DE2503377B2 - Verfahren zur herstellung von 1,4-naphthalindicarbonsaeureestern - Google Patents
Verfahren zur herstellung von 1,4-naphthalindicarbonsaeureesternInfo
- Publication number
- DE2503377B2 DE2503377B2 DE19752503377 DE2503377A DE2503377B2 DE 2503377 B2 DE2503377 B2 DE 2503377B2 DE 19752503377 DE19752503377 DE 19752503377 DE 2503377 A DE2503377 A DE 2503377A DE 2503377 B2 DE2503377 B2 DE 2503377B2
- Authority
- DE
- Germany
- Prior art keywords
- acid esters
- production
- naphthalindicarbonic
- solvent
- pyrrolidinocyclohexene
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000002148 esters Chemical class 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 title 1
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical class C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- TXXHDPDFNKHHGW-UHFFFAOYSA-N muconic acid Chemical compound OC(=O)C=CC=CC(O)=O TXXHDPDFNKHHGW-UHFFFAOYSA-N 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- TXXHDPDFNKHHGW-CCAGOZQPSA-N Muconic acid Natural products OC(=O)\C=C/C=C\C(O)=O TXXHDPDFNKHHGW-CCAGOZQPSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- -1 hexahydronaphthalene-1,4-dicarboxylic acid ester Chemical class 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OTSZYGOOKXGLED-UHFFFAOYSA-N 1-methoxycarbonylnaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(C(=O)OC)=C(C(O)=O)C=CC2=C1 OTSZYGOOKXGLED-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007269 dehydrobromination reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 238000004949 mass spectrometry 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
- 230000003287 optical effect Effects 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752503377 DE2503377B2 (de) | 1975-01-28 | 1975-01-28 | Verfahren zur herstellung von 1,4-naphthalindicarbonsaeureestern |
| ES444541A ES444541A1 (es) | 1975-01-28 | 1976-01-22 | Procedimiento para la preparacion de esteres de acido 1,4- naftalendicarboxilico. |
| GB267676A GB1528223A (en) | 1975-01-28 | 1976-01-23 | Process for preparing 1,4-naphthalene-dicarboxylic acid esters |
| NL7600714A NL7600714A (nl) | 1975-01-28 | 1976-01-23 | Werkwijze voor de bereiding van 1,4-naftaleendi- carbonzuuresters. |
| IT1960376A IT1054501B (it) | 1975-01-28 | 1976-01-26 | Processo per la preparazione di esteri del acido i.4 naftalendi carbossilico |
| SE7600766A SE7600766L (sv) | 1975-01-28 | 1976-01-26 | Forfarande for framstellning av 1,4-naftalen-dikarbonsyraester |
| CH91676A CH598185A5 (OSRAM) | 1975-01-28 | 1976-01-26 | |
| LU74244A LU74244A1 (OSRAM) | 1975-01-28 | 1976-01-26 | |
| BR7600480A BR7600480A (pt) | 1975-01-28 | 1976-01-27 | Processo para a obtencao de esteres de acido 1,4-naftalenodicarboxilico |
| AU10576/76A AU491550B2 (en) | 1975-01-28 | 1976-01-27 | Process for preparing. 1, 4-napthalene-dicarboxylic acid esters |
| JP718776A JPS51100053A (ja) | 1975-01-28 | 1976-01-27 | 1*44nafutarinjikarubonsanesuterunoseiho |
| DK31776A DK31776A (da) | 1975-01-28 | 1976-01-27 | Fremgangsmade til fremstilling af 1,4-naphthalendicarboxylsyrestere |
| FR7602253A FR2299308A1 (fr) | 1975-01-28 | 1976-01-28 | Procede de preparation d'esters d'un acide aromatique dicarboxylique |
| BE163868A BE837993A (fr) | 1975-01-28 | 1976-01-28 | Procede de preparation d'ester d'un acide aromatique dicarboxylique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752503377 DE2503377B2 (de) | 1975-01-28 | 1975-01-28 | Verfahren zur herstellung von 1,4-naphthalindicarbonsaeureestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2503377A1 DE2503377A1 (de) | 1976-08-05 |
| DE2503377B2 true DE2503377B2 (de) | 1976-11-11 |
Family
ID=5937490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752503377 Granted DE2503377B2 (de) | 1975-01-28 | 1975-01-28 | Verfahren zur herstellung von 1,4-naphthalindicarbonsaeureestern |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS51100053A (OSRAM) |
| BE (1) | BE837993A (OSRAM) |
| BR (1) | BR7600480A (OSRAM) |
| CH (1) | CH598185A5 (OSRAM) |
| DE (1) | DE2503377B2 (OSRAM) |
| DK (1) | DK31776A (OSRAM) |
| ES (1) | ES444541A1 (OSRAM) |
| FR (1) | FR2299308A1 (OSRAM) |
| GB (1) | GB1528223A (OSRAM) |
| IT (1) | IT1054501B (OSRAM) |
| LU (1) | LU74244A1 (OSRAM) |
| NL (1) | NL7600714A (OSRAM) |
| SE (1) | SE7600766L (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012082727A1 (en) * | 2010-12-15 | 2012-06-21 | Amyris, Inc. | Biobased polyamides |
| WO2014051021A1 (ja) * | 2012-09-28 | 2014-04-03 | 三菱瓦斯化学株式会社 | １，４－テトラリンジカルボン酸ジアルキルエステルとその製造方法 |
-
1975
- 1975-01-28 DE DE19752503377 patent/DE2503377B2/de active Granted
-
1976
- 1976-01-22 ES ES444541A patent/ES444541A1/es not_active Expired
- 1976-01-23 GB GB267676A patent/GB1528223A/en not_active Expired
- 1976-01-23 NL NL7600714A patent/NL7600714A/xx not_active Application Discontinuation
- 1976-01-26 CH CH91676A patent/CH598185A5/xx not_active IP Right Cessation
- 1976-01-26 LU LU74244A patent/LU74244A1/xx unknown
- 1976-01-26 IT IT1960376A patent/IT1054501B/it active
- 1976-01-26 SE SE7600766A patent/SE7600766L/xx not_active Application Discontinuation
- 1976-01-27 DK DK31776A patent/DK31776A/da not_active Application Discontinuation
- 1976-01-27 BR BR7600480A patent/BR7600480A/pt unknown
- 1976-01-27 JP JP718776A patent/JPS51100053A/ja active Pending
- 1976-01-28 FR FR7602253A patent/FR2299308A1/fr active Granted
- 1976-01-28 BE BE163868A patent/BE837993A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2299308A1 (fr) | 1976-08-27 |
| AU1057676A (en) | 1977-08-04 |
| BE837993A (fr) | 1976-07-28 |
| GB1528223A (en) | 1978-10-11 |
| ES444541A1 (es) | 1977-05-16 |
| CH598185A5 (OSRAM) | 1978-04-28 |
| IT1054501B (it) | 1981-11-10 |
| LU74244A1 (OSRAM) | 1976-12-31 |
| JPS51100053A (ja) | 1976-09-03 |
| SE7600766L (sv) | 1976-07-29 |
| DE2503377A1 (de) | 1976-08-05 |
| NL7600714A (nl) | 1976-07-30 |
| FR2299308B1 (OSRAM) | 1979-07-27 |
| BR7600480A (pt) | 1976-08-31 |
| DK31776A (da) | 1976-07-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |