DE102004005318A1 - Verfahren zur Herstellung von 2,5-Dimethylphenylessigsäure - Google Patents
Verfahren zur Herstellung von 2,5-Dimethylphenylessigsäure Download PDFInfo
- Publication number
- DE102004005318A1 DE102004005318A1 DE102004005318A DE102004005318A DE102004005318A1 DE 102004005318 A1 DE102004005318 A1 DE 102004005318A1 DE 102004005318 A DE102004005318 A DE 102004005318A DE 102004005318 A DE102004005318 A DE 102004005318A DE 102004005318 A1 DE102004005318 A1 DE 102004005318A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- xylene
- mixture
- water
- mol
- 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.)
- Withdrawn
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- RUSCTNYOPQOXDJ-UHFFFAOYSA-N 2-(2,5-dimethylphenyl)acetic acid Chemical compound CC1=CC=C(C)C(CC(O)=O)=C1 RUSCTNYOPQOXDJ-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title abstract description 52
- 238000002360 preparation method Methods 0.000 title description 13
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims abstract description 15
- JVDITFWYVNXMQP-UHFFFAOYSA-N 2-chloro-1-(2,5-dimethylphenyl)ethanone Chemical compound CC1=CC=C(C)C(C(=O)CCl)=C1 JVDITFWYVNXMQP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 5
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 3
- 101150065749 Churc1 gene Proteins 0.000 claims description 3
- 102100038239 Protein Churchill Human genes 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 15
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 14
- 239000008096 xylene Substances 0.000 description 14
- 235000011121 sodium hydroxide Nutrition 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- -1 2,5-Dimethylphenylessigsäure hydroxyalkyl ester Chemical class 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- GAAXRHSFPCLNEV-UHFFFAOYSA-N 2-(chloromethyl)-2-(2,5-dimethylphenyl)-5,5-dimethyl-1,3-dioxane Chemical compound CC1=CC=C(C)C(C2(CCl)OCC(C)(C)CO2)=C1 GAAXRHSFPCLNEV-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical class COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Chemical class 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- DHJPEGRMZQBUMM-UHFFFAOYSA-N 2-(bromomethyl)-1,4-dimethylbenzene Chemical compound CC1=CC=C(C)C(CBr)=C1 DHJPEGRMZQBUMM-UHFFFAOYSA-N 0.000 description 2
- PECXPZGFZFGDRD-UHFFFAOYSA-N 2-(chloromethyl)-1,4-dimethylbenzene Chemical compound CC1=CC=C(C)C(CCl)=C1 PECXPZGFZFGDRD-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 238000007265 chloromethylation reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- AWKBVLVKQQRRFQ-UHFFFAOYSA-N 1-(2,5-dimethylphenyl)ethanone Chemical compound CC(=O)C1=CC(C)=CC=C1C AWKBVLVKQQRRFQ-UHFFFAOYSA-N 0.000 description 1
- XIRZJAAXABSUAY-UHFFFAOYSA-N 2-(2,5-dimethylphenyl)-1-phenylethanone Chemical compound CC1=CC=C(C)C(CC(=O)C=2C=CC=CC=2)=C1 XIRZJAAXABSUAY-UHFFFAOYSA-N 0.000 description 1
- FVCFAMCEPNIAKS-UHFFFAOYSA-N 2-(chloromethyl)-2-(2,5-dimethylphenyl)-1,3-dioxane Chemical compound CC1=CC=C(C)C(C2(CCl)OCCCO2)=C1 FVCFAMCEPNIAKS-UHFFFAOYSA-N 0.000 description 1
- JYUNAOFNZLUGSW-UHFFFAOYSA-N 2-(chloromethyl)-2-(2,5-dimethylphenyl)-1,3-dioxolane Chemical compound CC1=CC=C(C)C(C2(CCl)OCCO2)=C1 JYUNAOFNZLUGSW-UHFFFAOYSA-N 0.000 description 1
- YEGWOSYSXNHSAZ-UHFFFAOYSA-N 2-(chloromethyl)-2-(2,5-dimethylphenyl)-4-methyl-1,3-dioxolane Chemical compound O1C(C)COC1(CCl)C1=CC(C)=CC=C1C YEGWOSYSXNHSAZ-UHFFFAOYSA-N 0.000 description 1
- YHXHKYRQLYQUIH-UHFFFAOYSA-N 4-hydroxymandelic acid Chemical class OC(=O)C(O)C1=CC=C(O)C=C1 YHXHKYRQLYQUIH-UHFFFAOYSA-N 0.000 description 1
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical class OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 238000005672 Willgerodt-Kindler rearrangement reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 1
- 229950006800 prenderol Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 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
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/16—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
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)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004005318A DE102004005318A1 (de) | 2004-02-04 | 2004-02-04 | Verfahren zur Herstellung von 2,5-Dimethylphenylessigsäure |
| PCT/EP2005/000617 WO2005075401A1 (de) | 2004-02-04 | 2005-01-22 | Verfahren zur herstellung von 2,5-dimethylphenylessigsäure |
| JP2006551756A JP4668212B2 (ja) | 2004-02-04 | 2005-01-22 | ２，５−ジメチルフェニル酢酸の調製方法 |
| CN2005800041299A CN1918103B (zh) | 2004-02-04 | 2005-01-22 | 2,5-二甲基苯乙酸的制备方法 |
| US10/586,491 US7579500B2 (en) | 2004-02-04 | 2005-01-22 | Method for producing 2,5-dimethylphenyl acetic acid |
| DE502005008867T DE502005008867D1 (de) | 2004-02-04 | 2005-01-22 | Verfahren zur herstellung von 2,5-dimethylphenylessigsäure |
| EP05701122A EP1713755B1 (de) | 2004-02-04 | 2005-01-22 | Verfahren zur herstellung von 2,5-dimethylphenylessigsäure |
| BRPI0507422-3A BRPI0507422A (pt) | 2004-02-04 | 2005-01-22 | processo para produção de ácido 2,5-dimetilfenilacético |
| AT05701122T ATE455087T1 (de) | 2004-02-04 | 2005-01-22 | Verfahren zur herstellung von 2,5- dimethylphenylessigsäure |
| US12/388,274 US7629476B2 (en) | 2004-02-04 | 2009-02-18 | Method for producing 2,5-dimethylphenyl acetic acid |
| IN3160DEN2012 IN2012DN03160A (https=) | 2004-02-04 | 2012-04-12 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004005318A DE102004005318A1 (de) | 2004-02-04 | 2004-02-04 | Verfahren zur Herstellung von 2,5-Dimethylphenylessigsäure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102004005318A1 true DE102004005318A1 (de) | 2005-08-25 |
Family
ID=34801503
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102004005318A Withdrawn DE102004005318A1 (de) | 2004-02-04 | 2004-02-04 | Verfahren zur Herstellung von 2,5-Dimethylphenylessigsäure |
| DE502005008867T Expired - Lifetime DE502005008867D1 (de) | 2004-02-04 | 2005-01-22 | Verfahren zur herstellung von 2,5-dimethylphenylessigsäure |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE502005008867T Expired - Lifetime DE502005008867D1 (de) | 2004-02-04 | 2005-01-22 | Verfahren zur herstellung von 2,5-dimethylphenylessigsäure |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US7579500B2 (https=) |
| EP (1) | EP1713755B1 (https=) |
| JP (1) | JP4668212B2 (https=) |
| CN (1) | CN1918103B (https=) |
| AT (1) | ATE455087T1 (https=) |
| BR (1) | BRPI0507422A (https=) |
| DE (2) | DE102004005318A1 (https=) |
| IN (1) | IN2012DN03160A (https=) |
| WO (1) | WO2005075401A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008291008A (ja) | 2007-04-24 | 2008-12-04 | Daicel Chem Ind Ltd | ２，５−ジメチルアセトフェノン誘導体、２，５−ジメチルアセトフェノン誘導体から得られる２，５−ジメチルフェニル酢酸及びその誘導体の製造方法 |
| EP2204366A1 (de) | 2008-12-19 | 2010-07-07 | Bayer CropScience AG | Herbizid und insektizid wirksame phenylsubstituierte Pyridazinone |
| WO2011035878A1 (de) | 2009-09-25 | 2011-03-31 | Bayer Cropscience Ag | Herbizid wirksame phenylsubstituierte pyridazinone |
| WO2011045271A1 (de) | 2009-10-15 | 2011-04-21 | Bayer Cropscience Ag | Herbizid wirksame heterocyclylsubstituierte pyridazinone |
| JP5990170B2 (ja) | 2010-09-01 | 2016-09-07 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 除草活性を有するケトスルタム類及びジケトピリジン類 |
| JP2012087113A (ja) * | 2010-09-22 | 2012-05-10 | Daicel Corp | フェニル酢酸化合物 |
| CN102140062B (zh) * | 2011-03-13 | 2012-11-14 | 联化科技股份有限公司 | 一种2，5-二甲基苯乙酸的制备方法 |
| CN104628551A (zh) * | 2015-02-13 | 2015-05-20 | 中国药科大学 | 一种2,5-二甲基苯乙酸的制备方法 |
| CN110305010B (zh) * | 2019-07-17 | 2022-05-13 | 江苏中旗科技股份有限公司 | 一种2,5-二甲基苯乙酸的制备方法 |
| CN115023413B (zh) * | 2020-02-03 | 2024-11-15 | 帝斯曼知识产权资产管理有限公司 | 二甲基苯基丙烯酸酯使用沸石的重排 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE50897B1 (en) | 1980-02-26 | 1986-08-06 | Blaschim Spa | Process for preparing esters of alkanoic acids via rearrangement of alpha-haloketals |
| US4632736A (en) * | 1982-06-25 | 1986-12-30 | Westfall Richard M | Electrolytic preparation of tin |
| US4623736A (en) * | 1982-07-09 | 1986-11-18 | The Upjohn Company | Arylalkanoic acid process improvement |
| IT1212709B (it) * | 1983-03-07 | 1989-11-30 | Zambon Spa | Alfa-alogenoalchilarilchetali particolarmente utili per la sintesi di acidi alfa-arilalcanoici. |
| IT1210917B (it) * | 1982-08-06 | 1989-09-29 | Zambon Spa | Procedimento per preparare esteri di acidi aril-alcanoici. |
| EP0101124B1 (en) * | 1982-08-06 | 1986-01-29 | ZAMBON S.p.A. | Process for preparing alpha arylalkanoic acids |
| BR9708425B1 (pt) | 1996-04-02 | 2012-02-22 | fenilcetoenóis substituìdos, processo para preparação e uso dos mesmos, bem como pesticidas ou herbicidas e método para controle de pragas e ervas daninhas. |
-
2004
- 2004-02-04 DE DE102004005318A patent/DE102004005318A1/de not_active Withdrawn
-
2005
- 2005-01-22 WO PCT/EP2005/000617 patent/WO2005075401A1/de not_active Ceased
- 2005-01-22 BR BRPI0507422-3A patent/BRPI0507422A/pt not_active IP Right Cessation
- 2005-01-22 CN CN2005800041299A patent/CN1918103B/zh not_active Expired - Fee Related
- 2005-01-22 JP JP2006551756A patent/JP4668212B2/ja not_active Expired - Fee Related
- 2005-01-22 US US10/586,491 patent/US7579500B2/en not_active Expired - Fee Related
- 2005-01-22 DE DE502005008867T patent/DE502005008867D1/de not_active Expired - Lifetime
- 2005-01-22 AT AT05701122T patent/ATE455087T1/de not_active IP Right Cessation
- 2005-01-22 EP EP05701122A patent/EP1713755B1/de not_active Expired - Lifetime
-
2009
- 2009-02-18 US US12/388,274 patent/US7629476B2/en not_active Expired - Fee Related
-
2012
- 2012-04-12 IN IN3160DEN2012 patent/IN2012DN03160A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE502005008867D1 (de) | 2010-03-04 |
| US7579500B2 (en) | 2009-08-25 |
| EP1713755A1 (de) | 2006-10-25 |
| IN2012DN03160A (https=) | 2015-09-18 |
| WO2005075401A1 (de) | 2005-08-18 |
| US7629476B2 (en) | 2009-12-08 |
| CN1918103B (zh) | 2012-08-08 |
| EP1713755B1 (de) | 2010-01-13 |
| BRPI0507422A (pt) | 2007-06-26 |
| US20090156839A1 (en) | 2009-06-18 |
| JP2007522139A (ja) | 2007-08-09 |
| JP4668212B2 (ja) | 2011-04-13 |
| US20080234501A1 (en) | 2008-09-25 |
| CN1918103A (zh) | 2007-02-21 |
| ATE455087T1 (de) | 2010-01-15 |
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Legal Events
| Date | Code | Title | Description |
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| 8141 | Disposal/no request for examination | ||
| R005 | Application deemed withdrawn due to failure to request examination |
Effective date: 20110205 |