DE2214690A1 - Verfahren zur Herstellung von Diphensäure und 2-Phenylbenzoesäure - Google Patents
Verfahren zur Herstellung von Diphensäure und 2-PhenylbenzoesäureInfo
- Publication number
- DE2214690A1 DE2214690A1 DE19722214690 DE2214690A DE2214690A1 DE 2214690 A1 DE2214690 A1 DE 2214690A1 DE 19722214690 DE19722214690 DE 19722214690 DE 2214690 A DE2214690 A DE 2214690A DE 2214690 A1 DE2214690 A1 DE 2214690A1
- Authority
- DE
- Germany
- Prior art keywords
- copper
- pharmaceuticals
- acid
- plasticisers
- acids
- 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.)
- Pending
Links
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 title claims abstract description 6
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 title claims description 14
- 239000003814 drug Substances 0.000 title abstract description 5
- 239000004014 plasticizer Substances 0.000 title abstract description 5
- 239000000314 lubricant Substances 0.000 title abstract description 3
- 229920000642 polymer Polymers 0.000 title abstract description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 11
- 150000007513 acids Chemical class 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 5
- GWZCCUDJHOGOSO-UHFFFAOYSA-N diphenic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1C(O)=O GWZCCUDJHOGOSO-UHFFFAOYSA-N 0.000 claims description 10
- PEDPADYOGWOSPR-UHFFFAOYSA-L copper(1+);phthalate Chemical compound [Cu+].[Cu+].[O-]C(=O)C1=CC=CC=C1C([O-])=O PEDPADYOGWOSPR-UHFFFAOYSA-L 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 5
- -1 alkyl pyridine Chemical compound 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 239000004952 Polyamide Substances 0.000 abstract description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract description 2
- 229920000728 polyester Polymers 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000001569 carbon dioxide Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- 229940112669 cuprous oxide Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- CGTYPNOFVGYUED-UHFFFAOYSA-N methyl 2-(2-methoxycarbonylphenyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1C1=CC=CC=C1C(=O)OC CGTYPNOFVGYUED-UHFFFAOYSA-N 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/33—Polycyclic acids
- C07C63/331—Polycyclic acids with all carboxyl groups bound to non-condensed rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE430471A SE355179B (OSRAM) | 1971-04-02 | 1971-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2214690A1 true DE2214690A1 (de) | 1972-10-19 |
Family
ID=20263891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722214690 Pending DE2214690A1 (de) | 1971-04-02 | 1972-03-25 | Verfahren zur Herstellung von Diphensäure und 2-Phenylbenzoesäure |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE2214690A1 (OSRAM) |
| SE (1) | SE355179B (OSRAM) |
-
1971
- 1971-04-02 SE SE430471A patent/SE355179B/xx unknown
-
1972
- 1972-03-25 DE DE19722214690 patent/DE2214690A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| SE355179B (OSRAM) | 1973-04-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3006277C2 (OSRAM) | ||
| EP0176026B1 (de) | Verfahren zur Herstellung von 2,4-Dichlor-5-fluor-benzoesäure | |
| DE2214690A1 (de) | Verfahren zur Herstellung von Diphensäure und 2-Phenylbenzoesäure | |
| DE3625269C2 (OSRAM) | ||
| DE10025700A1 (de) | Verfahren zur Herstellung von trifluorethoxysubstituierten Benzoesäuren | |
| DE2407003A1 (de) | Neue naphthalin-tetracarbonsaeurederivate und verfahren zu ihrer herstellung | |
| CH650488A5 (de) | Verfahren zur herstellung des m-phenoxy-benzyl-alkohols. | |
| DE1768114A1 (de) | Verfahren zur Herstellung von alpha-Ketoglutarsaeure | |
| DE953072C (de) | Verfahren zur Herstellung von Naphthalin-2, 6-dicarbonsaeure bzw. von deren Salzen und Derivaten | |
| DE3813452A1 (de) | Verfahren zur herstellung von trifluormethylbenzoesaeure aus hexafluorxylol | |
| DE2257442C3 (de) | 1,8,9-Trihydroxyanthracenderivate und Verfahren zu ihrer Herstellung | |
| DE1187233B (de) | Verfahren zur Herstellung von Benzolpolycarbonsaeuren | |
| DE1935725C3 (de) | Verfahren zur Herstellung von Chlorphenylestern | |
| DE3126057C2 (de) | Verfahren zur Herstellung von Naphtholactonen | |
| DE1283832B (de) | Verfahren zur Herstellung von Anhydriden der Sorbinsaeure | |
| CH646430A5 (de) | Verfahren zur herstellung von naphtholactonen. | |
| DE2122314A1 (en) | Chromone-3-aldehydes - from ortho-hydroxyacetyl cpds using a vilsmeier reagent | |
| AT240842B (de) | Verfahren zur Herstellung von ausschließlich im Kern chlorierten Estern von Alkylbenzolmonocarbonsäuren | |
| DE3105485C2 (de) | Verfahren zur Herstellung von Naphtholacton | |
| AT238380B (de) | Verfahren zur Herstellung von 9(11), 16-Pregnadienen | |
| DE2612842B2 (de) | Bis-(carbalkoxy-phenoxymethyl)-benzole | |
| DE1668387B2 (de) | a-Methylsulfonyl-S-hydroxy-S-(3-dimethyl-aminopropyl)-5H-di benzo eckige Klammer auf a, d eckige Klammer zu -cycloheptene und Verfahren zu deren Herstellung | |
| DEH0022699MA (OSRAM) | ||
| DE2257442B2 (de) | 1,8,9-trihydroxyanthracenderivate und verfahren zu ihrer herstellung | |
| DD275666A1 (de) | Verfahren zur herstellung von phenoxyessigsaeure |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |