DE2510019C3 - Verfahren zur Herstellung von 2,6-Naphthalindicarbonsäure-dimethylester - Google Patents
Verfahren zur Herstellung von 2,6-Naphthalindicarbonsäure-dimethylesterInfo
- Publication number
- DE2510019C3 DE2510019C3 DE2510019A DE2510019A DE2510019C3 DE 2510019 C3 DE2510019 C3 DE 2510019C3 DE 2510019 A DE2510019 A DE 2510019A DE 2510019 A DE2510019 A DE 2510019A DE 2510019 C3 DE2510019 C3 DE 2510019C3
- Authority
- DE
- Germany
- Prior art keywords
- nda
- esterification
- methanol
- minutes
- naphthalenedicarboxylic acid
- 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 22
- 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 claims description 15
- 230000008569 process Effects 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 150
- 238000005886 esterification reaction Methods 0.000 claims description 62
- 230000032050 esterification Effects 0.000 claims description 42
- 239000002245 particle Substances 0.000 claims description 30
- 239000007787 solid Substances 0.000 claims description 26
- 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 15
- 239000003054 catalyst Substances 0.000 claims description 9
- 239000002002 slurry Substances 0.000 description 32
- 239000000725 suspension Substances 0.000 description 26
- 230000000903 blocking effect Effects 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 12
- 229910052753 mercury Inorganic materials 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 230000005587 bubbling Effects 0.000 description 4
- 230000005484 gravity Effects 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011343 solid material Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- -1 dimethyl 2,6-naphthalenedicarboxylic acid ester Chemical class 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
- 239000010419 fine particle Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 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
- 238000004064 recycling Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- UFMBOFGKHIXOTA-UHFFFAOYSA-N 2-methylterephthalic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C(O)=O UFMBOFGKHIXOTA-UHFFFAOYSA-N 0.000 description 1
- 235000014277 Clidemia hirta Nutrition 0.000 description 1
- 241000069219 Henriettea Species 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229940059904 light mineral oil Drugs 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 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 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001007 puffing effect Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2633874A JPS5710862B2 (OSRAM) | 1974-03-08 | 1974-03-08 | |
| JP11282274A JPS5139658A (en) | 1974-10-02 | 1974-10-02 | 2*66 nafutarinjikarubonsanno renzokuesuterukaho |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2510019A1 DE2510019A1 (de) | 1975-09-11 |
| DE2510019B2 DE2510019B2 (de) | 1978-04-06 |
| DE2510019C3 true DE2510019C3 (de) | 1978-12-07 |
Family
ID=26364106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2510019A Expired DE2510019C3 (de) | 1974-03-08 | 1975-03-07 | Verfahren zur Herstellung von 2,6-Naphthalindicarbonsäure-dimethylester |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4003948A (OSRAM) |
| DE (1) | DE2510019C3 (OSRAM) |
| FR (1) | FR2272973B1 (OSRAM) |
| GB (1) | GB1479845A (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5350874A (en) * | 1992-11-24 | 1994-09-27 | Amoco Corporation | Process for preparing diesters of naphthalenedicarboxylic acids |
| US6211398B1 (en) | 1997-10-03 | 2001-04-03 | Eastman Chemical Company | Process for the preparation of dialkyl esters of naphthalenedicarboxylic acids |
| CN112441918A (zh) * | 2019-09-04 | 2021-03-05 | 中国石油化工股份有限公司 | 合成2,6-萘二甲酸二甲酯的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3431243A (en) * | 1963-12-04 | 1969-03-04 | Teijin Ltd | Process for preparation of poly(ethylene terphthalate) from compressed terephthalic acid |
| US3655729A (en) * | 1968-07-18 | 1972-04-11 | Gen Tire & Rubber Co | Process for preparing esters of terephthalic acid |
-
1975
- 1975-03-04 US US05/555,125 patent/US4003948A/en not_active Expired - Lifetime
- 1975-03-07 GB GB9643/75A patent/GB1479845A/en not_active Expired
- 1975-03-07 DE DE2510019A patent/DE2510019C3/de not_active Expired
- 1975-03-10 FR FR7507405A patent/FR2272973B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2510019B2 (de) | 1978-04-06 |
| US4003948A (en) | 1977-01-18 |
| GB1479845A (en) | 1977-07-13 |
| FR2272973B1 (OSRAM) | 1978-08-18 |
| DE2510019A1 (de) | 1975-09-11 |
| FR2272973A1 (OSRAM) | 1975-12-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHJ | Ceased/non-payment of the annual fee |