DE3529381A1 - Verfahren zur herstellung von 2,6-naphthalindicarbonsaeure - Google Patents
Verfahren zur herstellung von 2,6-naphthalindicarbonsaeureInfo
- Publication number
- DE3529381A1 DE3529381A1 DE19853529381 DE3529381A DE3529381A1 DE 3529381 A1 DE3529381 A1 DE 3529381A1 DE 19853529381 DE19853529381 DE 19853529381 DE 3529381 A DE3529381 A DE 3529381A DE 3529381 A1 DE3529381 A1 DE 3529381A1
- Authority
- DE
- Germany
- Prior art keywords
- oxidation
- alkylnaphthalene
- acyl
- oxidation stage
- solvent
- 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
- 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 claims abstract description 16
- 238000000034 method Methods 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 68
- 230000003647 oxidation Effects 0.000 claims abstract description 67
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 18
- 239000001301 oxygen Substances 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 13
- 239000010941 cobalt Substances 0.000 claims abstract description 13
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 13
- SPAYGOAEIJHIDE-UHFFFAOYSA-N 1-(6-methylnaphthalen-2-yl)ethanone Chemical compound C1=C(C)C=CC2=CC(C(=O)C)=CC=C21 SPAYGOAEIJHIDE-UHFFFAOYSA-N 0.000 claims abstract description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000011572 manganese Substances 0.000 claims abstract description 9
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 75
- 239000000047 product Substances 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 11
- 239000007789 gas Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 9
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims description 7
- 239000011877 solvent mixture Substances 0.000 claims description 7
- 150000002697 manganese compounds Chemical class 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 239000012452 mother liquor Substances 0.000 claims description 6
- 150000001869 cobalt compounds Chemical class 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- VNNDVNZCGCCIPA-FDGPNNRMSA-N (z)-4-hydroxypent-3-en-2-one;manganese Chemical compound [Mn].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O VNNDVNZCGCCIPA-FDGPNNRMSA-N 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 1
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 12
- -1 bromine compound Chemical class 0.000 description 8
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229940011182 cobalt acetate Drugs 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- BZRRQSJJPUGBAA-UHFFFAOYSA-L cobalt(ii) bromide Chemical compound Br[Co]Br BZRRQSJJPUGBAA-UHFFFAOYSA-L 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YGYNBBAUIYTWBF-UHFFFAOYSA-N 2,6-dimethylnaphthalene Chemical compound C1=C(C)C=CC2=CC(C)=CC=C21 YGYNBBAUIYTWBF-UHFFFAOYSA-N 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853529381 DE3529381A1 (de) | 1985-08-16 | 1985-08-16 | Verfahren zur herstellung von 2,6-naphthalindicarbonsaeure |
| EP86109528A EP0212221B1 (de) | 1985-08-16 | 1986-07-11 | Verfahren zur Herstellung von 2,6-Naphthalindicarbonsäure |
| DE8686109528T DE3671009D1 (de) | 1985-08-16 | 1986-07-11 | Verfahren zur herstellung von 2,6-naphthalindicarbonsaeure. |
| US06/896,116 US4764638A (en) | 1985-08-16 | 1986-08-12 | Method for the preparation of 2,6-naphthalene dicarboxylic acid |
| JP19069686A JPS6242946A (ja) | 1985-08-16 | 1986-08-15 | ２，６−ナフタリンジカルボン酸の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853529381 DE3529381A1 (de) | 1985-08-16 | 1985-08-16 | Verfahren zur herstellung von 2,6-naphthalindicarbonsaeure |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3529381A1 true DE3529381A1 (de) | 1987-02-19 |
| DE3529381C2 DE3529381C2 (enrdf_load_stackoverflow) | 1987-07-23 |
Family
ID=6278657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853529381 Granted DE3529381A1 (de) | 1985-08-16 | 1985-08-16 | Verfahren zur herstellung von 2,6-naphthalindicarbonsaeure |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS6242946A (enrdf_load_stackoverflow) |
| DE (1) | DE3529381A1 (enrdf_load_stackoverflow) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54135756A (en) * | 1978-04-08 | 1979-10-22 | Maruzen Sekiyu Kagaku Kk | Manufacture of 22alkyll66acylnaphthalene and 2*66naphthalenedicarboxylic acid and said ester |
| EP0142719A1 (en) * | 1983-10-24 | 1985-05-29 | Teijin Petrochemical Industries Ltd. | Process for producing 2,6-naphthalenedicarboxylic acid |
-
1985
- 1985-08-16 DE DE19853529381 patent/DE3529381A1/de active Granted
-
1986
- 1986-08-15 JP JP19069686A patent/JPS6242946A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54135756A (en) * | 1978-04-08 | 1979-10-22 | Maruzen Sekiyu Kagaku Kk | Manufacture of 22alkyll66acylnaphthalene and 2*66naphthalenedicarboxylic acid and said ester |
| EP0142719A1 (en) * | 1983-10-24 | 1985-05-29 | Teijin Petrochemical Industries Ltd. | Process for producing 2,6-naphthalenedicarboxylic acid |
Non-Patent Citations (1)
| Title |
|---|
| Chem.Abstr., Vol. 87, Ref. 134813 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3529381C2 (enrdf_load_stackoverflow) | 1987-07-23 |
| JPS6242946A (ja) | 1987-02-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| AG | Has addition no. |
Ref country code: DE Ref document number: 3543879 Format of ref document f/p: P |
|
| AG | Has addition no. |
Ref country code: DE Ref document number: 3543879 Format of ref document f/p: P |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: HUELS TROISDORF AG, 5210 TROISDORF, DE |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: HUELS AG, 4370 MARL, DE |
|
| 8339 | Ceased/non-payment of the annual fee |