DE2407003A1 - Neue naphthalin-tetracarbonsaeurederivate und verfahren zu ihrer herstellung - Google Patents
Neue naphthalin-tetracarbonsaeurederivate und verfahren zu ihrer herstellungInfo
- Publication number
- DE2407003A1 DE2407003A1 DE19742407003 DE2407003A DE2407003A1 DE 2407003 A1 DE2407003 A1 DE 2407003A1 DE 19742407003 DE19742407003 DE 19742407003 DE 2407003 A DE2407003 A DE 2407003A DE 2407003 A1 DE2407003 A1 DE 2407003A1
- Authority
- DE
- Germany
- Prior art keywords
- naphthalene
- tetracarboxylate
- alkali metal
- acid
- water
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 94
- 230000008569 process Effects 0.000 title claims description 45
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 133
- 239000000203 mixture Substances 0.000 claims description 89
- 229910052783 alkali metal Inorganic materials 0.000 claims description 78
- -1 alkali metal salts Chemical class 0.000 claims description 75
- 239000002253 acid Substances 0.000 claims description 67
- YSRFBCIGFNFMPS-UHFFFAOYSA-N naphthalene-1,3,5,7-tetracarboxylic acid Chemical compound C1=C(C(O)=O)C=C(C(O)=O)C2=CC(C(=O)O)=CC(C(O)=O)=C21 YSRFBCIGFNFMPS-UHFFFAOYSA-N 0.000 claims description 65
- 239000007864 aqueous solution Substances 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 40
- 150000002148 esters Chemical class 0.000 claims description 35
- 239000007787 solid Substances 0.000 claims description 35
- 239000011541 reaction mixture Substances 0.000 claims description 34
- 150000002500 ions Chemical class 0.000 claims description 31
- 150000001340 alkali metals Chemical class 0.000 claims description 29
- 239000003513 alkali Substances 0.000 claims description 28
- 229910052751 metal Inorganic materials 0.000 claims description 26
- 239000002184 metal Substances 0.000 claims description 26
- 239000002244 precipitate Substances 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000002609 medium Substances 0.000 claims description 23
- 239000012736 aqueous medium Substances 0.000 claims description 21
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 19
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 16
- 239000011707 mineral Substances 0.000 claims description 16
- 150000001447 alkali salts Chemical class 0.000 claims description 15
- 239000000706 filtrate Substances 0.000 claims description 15
- 150000007524 organic acids Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 11
- 150000004820 halides Chemical class 0.000 claims description 11
- 239000011261 inert gas Substances 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 8
- 239000012298 atmosphere Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 6
- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000001661 cadmium Chemical class 0.000 claims description 5
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 5
- 150000003751 zinc Chemical class 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- GAWQSSFXFKROAE-UHFFFAOYSA-J tetrasodium;naphthalene-1,3,5,7-tetracarboxylate Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(C([O-])=O)C=C(C([O-])=O)C2=CC(C(=O)[O-])=CC(C([O-])=O)=C21 GAWQSSFXFKROAE-UHFFFAOYSA-J 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 144
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 70
- 239000013078 crystal Substances 0.000 description 42
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 40
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 40
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 35
- 239000000243 solution Substances 0.000 description 32
- JQKBWPDRRSJVDN-UHFFFAOYSA-J tetrapotassium;naphthalene-1,3,5,7-tetracarboxylate Chemical compound [K+].[K+].[K+].[K+].C1=C(C([O-])=O)C=C(C([O-])=O)C2=CC(C(=O)[O-])=CC(C([O-])=O)=C21 JQKBWPDRRSJVDN-UHFFFAOYSA-J 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- 238000005886 esterification reaction Methods 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 239000007789 gas Substances 0.000 description 21
- 239000001569 carbon dioxide Substances 0.000 description 20
- 229910002092 carbon dioxide Inorganic materials 0.000 description 20
- 230000032050 esterification Effects 0.000 description 20
- 229910000027 potassium carbonate Inorganic materials 0.000 description 20
- 238000000926 separation method Methods 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- 235000011181 potassium carbonates Nutrition 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 239000007795 chemical reaction product Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 238000007323 disproportionation reaction Methods 0.000 description 15
- 239000012535 impurity Substances 0.000 description 15
- 239000003960 organic solvent Substances 0.000 description 15
- 238000006462 rearrangement reaction Methods 0.000 description 15
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 235000010755 mineral Nutrition 0.000 description 14
- 230000008707 rearrangement Effects 0.000 description 14
- 235000012970 cakes Nutrition 0.000 description 13
- 238000000605 extraction Methods 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- 239000012452 mother liquor Substances 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 238000000921 elemental analysis Methods 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical class C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 11
- 238000003916 acid precipitation Methods 0.000 description 11
- 238000009835 boiling Methods 0.000 description 11
- 230000007423 decrease Effects 0.000 description 11
- 229910052700 potassium Inorganic materials 0.000 description 11
- NPZDDYUXAQBRCJ-UHFFFAOYSA-M potassium;naphthalene-2-carboxylate Chemical compound [K+].C1=CC=CC2=CC(C(=O)[O-])=CC=C21 NPZDDYUXAQBRCJ-UHFFFAOYSA-M 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 10
- 238000000862 absorption spectrum Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 9
- 159000000001 potassium salts Chemical class 0.000 description 9
- 239000002002 slurry Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 8
- QAYXDWGFSMUTBJ-UHFFFAOYSA-L dipotassium;naphthalene-2,6-dicarboxylate Chemical compound [K+].[K+].C1=C(C([O-])=O)C=CC2=CC(C(=O)[O-])=CC=C21 QAYXDWGFSMUTBJ-UHFFFAOYSA-L 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000011591 potassium Substances 0.000 description 8
- 229960003975 potassium Drugs 0.000 description 8
- ZVUVJTQITHFYHV-UHFFFAOYSA-M potassium;naphthalene-1-carboxylate Chemical compound [K+].C1=CC=C2C(C(=O)[O-])=CC=CC2=C1 ZVUVJTQITHFYHV-UHFFFAOYSA-M 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 229910001414 potassium ion Inorganic materials 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 150000003628 tricarboxylic acids Chemical class 0.000 description 6
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000001103 potassium chloride Substances 0.000 description 5
- 235000011164 potassium chloride Nutrition 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- OKIIEJOIXGHUKX-UHFFFAOYSA-L cadmium iodide Chemical compound [Cd+2].[I-].[I-] OKIIEJOIXGHUKX-UHFFFAOYSA-L 0.000 description 4
- 238000001103 continuous-wave nuclear magnetic resonance spectrum Methods 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- 229940093915 gynecological organic acid Drugs 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000003575 carbonaceous material Substances 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 150000004683 dihydrates Chemical class 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical class C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- OCSRTSMJGCJOAO-UHFFFAOYSA-N tetramethyl naphthalene-1,3,5,7-tetracarboxylate Chemical compound C1=C(C(=O)OC)C=C(C(=O)OC)C2=CC(C(=O)OC)=CC(C(=O)OC)=C21 OCSRTSMJGCJOAO-UHFFFAOYSA-N 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 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 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 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
- 229940075417 cadmium iodide Drugs 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- JGJWEXOAAXEJMW-UHFFFAOYSA-N dimethyl naphthalene-1,2-dicarboxylate Chemical compound C1=CC=CC2=C(C(=O)OC)C(C(=O)OC)=CC=C21 JGJWEXOAAXEJMW-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- HZCVHZNSPYVRST-UHFFFAOYSA-L dipotassium;4,8-dicarboxynaphthalene-2,6-dicarboxylate Chemical compound [K+].[K+].C1=C(C([O-])=O)C=C2C(C(=O)O)=CC(C([O-])=O)=CC2=C1C(O)=O HZCVHZNSPYVRST-UHFFFAOYSA-L 0.000 description 2
- AVTWCKQWICBEPN-UHFFFAOYSA-L dipotassium;naphthalene-1,8-dicarboxylate Chemical compound [K+].[K+].C1=CC(C([O-])=O)=C2C(C(=O)[O-])=CC=CC2=C1 AVTWCKQWICBEPN-UHFFFAOYSA-L 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- HMRROBKAACRWBP-UHFFFAOYSA-N methyl naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=CC=CC2=C1 HMRROBKAACRWBP-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- KVQQRFDIKYXJTJ-UHFFFAOYSA-N naphthalene-1,2,3-tricarboxylic acid Chemical compound C1=CC=C2C(C(O)=O)=C(C(O)=O)C(C(=O)O)=CC2=C1 KVQQRFDIKYXJTJ-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
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- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/33—Polycyclic acids
- C07C63/337—Polycyclic acids with carboxyl groups bound to condensed ring systems
- C07C63/34—Polycyclic acids with carboxyl groups bound to condensed ring systems containing two condensed rings
- C07C63/40—Polycyclic acids with carboxyl groups bound to condensed ring systems containing two condensed rings containing three or more carboxyl groups all bound to carbon atoms of the condensed ring system
Landscapes
- 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)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1742073A JPS49102656A (enExample) | 1973-02-14 | 1973-02-14 | |
| JP1789473A JPS49102657A (enExample) | 1973-02-15 | 1973-02-15 | |
| JP2539973A JPS5062962A (enExample) | 1973-03-03 | 1973-03-03 | |
| JP2540073A JPS49132045A (enExample) | 1973-03-03 | 1973-03-03 | |
| JP3087373A JPS49132048A (enExample) | 1973-03-19 | 1973-03-19 | |
| JP3087273A JPS49132047A (enExample) | 1973-03-19 | 1973-03-19 | |
| JP3503573A JPS49132054A (enExample) | 1973-03-29 | 1973-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2407003A1 true DE2407003A1 (de) | 1974-09-12 |
Family
ID=27563779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742407003 Pending DE2407003A1 (de) | 1973-02-14 | 1974-02-14 | Neue naphthalin-tetracarbonsaeurederivate und verfahren zu ihrer herstellung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3954840A (enExample) |
| DE (1) | DE2407003A1 (enExample) |
| FR (1) | FR2217308B1 (enExample) |
| GB (1) | GB1453376A (enExample) |
| IT (1) | IT1007342B (enExample) |
| NL (1) | NL7402034A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0359098A1 (en) * | 1988-09-05 | 1990-03-21 | Nkk Corporation | Method of manufacturing alkali metal salt of 2,3,6,7-naphthalenetetracarboxylic acid |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4139577A (en) * | 1976-12-07 | 1979-02-13 | Ici Americas Inc. | Polymerizable composition comprising a tetracarboxylic ester monomer useful for imparting flame retardance to resin polymers |
| US4339595A (en) * | 1980-06-27 | 1982-07-13 | Standard Oil Company (Indiana) | Hexa(meta-,para-carboxyphenyl)benzene compounds |
| JPH07116352B2 (ja) * | 1986-10-07 | 1995-12-13 | 三菱化学株式会社 | 熱可塑性ポリエステル樹脂組成物 |
| US5175354A (en) * | 1990-03-30 | 1992-12-29 | Nippon Steel Chemical Co., Ltd. | Process for preparing 2,6-naphthalene-dicarboxylic acid |
| US6320073B1 (en) * | 1999-08-30 | 2001-11-20 | Shell Oil Company | Process for separation of the dipotassium salt of naphthalene dicarboxylic acid using activated carbon beds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2849482A (en) * | 1955-11-19 | 1958-08-26 | Henkel & Cie Gmbh | Production of naphthalene-2, 6-dicarboxylic acid |
| US3101368A (en) * | 1956-01-03 | 1963-08-20 | Henkel & Cie Gmbh | Process for the preparation of cyclic dicarboxylic acids |
| US3042717A (en) * | 1961-02-15 | 1962-07-03 | Henkel & Cie Gmbh | Process for the production of aromatic dicarboxylic and polycarboxylic acids |
| BE629973A (enExample) * | 1962-03-23 | |||
| NL294054A (enExample) * | 1962-06-15 | |||
| JPS545814Y2 (enExample) * | 1971-05-26 | 1979-03-15 | ||
| US3746752A (en) * | 1971-10-18 | 1973-07-17 | Phillips Petroleum Co | Process for preparation of aromatic carboxylates |
-
1974
- 1974-02-11 US US05/441,626 patent/US3954840A/en not_active Expired - Lifetime
- 1974-02-11 IT IT20424/74A patent/IT1007342B/it active
- 1974-02-14 GB GB674074A patent/GB1453376A/en not_active Expired
- 1974-02-14 FR FR7404977A patent/FR2217308B1/fr not_active Expired
- 1974-02-14 DE DE19742407003 patent/DE2407003A1/de active Pending
- 1974-02-14 NL NL7402034A patent/NL7402034A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0359098A1 (en) * | 1988-09-05 | 1990-03-21 | Nkk Corporation | Method of manufacturing alkali metal salt of 2,3,6,7-naphthalenetetracarboxylic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1007342B (it) | 1976-10-30 |
| FR2217308A1 (enExample) | 1974-09-06 |
| NL7402034A (enExample) | 1974-08-16 |
| GB1453376A (en) | 1976-10-20 |
| US3954840A (en) | 1976-05-04 |
| FR2217308B1 (enExample) | 1976-06-25 |
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