JPS5829291B2 - ２，６− ナフタリンジカルボンサンジメチルエステル ノ セイセイホウ - Google Patents
２，６− ナフタリンジカルボンサンジメチルエステル ノ セイセイホウInfo
- Publication number
- JPS5829291B2 JPS5829291B2 JP1630774A JP1630774A JPS5829291B2 JP S5829291 B2 JPS5829291 B2 JP S5829291B2 JP 1630774 A JP1630774 A JP 1630774A JP 1630774 A JP1630774 A JP 1630774A JP S5829291 B2 JPS5829291 B2 JP S5829291B2
- Authority
- JP
- Japan
- Prior art keywords
- dicarboxylic acid
- naphthalene dicarboxylic
- dimethyl ester
- ester
- acid dimethyl
- 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
- 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 42
- 238000004821 distillation Methods 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 15
- 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 claims description 13
- HMRROBKAACRWBP-UHFFFAOYSA-N methyl naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=CC=CC2=C1 HMRROBKAACRWBP-UHFFFAOYSA-N 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000004040 coloring Methods 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 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 description 9
- 239000000047 product Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- YGYNBBAUIYTWBF-UHFFFAOYSA-N 2,6-dimethylnaphthalene Chemical compound C1=C(C)C=CC2=CC(C)=CC=C21 YGYNBBAUIYTWBF-UHFFFAOYSA-N 0.000 description 6
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- -1 for example Chemical compound 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 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 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 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 3
- 238000001577 simple distillation Methods 0.000 description 3
- 238000005979 thermal decomposition reaction Methods 0.000 description 3
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 2
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1630774A JPS5829291B2 (ja) | 1974-02-12 | 1974-02-12 | ２，６− ナフタリンジカルボンサンジメチルエステル ノ セイセイホウ |
| GB601075A GB1464241A (en) | 1974-02-12 | 1975-02-12 | Purification of aromatic esters |
| FR7504302A FR2260561B1 (en, 2012) | 1974-02-12 | 1975-02-12 | |
| DE19752505831 DE2505831C3 (de) | 1974-02-12 | 1975-02-12 | Verfahren zur Reinigung von rohem 2,6-Naphthalindicarbonsäuredimetliylester |
| US05/725,834 US4048021A (en) | 1974-02-12 | 1976-09-23 | Method of purifying crude 2,6-naphthalenedicarboxylic acid dimethyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1630774A JPS5829291B2 (ja) | 1974-02-12 | 1974-02-12 | ２，６− ナフタリンジカルボンサンジメチルエステル ノ セイセイホウ |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS50108248A JPS50108248A (en, 2012) | 1975-08-26 |
| JPS5829291B2 true JPS5829291B2 (ja) | 1983-06-22 |
Family
ID=11912867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1630774A Expired JPS5829291B2 (ja) | 1974-02-12 | 1974-02-12 | ２，６− ナフタリンジカルボンサンジメチルエステル ノ セイセイホウ |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5829291B2 (en, 2012) |
| DE (1) | DE2505831C3 (en, 2012) |
| FR (1) | FR2260561B1 (en, 2012) |
| GB (1) | GB1464241A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5868226U (ja) * | 1981-11-04 | 1983-05-10 | 伊藤 公政 | 中央に穴のあいたハム及びソ−セ−ジ、かまぼこ等練食品 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0450621A3 (en) * | 1990-04-05 | 1993-05-12 | Sumikin Chemical Co., Ltd. | Process for the preparation of high-purity naphthalenecarboxylic acid esters |
-
1974
- 1974-02-12 JP JP1630774A patent/JPS5829291B2/ja not_active Expired
-
1975
- 1975-02-12 GB GB601075A patent/GB1464241A/en not_active Expired
- 1975-02-12 FR FR7504302A patent/FR2260561B1/fr not_active Expired
- 1975-02-12 DE DE19752505831 patent/DE2505831C3/de not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5868226U (ja) * | 1981-11-04 | 1983-05-10 | 伊藤 公政 | 中央に穴のあいたハム及びソ−セ−ジ、かまぼこ等練食品 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2505831B2 (de) | 1978-07-13 |
| DE2505831A1 (de) | 1975-08-14 |
| FR2260561B1 (en, 2012) | 1978-10-06 |
| JPS50108248A (en, 2012) | 1975-08-26 |
| FR2260561A1 (en, 2012) | 1975-09-05 |
| GB1464241A (en) | 1977-02-09 |
| DE2505831C3 (de) | 1979-03-15 |
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