GB730923A - Process for the preparation of a new aldehyde derivative - Google Patents

Process for the preparation of a new aldehyde derivative

Info

Publication number
GB730923A
GB730923A GB12321/53A GB1232153A GB730923A GB 730923 A GB730923 A GB 730923A GB 12321/53 A GB12321/53 A GB 12321/53A GB 1232153 A GB1232153 A GB 1232153A GB 730923 A GB730923 A GB 730923A
Authority
GB
United Kingdom
Prior art keywords
methionine
hydroxymethyl
formaldehyde
reacted
give
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
Application number
GB12321/53A
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.)
Hamol A -G
Original Assignee
Hamol A -G
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
Application filed by Hamol A -G filed Critical Hamol A -G
Publication of GB730923A publication Critical patent/GB730923A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/04—Alpha- or beta- amino acids
    • C12P13/12—Methionine; Cysteine; Cystine

Abstract

The invention comprises as new compounds N-hydroxymethyl-methionine and its sodium, potassium, barium and calcium salts. Such compounds are obtained by reacting methionine with formaldehyde in alkaline solution at a pH value greater than 7. When the product is obtained as a salt, the latter may be converted to N - hydroxymethyl - methionine itself. In examples: (1) methionine and formaldehyde are reacted in the presence of aqueous sodium hydroxide, and the solution obtained is treated with a cation-exchange resin and evaporated to dryness, and the product is redissolved and precipitated by adding acetone to give N-hydroxymethyl - methionine. If sodium or potassium hydroxides are added to the reaction in equivalent amounts to the reactants, and the treatment with the cation-exchange resin is omitted the corresponding salts are obtained; (2) methionine and formaldehyde are reacted in aqueous baryta solution to give the barium salt of N-hydroxymethyl-methionine from which the free compound is liberated by the addition of sulphuric acid; (3) methionine and formaldehyde are reacted in the presence of aqueous calcium hydroxide to give the calcium salt of N-hydroxymethyl-methionine, from which the free compound is liberated by the passage of carbon dioxide.
GB12321/53A 1952-07-05 1953-05-04 Process for the preparation of a new aldehyde derivative Expired GB730923A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH730923X 1952-07-05

Publications (1)

Publication Number Publication Date
GB730923A true GB730923A (en) 1955-06-01

Family

ID=4532351

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12321/53A Expired GB730923A (en) 1952-07-05 1953-05-04 Process for the preparation of a new aldehyde derivative

Country Status (1)

Country Link
GB (1) GB730923A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3968253A (en) 1973-02-16 1976-07-06 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler Feed additive for ruminants
US4044169A (en) 1973-02-16 1977-08-23 Duetsche Gold- Und Silber-Scheideanstalt Vormals Roessler Feed additive for ruminants
CN102702049A (en) * 2012-06-18 2012-10-03 山东轻工业学院 Method for preparing solid 2-hydroxy-4-(methylthio) butanoic acid
CN102796032A (en) * 2012-07-26 2012-11-28 江苏畜牧兽医职业技术学院 Method for synthesizing rumen bypass protective methionine

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3968253A (en) 1973-02-16 1976-07-06 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler Feed additive for ruminants
US4044169A (en) 1973-02-16 1977-08-23 Duetsche Gold- Und Silber-Scheideanstalt Vormals Roessler Feed additive for ruminants
CN102702049A (en) * 2012-06-18 2012-10-03 山东轻工业学院 Method for preparing solid 2-hydroxy-4-(methylthio) butanoic acid
CN102702049B (en) * 2012-06-18 2013-11-13 山东轻工业学院 Method for preparing solid 2-hydroxy-4-(methylthio) butanoic acid
CN102796032A (en) * 2012-07-26 2012-11-28 江苏畜牧兽医职业技术学院 Method for synthesizing rumen bypass protective methionine

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