SU591135A3 - Способ получени диметилового эфира 2,6-нафталиндикарбоновой кислоты - Google Patents
Способ получени диметилового эфира 2,6-нафталиндикарбоновой кислотыInfo
- Publication number
- SU591135A3 SU591135A3 SU752116037A SU2116037A SU591135A3 SU 591135 A3 SU591135 A3 SU 591135A3 SU 752116037 A SU752116037 A SU 752116037A SU 2116037 A SU2116037 A SU 2116037A SU 591135 A3 SU591135 A3 SU 591135A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- oxidation
- esterification
- methanol
- mol
- crude
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 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 title description 7
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 title description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- 238000007254 oxidation reaction Methods 0.000 claims description 40
- 230000003647 oxidation Effects 0.000 claims description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 230000032050 esterification Effects 0.000 claims description 15
- 238000005886 esterification reaction Methods 0.000 claims description 15
- YGYNBBAUIYTWBF-UHFFFAOYSA-N 2,6-dimethylnaphthalene Chemical compound C1=C(C)C=CC2=CC(C)=CC=C21 YGYNBBAUIYTWBF-UHFFFAOYSA-N 0.000 claims description 12
- 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 8
- 238000000926 separation method Methods 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- BZRRQSJJPUGBAA-UHFFFAOYSA-L cobalt(ii) bromide Chemical compound Br[Co]Br BZRRQSJJPUGBAA-UHFFFAOYSA-L 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 26
- 239000000706 filtrate Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 7
- -1 aldehyde ester Chemical class 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000005406 washing Methods 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 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- IWEATXLWFWACOA-UHFFFAOYSA-N 2,6-dimethylnaphthalene-1-carboxylic acid Chemical compound OC(=O)C1=C(C)C=CC2=CC(C)=CC=C21 IWEATXLWFWACOA-UHFFFAOYSA-N 0.000 description 1
- WQFZWQFTPVEXQQ-UHFFFAOYSA-N 2-formylnaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(C=O)C=CC2=C1 WQFZWQFTPVEXQQ-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
- VOCNMTIGMYPFPY-UHFFFAOYSA-N 6-methylnaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C)=CC=C21 VOCNMTIGMYPFPY-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 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 1
- 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 1
- ZBXAEINYNSCHFO-UHFFFAOYSA-N methyl 6-methylnaphthalene-2-carboxylate Chemical compound C1=C(C)C=CC2=CC(C(=O)OC)=CC=C21 ZBXAEINYNSCHFO-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742414363 DE2414363C3 (de) | 1974-03-26 | 1974-03-26 | Verfahren zur Herstellung von 2,6-Naphthalindicarbonsäuredimethylester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU591135A3 true SU591135A3 (ru) | 1978-01-30 |
Family
ID=5911120
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752116037A SU591135A3 (ru) | 1974-03-26 | 1975-03-21 | Способ получени диметилового эфира 2,6-нафталиндикарбоновой кислоты |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS50142545A (enExample) |
| DE (1) | DE2414363C3 (enExample) |
| FR (1) | FR2265718B1 (enExample) |
| GB (1) | GB1462317A (enExample) |
| IT (1) | IT1029662B (enExample) |
| NL (1) | NL7503622A (enExample) |
| SU (1) | SU591135A3 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007213814A (ja) * | 2006-02-07 | 2007-08-23 | Micro Denshi Kk | マイクロ波発振装置 |
-
1974
- 1974-03-26 DE DE19742414363 patent/DE2414363C3/de not_active Expired
-
1975
- 1975-02-07 IT IT4807275A patent/IT1029662B/it active
- 1975-02-20 JP JP2138575A patent/JPS50142545A/ja active Pending
- 1975-03-21 SU SU752116037A patent/SU591135A3/ru active
- 1975-03-24 FR FR7509169A patent/FR2265718B1/fr not_active Expired
- 1975-03-24 GB GB1227775A patent/GB1462317A/en not_active Expired
- 1975-03-26 NL NL7503622A patent/NL7503622A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2414363B2 (de) | 1979-02-01 |
| DE2414363C3 (de) | 1979-09-27 |
| JPS50142545A (enExample) | 1975-11-17 |
| NL7503622A (nl) | 1975-09-30 |
| IT1029662B (it) | 1979-03-20 |
| DE2414363A1 (de) | 1975-10-16 |
| FR2265718A1 (enExample) | 1975-10-24 |
| FR2265718B1 (enExample) | 1980-04-30 |
| GB1462317A (en) | 1977-01-26 |
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