DE2505831C3 - Verfahren zur Reinigung von rohem 2,6-Naphthalindicarbonsäuredimetliylester - Google Patents
Verfahren zur Reinigung von rohem 2,6-NaphthalindicarbonsäuredimetliylesterInfo
- Publication number
- DE2505831C3 DE2505831C3 DE19752505831 DE2505831A DE2505831C3 DE 2505831 C3 DE2505831 C3 DE 2505831C3 DE 19752505831 DE19752505831 DE 19752505831 DE 2505831 A DE2505831 A DE 2505831A DE 2505831 C3 DE2505831 C3 DE 2505831C3
- Authority
- DE
- Germany
- Prior art keywords
- nda
- distillation
- dimethyl ester
- crude
- acid number
- 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
- 238000000034 method Methods 0.000 title claims description 24
- 230000008569 process Effects 0.000 title description 14
- 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 title description 8
- 238000000746 purification Methods 0.000 title description 7
- 238000004821 distillation Methods 0.000 claims description 56
- 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 6
- 239000007791 liquid phase Substances 0.000 claims description 5
- 238000005292 vacuum distillation Methods 0.000 claims description 2
- 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 1
- 239000002253 acid Substances 0.000 description 31
- 238000002845 discoloration Methods 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 14
- 239000007788 liquid Substances 0.000 description 14
- HMRROBKAACRWBP-UHFFFAOYSA-N methyl naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=CC=CC2=C1 HMRROBKAACRWBP-UHFFFAOYSA-N 0.000 description 13
- 239000012071 phase Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000005886 esterification reaction Methods 0.000 description 9
- 230000032050 esterification Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical class C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 238000001577 simple distillation Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 238000005979 thermal decomposition reaction Methods 0.000 description 3
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004140 cleaning Methods 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
- 238000007323 disproportionation reaction Methods 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 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 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 206010039509 Scab Diseases 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- HQKSINSCHCDMLS-UHFFFAOYSA-N ethyl naphthalene-2-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)OCC)=CC=C21 HQKSINSCHCDMLS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- -1 monomethyl ester Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000011364 vaporized material Substances 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)
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 (3)
| Publication Number | Publication Date |
|---|---|
| DE2505831A1 DE2505831A1 (de) | 1975-08-14 |
| DE2505831B2 DE2505831B2 (de) | 1978-07-13 |
| DE2505831C3 true DE2505831C3 (de) | 1979-03-15 |
Family
ID=11912867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752505831 Expired DE2505831C3 (de) | 1974-02-12 | 1975-02-12 | Verfahren zur Reinigung von rohem 2,6-Naphthalindicarbonsäuredimetliylester |
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) |
Families Citing this family (2)
| 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 |
| 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
Also Published As
| Publication number | Publication date |
|---|---|
| DE2505831A1 (de) | 1975-08-14 |
| FR2260561A1 (en, 2012) | 1975-09-05 |
| GB1464241A (en) | 1977-02-09 |
| FR2260561B1 (en, 2012) | 1978-10-06 |
| DE2505831B2 (de) | 1978-07-13 |
| JPS5829291B2 (ja) | 1983-06-22 |
| JPS50108248A (en, 2012) | 1975-08-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EI | Miscellaneous see part 3 | ||
| 8339 | Ceased/non-payment of the annual fee |