-2-yl) acetate Chemical compound CC1OC(OC(C)=O)C=CC1=O GMRFAZZMYGJAQO-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- PLIHKNUTGDTARM-UHFFFAOYSA-N 2-butyl-3-hydroxypyran-4-one Chemical compound CCCCC=1OC=CC(=O)C=1O PLIHKNUTGDTARM-UHFFFAOYSA-N 0.000 description 2
- JCSZMSVNGHLLNB-UHFFFAOYSA-N 2-ethoxy-4-hexyl-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound O=C1C(CCCCCC)OC(OCC)C2OC21 JCSZMSVNGHLLNB-UHFFFAOYSA-N 0.000 description 2
- RZZDSHGXUWNGAV-UHFFFAOYSA-N 2-ethoxy-6-methyl-2h-pyran-5-one Chemical compound CCOC1OC(C)C(=O)C=C1 RZZDSHGXUWNGAV-UHFFFAOYSA-N 0.000 description 2
- OTFUSKNZLQKSFF-UHFFFAOYSA-N 2-ethoxy-6-octyl-2h-pyran-5-one Chemical compound CCCCCCCCC1OC(OCC)C=CC1=O OTFUSKNZLQKSFF-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- XIPGMIWMZXBKGS-UHFFFAOYSA-N 4-butyl-2-ethoxy-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound O=C1C(CCCC)OC(OCC)C2OC21 XIPGMIWMZXBKGS-UHFFFAOYSA-N 0.000 description 2
- FPJQUXXJCTZHSU-UHFFFAOYSA-N 4-ethyl-2-methoxy-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound O=C1C(CC)OC(OC)C2OC21 FPJQUXXJCTZHSU-UHFFFAOYSA-N 0.000 description 2
- REGQVCXIQLCNMD-UHFFFAOYSA-N 6-decyl-2-methoxy-2h-pyran-5-one Chemical compound CCCCCCCCCCC1OC(OC)C=CC1=O REGQVCXIQLCNMD-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical class OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- UPKHZBKHPNXGTF-UHFFFAOYSA-N (4-butyl-5-oxo-3,7-dioxabicyclo[4.1.0]heptan-2-yl) acetate Chemical compound O=C1C(CCCC)OC(OC(C)=O)C2OC21 UPKHZBKHPNXGTF-UHFFFAOYSA-N 0.000 description 1
- YLHVJOCZQOYFOZ-UHFFFAOYSA-N (4-decyl-5-oxo-3,7-dioxabicyclo[4.1.0]heptan-2-yl) acetate Chemical compound O=C1C(CCCCCCCCCC)OC(OC(C)=O)C2OC21 YLHVJOCZQOYFOZ-UHFFFAOYSA-N 0.000 description 1
- HUBNORDNGQUGNN-UHFFFAOYSA-N (4-methyl-5-oxo-3,7-dioxabicyclo[4.1.0]heptan-2-yl) acetate Chemical compound O=C1C(C)OC(OC(C)=O)C2OC21 HUBNORDNGQUGNN-UHFFFAOYSA-N 0.000 description 1
- BLANHKLOWLGAFA-UHFFFAOYSA-N (4-octyl-5-oxo-3,7-dioxabicyclo[4.1.0]heptan-2-yl) acetate Chemical compound O=C1C(CCCCCCCC)OC(OC(C)=O)C2OC21 BLANHKLOWLGAFA-UHFFFAOYSA-N 0.000 description 1
- JJVMFCRCFSJODB-UHFFFAOYSA-N (5-oxo-2h-pyran-2-yl) acetate Chemical compound CC(=O)OC1OCC(=O)C=C1 JJVMFCRCFSJODB-UHFFFAOYSA-N 0.000 description 1
- WGHYPCKIPVFCCA-UHFFFAOYSA-N (5-oxo-3,7-dioxabicyclo[4.1.0]heptan-2-yl) acetate Chemical compound CC(=O)OC1OCC(=O)C2OC12 WGHYPCKIPVFCCA-UHFFFAOYSA-N 0.000 description 1
- FNWCVHDSZFUCPX-UHFFFAOYSA-N (5-oxo-4-propan-2-yl-3,7-dioxabicyclo[4.1.0]heptan-2-yl) acetate Chemical compound O=C1C(C(C)C)OC(OC(C)=O)C2OC21 FNWCVHDSZFUCPX-UHFFFAOYSA-N 0.000 description 1
- BOHBUQCFLFIXDJ-UHFFFAOYSA-N (6-butyl-5-oxo-2h-pyran-2-yl) acetate Chemical compound CCCCC1OC(OC(C)=O)C=CC1=O BOHBUQCFLFIXDJ-UHFFFAOYSA-N 0.000 description 1
- GPFXVUVIEANTCR-UHFFFAOYSA-N (6-decyl-5-oxo-2h-pyran-2-yl) acetate Chemical compound CCCCCCCCCCC1OC(OC(C)=O)C=CC1=O GPFXVUVIEANTCR-UHFFFAOYSA-N 0.000 description 1
- BGMARPRSJZJOIP-UHFFFAOYSA-N (6-hexyl-5-oxo-2h-pyran-2-yl) acetate Chemical compound CCCCCCC1OC(OC(C)=O)C=CC1=O BGMARPRSJZJOIP-UHFFFAOYSA-N 0.000 description 1
- FOUSHPDYNDVYNP-UHFFFAOYSA-N (6-octyl-5-oxo-2h-pyran-2-yl) acetate Chemical compound CCCCCCCCC1OC(OC(C)=O)C=CC1=O FOUSHPDYNDVYNP-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- SGJBIFUEFLWXJY-UHFFFAOYSA-N 1-(dibutoxymethoxy)butane Chemical compound CCCCOC(OCCCC)OCCCC SGJBIFUEFLWXJY-UHFFFAOYSA-N 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- ZXNQSMFGPQEBKM-UHFFFAOYSA-N 2-butoxy-2h-pyran-5-one Chemical compound CCCCOC1OCC(=O)C=C1 ZXNQSMFGPQEBKM-UHFFFAOYSA-N 0.000 description 1
- ZXCHFKBTTMLMPE-UHFFFAOYSA-N 2-butoxy-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound CCCCOC1OCC(=O)C2OC12 ZXCHFKBTTMLMPE-UHFFFAOYSA-N 0.000 description 1
- RHKBDXALMKTDRQ-UHFFFAOYSA-N 2-butoxy-4-methyl-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound CCCCOC1OC(C)C(=O)C2OC12 RHKBDXALMKTDRQ-UHFFFAOYSA-N 0.000 description 1
- FQLSTCHYHZIPQL-UHFFFAOYSA-N 2-butoxy-6-ethyl-2h-pyran-5-one Chemical compound CCCCOC1OC(CC)C(=O)C=C1 FQLSTCHYHZIPQL-UHFFFAOYSA-N 0.000 description 1
- NYXUJEINQSITPQ-UHFFFAOYSA-N 2-butoxy-6-methyl-2h-pyran-5-one Chemical compound CCCCOC1OC(C)C(=O)C=C1 NYXUJEINQSITPQ-UHFFFAOYSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- YFWBNHSYXGFXLE-UHFFFAOYSA-N 2-ethoxy-2h-pyran-5-one Chemical compound CCOC1OCC(=O)C=C1 YFWBNHSYXGFXLE-UHFFFAOYSA-N 0.000 description 1
- ANBGMFVCPREODB-UHFFFAOYSA-N 2-ethoxy-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound CCOC1OCC(=O)C2OC12 ANBGMFVCPREODB-UHFFFAOYSA-N 0.000 description 1
- BLBNCIKXDSXUIC-UHFFFAOYSA-N 2-ethoxy-4-ethyl-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound CCOC1OC(CC)C(=O)C2OC12 BLBNCIKXDSXUIC-UHFFFAOYSA-N 0.000 description 1
- KSANYIRJYQFYFX-UHFFFAOYSA-N 2-ethoxy-4-octyl-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound O=C1C(CCCCCCCC)OC(OCC)C2OC21 KSANYIRJYQFYFX-UHFFFAOYSA-N 0.000 description 1
- DOTWDAISILQJDX-UHFFFAOYSA-N 2-ethoxy-4-propan-2-yl-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound CCOC1OC(C(C)C)C(=O)C2OC12 DOTWDAISILQJDX-UHFFFAOYSA-N 0.000 description 1
- BUCSXABEHCBNTH-UHFFFAOYSA-N 2-ethoxy-6-ethyl-2h-pyran-5-one Chemical compound CCOC1OC(CC)C(=O)C=C1 BUCSXABEHCBNTH-UHFFFAOYSA-N 0.000 description 1
- GFUMRMDKDPCWSE-UHFFFAOYSA-N 2-ethoxy-6-hexyl-2h-pyran-5-one Chemical compound CCCCCCC1OC(OCC)C=CC1=O GFUMRMDKDPCWSE-UHFFFAOYSA-N 0.000 description 1
- KHAFJIWMWPWOEH-UHFFFAOYSA-N 2-ethoxy-6-propan-2-yl-2h-pyran-5-one Chemical compound CCOC1OC(C(C)C)C(=O)C=C1 KHAFJIWMWPWOEH-UHFFFAOYSA-N 0.000 description 1
- RYQBXDFWRORCAU-UHFFFAOYSA-N 2-hydroxy-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound OC1OCC(=O)C2OC12 RYQBXDFWRORCAU-UHFFFAOYSA-N 0.000 description 1
- CTXWEZMUHDMKTC-UHFFFAOYSA-N 2-hydroxy-4-methyl-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound O=C1C(C)OC(O)C2OC21 CTXWEZMUHDMKTC-UHFFFAOYSA-N 0.000 description 1
- AFMDMDCKEUYPDG-UHFFFAOYSA-N 2-methoxy-2h-pyran-5-one Chemical compound COC1OCC(=O)C=C1 AFMDMDCKEUYPDG-UHFFFAOYSA-N 0.000 description 1
- KAQJMJUNNHECSH-UHFFFAOYSA-N 2-methoxy-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound COC1OCC(=O)C2OC12 KAQJMJUNNHECSH-UHFFFAOYSA-N 0.000 description 1
- BYIAIFISPQYESO-UHFFFAOYSA-N 2-methoxy-4-octyl-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound O=C1C(CCCCCCCC)OC(OC)C2OC21 BYIAIFISPQYESO-UHFFFAOYSA-N 0.000 description 1
- IFARUJDUXZXDAS-UHFFFAOYSA-N 2-methoxy-4-propan-2-yl-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound COC1OC(C(C)C)C(=O)C2OC12 IFARUJDUXZXDAS-UHFFFAOYSA-N 0.000 description 1
- CSEDVMRKXMDBAK-UHFFFAOYSA-N 2-methoxy-6-methyl-2h-pyran-5-one Chemical compound COC1OC(C)C(=O)C=C1 CSEDVMRKXMDBAK-UHFFFAOYSA-N 0.000 description 1
- SOPBORCOCVQHJW-UHFFFAOYSA-N 2-methoxy-6-octyl-2h-pyran-5-one Chemical compound CCCCCCCCC1OC(OC)C=CC1=O SOPBORCOCVQHJW-UHFFFAOYSA-N 0.000 description 1
- YFMMAOAKQVZOHZ-UHFFFAOYSA-N 2-methoxy-6-propan-2-yl-2h-pyran-5-one Chemical compound COC1OC(C(C)C)C(=O)C=C1 YFMMAOAKQVZOHZ-UHFFFAOYSA-N 0.000 description 1
- HYMLWHLQFGRFIY-UHFFFAOYSA-N 2-methylpyran-3,4-dione Chemical compound CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 1
- QOBVYDFJCWOWOW-UHFFFAOYSA-N 2-propan-2-yloxy-2h-pyran-5-one Chemical compound CC(C)OC1OCC(=O)C=C1 QOBVYDFJCWOWOW-UHFFFAOYSA-N 0.000 description 1
- WFQUNQZHPYOKKD-UHFFFAOYSA-N 2-propan-2-yloxy-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound CC(C)OC1OCC(=O)C2OC12 WFQUNQZHPYOKKD-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- BYAVMBAAZQAOHB-UHFFFAOYSA-N 3-hydroxy-2-(2-methylpropyl)pyran-4-one Chemical compound CC(C)CC=1OC=CC(=O)C=1O BYAVMBAAZQAOHB-UHFFFAOYSA-N 0.000 description 1
- MWSOWPCDOJLHGS-UHFFFAOYSA-N 3-hydroxy-2-(3-methylbutyl)pyran-4-one Chemical compound CC(C)CCC=1OC=CC(=O)C=1O MWSOWPCDOJLHGS-UHFFFAOYSA-N 0.000 description 1
- ONIMUPYFIMWJFC-UHFFFAOYSA-N 3-hydroxy-2-propan-2-ylpyran-4-one Chemical compound CC(C)C=1OC=CC(=O)C=1O ONIMUPYFIMWJFC-UHFFFAOYSA-N 0.000 description 1
- DWAFWTJANIITML-UHFFFAOYSA-N 3-hydroxy-2-propylpyran-4-one Chemical compound CCCC=1OC=CC(=O)C=1O DWAFWTJANIITML-UHFFFAOYSA-N 0.000 description 1
- ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- SJDJEIJDOHJHKG-UHFFFAOYSA-N 4-butyl-2-methoxy-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound O=C1C(CCCC)OC(OC)C2OC21 SJDJEIJDOHJHKG-UHFFFAOYSA-N 0.000 description 1
- STABAPSYCQFWOK-UHFFFAOYSA-N 4-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=C(Cl)C=C1 STABAPSYCQFWOK-UHFFFAOYSA-N 0.000 description 1
- VCJKJBOIOLWPHR-UHFFFAOYSA-N 4-decyl-2-ethoxy-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound O=C1C(CCCCCCCCCC)OC(OCC)C2OC21 VCJKJBOIOLWPHR-UHFFFAOYSA-N 0.000 description 1
- BZGQCAQCKMHKAB-UHFFFAOYSA-N 4-decyl-2-methoxy-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound O=C1C(CCCCCCCCCC)OC(OC)C2OC21 BZGQCAQCKMHKAB-UHFFFAOYSA-N 0.000 description 1
- ZPENBSDUVNPGDF-UHFFFAOYSA-N 4-ethyl-2-hexoxy-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound CCCCCCOC1OC(CC)C(=O)C2OC12 ZPENBSDUVNPGDF-UHFFFAOYSA-N 0.000 description 1
- NGRZZJNAJUAHJL-UHFFFAOYSA-N 4-ethyl-2-propan-2-yloxy-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound O=C1C(CC)OC(OC(C)C)C2OC21 NGRZZJNAJUAHJL-UHFFFAOYSA-N 0.000 description 1
- IUCHKCADBOOSBB-UHFFFAOYSA-N 4-hexyl-2-methoxy-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound O=C1C(CCCCCC)OC(OC)C2OC21 IUCHKCADBOOSBB-UHFFFAOYSA-N 0.000 description 1
- PMLAPEXVPGZDNG-UHFFFAOYSA-N 4-methyl-2-propan-2-yloxy-3,7-dioxabicyclo[4.1.0]heptan-5-one Chemical compound CC(C)OC1OC(C)C(=O)C2OC12 PMLAPEXVPGZDNG-UHFFFAOYSA-N 0.000 description 1
- MALOBWMOORWUQW-UHFFFAOYSA-N 4h-pyran-3-one Chemical group O=C1COC=CC1 MALOBWMOORWUQW-UHFFFAOYSA-N 0.000 description 1
- OYRWCMASLRNSFD-UHFFFAOYSA-N 6-butyl-2-ethoxy-2h-pyran-5-one Chemical compound CCCCC1OC(OCC)C=CC1=O OYRWCMASLRNSFD-UHFFFAOYSA-N 0.000 description 1
- ATBJWHYEJAHPHD-UHFFFAOYSA-N 6-butyl-2-methoxy-2h-pyran-5-one Chemical compound CCCCC1OC(OC)C=CC1=O ATBJWHYEJAHPHD-UHFFFAOYSA-N 0.000 description 1
- BLVHQERCCDOEJG-UHFFFAOYSA-N 6-decyl-2-ethoxy-2h-pyran-5-one Chemical compound CCCCCCCCCCC1OC(OCC)C=CC1=O BLVHQERCCDOEJG-UHFFFAOYSA-N 0.000 description 1
- CQAVRCRSSMIRJD-UHFFFAOYSA-N 6-ethyl-2-hexoxy-2h-pyran-5-one Chemical compound CCCCCCOC1OC(CC)C(=O)C=C1 CQAVRCRSSMIRJD-UHFFFAOYSA-N 0.000 description 1
- IIWAANFFGGRNNT-UHFFFAOYSA-N 6-ethyl-2-pentoxy-2h-pyran-5-one Chemical compound CCCCCOC1OC(CC)C(=O)C=C1 IIWAANFFGGRNNT-UHFFFAOYSA-N 0.000 description 1
- UTKZHBLVNRCIDQ-UHFFFAOYSA-N 6-ethyl-2-propan-2-yloxy-2h-pyran-5-one Chemical compound CCC1OC(OC(C)C)C=CC1=O UTKZHBLVNRCIDQ-UHFFFAOYSA-N 0.000 description 1
- ZNKRRBNQUWFLGX-UHFFFAOYSA-N 6-hexyl-2-methoxy-2h-pyran-5-one Chemical compound CCCCCCC1OC(OC)C=CC1=O ZNKRRBNQUWFLGX-UHFFFAOYSA-N 0.000 description 1
- YOLAEXBJDBWVEL-UHFFFAOYSA-N 6-hydroxy-2h-pyran-5-one Chemical class OC1OCC=CC1=O YOLAEXBJDBWVEL-UHFFFAOYSA-N 0.000 description 1
- SUPZZYDCRJUUFP-UHFFFAOYSA-N 6-methyl-2-(2-methylpropoxy)-2h-pyran-5-one Chemical compound CC(C)COC1OC(C)C(=O)C=C1 SUPZZYDCRJUUFP-UHFFFAOYSA-N 0.000 description 1
- YBTLDMRFLOSXSU-UHFFFAOYSA-N 6-methyl-2-propan-2-yloxy-2h-pyran-5-one Chemical compound CC(C)OC1OC(C)C(=O)C=C1 YBTLDMRFLOSXSU-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 235000011147 magnesium chloride Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003385 ring cleavage reaction Methods 0.000 description 1
- 238000006049 ring expansion reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyrane Compounds (AREA)
- Epoxy Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50087940A JPS5212166A (en) | 1975-07-17 | 1975-07-17 | Process for preparation of 4-pyron derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH619700A5 true CH619700A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-10-15 |
Family
ID=13928886
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH281676A CH617200A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-07-17 | 1976-03-05 | |
| CH281776A CH619700A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-07-17 | 1976-03-05 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH281676A CH617200A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-07-17 | 1976-03-05 |
Country Status (8)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4342697A (en) * | 1975-08-28 | 1982-08-03 | Pfizer Inc. | Preparation of gamma-pyrones |
| IE42789B1 (en) * | 1975-08-28 | 1980-10-22 | Pfizer | Preparation of gamma-pyrones |
| JPS532468A (en) * | 1976-06-15 | 1978-01-11 | Otsuka Chem Co Ltd | 2,2-bis(3,4-epoxy-5-oxotetrahydropyrane)-ethers and method of preparing the same |
| CA1095921A (en) * | 1976-08-02 | 1981-02-17 | Thomas M. Brennan | Preparation of gamma-pyrones |
| JPS5353613U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1976-10-11 | 1978-05-09 | ||
| US4390709A (en) * | 1976-11-11 | 1983-06-28 | Pfizer Inc. | Preparation of gamma-pyrones |
| US4191693A (en) * | 1976-11-12 | 1980-03-04 | Pfizer, Inc. | Preparation of gamma-pyrones from 3-substituted furans |
| JPS5481273A (en) * | 1977-12-12 | 1979-06-28 | Shin Etsu Chem Co Ltd | Preparation of pyranone halide |
| US4451661A (en) * | 1982-04-26 | 1984-05-29 | Pfizer Inc. | Preparation of gamma-pyrone intermediates |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3159652A (en) * | 1962-06-13 | 1964-12-01 | Pfizer & Co C | Preparation of gamma-pyrones |
| US3476778A (en) * | 1966-05-16 | 1969-11-04 | Monsanto Co | Gamma-pyrone synthesis |
| US3491122A (en) * | 1966-09-14 | 1970-01-20 | Monsanto Co | Synthesis of 4-pyrones |
| JPS5145565B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1968-10-12 | 1976-12-04 |
-
1975
- 1975-07-17 JP JP50087940A patent/JPS5212166A/ja active Granted
-
1976
- 1976-02-25 GB GB7539/76A patent/GB1498365A/en not_active Expired
- 1976-02-26 GB GB7540/76A patent/GB1496992A/en not_active Expired
- 1976-02-26 US US05/661,823 patent/US4059595A/en not_active Expired - Lifetime
- 1976-03-04 DE DE2608932A patent/DE2608932C2/de not_active Expired
- 1976-03-05 CH CH281676A patent/CH617200A5/de not_active IP Right Cessation
- 1976-03-05 FR FR7606288A patent/FR2318161A1/fr active Granted
- 1976-03-05 IT IT20921/76A patent/IT1063916B/it active
- 1976-03-05 CH CH281776A patent/CH619700A5/de not_active IP Right Cessation
- 1976-03-09 IT IT21011/76A patent/IT1063914B/it active
- 1976-03-10 DE DE2609888A patent/DE2609888C3/de not_active Expired
- 1976-03-10 FR FR7606779A patent/FR2317921A1/fr active Granted
- 1976-07-16 BE BE2055186A patent/BE844193A/xx not_active IP Right Cessation
- 1976-07-16 BE BE2055187A patent/BE844194A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5412465B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-05-23 |
| DE2608932C2 (de) | 1982-07-08 |
| FR2318161B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-08-25 |
| FR2317921A1 (fr) | 1977-02-11 |
| DE2608932A1 (de) | 1977-01-20 |
| DE2609888C3 (de) | 1979-05-10 |
| FR2317921B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-09-22 |
| BE844194A (fr) | 1976-11-16 |
| US4059595A (en) | 1977-11-22 |
| DE2609888B2 (de) | 1978-09-07 |
| JPS5212166A (en) | 1977-01-29 |
| GB1496992A (en) | 1978-01-05 |
| FR2318161A1 (fr) | 1977-02-11 |
| IT1063914B (it) | 1985-02-18 |
| CH617200A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-05-14 |
| GB1498365A (en) | 1978-01-18 |
| BE844193A (fr) | 1976-11-16 |
| IT1063916B (it) | 1985-02-18 |
| DE2609888A1 (de) | 1977-01-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2954373C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2721264A1 (de) | Verfahren zur herstellung von di-n- propylessigsaeure | |
| DE2760220C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| CH619700A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| EP0779285B1 (de) | Verfahren zur Herstellung von Ascorbinsäure | |
| DE2715080A1 (de) | Verfahren zur herstellung von cyclopentenon-derivaten | |
| DE2834117C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2750553C2 (de) | Verfahren zur Herstellung von gamma-Pyronen | |
| DE69016647T2 (de) | Verfahren zur herstellung von alpha-beta-ungesättigten ketonen. | |
| DE60101020T2 (de) | Verfahren zur Herstellung von Sesamol Ameisensäure Ester und Sesamol | |
| DE69900528T2 (de) | Herstellung von Di-tert-peroxiden | |
| DE2918900A1 (de) | Verfahren zur herstellung von 1,5- dimethyl-bicyclo- eckige klammer auf 3,2,1 eckige klammer zu octanol-8 und dessen ester | |
| DE1618861B2 (de) | Verfahren zur herstellung von ungesaettigten esteralkoholen | |
| EP0512348B1 (de) | Derivate cyclischer Lactone, Verfahren zu ihrer Herstellung und Verfahren zur Herstellung von 15-Pentadecanolid und seinen Homologen | |
| DD213437A5 (de) | Verfahren zur herstellung von cyclopentenderivaten | |
| DE3132687A1 (de) | "verfahren zur herstellung von ketosaeuren aus (alpha), ss-ungesaettigten cyclischen ketonen" | |
| DE3247255A1 (de) | Verfahren zur herstellung von isolierung von polyglycidylverbindungen | |
| DE3112056A1 (de) | Verbessertes verfahren zur herstellung von cyclohexan-1,3-dionen sowie einige neue bicyclische cyclohexan-1,3-dione | |
| EP0735032B1 (de) | Verfahren zur Herstellung von 5-Hydroxy-4-methyl-2(5H)-furanon | |
| EP0579113A1 (de) | Verbessertes Verfahren zur Herstellung von cyclischen Acetalen von 3-formyl-2-butenyl-triphenylphosphoniumchlorid | |
| DE2833967A1 (de) | Verfahren zur herstellung von apovincamin | |
| DE2824841B2 (de) | Verfahren zur Herstellung von 2-Cyclopentenonderivaten sowie diese enthaltende Parfüm-Kompositionen | |
| DE2440745C3 (de) | Verfahren zur Abtrennung von cis-Chrysanthemummonocarbonsäure | |
| DE3123177C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE1919504C3 (de) | Verfahren zur Herstellung von 1- Thiacyclo-A3 -hexenal (3) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |