JP3730659B2 - ナフタリンジカルボン酸のジエステルの製造方法 - Google Patents
ナフタリンジカルボン酸のジエステルの製造方法 Download PDFInfo
- Publication number
- JP3730659B2 JP3730659B2 JP51329594A JP51329594A JP3730659B2 JP 3730659 B2 JP3730659 B2 JP 3730659B2 JP 51329594 A JP51329594 A JP 51329594A JP 51329594 A JP51329594 A JP 51329594A JP 3730659 B2 JP3730659 B2 JP 3730659B2
- Authority
- JP
- Japan
- Prior art keywords
- dicarboxylic acid
- naphthalene dicarboxylic
- reactor
- alcohol
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 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 title claims description 91
- 150000005690 diesters Chemical class 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 189
- 238000006243 chemical reaction Methods 0.000 claims description 105
- 238000005886 esterification reaction Methods 0.000 claims description 82
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 75
- 238000000034 method Methods 0.000 claims description 62
- 239000011541 reaction mixture Substances 0.000 claims description 48
- 239000007791 liquid phase Substances 0.000 claims description 37
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 28
- 150000002148 esters Chemical class 0.000 claims description 26
- 239000000047 product Substances 0.000 claims description 24
- 239000002002 slurry Substances 0.000 claims description 17
- GYUVMLBYMPKZAZ-UHFFFAOYSA-N dimethyl naphthalene-2,6-dicarboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(C(=O)OC)=CC=C21 GYUVMLBYMPKZAZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000012071 phase Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 8
- 238000011144 upstream manufacturing Methods 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000010924 continuous production Methods 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 description 42
- 230000032050 esterification Effects 0.000 description 34
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 33
- 230000003647 oxidation Effects 0.000 description 28
- YGYNBBAUIYTWBF-UHFFFAOYSA-N 2,6-dimethylnaphthalene Chemical compound C1=C(C)C=CC2=CC(C)=CC=C21 YGYNBBAUIYTWBF-UHFFFAOYSA-N 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 24
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 24
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- 239000010941 cobalt Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 229910017052 cobalt Inorganic materials 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- 229910052794 bromium Inorganic materials 0.000 description 16
- -1 methanol Chemical class 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 229910052748 manganese Inorganic materials 0.000 description 14
- 239000011572 manganese Substances 0.000 description 14
- 239000007789 gas Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 12
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 8
- 239000011112 polyethylene naphthalate Substances 0.000 description 8
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 229910001385 heavy metal Inorganic materials 0.000 description 5
- 238000004811 liquid chromatography Methods 0.000 description 5
- 239000012808 vapor phase Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 150000001983 dialkylethers Chemical class 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 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 4
- 239000000463 material Substances 0.000 description 4
- 238000005192 partition Methods 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 3
- SHFLOIUZUDNHFB-UHFFFAOYSA-N 6-formylnaphthalene-2-carboxylic acid Chemical compound C1=C(C=O)C=CC2=CC(C(=O)O)=CC=C21 SHFLOIUZUDNHFB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 229910001882 dioxygen Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RVHSTXJKKZWWDQ-UHFFFAOYSA-N 1,1,1,2-tetrabromoethane Chemical compound BrCC(Br)(Br)Br RVHSTXJKKZWWDQ-UHFFFAOYSA-N 0.000 description 2
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- APQSQLNWAIULLK-UHFFFAOYSA-N 1,4-dimethylnaphthalene Chemical compound C1=CC=C2C(C)=CC=C(C)C2=C1 APQSQLNWAIULLK-UHFFFAOYSA-N 0.000 description 2
- SPAYGOAEIJHIDE-UHFFFAOYSA-N 1-(6-methylnaphthalen-2-yl)ethanone Chemical compound C1=C(C)C=CC2=CC(C(=O)C)=CC=C21 SPAYGOAEIJHIDE-UHFFFAOYSA-N 0.000 description 2
- RSZZOYYYZOWNCO-UHFFFAOYSA-N 1-methyl-naphthalene-2,6-dicarboxylic acid Natural products OC(=O)C1=CC=C2C(C)=C(C(O)=O)C=CC2=C1 RSZZOYYYZOWNCO-UHFFFAOYSA-N 0.000 description 2
- WWGUMAYGTYQSGA-UHFFFAOYSA-N 2,3-dimethylnaphthalene Chemical compound C1=CC=C2C=C(C)C(C)=CC2=C1 WWGUMAYGTYQSGA-UHFFFAOYSA-N 0.000 description 2
- CJJFFBINNGWEBO-UHFFFAOYSA-N 2,6-diethylnaphthalene Chemical compound C1=C(CC)C=CC2=CC(CC)=CC=C21 CJJFFBINNGWEBO-UHFFFAOYSA-N 0.000 description 2
- GWLLTEXUIOFAFE-UHFFFAOYSA-N 2,6-diisopropylnaphthalene Chemical compound C1=C(C(C)C)C=CC2=CC(C(C)C)=CC=C21 GWLLTEXUIOFAFE-UHFFFAOYSA-N 0.000 description 2
- SKTKMAWOMQFTNS-UHFFFAOYSA-N 6-methoxycarbonylnaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)OC)=CC=C21 SKTKMAWOMQFTNS-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000004429 atom 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
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-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
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- RHOUYXUGJXVYJF-UHFFFAOYSA-N methyl 6-formylnaphthalene-2-carboxylate Chemical compound C1=C(C=O)C=CC2=CC(C(=O)OC)=CC=C21 RHOUYXUGJXVYJF-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- MJHNUUNSCNRGJE-UHFFFAOYSA-N trimethyl benzene-1,2,4-tricarboxylate Chemical group COC(=O)C1=CC=C(C(=O)OC)C(C(=O)OC)=C1 MJHNUUNSCNRGJE-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- 239000005967 1,4-Dimethylnaphthalene Substances 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- UDDBXEBZOSFUQE-UHFFFAOYSA-N 2-butyl-6-methylnaphthalene Chemical compound C1=C(C)C=CC2=CC(CCCC)=CC=C21 UDDBXEBZOSFUQE-UHFFFAOYSA-N 0.000 description 1
- ZSPDYGICHBLYSD-UHFFFAOYSA-N 2-methylnaphthalene-1-carboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C)=CC=C21 ZSPDYGICHBLYSD-UHFFFAOYSA-N 0.000 description 1
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
- CYOMKTVNSWQGGQ-UHFFFAOYSA-N [Mn].[Br] Chemical compound [Mn].[Br] CYOMKTVNSWQGGQ-UHFFFAOYSA-N 0.000 description 1
- DJTZIDSZSYWGKR-UHFFFAOYSA-N acetic acid tetrahydrate Chemical compound O.O.O.O.CC(O)=O DJTZIDSZSYWGKR-UHFFFAOYSA-N 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical group O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910021446 cobalt carbonate Inorganic materials 0.000 description 1
- MZZUATUOLXMCEY-UHFFFAOYSA-N cobalt manganese Chemical compound [Mn].[Co] MZZUATUOLXMCEY-UHFFFAOYSA-N 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- REQPQFUJGGOFQL-UHFFFAOYSA-N dimethylcarbamothioyl n,n-dimethylcarbamodithioate Chemical compound CN(C)C(=S)SC(=S)N(C)C REQPQFUJGGOFQL-UHFFFAOYSA-N 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000011656 manganese carbonate Substances 0.000 description 1
- 229940093474 manganese carbonate Drugs 0.000 description 1
- 235000006748 manganese carbonate Nutrition 0.000 description 1
- 229910000016 manganese(II) carbonate Inorganic materials 0.000 description 1
- XMWCXZJXESXBBY-UHFFFAOYSA-L manganese(ii) carbonate Chemical compound [Mn+2].[O-]C([O-])=O XMWCXZJXESXBBY-UHFFFAOYSA-L 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000012264 purified product Substances 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
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US981,184 | 1992-11-24 | ||
| US07/981,184 US5350874A (en) | 1992-11-24 | 1992-11-24 | Process for preparing diesters of naphthalenedicarboxylic acids |
| PCT/US1993/011299 WO1994012462A1 (en) | 1992-11-24 | 1993-11-19 | Process for preparing diesters of naphthalenedicarboxylic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH07503259A JPH07503259A (ja) | 1995-04-06 |
| JP3730659B2 true JP3730659B2 (ja) | 2006-01-05 |
Family
ID=25528181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51329594A Expired - Lifetime JP3730659B2 (ja) | 1992-11-24 | 1993-11-19 | ナフタリンジカルボン酸のジエステルの製造方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5350874A (cg-RX-API-DMAC10.html) |
| EP (1) | EP0624153B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP3730659B2 (cg-RX-API-DMAC10.html) |
| KR (1) | KR100276936B1 (cg-RX-API-DMAC10.html) |
| CN (1) | CN1041084C (cg-RX-API-DMAC10.html) |
| AU (1) | AU5615294A (cg-RX-API-DMAC10.html) |
| CA (1) | CA2117418C (cg-RX-API-DMAC10.html) |
| DE (1) | DE69321577T2 (cg-RX-API-DMAC10.html) |
| ES (1) | ES2122219T3 (cg-RX-API-DMAC10.html) |
| MX (1) | MX9307310A (cg-RX-API-DMAC10.html) |
| RU (1) | RU2123996C1 (cg-RX-API-DMAC10.html) |
| TW (1) | TW284756B (cg-RX-API-DMAC10.html) |
| WO (1) | WO1994012462A1 (cg-RX-API-DMAC10.html) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW346555B (en) * | 1994-04-19 | 1998-12-01 | Teijin Ltd | Base film for photographic film |
| US6211398B1 (en) | 1997-10-03 | 2001-04-03 | Eastman Chemical Company | Process for the preparation of dialkyl esters of naphthalenedicarboxylic acids |
| MXPA02006832A (es) * | 2000-01-14 | 2002-10-23 | Bp Corp North America Inc | Sintesis y uso de los 1,5-naftalenodicarboxilatos dimetilicos y sus intermediarios. |
| US6906164B2 (en) * | 2000-12-07 | 2005-06-14 | Eastman Chemical Company | Polyester process using a pipe reactor |
| US7074879B2 (en) * | 2003-06-06 | 2006-07-11 | Eastman Chemical Company | Polyester process using a pipe reactor |
| US7247742B2 (en) * | 2004-05-20 | 2007-07-24 | Bp Corporation North America Inc. | Recycling polyethylene naphthalate containing materials in a process to produce diesters |
| EP2748142B1 (de) * | 2011-08-24 | 2015-08-05 | Basf Se | Verfahren zur herstellung von mercaptoalkylcarboxylaten |
| US10556214B2 (en) * | 2017-12-20 | 2020-02-11 | Uop Llc | Apparatuses for mixing of staged methanol injection |
| CN114805071A (zh) * | 2022-05-23 | 2022-07-29 | 煤炭科学技术研究院有限公司 | 一种连续精制2,6-萘二甲酸二甲酯的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2885432A (en) * | 1954-10-06 | 1959-05-05 | Huels Chemische Werke Ag | Process for the production of alkyl esters of aromatic dicarboxylic acids |
| JPS4896574A (cg-RX-API-DMAC10.html) * | 1972-03-14 | 1973-12-10 | ||
| JPS5076057A (cg-RX-API-DMAC10.html) * | 1973-11-09 | 1975-06-21 | ||
| JPS5076055A (cg-RX-API-DMAC10.html) * | 1973-11-09 | 1975-06-21 | ||
| JPS5647893B2 (cg-RX-API-DMAC10.html) * | 1973-11-27 | 1981-11-12 | ||
| JPS5095253A (cg-RX-API-DMAC10.html) * | 1973-12-25 | 1975-07-29 | ||
| US4003948A (en) * | 1974-03-08 | 1977-01-18 | Teijin Limited | Process for preparing dimethyl 2,6-naphthalenedicarboxylate |
-
1992
- 1992-11-24 US US07/981,184 patent/US5350874A/en not_active Expired - Lifetime
-
1993
- 1993-11-19 ES ES94901630T patent/ES2122219T3/es not_active Expired - Lifetime
- 1993-11-19 WO PCT/US1993/011299 patent/WO1994012462A1/en not_active Ceased
- 1993-11-19 DE DE69321577T patent/DE69321577T2/de not_active Expired - Lifetime
- 1993-11-19 CA CA002117418A patent/CA2117418C/en not_active Expired - Fee Related
- 1993-11-19 AU AU56152/94A patent/AU5615294A/en not_active Abandoned
- 1993-11-19 RU RU94040188A patent/RU2123996C1/ru not_active IP Right Cessation
- 1993-11-19 EP EP94901630A patent/EP0624153B1/en not_active Expired - Lifetime
- 1993-11-19 JP JP51329594A patent/JP3730659B2/ja not_active Expired - Lifetime
- 1993-11-19 KR KR1019940702514A patent/KR100276936B1/ko not_active Expired - Lifetime
- 1993-11-23 TW TW082109886A patent/TW284756B/zh not_active IP Right Cessation
- 1993-11-23 MX MX9307310A patent/MX9307310A/es not_active IP Right Cessation
- 1993-11-24 CN CN93114834A patent/CN1041084C/zh not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| MX9307310A (es) | 1994-05-31 |
| CA2117418C (en) | 2004-04-06 |
| AU5615294A (en) | 1994-06-22 |
| CN1041084C (zh) | 1998-12-09 |
| DE69321577D1 (de) | 1998-11-19 |
| WO1994012462A1 (en) | 1994-06-09 |
| KR950700232A (ko) | 1995-01-16 |
| RU2123996C1 (ru) | 1998-12-27 |
| EP0624153B1 (en) | 1998-10-14 |
| TW284756B (cg-RX-API-DMAC10.html) | 1996-09-01 |
| RU94040188A (ru) | 1996-07-10 |
| EP0624153A1 (en) | 1994-11-17 |
| JPH07503259A (ja) | 1995-04-06 |
| CA2117418A1 (en) | 1994-06-09 |
| CN1092761A (zh) | 1994-09-28 |
| ES2122219T3 (es) | 1998-12-16 |
| KR100276936B1 (ko) | 2001-02-01 |
| DE69321577T2 (de) | 1999-06-17 |
| US5350874A (en) | 1994-09-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0021747B1 (en) | Process for the preparation of terephthalic acid | |
| US5292934A (en) | Method for preparing aromatic carboxylic acids | |
| US6153790A (en) | Method to produce aromatic dicarboxylic acids using cobalt and zirconium catalysts | |
| US4777287A (en) | Recycle of vaporized solvent in liquid phase oxidation of an alkyl aromatic | |
| EP0261892B1 (en) | The production of aromatic carboxylic acids | |
| EP0601177B1 (en) | Method for preparing aromatic carboxylic acids | |
| WO1999031038A1 (en) | Method to produce aromatic carboxylic acids | |
| US5256817A (en) | Method for purifying a naphthalenedicarboxylic acid | |
| KR100276936B1 (ko) | 나프탈렌디카복실산의 디에스테르의 제조방법 | |
| CA2329258C (en) | Improved process for producing pure carboxylic acids | |
| US5629446A (en) | Process for preparing purified 2,6-naphthalenedicarboxylic acid | |
| US5770764A (en) | Process for preparing purified aromatic polycarboxylic acids | |
| EP0046397B1 (en) | Process for producing trimellitic acid or pyromellitic acid | |
| CA2562246C (en) | Recycling 2,6-naphthalenedicarboxylic acid (2,6-nda) contained in polyethylene naphthalate in a process to produce diesters | |
| JP3199104B2 (ja) | ２，６−ナフタレンジカルボン酸及びそのエステルの製造法 | |
| EP0041778B2 (en) | Oxidation of meta- or para-xylene to iso- or tere-phthalic acid | |
| JPH1129521A (ja) | ナフタレンジカルボン酸の製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20040217 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20040405 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20040518 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20040706 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20041006 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20050920 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20051007 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R154 | Certificate of patent or utility model (reissue) |
Free format text: JAPANESE INTERMEDIATE CODE: R154 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20091014 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20091014 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20101014 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20111014 Year of fee payment: 6 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121014 Year of fee payment: 7 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20131014 Year of fee payment: 8 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |