JP2007521229A - テトラブロモ安息香酸エステルの製造方法 - Google Patents
テトラブロモ安息香酸エステルの製造方法 Download PDFInfo
- Publication number
- JP2007521229A JP2007521229A JP2005507850A JP2005507850A JP2007521229A JP 2007521229 A JP2007521229 A JP 2007521229A JP 2005507850 A JP2005507850 A JP 2005507850A JP 2005507850 A JP2005507850 A JP 2005507850A JP 2007521229 A JP2007521229 A JP 2007521229A
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- JP
- Japan
- Prior art keywords
- tetrabromobenzoate
- reactor
- alcohol
- mixture
- esterification
- 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.)
- Granted
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 63
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 238000006114 decarboxylation reaction Methods 0.000 claims abstract description 56
- 238000005886 esterification reaction Methods 0.000 claims abstract description 56
- 239000000203 mixture Substances 0.000 claims abstract description 52
- 230000032050 esterification Effects 0.000 claims abstract description 51
- 239000003054 catalyst Substances 0.000 claims abstract description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 41
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 claims abstract description 41
- XIRDTMSOGDWMOX-UHFFFAOYSA-N 3,4,5,6-tetrabromophthalic acid Chemical compound OC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(O)=O XIRDTMSOGDWMOX-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims description 63
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 27
- 238000009835 boiling Methods 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 14
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 9
- 239000003063 flame retardant Substances 0.000 claims description 9
- 239000012442 inert solvent Substances 0.000 claims description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 6
- 239000004800 polyvinyl chloride Substances 0.000 claims description 6
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 239000002952 polymeric resin Substances 0.000 claims description 4
- 239000004814 polyurethane Substances 0.000 claims description 4
- 229920002635 polyurethane Polymers 0.000 claims description 4
- 229920003002 synthetic resin Polymers 0.000 claims description 4
- 125000001033 ether group Chemical group 0.000 claims 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 30
- -1 tetrabromophthalic acid diester Chemical class 0.000 description 26
- 150000001298 alcohols Chemical class 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 16
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 12
- 239000007858 starting material Substances 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- 150000005690 diesters Chemical class 0.000 description 7
- 230000002349 favourable effect Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N (2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 6
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 6
- HVDXCGSGEQKWGB-UHFFFAOYSA-N 2-ethylhexyl 2,3,4,5-tetrabromobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC(Br)=C(Br)C(Br)=C1Br HVDXCGSGEQKWGB-UHFFFAOYSA-N 0.000 description 6
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- FBCNRCVXBGRPQU-UHFFFAOYSA-N bromo benzoate Chemical compound BrOC(=O)C1=CC=CC=C1 FBCNRCVXBGRPQU-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- BVOSSZSHBZQJOI-UHFFFAOYSA-N 1-Hexen-3-ol Chemical compound CCCC(O)C=C BVOSSZSHBZQJOI-UHFFFAOYSA-N 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 4
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 4
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 4
- NGDNVOAEIVQRFH-UHFFFAOYSA-N 2-nonanol Chemical compound CCCCCCCC(C)O NGDNVOAEIVQRFH-UHFFFAOYSA-N 0.000 description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- XNDZQQSKSQTQQD-UHFFFAOYSA-N 3-methylcyclohex-2-en-1-ol Chemical compound CC1=CC(O)CCC1 XNDZQQSKSQTQQD-UHFFFAOYSA-N 0.000 description 4
- HTSABYAWKQAHBT-UHFFFAOYSA-N 3-methylcyclohexanol Chemical compound CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 4
- IWTBVKIGCDZRPL-UHFFFAOYSA-N 3-methylpentanol Chemical compound CCC(C)CCO IWTBVKIGCDZRPL-UHFFFAOYSA-N 0.000 description 4
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 4
- WRYLYDPHFGVWKC-UHFFFAOYSA-N 4-terpineol Chemical compound CC(C)C1(O)CCC(C)=CC1 WRYLYDPHFGVWKC-UHFFFAOYSA-N 0.000 description 4
- FCOUHTHQYOMLJT-UHFFFAOYSA-N 6-methylheptan-2-ol Chemical compound CC(C)CCCC(C)O FCOUHTHQYOMLJT-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000008378 aryl ethers Chemical class 0.000 description 4
- 238000010923 batch production Methods 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 4
- STJIISDMSMJQQK-UHFFFAOYSA-N furan-3-ylmethanol Chemical compound OCC=1C=COC=1 STJIISDMSMJQQK-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- ODEHKVYXWLXRRR-UHFFFAOYSA-N hex-3-yn-1-ol Chemical compound CCC#CCCO ODEHKVYXWLXRRR-UHFFFAOYSA-N 0.000 description 4
- VTIODUHBZHNXFP-UHFFFAOYSA-N hex-4-en-1-ol Chemical compound CC=CCCCO VTIODUHBZHNXFP-UHFFFAOYSA-N 0.000 description 4
- GOQJMMHTSOQIEI-UHFFFAOYSA-N hex-5-yn-1-ol Chemical compound OCCCCC#C GOQJMMHTSOQIEI-UHFFFAOYSA-N 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 4
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 description 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 4
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 4
- ZYTMANIQRDEHIO-KXUCPTDWSA-N isopulegol Chemical compound C[C@@H]1CC[C@@H](C(C)=C)[C@H](O)C1 ZYTMANIQRDEHIO-KXUCPTDWSA-N 0.000 description 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 4
- VSMOENVRRABVKN-UHFFFAOYSA-N oct-1-en-3-ol Chemical compound CCCCCC(O)C=C VSMOENVRRABVKN-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 3
- OTJZCIYGRUNXTP-UHFFFAOYSA-N but-3-yn-1-ol Chemical compound OCCC#C OTJZCIYGRUNXTP-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- UIZVMOZAXAMASY-UHFFFAOYSA-N hex-5-en-1-ol Chemical compound OCCCCC=C UIZVMOZAXAMASY-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- APALRPYIDIBHQN-UHFFFAOYSA-N (1-phenylcyclopropyl)methanol Chemical compound C=1C=CC=CC=1C1(CO)CC1 APALRPYIDIBHQN-UHFFFAOYSA-N 0.000 description 2
- 239000001871 (1R,2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol Substances 0.000 description 2
- YBRHBMHQQIEOOL-RMKNXTFCSA-N (2e)-2,4-dimethylhepta-2,6-dien-1-ol Chemical compound C=CCC(C)\C=C(/C)CO YBRHBMHQQIEOOL-RMKNXTFCSA-N 0.000 description 2
- 239000001618 (3R)-3-methylpentan-1-ol Substances 0.000 description 2
- BTSIZIIPFNVMHF-ONEGZZNKSA-N (E)-2-penten-1-ol Chemical compound CC\C=C\CO BTSIZIIPFNVMHF-ONEGZZNKSA-N 0.000 description 2
- UFLHIIWVXFIJGU-ONEGZZNKSA-N (E)-3-Hexenol Natural products CC\C=C\CCO UFLHIIWVXFIJGU-ONEGZZNKSA-N 0.000 description 2
- 239000001714 (E)-hex-2-en-1-ol Substances 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 2
- WRYLYDPHFGVWKC-JTQLQIEISA-N (R)-(-)-p-Menth-1-en-4-ol Natural products CC(C)[C@@]1(O)CCC(C)=CC1 WRYLYDPHFGVWKC-JTQLQIEISA-N 0.000 description 2
- 239000000267 (Z)-hex-3-en-1-ol Substances 0.000 description 2
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- 239000001586 (Z)-pent-2-en-1-ol Substances 0.000 description 2
- BRTBTJVSPJZQIT-GQCTYLIASA-N (e)-3-trimethylsilylprop-2-en-1-ol Chemical compound C[Si](C)(C)\C=C\CO BRTBTJVSPJZQIT-GQCTYLIASA-N 0.000 description 2
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- LQMDOONLLAJAPZ-UHFFFAOYSA-N 1-ethynylcyclopentan-1-ol Chemical compound C#CC1(O)CCCC1 LQMDOONLLAJAPZ-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
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- RXAMIWOJDOJSTB-UHFFFAOYSA-N 2,2-dimethoxycyclohexan-1-ol Chemical compound COC1(OC)CCCCC1O RXAMIWOJDOJSTB-UHFFFAOYSA-N 0.000 description 2
- KMVFQKNNDPKWOX-UHFFFAOYSA-N 2,3-dimethylcyclohexan-1-ol Chemical compound CC1CCCC(O)C1C KMVFQKNNDPKWOX-UHFFFAOYSA-N 0.000 description 2
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- PRNCMAKCNVRZFX-UHFFFAOYSA-N 3,7-dimethyloctan-1-ol Chemical compound CC(C)CCCC(C)CCO PRNCMAKCNVRZFX-UHFFFAOYSA-N 0.000 description 2
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- NMRPBPVERJPACX-QMMMGPOBSA-N 3-Octanol Natural products CCCCC[C@@H](O)CC NMRPBPVERJPACX-QMMMGPOBSA-N 0.000 description 2
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- ZSPTYLOMNJNZNG-UHFFFAOYSA-N 3-Buten-1-ol Chemical compound OCCC=C ZSPTYLOMNJNZNG-UHFFFAOYSA-N 0.000 description 1
- HFYAEUXHCMTPOL-UHFFFAOYSA-N 3-Methyl-1-penten-3-ol Chemical compound CCC(C)(O)C=C HFYAEUXHCMTPOL-UHFFFAOYSA-N 0.000 description 1
- BOWIFWCBNWWZOG-UHFFFAOYSA-N 3-Thiophenemethanol Chemical compound OCC=1C=CSC=1 BOWIFWCBNWWZOG-UHFFFAOYSA-N 0.000 description 1
- KQOQXYPZBYTICM-UHFFFAOYSA-N 3-bromo-2,2-dimethylpropan-1-ol Chemical compound OCC(C)(C)CBr KQOQXYPZBYTICM-UHFFFAOYSA-N 0.000 description 1
- RTKMFQOHBDVEBC-UHFFFAOYSA-N 3-bromo-3-buten-1-ol Chemical compound OCCC(Br)=C RTKMFQOHBDVEBC-UHFFFAOYSA-N 0.000 description 1
- CAZPRAORHCOIHC-UHFFFAOYSA-N 3-chloro-2,2-dimethylpropan-1-ol Chemical compound OCC(C)(C)CCl CAZPRAORHCOIHC-UHFFFAOYSA-N 0.000 description 1
- DOANJBQUOFJQHC-UHFFFAOYSA-N 3-chloro-2-(chloromethyl)-2-methylpropan-1-ol Chemical compound OCC(C)(CCl)CCl DOANJBQUOFJQHC-UHFFFAOYSA-N 0.000 description 1
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 1
- XHMWPVBQGARKQM-UHFFFAOYSA-N 3-ethoxy-1-propanol Chemical compound CCOCCCO XHMWPVBQGARKQM-UHFFFAOYSA-N 0.000 description 1
- CZUGFKJYCPYHHV-UHFFFAOYSA-N 3-methylthiopropanol Chemical compound CSCCCO CZUGFKJYCPYHHV-UHFFFAOYSA-N 0.000 description 1
- JNTVUHZXIJFHAU-UHFFFAOYSA-N 4-(Methylthio)-1-butanol Chemical compound CSCCCCO JNTVUHZXIJFHAU-UHFFFAOYSA-N 0.000 description 1
- HXHGULXINZUGJX-UHFFFAOYSA-N 4-chlorobutanol Chemical compound OCCCCCl HXHGULXINZUGJX-UHFFFAOYSA-N 0.000 description 1
- LLUQZGDMUIMPTC-UHFFFAOYSA-N 4-methylheptan-1-ol Chemical compound CCCC(C)CCCO LLUQZGDMUIMPTC-UHFFFAOYSA-N 0.000 description 1
- KFARNLMRENFOHE-UHFFFAOYSA-N 5-methylheptan-1-ol Chemical compound CCC(C)CCCCO KFARNLMRENFOHE-UHFFFAOYSA-N 0.000 description 1
- FCMCSZXRVWDVAW-UHFFFAOYSA-N 6-bromo-1-hexanol Chemical compound OCCCCCCBr FCMCSZXRVWDVAW-UHFFFAOYSA-N 0.000 description 1
- JNTPTNNCGDAGEJ-UHFFFAOYSA-N 6-chlorohexan-1-ol Chemical compound OCCCCCCCl JNTPTNNCGDAGEJ-UHFFFAOYSA-N 0.000 description 1
- MMXRRNUXCHUHOE-UHFFFAOYSA-N 7-bromoheptan-1-ol Chemical compound OCCCCCCCBr MMXRRNUXCHUHOE-UHFFFAOYSA-N 0.000 description 1
- CLQHEYPLKXTCBT-UHFFFAOYSA-N CC(CCCCCC)O.CC(CCCO)CCC Chemical compound CC(CCCCCC)O.CC(CCCO)CCC CLQHEYPLKXTCBT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004609 Impact Modifier Substances 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropanol Chemical compound CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000013036 UV Light Stabilizer Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- UUEDINPOVKWVAZ-UHFFFAOYSA-N bis(2-ethylhexyl) 3,4,5,6-tetrabromobenzene-1,2-dicarboxylate Chemical compound CCCCC(CC)COC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(=O)OCC(CC)CCCC UUEDINPOVKWVAZ-UHFFFAOYSA-N 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- KTHXBEHDVMTNOH-UHFFFAOYSA-N cyclobutanol Chemical compound OC1CCC1 KTHXBEHDVMTNOH-UHFFFAOYSA-N 0.000 description 1
- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 description 1
- 229930008394 dihydromyrcenol Natural products 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229910021478 group 5 element Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- QXLPXWSKPNOQLE-UHFFFAOYSA-N methylpentynol Chemical compound CCC(C)(O)C#C QXLPXWSKPNOQLE-UHFFFAOYSA-N 0.000 description 1
- ZYWUVGFIXPNBDL-UHFFFAOYSA-N n,n-diisopropylaminoethanol Chemical compound CC(C)N(C(C)C)CCO ZYWUVGFIXPNBDL-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- WPSTUUQRKZWQIO-UHFFFAOYSA-N octan-3-yl 2,3,4,5-tetrabromobenzoate Chemical compound CCCCCC(CC)OC(=O)C1=CC(Br)=C(Br)C(Br)=C1Br WPSTUUQRKZWQIO-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- ROTONRWJLXYJBD-UHFFFAOYSA-N oxan-2-ylmethanol Chemical compound OCC1CCCCO1 ROTONRWJLXYJBD-UHFFFAOYSA-N 0.000 description 1
- LMYJGUNNJIDROI-UHFFFAOYSA-N oxan-4-ol Chemical compound OC1CCOCC1 LMYJGUNNJIDROI-UHFFFAOYSA-N 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- ZHZCYWWNFQUZOR-UHFFFAOYSA-N pent-4-en-2-ol Chemical compound CC(O)CC=C ZHZCYWWNFQUZOR-UHFFFAOYSA-N 0.000 description 1
- ICMWSAALRSINTC-UHFFFAOYSA-N penta-1,4-dien-3-ol Chemical compound C=CC(O)C=C ICMWSAALRSINTC-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- DFOXKPDFWGNLJU-UHFFFAOYSA-N pinacolyl alcohol Chemical compound CC(O)C(C)(C)C DFOXKPDFWGNLJU-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
- JSASXSHMJYRPCM-UHFFFAOYSA-N r-3-(methylthio)-1-hexanol Chemical compound CCCC(SC)CCO JSASXSHMJYRPCM-UHFFFAOYSA-N 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZQKNBDOVPOZPLY-UHFFFAOYSA-N trimethylsilylmethanol Chemical compound C[Si](C)(C)CO ZQKNBDOVPOZPLY-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C67/32—Decarboxylation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
(スキームI)
これらのうち、3−フランメタノール、フルフリルアルコール、テトラヒドロフルフリルアルコール、3−アセチル−1−プロパノール、2−イソプロポキシエタノール、3−メトキシ−1−ブタノール、2−シクロヘキセン−1−オール、1,5−ヘキサジエン−3−オール、t,t−2,4−ヘキサジエン−1−オール、3−ヘキシン−1−オール、5−ヘキシン−1−オール、シクロペンタンメタノール、4−メチル−1−ペンタノール、3−(トリメチルシリル)アリルアルコール、シクロヘキシルメタノール、3−トリメチルシリル−1−プロパノール、ベンジルアルコール、3−シクロヘキセン−1−メタノール、3−メチル−2−シクロヘキセン−1−オール、シクロヘプタノール、1−メチルシクロヘキサノール、2−メチルシクロヘキサノール、3−メチルシクロヘキサノール、4−メチルシクロヘキサノール、1−ヘプタノール、2−ヘプタノール、プロピレングリコールブチルエーテル、2−メチルベンジルアルコール、3−メチルベンジルアルコール、4−メチルベンジルアルコール、フェネチルアルコール、sec−フェネチルアルコール、1−オクチン−3−オール、シクロヘプタンメタノール、2−シクロヘキシルエタノール、1−シクロヘキシルエタノール、シクロオクタノール、3−シクロペンチル−1−プロパノール、2,3−ジメチルシクロヘキサノール、2,6−ジメチルシクロヘキサノール、3,5−ジメチルシクロヘキサノール、2−エチルシクロヘキサノール、4−エチルシクロヘキサノール、6−メチル−5−ヘプテン−2−オール、1−オクテン−3−オール、2−(シクロヘキシルオキシ)エタノール、2,2−ジメトキシシクロヘキサノール、6−メチル−2−ヘプタノール、1−オクタノール、2,4,4−トリメチル−1−ペンタノール、1−フェニル−1−プロパノール、1−フェニル−2−プロパノール、2−フェニル−2−プロパノール、2,4−ジメチル−2,6−ヘプタジエン−1−オール、3−ノニン−1−オール、3,5,5−トリメチル−2−シクロヘキセン−1−オール、3−シクロヘキシル−1−プロパノール、3−ノネン−1−オール、1−ノナノール、3−エチル−2,2−ジメチル−3−ペンタノール、2−フェニル−3−ブチン−2−オール、1−フェニル−1−シクロプロパンメタノール、1−ミルテノール、イソプレゴール、2−メチル−1−フェニル−2−プロパノール、リナロオール、1−ミルテノール、ネロール、テルピネオール、テルピネン−4−オール、シトロネロール、2−デカノール、4−デカノール、4−シクロヘキシル−1−ブタノール、混合C7/C11アルコール、イソデシルアルコール及びヘキシルデシルアルコールが好ましいが、3,3−ジエトキシ−1−プロパノール、2−(2−メトキシ)エトキシエタノール、3,4−ジメチル−1−ヘキサノール、2−ブトキシエタノール、ジ(プロピレングリコール)メチルエーテル、3−エチル−1−ヘキサノール、2−エチル−1−ヘキサノール、3,5−ジメチル−1−ヘキサノール、3−メチル−1−ヘプタノール、4−メチル−1−ヘプタノール、5−メチル−1−ヘプタノール、2−オクタノール、3−オクタノール、2−プロピル−1−ペンタノール、2,6−ジメチル4−ヘプタノール、2−ノナノール、3,5,5−トリメチル−1−ヘキサノール、ジヒドロミルセノール、3,7−ジメチル1−オクタノール、3,7−ジメチル−3−オクタノール、混合C7/C9アルコール、イソオクチルアルコール及び混合C9アルコールが最も好ましい。
この実施例では、2−エチルヘキシルテトラブロモ安息香酸エステルを、以下に説明する米国特許第5637757号に教示の既知の回分プロセスを用いて作製した。この回分プロセスで用いた反応物とその量を表1に示す。結果を表2に示す。
この実施例では、2−エチルヘキシルテトラブロモ安息香酸エステルを本発明の方法と表1に示した反応物を用いて作製した。結果を表2に示す。
本発明のこの実施例では、本発明の一実施形態による別の非連続式プロセスを用いて2−エチルヘキシルテトラブロモ安息香酸エステルを調製した。反応物を表3に示す。
Claims (35)
- テトラブロモフタル酸無水物からテトラブロモ安息香酸エステルを調製する方法であって、
少なくとも1基の反応容器中で前記テトラブロモフタル酸無水物とアルコールとを混合して第1の反応混合物を形成するステップと、
前記第1の反応混合物を、完全エステル化より部分エステル化に有利な温度に加熱してテトラブロモフタル酸半エステル中間体混合物を形成するステップと、
前記テトラブロモフタル酸半エステル中間体混合物と触媒とを、エステル化より脱炭酸に有利な温度を有する少なくとも1基の加熱された反応器に供給するステップと、
前記少なくとも1基の反応器をエステル化より脱炭酸に有利な温度に保持してテトラブロモ安息香酸エステル含有生成物を製造するステップと
を含む方法。 - 完全エステル化より部分エステル化に有利な前記温度が約70℃を超える請求項1に記載の方法。
- 完全エステル化より部分エステル化に有利な前記温度が約90℃〜約130℃である請求項2に記載の方法。
- エステル化より脱炭酸に有利な前記温度が約190℃を超える請求項1に記載の方法。
- エステル化より脱炭酸に有利な前記温度が約190℃〜約205℃である請求項4に記載の方法。
- 前記アルコールが約100℃〜約230℃の沸点を有する請求項1に記載の方法。
- 前記アルコールが一般式ROHを有し、式中、Rが最大で約30個の炭素原子を有する有機基である請求項1に記載の方法。
- 前記テトラブロモフタル酸無水物とアルコールとを混合する前記ステップを不活性溶媒中で実施する請求項1に記載の方法。
- 前記不活性溶媒が約160℃〜230℃の沸点を有するエーテルである請求項8に記載の方法。
- 前記触媒が炭酸塩、重炭酸アルカリ、アルカリ及びその混合物からなる群から選択される化合物である請求項1に記載の方法。
- 前記テトラブロモ安息香酸エステル含有生成物が少なくとも約85%のテトラブロモ安息香酸エステルを含む請求項1に記載の方法。
- 少なくとも1基の加熱された反応器に前記テトラブロモフタル酸半エステル中間体混合物を供給する際に、前記少なくとも1基の反応器がテトラブロモ安息香酸エステルを含む請求項1に記載の方法。
- 前記少なくとも1基の反応器が、互いに直列に連結された複数の加熱された反応器を含む請求項1に記載の方法。
- 少なくとも1基の加熱された反応器に前記テトラブロモフタル酸半エステル中間体混合物を供給する際に、前記複数の加熱された反応器のうちの第1の反応器がテトラブロモ安息香酸エステルを含む請求項13に記載の方法。
- 前記テトラブロモフタル酸半エステル中間体混合物を供給する前記ステップが連続的であり、それによって前記半エステル中間体混合物が前記少なくとも1基の反応器に連続的に供給され、同時に前記テトラブロモ安息香酸エステル含有生成物が前記少なくとも1基の反応器から連続的に抜き出される請求項1に記載の方法。
- 請求項1に記載の方法によって製造された前記テトラブロモ安息香酸エステル含有化合物のテトラブロモ安息香酸エステルを含む難燃性混合物。
- 請求項1に記載の方法によって製造された前記テトラブロモ安息香酸エステル含有化合物のテトラブロモ安息香酸エステルを含む難燃化ポリマー樹脂。
- 請求項1に記載の方法によって製造された前記テトラブロモ安息香酸エステル含有化合物のテトラブロモ安息香酸エステルを含む、難燃化されたポリ塩化ビニル又はポリウレタン。
- 少なくとも1基の反応器に、テトラブロモフタル酸無水物、テトラブロモフタル二酸又はその混合物のいずれかとアルコールとを供給するステップであって、前記少なくとも1基の反応器の第1の反応器が、テトラブロモ安息香酸エステルを含んだ生成混合物を含み、前記少なくとも1基の反応器がエステル化より脱炭酸に有利な温度を有する、ステップと、
前記少なくとも1基の反応器を、エステル化より脱炭酸に有利な温度に保持してテトラブロモ安息香酸エステル含有生成物を製造するステップと、
を含むテトラブロモ安息香酸エステルの調製方法。 - 前記生成混合物が脱炭酸触媒を含む請求項19に記載の方法。
- 前記脱炭酸触媒が炭酸塩、重炭酸アルカリ、アルカリ及びその混合物からなる群から選択される化合物である請求項20に記載の方法。
- テトラブロモフタル酸無水物、テトラブロモフタル二酸又はその混合物のいずれかとアルコールとを、少なくとも1基の反応器に供給する前記ステップが、脱炭酸触媒を前記少なくとも1基の反応器に供給するステップをさらに含む請求項19に記載の方法。
- 前記触媒が炭酸塩、重炭酸アルカリ、アルカリ及びその混合物からなる群から選択される化合物である請求項22に記載の方法。
- エステル化より脱炭酸に有利な前記温度が約190℃を超える請求項19に記載の方法。
- エステル化より脱炭酸に有利な前記温度が約190℃〜約205℃である請求項24に記載の方法。
- 前記アルコールが約100℃〜約230℃の沸点を有する請求項19に記載の方法。
- 前記アルコールが一般式ROHを有し、式中、Rが最大で約30個の炭素原子を有する有機基である請求項19に記載の方法。
- 不活性溶媒を前記少なくとも1基の反応器に加えるステップをさらに含み、前記不活性溶媒が約160℃を超える沸点を有する請求項19に記載の方法。
- 前記不活性溶媒がエーテルである請求項28に記載の方法。
- 前記少なくとも1基の反応器が、互いに直列に連結された複数の反応器を含む請求項19に記載の方法。
- 前記テトラブロモフタル酸無水物、テトラブロモフタル二酸又はその混合物と前記アルコールとを供給する前記ステップの前に、前記テトラブロモフタル酸無水物、テトラブロモフタル二酸又はその混合物のいずれかと前記アルコールとを混合して第1の反応混合物を形成するステップをさらに含む請求項19に記載の方法。
- 前記テトラブロモフタル酸無水物、テトラブロモフタル二酸又はその混合物と前記アルコールとを少なくとも1基の反応器に供給する前記ステップが連続的であり、それによってテトラブロモフタル酸無水物、テトラブロモフタル二酸又はその混合物のいずれかとアルコールとが前記少なくとも1基の反応器に連続的に供給され、同時に前記テトラブロモ安息香酸エステル含有生成物が前記少なくとも1基の反応器から連続的に抜き出される請求項19に記載の方法。
- 請求項19に記載の方法によって製造された前記テトラブロモ安息香酸エステル含有化合物のテトラブロモ安息香酸エステルを含む難燃性混合物。
- 請求項19に記載の方法によって製造された前記テトラブロモ安息香酸エステル含有化合物のテトラブロモ安息香酸エステルを含む難燃化ポリマー樹脂。
- 請求項19に記載の方法によって製造された前記テトラブロモ安息香酸エステル含有化合物のテトラブロモ安息香酸エステルを含む、難燃化されたポリ塩化ビニル又はポリウレタン。
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US20200024537A1 (en) * | 2018-02-22 | 2020-01-23 | Exxonmobil Research And Engineering Company | Low viscosity low volatility benzoate monoester lubricating oil base stocks and methods of use thereof |
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