FR2495137A1 - Procede industriel de preparation en continu de l'acide p-hydroxymandelique racemique - Google Patents
Procede industriel de preparation en continu de l'acide p-hydroxymandelique racemique Download PDFInfo
- Publication number
- FR2495137A1 FR2495137A1 FR8025333A FR8025333A FR2495137A1 FR 2495137 A1 FR2495137 A1 FR 2495137A1 FR 8025333 A FR8025333 A FR 8025333A FR 8025333 A FR8025333 A FR 8025333A FR 2495137 A1 FR2495137 A1 FR 2495137A1
- Authority
- FR
- France
- Prior art keywords
- sep
- phenol
- moles
- reactor
- acid
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 title claims abstract description 42
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 25
- YHXHKYRQLYQUIH-UHFFFAOYSA-N 4-hydroxymandelic acid Chemical compound OC(=O)C(O)C1=CC=C(O)C=C1 YHXHKYRQLYQUIH-UHFFFAOYSA-N 0.000 title claims abstract description 15
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 title claims description 54
- 238000009833 condensation Methods 0.000 claims abstract description 13
- 230000005494 condensation Effects 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 239000007864 aqueous solution Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 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 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 9
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 abstract description 8
- AYKYOOPFBCOXSL-UHFFFAOYSA-N (4-hydroxyphenyl)acetonitrile Chemical compound OC1=CC=C(CC#N)C=C1 AYKYOOPFBCOXSL-UHFFFAOYSA-N 0.000 abstract description 4
- 238000004064 recycling Methods 0.000 abstract description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229960003742 phenol Drugs 0.000 description 17
- 239000000243 solution Substances 0.000 description 6
- 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 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000012527 feed solution Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- FEUATHOQKVGPEK-UHFFFAOYSA-N 4-hydroxybenzene-1,3-dicarbaldehyde Chemical compound OC1=CC=C(C=O)C=C1C=O FEUATHOQKVGPEK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000911 decarboxylating effect Effects 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 241000288748 Chrysochloridae Species 0.000 description 1
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002913 oxalic acids Chemical class 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 235000009048 phenolic acids Nutrition 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- HPQVZCCKGRTPLU-UHFFFAOYSA-M sodium;2-hydroxy-2-(4-hydroxyphenyl)acetate Chemical compound [Na+].[O-]C(=O)C(O)C1=CC=C(O)C=C1 HPQVZCCKGRTPLU-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8025333A FR2495137A1 (fr) | 1980-11-28 | 1980-11-28 | Procede industriel de preparation en continu de l'acide p-hydroxymandelique racemique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8025333A FR2495137A1 (fr) | 1980-11-28 | 1980-11-28 | Procede industriel de preparation en continu de l'acide p-hydroxymandelique racemique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2495137A1 true FR2495137A1 (fr) | 1982-06-04 |
| FR2495137B1 FR2495137B1 (cg-RX-API-DMAC7.html) | 1983-02-11 |
Family
ID=9248473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8025333A Granted FR2495137A1 (fr) | 1980-11-28 | 1980-11-28 | Procede industriel de preparation en continu de l'acide p-hydroxymandelique racemique |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2495137A1 (cg-RX-API-DMAC7.html) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5248816A (en) * | 1991-10-11 | 1993-09-28 | Imperial Chemical Industries Plc | Process for making 2-hydroxymandelic acid and 2-hydroxybenzaldehydes |
| US5395964A (en) * | 1993-05-28 | 1995-03-07 | Societe Francaise Hoechst | Preparation process for hydroxyphenylacetic acids |
| EP0864557A1 (fr) * | 1997-03-11 | 1998-09-16 | Clariant (France) S.A. | Procédé industriel de préparation en continu de l'orthohydroxymandélate de sodium |
| EP2796441A3 (fr) * | 2014-05-26 | 2015-02-25 | Rhodia Opérations | Procédé de préparation de composés p-hydroxymandéliques en réacteurs agités |
| CN108047033B (zh) * | 2017-12-20 | 2023-12-01 | 江西科苑生物药业有限公司 | 一种制备扁桃酸类化合物的反应装置及其方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2440350A1 (fr) * | 1978-11-03 | 1980-05-30 | Hoechst France | Procede de fabrication de l'acide parahydroxymandelique racemique |
-
1980
- 1980-11-28 FR FR8025333A patent/FR2495137A1/fr active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2440350A1 (fr) * | 1978-11-03 | 1980-05-30 | Hoechst France | Procede de fabrication de l'acide parahydroxymandelique racemique |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5248816A (en) * | 1991-10-11 | 1993-09-28 | Imperial Chemical Industries Plc | Process for making 2-hydroxymandelic acid and 2-hydroxybenzaldehydes |
| US5395964A (en) * | 1993-05-28 | 1995-03-07 | Societe Francaise Hoechst | Preparation process for hydroxyphenylacetic acids |
| EP0864557A1 (fr) * | 1997-03-11 | 1998-09-16 | Clariant (France) S.A. | Procédé industriel de préparation en continu de l'orthohydroxymandélate de sodium |
| FR2760745A1 (fr) * | 1997-03-11 | 1998-09-18 | Hoechst France | Procede industriel de preparation en continu de l'orthohydroxymandelate de sodium |
| US5914429A (en) * | 1997-03-11 | 1999-06-22 | Clariant (France) S. A. | Industrial process for the continuous preparation of sodium orthohydroxymandelate |
| CN1119312C (zh) * | 1997-03-11 | 2003-08-27 | 科莱恩(法国)公司 | 邻羟基扁桃酸钠的工业化连续制备方法 |
| EP2796441A3 (fr) * | 2014-05-26 | 2015-02-25 | Rhodia Opérations | Procédé de préparation de composés p-hydroxymandéliques en réacteurs agités |
| FR3021314A1 (fr) * | 2014-05-26 | 2015-11-27 | Rhodia Operations | Procede de preparation de composes p-hydroxymandeliques en reacteurs agites |
| WO2015181023A1 (fr) | 2014-05-26 | 2015-12-03 | Rhodia Operations | Procede de preparation de composes p-hydroxymandeliques en reacteurs agites |
| CN108047033B (zh) * | 2017-12-20 | 2023-12-01 | 江西科苑生物药业有限公司 | 一种制备扁桃酸类化合物的反应装置及其方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2495137B1 (cg-RX-API-DMAC7.html) | 1983-02-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |