DE2547267C3 - Verfahren zur Herstellung von cyclischen Diestern der Dodecandisäure - Google Patents
Verfahren zur Herstellung von cyclischen Diestern der DodecandisäureInfo
- Publication number
- DE2547267C3 DE2547267C3 DE2547267A DE2547267A DE2547267C3 DE 2547267 C3 DE2547267 C3 DE 2547267C3 DE 2547267 A DE2547267 A DE 2547267A DE 2547267 A DE2547267 A DE 2547267A DE 2547267 C3 DE2547267 C3 DE 2547267C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- carbon atoms
- polyester
- thermolysis
- tin
- 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
Links
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 title claims description 26
- -1 cyclic diesters Chemical class 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 6
- 229920000728 polyester Polymers 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 18
- 238000001149 thermolysis Methods 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 150000002009 diols Chemical class 0.000 claims description 3
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- 239000011135 tin Substances 0.000 description 11
- 238000004821 distillation Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 238000005292 vacuum distillation Methods 0.000 description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VPPWQRIBARKZNY-UHFFFAOYSA-N oxo(diphenyl)tin Chemical compound C=1C=CC=CC=1[Sn](=O)C1=CC=CC=C1 VPPWQRIBARKZNY-UHFFFAOYSA-N 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- NXMNIHPHNSDPTN-UHFFFAOYSA-N didodecyl(oxo)tin Chemical compound CCCCCCCCCCCC[Sn](=O)CCCCCCCCCCCC NXMNIHPHNSDPTN-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- JZZJEVTXJXXPOD-UHFFFAOYSA-N dioctadecyl(oxo)tin Chemical compound CCCCCCCCCCCCCCCCCC[Sn](=O)CCCCCCCCCCCCCCCCCC JZZJEVTXJXXPOD-UHFFFAOYSA-N 0.000 description 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 150000002611 lead compounds Chemical class 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- LLAQOKIZCDUINH-UHFFFAOYSA-N 1,5-dioxacycloheptadecane-6,17-dione Chemical compound O=C1CCCCCCCCCCC(=O)OCCCO1 LLAQOKIZCDUINH-UHFFFAOYSA-N 0.000 description 1
- WDCPTDRLVGJRDK-UHFFFAOYSA-N 1,6-dioxacyclooctadecane-7,18-dione Chemical compound O=C1CCCCCCCCCCC(=O)OCCCCO1 WDCPTDRLVGJRDK-UHFFFAOYSA-N 0.000 description 1
- VPNRJIKJACGVJW-UHFFFAOYSA-N 1,8-dioxacycloicosane-9,20-dione Chemical compound O=C1CCCCCCCCCCC(=O)OCCCCCCO1 VPNRJIKJACGVJW-UHFFFAOYSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- WRIREHMDTACSLC-UHFFFAOYSA-L 2-hydroxypropanoate;tin(2+) Chemical compound [Sn+2].CC(O)C([O-])=O.CC(O)C([O-])=O WRIREHMDTACSLC-UHFFFAOYSA-L 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 101100513612 Microdochium nivale MnCO gene Proteins 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 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
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 235000015165 citric acid Nutrition 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
- 239000002537 cosmetic Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- SMUSIFOACPPWGZ-UHFFFAOYSA-L di(hexadecanoyloxy)tin Chemical compound [Sn+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O SMUSIFOACPPWGZ-UHFFFAOYSA-L 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- DRNWASHEONIABT-UHFFFAOYSA-N dibenzyl(oxo)tin Chemical compound C=1C=CC=CC=1C[Sn](=O)CC1=CC=CC=C1 DRNWASHEONIABT-UHFFFAOYSA-N 0.000 description 1
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 1
- TVIDDXQYHWJXFK-UHFFFAOYSA-L dodecanedioate(2-) Chemical compound [O-]C(=O)CCCCCCCCCCC([O-])=O TVIDDXQYHWJXFK-UHFFFAOYSA-L 0.000 description 1
- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 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
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- LTCDUZSZNPSELB-UHFFFAOYSA-L hexanedioate;tin(2+) Chemical compound [Sn+2].[O-]C(=O)CCCCC([O-])=O LTCDUZSZNPSELB-UHFFFAOYSA-L 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052742 iron Inorganic materials 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
- RLJMLMKIBZAXJO-UHFFFAOYSA-N lead nitrate Chemical compound [O-][N+](=O)O[Pb]O[N+]([O-])=O RLJMLMKIBZAXJO-UHFFFAOYSA-N 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- 229910052749 magnesium 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- CYCFYXLDTSNTGP-UHFFFAOYSA-L octadecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CYCFYXLDTSNTGP-UHFFFAOYSA-L 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 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
- 235000006408 oxalic acid Nutrition 0.000 description 1
- NGUVWBCPUIQUAH-UHFFFAOYSA-N oxo-di(pentadecyl)tin Chemical compound CCCCCCCCCCCCCCC[Sn](=O)CCCCCCCCCCCCCCC NGUVWBCPUIQUAH-UHFFFAOYSA-N 0.000 description 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 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 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 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
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fats And Perfumes (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2547267A DE2547267C3 (de) | 1975-10-22 | 1975-10-22 | Verfahren zur Herstellung von cyclischen Diestern der Dodecandisäure |
| FR7630864A FR2328704A1 (fr) | 1975-10-22 | 1976-10-14 | Procede de preparation de diesters cycliques de l'acide dodecane-dioique |
| US05/734,013 US4105672A (en) | 1975-10-22 | 1976-10-19 | Process for the production of cyclic diesters of dodecanedioic acid |
| CH1327576A CH601283A5 (enExample) | 1975-10-22 | 1976-10-20 | |
| IT51812/76A IT1069968B (it) | 1975-10-22 | 1976-10-20 | Procedimento per produrre diesteri ciclici di acido dodecandioico |
| JP51125570A JPS5251385A (en) | 1975-10-22 | 1976-10-21 | Production of cyclic diester of doaecane diacid |
| GB43677/76A GB1560573A (en) | 1975-10-22 | 1976-10-21 | Process for the production of cyclic diesters or dodecanoic diacid |
| US05/867,566 US4157330A (en) | 1975-10-22 | 1978-01-06 | Process for the production of cyclic diesters of dodecanedioic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2547267A DE2547267C3 (de) | 1975-10-22 | 1975-10-22 | Verfahren zur Herstellung von cyclischen Diestern der Dodecandisäure |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2547267A1 DE2547267A1 (de) | 1977-05-05 |
| DE2547267B2 DE2547267B2 (de) | 1978-08-31 |
| DE2547267C3 true DE2547267C3 (de) | 1979-05-03 |
Family
ID=5959778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2547267A Expired DE2547267C3 (de) | 1975-10-22 | 1975-10-22 | Verfahren zur Herstellung von cyclischen Diestern der Dodecandisäure |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4105672A (enExample) |
| JP (1) | JPS5251385A (enExample) |
| CH (1) | CH601283A5 (enExample) |
| DE (1) | DE2547267C3 (enExample) |
| FR (1) | FR2328704A1 (enExample) |
| GB (1) | GB1560573A (enExample) |
| IT (1) | IT1069968B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3225431A1 (de) * | 1982-07-09 | 1984-01-12 | Nisso Petrochemical Industry Co., Ltd., Tokyo | Verfahren zur herstellung von makrocyclischen esterverbindungen |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2714564C2 (de) * | 1977-04-01 | 1986-01-02 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Herstellung von cyclischen Diestern der Undecandisäure |
| US4218379A (en) * | 1977-09-21 | 1980-08-19 | Emery Industries, Inc. | Process for the production of macrocyclic esters |
| DE2929864A1 (de) * | 1979-07-24 | 1981-02-19 | Haarmann & Reimer Gmbh | Makrocyclische diester, verfahren zu ihrer herstellung und ihre verwendung als riechstoffe |
| JPS5940393B2 (ja) * | 1979-10-03 | 1984-09-29 | 東レ株式会社 | 大環状ジエステルおよびそれを含む香料 |
| JPS5993072A (ja) * | 1982-11-17 | 1984-05-29 | Daicel Chem Ind Ltd | 大環状ジエステルおよびこれを含む付香剤組成物 |
| JPS5955881A (ja) * | 1982-09-22 | 1984-03-31 | Daicel Chem Ind Ltd | 大環状ジエステルおよびこれを含む付香剤組成物 |
| JPS5967282A (ja) * | 1982-10-12 | 1984-04-16 | Daicel Chem Ind Ltd | 大環状ジエステルおよびこれを含む付香剤組成物 |
| EP0103893A3 (en) * | 1982-09-22 | 1986-03-19 | Daicel Chemical Industries, Ltd. | Macrocyclic diesters |
| JPS6197244A (ja) * | 1984-10-16 | 1986-05-15 | Osaka Suiso Kogyo Kk | 重縮合物 |
| DE19515888A1 (de) * | 1995-04-29 | 1996-10-31 | Huels Chemische Werke Ag | Verfahren zur kontinuierlichen Herstellung von macrocyclischen Verbindungen |
| EP0870537B1 (de) * | 1997-04-09 | 2004-10-06 | Symrise GmbH & Co. KG | Verfahren zur Herstellung alkoholhaltiger Granulate |
| DE19742307A1 (de) * | 1997-09-25 | 1999-04-01 | Haarmann & Reimer Gmbh | Neue Moschus-Riechstoffe |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2092031A (en) * | 1937-09-07 | Process of preparing cycijc esters | ||
| US2163109A (en) * | 1936-04-03 | 1939-06-20 | Du Pont | Chemical process and products therefrom |
| NL282251A (enExample) * | 1961-08-18 | |||
| DD53074A1 (de) | 1965-12-18 | 1967-01-05 | Verfahren zur Herstellung cyclischer Esteranhydride von alpha-Hydroxycarbonsäuren | |
| US3431279A (en) * | 1966-03-01 | 1969-03-04 | Armstrong Cork Co | Cyclic esters of o-phthalic acid and a glycol ether |
| DE1929550A1 (de) * | 1968-06-28 | 1970-01-02 | Techni Chem Co The | Verfahren zur Herstellung von cyclischen Estern von Dicarbonsaeuren |
| JPS558977B2 (enExample) * | 1973-10-20 | 1980-03-07 | ||
| JPS5629647B2 (enExample) * | 1973-10-24 | 1981-07-09 |
-
1975
- 1975-10-22 DE DE2547267A patent/DE2547267C3/de not_active Expired
-
1976
- 1976-10-14 FR FR7630864A patent/FR2328704A1/fr active Granted
- 1976-10-19 US US05/734,013 patent/US4105672A/en not_active Expired - Lifetime
- 1976-10-20 CH CH1327576A patent/CH601283A5/xx not_active IP Right Cessation
- 1976-10-20 IT IT51812/76A patent/IT1069968B/it active
- 1976-10-21 JP JP51125570A patent/JPS5251385A/ja active Granted
- 1976-10-21 GB GB43677/76A patent/GB1560573A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3225431A1 (de) * | 1982-07-09 | 1984-01-12 | Nisso Petrochemical Industry Co., Ltd., Tokyo | Verfahren zur herstellung von makrocyclischen esterverbindungen |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1560573A (en) | 1980-02-06 |
| JPS5251385A (en) | 1977-04-25 |
| FR2328704A1 (fr) | 1977-05-20 |
| IT1069968B (it) | 1985-03-25 |
| US4105672A (en) | 1978-08-08 |
| DE2547267B2 (de) | 1978-08-31 |
| DE2547267A1 (de) | 1977-05-05 |
| JPS5543471B2 (enExample) | 1980-11-06 |
| CH601283A5 (enExample) | 1978-07-14 |
| FR2328704B1 (enExample) | 1982-06-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |