PL84513B1 - - Google Patents
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- Publication number
- PL84513B1 PL84513B1 PL1972154417A PL15441772A PL84513B1 PL 84513 B1 PL84513 B1 PL 84513B1 PL 1972154417 A PL1972154417 A PL 1972154417A PL 15441772 A PL15441772 A PL 15441772A PL 84513 B1 PL84513 B1 PL 84513B1
- Authority
- PL
- Poland
- Prior art keywords
- hydroxy
- acid
- solution
- phenylglycolic
- chloride
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 20
- -1 hydroxyaryl glycolic acids Chemical class 0.000 claims description 19
- 230000003647 oxidation Effects 0.000 claims description 19
- 238000007254 oxidation reaction Methods 0.000 claims description 19
- 239000007800 oxidant agent Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- CGQCWMIAEPEHNQ-UHFFFAOYSA-N Vanillylmandelic acid Chemical compound COC1=CC(C(O)C(O)=O)=CC=C1O CGQCWMIAEPEHNQ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 8
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- WINGEFIITRDOLJ-UHFFFAOYSA-N tert-butyl 2-hydroxyacetate Chemical compound CC(C)(C)OC(=O)CO WINGEFIITRDOLJ-UHFFFAOYSA-N 0.000 claims description 6
- YOIZTLBZAMFVPK-UHFFFAOYSA-N 2-(3-ethoxy-4-hydroxyphenyl)-2-hydroxyacetic acid Chemical compound CCOC1=CC(C(O)C(O)=O)=CC=C1O YOIZTLBZAMFVPK-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 claims description 3
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical group [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 claims description 2
- 229960003280 cupric chloride Drugs 0.000 claims description 2
- 238000006114 decarboxylation reaction Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910000159 nickel phosphate Inorganic materials 0.000 claims description 2
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 claims description 2
- JOCJYBPHESYFOK-UHFFFAOYSA-K nickel(3+);phosphate Chemical compound [Ni+3].[O-]P([O-])([O-])=O JOCJYBPHESYFOK-UHFFFAOYSA-K 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- 239000010941 cobalt Substances 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 claims 1
- 229910000358 iron sulfate Inorganic materials 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 41
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 16
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 16
- 230000001590 oxidative effect Effects 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 13
- 230000002378 acidificating effect Effects 0.000 description 12
- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 8
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 8
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 8
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 239000003929 acidic solution Substances 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229960001867 guaiacol Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 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 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229960002510 mandelic acid Drugs 0.000 description 3
- 150000004682 monohydrates Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000012485 toluene extract Substances 0.000 description 3
- TWLSOWAQVSIFIF-UHFFFAOYSA-N 2-hydroxy-2-(2-hydroxyphenyl)acetic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1O TWLSOWAQVSIFIF-UHFFFAOYSA-N 0.000 description 2
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000005569 Iron sulphate Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001868 cobalt Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 159000000014 iron salts Chemical class 0.000 description 2
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 2
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 2
- 150000002730 mercury Chemical class 0.000 description 2
- 150000002815 nickel Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- FBWPWWWZWKPJFL-QMMMGPOBSA-N (1r)-1-(4-hydroxy-3-methoxyphenyl)ethane-1,2-diol Chemical compound COC1=CC([C@@H](O)CO)=CC=C1O FBWPWWWZWKPJFL-QMMMGPOBSA-N 0.000 description 1
- RIPNKOPTCNHMOI-UHFFFAOYSA-N 2-(2-chloro-4-hydroxyphenyl)-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1=CC=C(O)C=C1Cl RIPNKOPTCNHMOI-UHFFFAOYSA-N 0.000 description 1
- VRBWLJOQTLYNPI-UHFFFAOYSA-N 2-(3,5-dichloro-4-hydroxyphenyl)-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1=CC(Cl)=C(O)C(Cl)=C1 VRBWLJOQTLYNPI-UHFFFAOYSA-N 0.000 description 1
- FGSBUNXNOPODEQ-UHFFFAOYSA-N 2-(3,5-diethyl-4-hydroxyphenyl)-2-hydroxyacetic acid Chemical compound CCC1=CC(C(O)C(O)=O)=CC(CC)=C1O FGSBUNXNOPODEQ-UHFFFAOYSA-N 0.000 description 1
- PIQHNLSUESMWBA-UHFFFAOYSA-N 2-(3-bromo-4-hydroxyphenyl)-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1=CC=C(O)C(Br)=C1 PIQHNLSUESMWBA-UHFFFAOYSA-N 0.000 description 1
- VDBWQCRJTMKEMJ-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1=CC=C(O)C(Cl)=C1 VDBWQCRJTMKEMJ-UHFFFAOYSA-N 0.000 description 1
- BVRWNHJYAKKXKH-UHFFFAOYSA-N 2-(4-chloro-3-hydroxyphenyl)-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1=CC=C(Cl)C(O)=C1 BVRWNHJYAKKXKH-UHFFFAOYSA-N 0.000 description 1
- HLBBQXTYDWELLT-UHFFFAOYSA-N 2-hydroxy-2-(2-hydroxy-4-methoxyphenyl)acetic acid Chemical compound COC1=CC=C(C(O)C(O)=O)C(O)=C1 HLBBQXTYDWELLT-UHFFFAOYSA-N 0.000 description 1
- PXMUSCHKJYFZFD-UHFFFAOYSA-N 2-hydroxy-2-(3-hydroxy-4-methoxyphenyl)acetic acid Chemical compound COC1=CC=C(C(O)C(O)=O)C=C1O PXMUSCHKJYFZFD-UHFFFAOYSA-N 0.000 description 1
- ASTGXUHKUFFOQX-UHFFFAOYSA-N 2-hydroxy-2-(3-methylphenyl)acetic acid Chemical compound CC1=CC=CC(C(O)C(O)=O)=C1 ASTGXUHKUFFOQX-UHFFFAOYSA-N 0.000 description 1
- OOPJZFNKCAXFEP-UHFFFAOYSA-N 2-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)acetic acid Chemical compound COC1=CC(C(O)C(O)=O)=CC(OC)=C1O OOPJZFNKCAXFEP-UHFFFAOYSA-N 0.000 description 1
- RZEFQGHPKYOLKG-UHFFFAOYSA-N 2-hydroxy-2-(4-hydroxy-3,5-dimethylphenyl)acetic acid Chemical compound CC1=CC(C(O)C(O)=O)=CC(C)=C1O RZEFQGHPKYOLKG-UHFFFAOYSA-N 0.000 description 1
- RBQYTVXHDIGUCS-UHFFFAOYSA-N 2-hydroxy-2-(4-hydroxy-3-methylphenyl)acetic acid Chemical compound CC1=CC(C(O)C(O)=O)=CC=C1O RBQYTVXHDIGUCS-UHFFFAOYSA-N 0.000 description 1
- HQDBRHNBKCRLNH-UHFFFAOYSA-N 2-hydroxy-2-methoxy-2-phenylacetic acid Chemical compound COC(O)(C(O)=O)C1=CC=CC=C1 HQDBRHNBKCRLNH-UHFFFAOYSA-N 0.000 description 1
- AXSZGQWPAAHKDH-UHFFFAOYSA-N 2-hydroxy-2-naphthalen-1-ylacetic acid Chemical compound C1=CC=C2C(C(C(O)=O)O)=CC=CC2=C1 AXSZGQWPAAHKDH-UHFFFAOYSA-N 0.000 description 1
- RGHMISIYKIHAJW-UHFFFAOYSA-N 3,4-dihydroxymandelic acid Chemical compound OC(=O)C(O)C1=CC=C(O)C(O)=C1 RGHMISIYKIHAJW-UHFFFAOYSA-N 0.000 description 1
- OLSDAJRAVOVKLG-UHFFFAOYSA-N 3-hydroxymandelic acid Chemical compound OC(=O)C(O)C1=CC=CC(O)=C1 OLSDAJRAVOVKLG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- MOHYGSBMXIJZBJ-UHFFFAOYSA-N [Ir+4] Chemical class [Ir+4] MOHYGSBMXIJZBJ-UHFFFAOYSA-N 0.000 description 1
- 229910001963 alkali metal nitrate Inorganic materials 0.000 description 1
- 238000007743 anodising Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- ITZXULOAYIAYNU-UHFFFAOYSA-N cerium(4+) Chemical class [Ce+4] ITZXULOAYIAYNU-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-M chlorate Inorganic materials [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical class [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 1
- 229910000361 cobalt sulfate Inorganic materials 0.000 description 1
- 229940044175 cobalt sulfate Drugs 0.000 description 1
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940073505 ethyl vanillin Drugs 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical class [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/204—Aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/296—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with lead derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/31—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with compounds containing mercury atoms, which may be regenerated in situ, e.g. by oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2115551A DE2115551C3 (de) | 1971-03-31 | 1971-03-31 | Verfahren zur Herstellung von aromatischen Hydroxyaldehyden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL84513B1 true PL84513B1 (en, 2012) | 1976-04-30 |
Family
ID=5803351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1972154417A PL84513B1 (en, 2012) | 1971-03-31 | 1972-03-30 |
Country Status (15)
| Country | Link |
|---|---|
| AT (1) | AT326636B (en, 2012) |
| BE (1) | BE781466A (en, 2012) |
| CA (1) | CA969556A (en, 2012) |
| CH (1) | CH566952A5 (en, 2012) |
| CS (1) | CS156536B2 (en, 2012) |
| DD (1) | DD95227A5 (en, 2012) |
| DE (1) | DE2115551C3 (en, 2012) |
| DK (1) | DK132400C (en, 2012) |
| FR (1) | FR2132364B1 (en, 2012) |
| GB (1) | GB1377243A (en, 2012) |
| IT (1) | IT952421B (en, 2012) |
| NL (1) | NL7204369A (en, 2012) |
| NO (1) | NO137891C (en, 2012) |
| PL (1) | PL84513B1 (en, 2012) |
| SU (1) | SU437270A3 (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2376112A1 (fr) * | 1976-12-30 | 1978-07-28 | Hoechst France | Procede de fabrication d'acides a-chloroarylacetiques et acides a-chloroarylacetiques nouveaux obtenus par ce procede |
| GB1576334A (en) * | 1977-05-26 | 1980-10-08 | Ici Ltd | N-alkyl and n,n-dialkyl derivatives thereof process for the manufacture of p-hydroxyphenylglycine and |
| JPS54125635A (en) * | 1978-02-20 | 1979-09-29 | Diamalt Ag | Manufacture of 44hydroxyphenylacetic acid |
| SE441524B (sv) * | 1978-05-19 | 1985-10-14 | Ici Ltd | Fast natrium- eller kalium-p-hydroximandelat-monohydrat och sett for dess framstellning |
| FR2440350A1 (fr) * | 1978-11-03 | 1980-05-30 | Hoechst France | Procede de fabrication de l'acide parahydroxymandelique racemique |
| FR2456722A1 (fr) * | 1979-05-14 | 1980-12-12 | Hoechst France | Parformylphenolate de sodium cristallise, son procede de preparation et son application |
| FR2427322A1 (fr) * | 1979-06-15 | 1979-12-28 | Hoechst France | Parahydroxymandelate de sodium racemique cristallise, son procede de preparation et son application a la preparation du paraformylphenolate de sodium cristallise |
| FR2461693A1 (fr) * | 1979-07-24 | 1981-02-06 | Brichima Spa | Procede pour la preparation d'hydroxy- et d'alcoxy-aldehydes aromatiques |
| DE3063330D1 (en) * | 1979-08-09 | 1983-07-07 | Beecham Group Plc | Process for the isolation of a solid salt of p-hydroxymandelic acid; some salts of p-hydroxymandelic acid |
| GB9121656D0 (en) * | 1991-10-11 | 1991-11-27 | Ici Plc | Chemical process |
| FR2931476B1 (fr) * | 2008-05-22 | 2012-12-28 | Rhodia Operations | Procede de separation d'un compose phenolique sous forme solifiee |
| FR2950886B1 (fr) | 2009-10-02 | 2011-10-28 | Rhodia Operations | Procede de separation de composes phenoliques sous forme salifiee |
| CN111848377B (zh) * | 2020-08-18 | 2022-12-06 | 重庆化工职业学院 | 乙基香兰素的制备方法 |
-
1971
- 1971-03-31 DE DE2115551A patent/DE2115551C3/de not_active Expired
-
1972
- 1972-03-27 AT AT261272A patent/AT326636B/de not_active IP Right Cessation
- 1972-03-28 IT IT49278/72A patent/IT952421B/it active
- 1972-03-29 SU SU1765201A patent/SU437270A3/ru active
- 1972-03-29 DK DK159072A patent/DK132400C/da active
- 1972-03-29 NO NO1089/72A patent/NO137891C/no unknown
- 1972-03-29 GB GB1475572A patent/GB1377243A/en not_active Expired
- 1972-03-29 CA CA138,405A patent/CA969556A/en not_active Expired
- 1972-03-30 DD DD161929A patent/DD95227A5/xx unknown
- 1972-03-30 PL PL1972154417A patent/PL84513B1/pl unknown
- 1972-03-30 NL NL7204369A patent/NL7204369A/xx not_active Application Discontinuation
- 1972-03-30 CH CH480872A patent/CH566952A5/xx not_active IP Right Cessation
- 1972-03-30 BE BE781466A patent/BE781466A/xx unknown
- 1972-03-31 FR FR7211597A patent/FR2132364B1/fr not_active Expired
- 1972-03-31 CS CS219672A patent/CS156536B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD95227A5 (en, 2012) | 1973-01-20 |
| FR2132364A1 (en, 2012) | 1972-11-17 |
| DE2115551C3 (de) | 1980-01-10 |
| CS156536B2 (en, 2012) | 1974-07-24 |
| AT326636B (de) | 1975-12-29 |
| GB1377243A (en) | 1974-12-11 |
| ATA261272A (de) | 1975-03-15 |
| CA969556A (en) | 1975-06-17 |
| DE2115551A1 (en, 2012) | 1972-10-12 |
| BE781466A (fr) | 1972-10-02 |
| FR2132364B1 (en, 2012) | 1976-03-05 |
| CH566952A5 (en, 2012) | 1975-09-30 |
| DE2115551B2 (de) | 1979-05-17 |
| NO137891C (no) | 1978-05-16 |
| SU437270A3 (ru) | 1974-07-25 |
| DK132400B (da) | 1975-12-01 |
| IT952421B (it) | 1973-07-20 |
| NL7204369A (en, 2012) | 1972-10-03 |
| NO137891B (no) | 1978-02-06 |
| DK132400C (da) | 1976-05-03 |
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