JP2789045B2 - パラヒドロキシマンデル酸ナトリウムの新規な工業的製造方法 - Google Patents
パラヒドロキシマンデル酸ナトリウムの新規な工業的製造方法Info
- Publication number
- JP2789045B2 JP2789045B2 JP1286017A JP28601789A JP2789045B2 JP 2789045 B2 JP2789045 B2 JP 2789045B2 JP 1286017 A JP1286017 A JP 1286017A JP 28601789 A JP28601789 A JP 28601789A JP 2789045 B2 JP2789045 B2 JP 2789045B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- sodium
- aqueous solution
- phenol
- parahydroxymandelic
- 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.)
- Expired - Lifetime
Links
- 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 19
- 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 title claims description 11
- 229910052708 sodium Inorganic materials 0.000 title claims description 11
- 239000011734 sodium Substances 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims abstract description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 24
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000007864 aqueous solution Substances 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 9
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 5
- YKGBNAGNNUEZQC-UHFFFAOYSA-N 6-methyl-n,n-bis(6-methylheptyl)heptan-1-amine Chemical compound CC(C)CCCCCN(CCCCCC(C)C)CCCCCC(C)C YKGBNAGNNUEZQC-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000008346 aqueous phase Substances 0.000 description 6
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- TWLSOWAQVSIFIF-UHFFFAOYSA-M 2-hydroxy-2-(2-hydroxyphenyl)acetate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1O TWLSOWAQVSIFIF-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- WAFRKUVMBWDGNY-UHFFFAOYSA-N 2-[3-[carboxy(hydroxy)methyl]-4-hydroxyphenyl]-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1=CC=C(O)C(C(O)C(O)=O)=C1 WAFRKUVMBWDGNY-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- -1 alkali metal salt Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- YSUHBROHWRSYSF-UHFFFAOYSA-N 2-[3-[carboxy(hydroxy)methyl]phenyl]-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1=CC=CC(C(O)C(O)=O)=C1 YSUHBROHWRSYSF-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- VNKYTQGIUYNRMY-UHFFFAOYSA-N methoxypropane Chemical compound CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010626 work up procedure 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8814575 | 1988-11-08 | ||
| FR8814575A FR2638740B1 (fr) | 1988-11-08 | 1988-11-08 | Nouveau procede de fabrication industrielle du parahydroxymandelate de sodium |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02178251A JPH02178251A (ja) | 1990-07-11 |
| JP2789045B2 true JP2789045B2 (ja) | 1998-08-20 |
Family
ID=9371685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1286017A Expired - Lifetime JP2789045B2 (ja) | 1988-11-08 | 1989-11-01 | パラヒドロキシマンデル酸ナトリウムの新規な工業的製造方法 |
Country Status (9)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2687143B1 (fr) * | 1992-02-12 | 1995-06-23 | Hoechst France | Procede d'obtention de l'acide orthohydroxymandelique et de ses sels. |
| FR2705669B1 (fr) * | 1993-05-28 | 1995-08-25 | Hoechst France | Procédé de préparation d'acides hydroxyphénylacétiques. |
| FR2760745B1 (fr) * | 1997-03-11 | 1999-05-28 | Hoechst France | Procede industriel de preparation en continu de l'orthohydroxymandelate de sodium |
| NL1010090C2 (nl) * | 1998-09-15 | 2000-03-17 | Gerard Kessels Sociedad Anonim | Werkwijze voor de bereiding van 2- en 4-hydroxyamandelzuur. |
| FR2901553B1 (fr) | 2006-05-24 | 2011-08-26 | Clariant Specialty Fine Chem F | Complexes metalliques comprenant un ligand derive d'acide 2-aryl-2-hydroxyacetique et un cation metallique divalent ou trivalent, et leur utilisation |
| FR3013351B1 (fr) * | 2013-11-15 | 2016-01-01 | Rhodia Operations | Procede de preparation de compose aromatique mandelique et de compose aldehyde aromatique |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6023659B2 (ja) * | 1977-10-20 | 1985-06-08 | 宇部興産株式会社 | ヒドロキシモノマンデル酸化合物の製造法 |
| 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 |
| HU182707B (en) * | 1979-08-09 | 1984-03-28 | Beecham Group Ltd | Process for isolating the salts of p-hydroxy-mandolic acid |
| JPS5668641A (en) * | 1979-11-07 | 1981-06-09 | Nippon Synthetic Chem Ind Co Ltd:The | Preparation of hydroxymandelic acids |
| JPS55102537A (en) * | 1980-01-16 | 1980-08-05 | Nippon Synthetic Chem Ind Co Ltd:The | Preparation of 4-hydroxymandelic acid |
-
1988
- 1988-11-08 FR FR8814575A patent/FR2638740B1/fr not_active Expired - Lifetime
-
1989
- 1989-10-10 AT AT89402790T patent/ATE77618T1/de not_active IP Right Cessation
- 1989-10-10 DE DE8989402790T patent/DE68901913T2/de not_active Expired - Lifetime
- 1989-10-10 EP EP89402790A patent/EP0368696B1/fr not_active Expired - Lifetime
- 1989-10-10 ES ES198989402790T patent/ES2033117T3/es not_active Expired - Lifetime
- 1989-10-25 US US07/426,352 patent/US4978784A/en not_active Expired - Lifetime
- 1989-11-01 JP JP1286017A patent/JP2789045B2/ja not_active Expired - Lifetime
- 1989-11-02 CA CA002002139A patent/CA2002139A1/en not_active Abandoned
-
1992
- 1992-06-25 GR GR920401220T patent/GR3005026T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2033117T3 (es) | 1993-03-01 |
| DE68901913D1 (de) | 1992-07-30 |
| JPH02178251A (ja) | 1990-07-11 |
| EP0368696B1 (fr) | 1992-06-24 |
| FR2638740B1 (fr) | 1991-07-12 |
| EP0368696A1 (fr) | 1990-05-16 |
| US4978784A (en) | 1990-12-18 |
| FR2638740A1 (fr) | 1990-05-11 |
| CA2002139A1 (en) | 1990-05-08 |
| ATE77618T1 (de) | 1992-07-15 |
| GR3005026T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-05-24 |
| DE68901913T2 (de) | 1992-12-17 |
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