EP0000518A1 - Procédé de dédoublement chimique du racémate de l'acide mandélique - Google Patents

Procédé de dédoublement chimique du racémate de l'acide mandélique Download PDF

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Publication number
EP0000518A1
EP0000518A1 EP78100393A EP78100393A EP0000518A1 EP 0000518 A1 EP0000518 A1 EP 0000518A1 EP 78100393 A EP78100393 A EP 78100393A EP 78100393 A EP78100393 A EP 78100393A EP 0000518 A1 EP0000518 A1 EP 0000518A1
Authority
EP
European Patent Office
Prior art keywords
mandelic acid
aminobutanol
optically active
mother liquor
acids
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
Application number
EP78100393A
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German (de)
English (en)
Other versions
EP0000518B1 (fr
Inventor
Wolfgang Dr. Dannenberg
Horst Dr. Schmand
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Honeywell Riedel de Haen AG
Original Assignee
Riedel de Haen AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6014738&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0000518(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Riedel de Haen AG filed Critical Riedel de Haen AG
Publication of EP0000518A1 publication Critical patent/EP0000518A1/fr
Application granted granted Critical
Publication of EP0000518B1 publication Critical patent/EP0000518B1/fr
Expired legal-status Critical Current

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Classifications

    • 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
    • C07C59/48—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings
    • C07C59/50—Mandelic acid

Definitions

  • the invention relates to a process for the chemical cleavage of racemic mandelic acid and the production, in particular, of D (-) - mandelic acid.
  • D (-) - mandelic acid is an important intermediate for the production of semisynthetic cephalosporins.
  • optically active amines used in the practically usable mandelic acid racemate cleavages are very expensive and moreover have relatively high molecular weights, so that the use of larger amounts is necessary.
  • the above object can be achieved by adding DL-mandelic acid in one or a mixture of a plurality of solvents from the group water, lower aliphatic alcohols and ketones with D (-) - 2-aminobutanol -. (1 ), the crystallizing diastereomeric salt is separated from the mother liquor and then the diastereomeric salts contained in crystals and mother liquor with acids or bases in each case into the optically active methods according to methods known per se Acids and D (-) - 2-aminobutanol separated.
  • D (-) - 2-aminobutanol- (1) can easily be obtained from racemic 2-aminobutanol- (1) by resolution with L (+) - tartaric acid (DE-PS 1 243 206). It shows a high resistance to racemization and can be easily cleaned by distillation.
  • 2-Aminobutanol- (1) has a comparatively low molecular weight and shows excellent dissolving properties in the solvents used for resolution. After successful cleavage, the amine used can be recovered using the usual methods and fed back into the process.
  • optically active forms of 2-aminobutanol (1) are already in use as racemate resolution reagents. However, based on the state of the art (e.g. tables of resolving agents and optical resolution), one had to expect that only bases which contain a large molecule, preferably a secondary or tertiary nitrogen atom, are suitable for the resolution of mandelic acid.
  • the optically active aminobutanol can be used in proportions between 0.5 and 1.0 equivalents. Equimolar amounts of mandelic acid and aminobutanol are preferably used, since the highest yields are achieved in this way.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP78100393A 1977-07-23 1978-07-14 Procédé de dédoublement chimique du racémate de l'acide mandélique Expired EP0000518B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2733425 1977-07-23
DE2733425A DE2733425C2 (de) 1977-07-23 1977-07-23 Verfahren zur Herstellung von D(-)-Mandelsäure aus DL-Mandelsäure durch racemische Spaltung

Publications (2)

Publication Number Publication Date
EP0000518A1 true EP0000518A1 (fr) 1979-02-07
EP0000518B1 EP0000518B1 (fr) 1981-01-07

Family

ID=6014738

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100393A Expired EP0000518B1 (fr) 1977-07-23 1978-07-14 Procédé de dédoublement chimique du racémate de l'acide mandélique

Country Status (3)

Country Link
EP (1) EP0000518B1 (fr)
JP (2) JPS5424849A (fr)
DE (2) DE2733425C2 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0025841A1 (fr) * 1979-08-22 1981-04-01 BASF Aktiengesellschaft Sels diastéréomériques de l'acide malique et de 2-amino-1-butanol et procédé de scission de l'acide malique racémique
EP0036265A1 (fr) * 1980-03-05 1981-09-23 Hiroyuki Nohira Procédé de résolution optique du (+/-)-2-amino-1-butanol et/ou de l'acide (+/-) mandélique
EP0202522A2 (fr) * 1985-05-11 1986-11-26 BASF Aktiengesellschaft Procédé pour la résolution racémique du D,L-2-aminobutane-1-ol
US6743944B1 (en) 1999-09-07 2004-06-01 Mitsubishi Rayon Co., Ltd. Process for producing optically active aminoalcohol

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS55115846A (en) * 1979-03-02 1980-09-06 Noyori Gentaro Optical resolution of dl-mandelic acid
US4322548A (en) 1980-02-13 1982-03-30 Kay Fries, Inc. Resolution of racemic mandelic acid
JPS5817733B2 (ja) * 1980-03-03 1983-04-09 野依 源太郎 Ｄｌ−マンデル酸の分割法
JPS6141245A (ja) * 1984-07-31 1986-02-27 Koonan Eng Kk 無線デ−タ伝送システム
DE102004035034A1 (de) * 2004-07-20 2006-02-16 Degussa Ag Racematspaltung von p-Hydroxyphenyl-2-alkoxy-propionsäuren
JP2015003861A (ja) * 2011-10-18 2015-01-08 株式会社カネカ （ｒ）−２−アミノ−２−エチルヘキサノールの製造法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE687555C (de) * 1937-07-21 1940-02-06 Chem Fab Vormals Sandoz Verfahren zur Herstellung von Aminoalkoholen
FR1439850A (fr) * 1963-08-10 1966-05-27 Zoja Lab Chim Farm Procédé pour la résolution de mélanges d'antipodes optiques
CA932720A (en) * 1968-08-20 1973-08-28 American Cyanamid Company Process for optical resolution and products resulting therefrom
US3686183A (en) * 1969-03-24 1972-08-22 Syntex Corp Preparation of optical isomers of arylalkylacetic acids
YU36484B (en) * 1973-06-07 1984-02-29 Pliva Pharm & Chem Works Process for preparing l-(-)-2-methyl-3-(3,4-dihydroxyphenyl)-alanine
JPS50130706A (fr) * 1974-04-04 1975-10-16

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
HELV. CHIM. ACTA, 26, 929-943 (1943) *
SAMUEL H. WILEN: "Tables of resolving agents and optical resolutions", 1972, University of Notre Dame Press, Notre Dame, Indiana, (USA) Seite 18 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0025841A1 (fr) * 1979-08-22 1981-04-01 BASF Aktiengesellschaft Sels diastéréomériques de l'acide malique et de 2-amino-1-butanol et procédé de scission de l'acide malique racémique
EP0036265A1 (fr) * 1980-03-05 1981-09-23 Hiroyuki Nohira Procédé de résolution optique du (+/-)-2-amino-1-butanol et/ou de l'acide (+/-) mandélique
EP0202522A2 (fr) * 1985-05-11 1986-11-26 BASF Aktiengesellschaft Procédé pour la résolution racémique du D,L-2-aminobutane-1-ol
EP0202522A3 (en) * 1985-05-11 1988-03-23 Basf Aktiengesellschaft Process for the racemic resolution of d,l-2-aminobutan-1-ol
US6743944B1 (en) 1999-09-07 2004-06-01 Mitsubishi Rayon Co., Ltd. Process for producing optically active aminoalcohol

Also Published As

Publication number Publication date
DE2860412D1 (en) 1981-02-26
JPS5843939A (ja) 1983-03-14
DE2733425C2 (de) 1982-08-26
JPS5424849A (en) 1979-02-24
DE2733425A1 (de) 1979-01-25
EP0000518B1 (fr) 1981-01-07

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