DE1150971B - Verfahren zur Herstellung von Polychlorbenzolcarbonsaeuremethylestern - Google Patents
Verfahren zur Herstellung von PolychlorbenzolcarbonsaeuremethylesternInfo
- Publication number
- DE1150971B DE1150971B DEC26442A DEC0026442A DE1150971B DE 1150971 B DE1150971 B DE 1150971B DE C26442 A DEC26442 A DE C26442A DE C0026442 A DEC0026442 A DE C0026442A DE 1150971 B DE1150971 B DE 1150971B
- Authority
- DE
- Germany
- Prior art keywords
- polychlorobenzenecarboxylic
- water
- methanol
- acid
- acid chlorides
- 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
- 239000002253 acid Substances 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 15
- 150000004702 methyl esters Chemical class 0.000 title claims description 15
- 230000008569 process Effects 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 79
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 150000001805 chlorine compounds Chemical class 0.000 claims description 14
- 238000009835 boiling Methods 0.000 claims description 12
- -1 iron halides Chemical class 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- 150000004706 metal oxides Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000002585 base Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- 238000007127 saponification reaction Methods 0.000 description 8
- YJIRZJAZKDWEIJ-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzene-1,4-dicarbonyl chloride Chemical compound ClC(=O)C1=C(Cl)C(Cl)=C(C(Cl)=O)C(Cl)=C1Cl YJIRZJAZKDWEIJ-UHFFFAOYSA-N 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- NPOJQCVWMSKXDN-UHFFFAOYSA-N Dacthal Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(C(=O)OC)C(Cl)=C1Cl NPOJQCVWMSKXDN-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical group ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- AAUSLOKBERXEER-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobenzoyl chloride Chemical compound ClC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl AAUSLOKBERXEER-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical class F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 150000002506 iron compounds Chemical class 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000036632 reaction speed Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- IROWIXYGGPOJFJ-UHFFFAOYSA-N 2,3,4,5-tetrachlorobenzoyl chloride Chemical class ClC(=O)C1=CC(Cl)=C(Cl)C(Cl)=C1Cl IROWIXYGGPOJFJ-UHFFFAOYSA-N 0.000 description 1
- OZGSEIVTQLXWRO-UHFFFAOYSA-N 2,4,6-trichlorobenzoyl chloride Chemical compound ClC(=O)C1=C(Cl)C=C(Cl)C=C1Cl OZGSEIVTQLXWRO-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- MBFGJFCYDDAKRD-UHFFFAOYSA-N O=C(C(C=C1)=CC=C1C(Cl)=O)Cl.Cl.Cl.Cl.Cl Chemical compound O=C(C(C=C1)=CC=C1C(Cl)=O)Cl.Cl.Cl.Cl.Cl MBFGJFCYDDAKRD-UHFFFAOYSA-N 0.000 description 1
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 239000004310 lactic acid Chemical class 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000012633 leachable Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- GMJLEFPTCWSZNE-UHFFFAOYSA-N methyl 2,3,4,5,6-pentachlorobenzoate Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl GMJLEFPTCWSZNE-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Chemical class 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 238000005292 vacuum distillation Methods 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 (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE629377D BE629377A (en, 2012) | 1962-03-09 | ||
| NL285685D NL285685A (en, 2012) | 1962-03-09 | ||
| NL122183D NL122183C (en, 2012) | 1962-03-09 | ||
| DEC26442A DE1150971B (de) | 1962-03-09 | 1962-03-09 | Verfahren zur Herstellung von Polychlorbenzolcarbonsaeuremethylestern |
| CH1317262A CH422753A (de) | 1962-03-09 | 1962-11-09 | Verfahren zur Herstellung von Methylestern aromatischer Polyhalogencarbonsäuren |
| US257869A US3334131A (en) | 1962-03-09 | 1963-02-12 | Process for the preparation of methyl esters of aromatic polyhalogen carboxylic acids |
| FR926670A FR1349721A (fr) | 1962-03-09 | 1963-03-04 | Procédé de préparation d'esters méthyliques d'acides carboxyliques aromatiques polyhalogénés |
| GB9560/63A GB973617A (en) | 1962-03-09 | 1963-03-11 | Improvements in or relating to the preparation of methyl esters of halogenated aromatic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC26442A DE1150971B (de) | 1962-03-09 | 1962-03-09 | Verfahren zur Herstellung von Polychlorbenzolcarbonsaeuremethylestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1150971B true DE1150971B (de) | 1963-07-04 |
Family
ID=7018130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC26442A Pending DE1150971B (de) | 1962-03-09 | 1962-03-09 | Verfahren zur Herstellung von Polychlorbenzolcarbonsaeuremethylestern |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3334131A (en, 2012) |
| BE (1) | BE629377A (en, 2012) |
| CH (1) | CH422753A (en, 2012) |
| DE (1) | DE1150971B (en, 2012) |
| GB (1) | GB973617A (en, 2012) |
| NL (2) | NL122183C (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4886901A (en) * | 1988-11-21 | 1989-12-12 | Amoco Corporation | Method for purifying a crude dimethyl naphthalene dicarboxylate |
-
0
- NL NL285685D patent/NL285685A/xx unknown
- BE BE629377D patent/BE629377A/xx unknown
- NL NL122183D patent/NL122183C/xx active
-
1962
- 1962-03-09 DE DEC26442A patent/DE1150971B/de active Pending
- 1962-11-09 CH CH1317262A patent/CH422753A/de unknown
-
1963
- 1963-02-12 US US257869A patent/US3334131A/en not_active Expired - Lifetime
- 1963-03-11 GB GB9560/63A patent/GB973617A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3334131A (en) | 1967-08-01 |
| BE629377A (en, 2012) | |
| CH422753A (de) | 1966-10-31 |
| GB973617A (en) | 1964-10-28 |
| NL285685A (en, 2012) | |
| NL122183C (en, 2012) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2050484C3 (de) | Verfahren zu deren Herstellung | |
| DE3308922A1 (de) | Verfahren zur herstellung von fettsaeureestern der ascorbinsaeure | |
| EP0176026B1 (de) | Verfahren zur Herstellung von 2,4-Dichlor-5-fluor-benzoesäure | |
| DE2015068A1 (de) | alpha Alkyl phosphonobernsteinsauren | |
| DE2627223C2 (en, 2012) | ||
| DE1150971B (de) | Verfahren zur Herstellung von Polychlorbenzolcarbonsaeuremethylestern | |
| EP0694556B1 (de) | Verfahren zur Herstellung von Diestern von Phosphonocarbonsäurederivaten | |
| AT232993B (de) | Verfahren zur Herstellung von Methylestern aromatischer Polyhalogencarbonsäuren | |
| EP0383130B1 (de) | Verfahren zur Herstellung von 2,4-Dihydroxybenzophenon | |
| DE1287079B (de) | Verfahren zur Herstellung von Monocarbonsaeureestern | |
| DE2728248A1 (de) | Nitroxolinderivate | |
| EP0159656B1 (de) | Verfahren zur Herstellung der Alkali- und Erdalkali-Salze von Diarylphosphinsäuren | |
| DE2065698A1 (de) | Verfahren zur herstellung von 2isopropyl-6-methyl-4(3h)-pyrimidon | |
| DE1101417B (de) | Verfahren zur Herstellung von sauren Dithiophosphonsaeureestern bzw. deren Alkalisalzen | |
| DE1034166B (de) | Verfahren zur Herstellung von 2, 2, 3, 3-Tetrachlor-1, 4-butandiol | |
| AT231471B (de) | Verfahren zur Herstellung von neuen Thionothiolphosphorsäureestern | |
| AT239211B (de) | Verfahren zur Herstellung von neuen halogenierten Polysäuren und Polyestern | |
| DE837700C (de) | Verfahren zur Herstellung von Furanderivaten | |
| DE2706823C2 (en, 2012) | ||
| DE650431C (de) | Verfahren zur Darstellung von trisubstituierten Barbitursaeuren | |
| AT217477B (de) | Verfahren zur Herstellung neuer Phosphinsäurederivate | |
| AT205480B (de) | Verfahren zur Herstellung von reinen aliphatischen N-Chlor-N-alkylacetamiden | |
| AT222653B (de) | Verfahren zur Herstellung von neuen Azepinderivaten | |
| DE1926942B2 (en, 2012) | ||
| DE2053735A1 (de) | Quaternäre Pyridiniumsalze |