FR1603611A - Method for the optical reaction of D-and-L-alpha-amino-caprolactam (D and L-I), wherein DL-I is mixed with beta-naphthalene-sulphonic acid (II) or 2-naphthylami - Google Patents

Method for the optical reaction of D-and-L-alpha-amino-caprolactam (D and L-I), wherein DL-I is mixed with beta-naphthalene-sulphonic acid (II) or 2-naphthylami

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Publication number
FR1603611A
FR1603611A FR1603611DA FR1603611A FR 1603611 A FR1603611 A FR 1603611A FR 1603611D A FR1603611D A FR 1603611DA FR 1603611 A FR1603611 A FR 1603611A
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France
Prior art keywords
sulphonic acid
isomer
seeded
caprolactam
naphthalene
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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
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French (fr)
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Publication of FR1603611A publication Critical patent/FR1603611A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D223/12—Nitrogen atoms not forming part of a nitro radical

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)

Abstract

Method for the optical reaction of D-and-L-alpha-amino-caprolactam (D and L-I), wherein DL-I is mixed with beta-naphthalene-sulphonic acid (II) or 2-naphthylamine-1-sulphonic acid (III) in a suitable warm solvent or solvent mixture eg. H2O, (1-5C) alkanol, (2-4C) alkyleneglycol, l. ether, l. carboxylic acid, di (l. alkyl) amide, etc., pref. a mixture of H2O and organic solvent in ratio 10:90 - 70:30, cooled, and seeded with one of the optical isomer salts (eg. D-I-II). If the mixture is already partly resolved, it is pref. seeded with the isomer present in excess. When crystallisation is complete, the product is filtered, and the mother-liquor seeded with the second isomer, the isomer isolated, and the filtrate recycled with more DL-I and acid. The resolved products may be purified by recrystn., and the sulphonic acid removed by treatment with ion exchange resin or inorganic base. The optically active lactam (I) or the salts, can be hydrolysed, e.g. by HCl to give D or L-lysine. The isolated D-I-sulphonate can be racemised by heating at 200-250 deg. under N2 or CO2, and recycled. Intermediates for lysine.
FR1603611D 1967-08-25 1968-08-23 Method for the optical reaction of D-and-L-alpha-amino-caprolactam (D and L-I), wherein DL-I is mixed with beta-naphthalene-sulphonic acid (II) or 2-naphthylami Expired FR1603611A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
JP5505267 1967-08-25
JP5505167 1967-08-25
JP5886667 1967-09-12
JP7891667 1967-12-09
JP3957768 1968-06-07

Publications (1)

Publication Number Publication Date
FR1603611A true FR1603611A (en) 1971-05-10

Family

ID=27522022

Family Applications (1)

Application Number Title Priority Date Filing Date
FR1603611D Expired FR1603611A (en) 1967-08-25 1968-08-23 Method for the optical reaction of D-and-L-alpha-amino-caprolactam (D and L-I), wherein DL-I is mixed with beta-naphthalene-sulphonic acid (II) or 2-naphthylami

Country Status (5)

Country Link
DE (1) DE1795225C3 (en)
FR (1) FR1603611A (en)
GB (1) GB1192097A (en)
IT (1) IT943037B (en)
NL (1) NL6812054A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3824231A (en) * 1972-10-27 1974-07-16 Allied Chem Resolution of alpha-aminocaprolactam

Also Published As

Publication number Publication date
GB1192097A (en) 1970-05-20
DE1795225B2 (en) 1974-02-21
DE1795225C3 (en) 1974-09-26
IT943037B (en) 1973-04-02
NL6812054A (en) 1969-02-27
DE1795225A1 (en) 1972-04-27

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