583-91-5

Usage

Uses

Used in Pharmaceutical Industry:
2-HYDROXY-4-(METHYLTHIO)BUTYRIC ACID is used as a pharmaceutical compound for its potential therapeutic effects. It is particularly known for its ability to improve stem cell activity, which can help in the treatment of deoxynivalenol-induced intestinal injury. This application highlights its potential in regenerative medicine and the development of novel treatments for gastrointestinal disorders.
Used in Nutritional Supplements:
As a Methionine hydroxy analogue, 2-HYDROXY-4-(METHYLTHIO)BUTYRIC ACID can be used as an additive in the nutritional supplement industry. It may provide benefits similar to Methionine, an essential amino acid, which plays a crucial role in various biological processes, including protein synthesis, detoxification, and the production of essential compounds like cysteine and taurine. Its use in this industry could contribute to the development of supplements that support overall health and well-being.

Reactivity Profile

An organosulfide, alcohol, and organic acid. Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt.

Health Hazard

Corrosive to the eyes and moderately irritating to the skin.

InChI:InChI=1/C5H10O3S/c1-9-3-2-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)

Synthetic route

3-hydroxyoxolan-2-one (19444-84-9) + sodium thiomethoxide (5188-07-8) → 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
Stage #1: 3-hydroxyoxolan-2-one; sodium thiomethoxide In N,N-dimethyl-formamide at 153℃; for 3h; Stage #2: With hydrogenchloride; water Product distribution / selectivity;	100%

2-hydroxy-4-(methylthio)butyronitrile (17773-41-0) → 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
With potassium phosphate buffer; nitrilase from Alcaligenes faecalis ATCC8750 at 30℃; for 48h; pH=7.3;	99%
Multi-step reaction with 2 steps 1: 83 percent / borax / KCN / H2O / 1.5 h / 80 °C 2: 90 percent / NaOH / H2O / 3 h / Heating View Scheme
Stage #1: 2-hydroxy-4-(methylthio)butyronitrile With sulfuric acid at 65℃; Stage #2: With water

α-hydroxy-4-methylthiobutyramide (49540-21-8) → 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
With sodium hydroxide In water for 3h; Heating;	90%
With sulfuric acid; water at 110℃; for 250 - 500h; Product distribution / selectivity;
With sulfuric acid; water at 100 - 105℃; Temperature;

phosphoric acid 1,1-dicyano-3-methylsulfanyl-propyl ester diethyl ester → 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
With hydrogenchloride for 5h; Heating;	85%

methylthiol (74-93-1) + vinyl glycolic acid (600-17-9) → 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
With triethyl borane at 20℃; UV-irradiation;	85%

2-hydroxy-4-(methylthio)butanoic acid calcium salt + sulfuric acid (7664-93-9) → 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
In water for 1.5h;	85%

2-hydroxy-4-(methylthio)butyronitrile (17773-41-0) → α-hydroxy-4-methylthiobutyramide (49540-21-8) + 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
With borax; potassium cyanide In water at 80℃; for 1.5h;	A 83% B 8%
With sulfuric acid; water at 35 - 112℃; for 1.5 - 3.16667h; Product distribution / selectivity;
With sulfuric acid; water at 40 - 125℃; under 1875.19 Torr; for 2.25h; Product distribution / selectivity;
With sulfuric acid; water at 50 - 110℃; under 12 Torr; Product distribution / selectivity; Continuous process;

hydrogen cyanide (74-90-8) + 3-(methylsulfenyl)propanal (3268-49-3) → 2-hydroxy 4-methylthiobutyric acid (583-91-5) + DL-methionine (59-51-8)

Conditions	Yield
With cerium(IV) oxide; ammonia In water at 75℃; for 6h;	A 62.1% B 34.9%
With cerium(IV) oxide; ammonia In water at 75℃; for 6h;	A 44.3% B 52.6%

4-(methylthio)-2-oxo-1-butanol (1003880-00-9) → 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
Stage #1: 4-(methylthio)-2-oxo-1-butanol With potassium hydroxide; oxygen; copper diacetate In water at 20℃; for 2h; Stage #2: With sulfuric acid; water	46%

DL-methionine (59-51-8) → 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
With silver(I) nitrite; water

L-methionine (63-68-3) → 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
With cis-nitrous acid; sodium bromide In water at 25℃; Rate constant;

2-acetoxy-4-methylthiobutanenitrile → 2-hydroxy 4-methylthiobutyric acid (583-91-5) + 2-acetyloxy-4-(methylthio)butanoic acid (138128-01-5)

Conditions	Yield
With potassium phosphate buffer; nitrilase from Alcaligenes faecalis ATCC8750 at 30℃; for 48h; pH=7.3; Title compound not separated from byproducts;	A 6 % Spectr. B 82 % Spectr.

hydrogen cyanide (74-90-8) + 3-(methylsulfenyl)propanal (3268-49-3) → 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
In water at 20 - 68℃; for 0.0833333h; pH=4.7 - 5.5;
Stage #1: hydrogen cyanide; 3-(methylsulfenyl)propanal With pyridine; acetic acid at 35 - 45℃; for 1.25h; Stage #2: With sulfuric acid; water at 60 - 90℃; for 2.91667h;

2-acetyloxy-4-(methylthio)butanoic acid (138128-01-5) → brucine salt + 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
With brucine In ethanol

1-acetyloxy-3-methylthiopropene + (PPh3)2 PdCl2 + L-menthoxyethyl acetyl-L-2-hydroxy-4-methylthiobutyrate + 2-(2-isopropyl-5-methylcyclohexyloxy)ethanol → 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
With hydrogenchloride; CO In tetrahydrofuran

1-carboxy-3-methylthiopropyl sulfate → 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
With water at 80℃; for 24h; Purification / work up;

α-hydroxy-4-methylthiobutyramide (49540-21-8) → 1-carboxy-3-methylthiopropyl sulfate + 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
With sulfuric acid; water at 109℃; for 4h; Heating / reflux;

2-hydroxy-4-methylthiobutyric acid ammonium salt (63302-72-7) → 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
In water; 4-methyl-2-pentanone at 80 - 117℃; Product distribution / selectivity; Inert atmosphere;

sodium α-keto-(γ-methylthio)butyrate (51828-97-8) → 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
With hydrogen; rhodium contaminated with carbon In water at 50℃; under 7500.75 Torr; for 6h; Product distribution / selectivity; autoclave;

sodium cyanide (773837-37-9) + 3-(methylsulfenyl)propanal (3268-49-3) + 3-(methylselenyl)-propanal (119353-03-6) → DL-α-hydroxyselenomethionine (873660-49-2) + 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
Stage #1: 3-(methylsulfenyl)propanal; 3-(methylselenyl)-propanal With sodium hydrogensulfite In water at 20℃; for 0.166667h; Stage #2: sodium cyanide In water at 20℃; for 2h; Reflux; Stage #3: With hydrogenchloride; water for 5h; Reflux;

methyl 2-hydroxy-4-(methylthio)butanoate (52703-96-5) → methylthiol (74-93-1) + 2-hydroxy 4-methylthiobutyric acid (583-91-5)

Conditions	Yield
With sodium hydrosulfide monohydrate In dimethyl sulfoxide at 50℃; for 24h; Temperature; Inert atmosphere; Schlenk technique;	A n/a B 93 %Spectr.

2-hydroxy 4-methylthiobutyric acid (583-91-5) → 2-hydroxy-4-(methylthio)butanoic acid calcium salt

Conditions	Yield
With calcium oxide In ethanol at 100℃; for 24h; Reagent/catalyst;	98.09%
Stage #1: 2-hydroxy 4-methylthiobutyric acid With sodium hydroxide In water at 20℃; pH=~ 9.0; Stage #2: With calcium chloride In water at 20℃; for 5.5h;	84%
With calcium oxide In water at 120℃; Reagent/catalyst; Temperature;
Multi-step reaction with 2 steps 1.1: sodium hydroxide / 0.5 h / 20 °C 2.1: sodium hydroxide; water / 45 - 50 °C 2.2: 0.5 h View Scheme
Multi-step reaction with 2 steps 1.1: potassium hydroxide / methanol / 1 h / 0 °C 1.2: 0 °C 2.1: sodium hydroxide; water / 45 - 50 °C 2.2: 0.5 h View Scheme

2-hydroxy 4-methylthiobutyric acid (583-91-5) + trichloromethyl chloroformate (503-38-8) → 5-(2-(methylthio)ethyl)-1,3-dioxolan-2,4-dione (1161721-72-7)

Conditions	Yield
In tetrahydrofuran	97%

methanol (67-56-1) + 2-hydroxy 4-methylthiobutyric acid (583-91-5) → methyl 2-hydroxy-4-(methylthio)butanoate (52703-96-5)

Conditions	Yield
With sodium hydroxide at 20℃; for 0.5h;	91.7%

2-hydroxy 4-methylthiobutyric acid (583-91-5) + methyl p-toluene sulfonate (80-48-8) → methyl 2-hydroxy-4-(methylthio)butanoate (52703-96-5)

Conditions	Yield
Stage #1: 2-hydroxy 4-methylthiobutyric acid With potassium hydroxide In ethanol at 20℃; for 0.5h; Stage #2: methyl p-toluene sulfonate In ethanol at 20℃;	90.3%

2-hydroxy 4-methylthiobutyric acid (583-91-5) + carbonic acid dimethyl ester (616-38-6) → methyl 2-hydroxy-4-(methylthio)butanoate (52703-96-5)

Conditions	Yield
Stage #1: 2-hydroxy 4-methylthiobutyric acid With potassium hydroxide In methanol at 0℃; for 1h; Stage #2: carbonic acid dimethyl ester In methanol at 0℃;	90.1%

2-hydroxy 4-methylthiobutyric acid (583-91-5) + 2,2-dimethoxy-propane (77-76-9) → 2,2-dimethyl-5-(2-(methylthio)ethyl)-1,3-dioxolan-4-one (1161721-65-8)

Conditions	Yield
In tetrahydrofuran	89%

BF3.2H2O + 2-hydroxy 4-methylthiobutyric acid (583-91-5) + MgBr2.2Et2O → 2,2-dimethyl-5-(2-(methylthio)ethyl)-1,3-dioxolan-4-one (1161721-65-8)

Conditions	Yield
zinc(II) chloride In diethyl ether; water; acetone	87%

dichlorotricarbonylruthenium(II) dimer + 2-hydroxy 4-methylthiobutyric acid (583-91-5) → Ru(CO)3Cl2(H3CS(CH2)2CH(OH)CO2H)

Conditions	Yield
In acetone at 20℃; for 24h; Inert atmosphere; Schlenk technique;	83%

2-hydroxy 4-methylthiobutyric acid (583-91-5) + tetradecanoyl chloride (112-64-1) → C14-HE + C14-HE

Conditions	Yield
at 65℃; Overall yield = 2.6 g;	A 80.5% B 19.5%

Triisopropyl borate (5419-55-6) + 2-hydroxy 4-methylthiobutyric acid (583-91-5) → D,L-2-hydroxy-4-(methylthio)-butanoic acid isopropyl ester (57296-04-5)

Conditions	Yield
at 95℃; for 10h;	72%

2-hydroxy 4-methylthiobutyric acid (583-91-5) + n-octanoic acid chloride (111-64-8) → C8-HE + C8-HE + C8-HE

Conditions	Yield
at 65℃;	A 25.6% B 5.3% C 68.4%

2-hydroxy 4-methylthiobutyric acid (583-91-5) + hexan-1-ol (111-27-3) → 2-hydroxy-4-(methylthio)butanoic acid hexyl ester (161193-00-6)

Conditions	Yield
With sodium hydrogen sulfate In toluene for 5.5h; Dean-Stark; Reflux;	64.1%
With sodium hydrogen sulfate In toluene Dean-Stark; Reflux;	61.1%

2-hydroxy 4-methylthiobutyric acid (583-91-5) + acetyl chloride (75-36-5) → 2-acetyloxy-4-(methylthio)butanoic acid (138128-01-5)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	63.1%
Stage #1: 2-hydroxy 4-methylthiobutyric acid With triethylamine In dichloromethane at 0℃; Stage #2: acetyl chloride In dichloromethane at 0 - 20℃;	63.1%
With triethylamine In dichloromethane at 0 - 20℃;
at 20℃; for 3h; Temperature; Large scale;

2-hydroxy 4-methylthiobutyric acid (583-91-5) + butan-1-ol (71-36-3) → 2-hydroxy-4-(methylthio)butanoic acid butyl ester

Conditions	Yield
With sodium hydrogen sulfate In toluene for 5h; Dean-Stark; Reflux;	62.3%

1-octadecanol (112-92-5) + 2-hydroxy 4-methylthiobutyric acid (583-91-5) → octadecyl 2-hydroxy-4-(methylthio)butanoate (1446404-60-9)

Conditions	Yield
With sodium hydrogen sulfate In toluene Dean-Stark; Reflux;	61%

Isopropyl acetate (108-21-4) + 2-hydroxy 4-methylthiobutyric acid (583-91-5) → D,L-2-hydroxy-4-(methylthio)-butanoic acid isopropyl ester (57296-04-5)

Conditions	Yield
With sulfuric acid at 80 - 90℃; for 6h; Temperature; Reagent/catalyst; Large scale;	57.5%

2-hydroxy 4-methylthiobutyric acid (583-91-5) + butanone (78-93-3) → 2-ethyl-2-methyl-5-(2-(methylthio)ethyl)-1,3-dioxolan-4-one (1161721-66-9)

Conditions	Yield
	56%

octanol (111-87-5) + 2-hydroxy 4-methylthiobutyric acid (583-91-5) → 2-hydroxy-4-(methylthio)butanoic acid octyl ester (1446404-55-2)

Conditions	Yield
With sodium hydrogen sulfate In toluene Dean-Stark; Reflux;	45%
With sodium hydrogen sulfate In toluene for 5.5h; Dean-Stark; Reflux;	45%

2-hydroxy 4-methylthiobutyric acid (583-91-5) + n-hexadecanoyl chloride (112-67-4) → 4-(methylthio)-2-(palmitoyloxy)butanoic acid

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃;	45%

1-Decanol (112-30-1) + 2-hydroxy 4-methylthiobutyric acid (583-91-5) → 2-hydroxy-4-(methylthio)butyric acid decyl ester (161193-01-7)

Conditions	Yield
With sodium hydrogen sulfate In toluene for 6h; Reflux;	44%
With sodium hydrogen sulfate In toluene Dean-Stark; Reflux;	43.5%
With sodium hydrogen sulfate In toluene for 6h; Dean-Stark;	43.5%

1-dodecyl alcohol (112-53-8) + 2-hydroxy 4-methylthiobutyric acid (583-91-5) → dodecyl 2-hydroxy-4-(methylthio)butanoate (1446404-58-5)

Conditions	Yield
With sodium hydrogen sulfate In toluene Dean-Stark; Reflux;	42%

Upstream product

• 59-51-8 DL-methionine 
• 63-68-3 L-methionine 
• 17773-41-0 2-hydroxy-4-(methylthio)butyronitrile 
• 74-90-8 hydrogen cyanide 
• 3268-49-3 3-(methylsulfenyl)propanal 
• 138128-01-5 2-acetyloxy-4-(methylthio)butanoic acid 
• 63302-72-7 2-hydroxy-4-methylthiobutyric acid ammonium salt 
• 52703-96-5 methyl 2-hydroxy-4-(methylthio)butanoate 
• 7664-93-9 sulfuric acid 
• 773837-37-9 sodium cyanide 
• 119353-03-6 3-(methylselenyl)-propanal 
• 51828-97-8 sodium α-keto-(γ-methylthio)butyrate 
• 19444-84-9 3-hydroxyoxolan-2-one 
• 5188-07-8 sodium thiomethoxide 

Downstream Products

• 557-41-5 zinc(II) formate 
• 57296-04-5 D,L-2-hydroxy-4-(methylthio)-butanoic acid isopropyl ester 
• 39638-34-1 (R)-2-hydroxy-4-(methylthio)butanoic acid 
• 38565-99-0 C₆H₁₃O₃S⁽¹⁺⁾*I^(1-) 
• 1374125-32-2 C₁₂H₁₇O₃S⁽¹⁺⁾*Br^(1-) 
• 19444-84-9 3-hydroxyoxolan-2-one 
• 138128-01-5 2-acetyloxy-4-(methylthio)butanoic acid 
• 75-52-5 Nitromethane 
• 25731-06-0 Nitro-methanol 

Relevant academic research and scientific papers

A contribution to the rational design of Ru(CO)3Cl2L complexes for in vivo delivery of CO

A few ruthenium based metal carbonyl complexes, e.g. CORM-2 and CORM-3, have therapeutic activity attributed to their ability to deliver CO to biological targets. In this work, a series of related complexes with the formula [Ru(CO)3Cl2L] (L = DMSO (3), l-H3CSO(CH2)2CH(NH2)CO2H) (6a); d,l-H3CSO(CH2)2CH(NH2)CO2H (6b); 3-NC5H4(CH2)2SO3Na (7); 4-NC5H4(CH2)2SO3Na (8); PTA (9); DAPTA (10); H3CS(CH2)2CH(OH)CO2H (11); CNCMe2CO2Me (12); CNCMeEtCO2Me (13); CN(c-C3H4)CO2Et) (14)) were designed, synthesized and studied. The effects of L on their stability, CO release profile, cytotoxicity and anti-inflammatory properties are described. The stability in aqueous solution depends on the nature of L as shown using HPLC and LC-MS studies. The isocyanide derivatives are the least stable complexes, and the S-bound methionine oxide derivative is the more stable one. The complexes do not release CO gas to the headspace, but release CO2 instead. X-ray diffraction of crystals of the model protein Hen Egg White Lysozyme soaked with 6b (4UWN) and 8 (4UWV) shows the addition of RuII(CO)(H2O)4 at the His15 binding site. Soakings with 7 (4UWU) produced the metallacarboxylate [Ru(COOH)(CO)(H2O)3]+ bound to the His15 site. The aqueous chemistry of these complexes is governed by the water-gas shift reaction initiated with the nucleophilic attack of HO- on coordinated CO. DFT calculations show this addition to be essentially barrierless. The complexes have low cytotoxicity and low hemolytic indices. Following i.v. administration of CORM-3, the in vivo bio-distribution of CO differs from that obtained with CO inhalation or with heme oxygenase stimulation. A mechanism for CO transport and delivery from these complexes is proposed. This journal is

METHOD FOR MANUFACTURING 2-HYDROXY-4-(METHYLTHIO)BUTYRIC ACID

A method for manufacturing 2-hydroxy-4-(methylthio)butyric acid (HMTBA) from 2-hydroxy-4-methylthio-butyronitrile (HMTBN), where HMTBN is hydrolyzed into HMTBA in the presence of a mineral acid in an aqueous medium, the medium is neutralized by addition of a base, a first phase including at least HMTBA and salts and a second phase containing salts are separated, the method including the separation of the HMTBA from the salts of the first phase, by subjecting the latter to a chromatography.

METHOD AND DEVICE FOR PREPARING 2-HYDROXY-4-METHYLTHIOBUTYRIC ACID AND INTERMEDIATES THEREOF

Provided by the present disclosure are a method and a device for preparing 2-hydroxy-4-methylthiobutyric acid and intermediates thereof; the intermediates for preparing 2-hydroxy-4-methylthiobutyric acid comprise 3-methylthiopropionaldehyde and 2-hydroxy-4-methylthiobutyronitrile. The method for preparing 2-hydroxy-4-methylthiobutyric acid provided by the present disclosure comprises: step (1), a step of reacting acrolein with methyl mercaptan to prepare 3-methylthiopropionaldehyde; step (2), a step of reacting 3-methylthiopropionaldehyde with hydrocyanic acid to prepare 2-hydroxy-4-methylthiobutyronitrile; and step (3), a step of hydrating 2-hydroxy-4-methylthiobutyronitrile by using sulfuric acid and then hydrolyzing to prepare 2-hydroxy-4-methylthiobutyric acid; wherein in steps (1), (2) and (3), the reaction status of the materials is detected online, and the proportions of the materials are controlled according to the detection results such that reactions are performed completely

Clean preparation method of high-purity methionine hydroxyl analogue calcium salt

The invention discloses a clean preparation method of high-purity methionine hydroxyl analogue calcium salt. The clean preparation method comprises the following specific steps: adding water into 2-hydroxy-4-methylthiobutyronitrile serving as a raw material, carrying out a hydration reaction under the catalytic action of solid acid/solid alkali, adding strong acid or strong alkali for hydrolysis to obtain 2-hydroxy-4-methylthiobutyric acid, then adding CaO or Ca(OH)2, carrying out a salt forming reaction to obtain an aqueous solution of a mixture, carrying out chromatographic desalination treatment on the aqueous solution of the mixture to obtain an aqueous solution of a methionine hydroxyl analogue, and finally carrying out spray drying on the aqueous solution of the methionine hydroxyl analogue to obtain a target product. Compared with a traditional method, the method disclosed by the invention has the advantages that the step of neutralizing and alkali washing after the reaction is finished is avoided, the generation of a byproduct, namely inorganic ammonium salt is avoided, reaction is simple, conditions are mild, and the method is safe and environment-friendly; and in addition, a catalyst, namely the solid acid or solid alkali adopted in the method can be recycled, so production cost is reduced.

DEMETHYLATION OF METHYL ESTER OF METHIONINE AND ITS HYDROXY ANALOG

The following invention regards a process of demethylating a methyl ester of methionine or its hydroxy analog and producing methane thiol as a side-product. The methionine and its hydroxy analog are suitable as an animal feed additive and as a food additive. The methane thiol may be consumed in a hydrothiolation step such as in a step of preparing the methyl ester of methio- nine or its hydroxy analog from from methyl vinyl glycolate.

METHOD FOR PRODUCING METHIONINE AND/OR 2-HYDROXY-4-(METHYLTHIO) BUTANOIC ACID

An object of the invention is to provide a simple method for producing methionine and/or 2-hydroxy-4-(methylthio)butanoic acid at a high yield using 3-(methylthio)propionaldehyde as a raw material. An oxide catalyst containing cerium, 3-(methylthio)propionaldehyde, a compound containing cyanide ion, ammonia or a compound containing ammonium ion, and water are contacted with each other to produce methionine and/or 2-hydroxy-4-(methylthio)butanoic acid.

Method for manufacturing methylmercaptopropionaldehyde and methionine using renewable raw materials

The present invention relates to a method for manufacturing methylmercaptopropionaldehyde (MMP) including at least the following steps: (a) dehydrating glycerol to acrolein from an aqueous solution of glycerol in the presence of an acid catalyst; (b) purifying the aqueous flux from step (a) to obtain a flux of acrolein containing at least 15 wt % of water relative to the acrolein; (c) causing a reaction of the acrolein flux obtained in step (b) with methylmercaptan in the presence of a catalyst; (d) optionally purifying the product obtained in step (c). The method of the invention can also include a reaction of the product obtained in step (c) or (d) with hydrocyanic acid, or sodium cyanide during a step (e) followed by a subsequent transformation to produce methionine or methionine hydroxyanalogue, which can then optionally be purified. The additional use of methylmercaptan and/or hydrocyanic acid derived from biomass as raw materials in the method according to the invention makes it possible to obtain MMP, methionine or methionine hydroxyanalogue made up of 100% organic carbon from renewable sources.

Process for preparing 2-hydroxy-4-methylselenobutyric acid, alone or as a mixture with its sulphur-containing analogue, and uses thereof in nutrition, in particular animal nutrition

The present invention relates to a novel process for preparing 2-hydroxy-4-methylselenobutyric acid from 3-methylselenoproprion-aldehyde. The 2-hydroxy-4-methylselenobutyric acid is obtained alone or as a mixture with its sulphur-containing analogue. The invention also relates to the compositions, in particular nutritional compositions, comprising a mixture of 2-hydroxy-4-methylselenobutyric acid and 2-hydroxy-4-methylthiobutyric acid, and a physiologically acceptable medium, and to the use of this mixture as a dietary ingredient.

PROCESS FOR THE PREPARATION OF HYDROXYCARBOXYLIC ACID COMPOUND OR SALT THEREOF

The present process can prepare a hydroxycarboxylic acid compound of Formula (1): or a salt thereof by reacting a ketocarboxylic acid compound of Formula (2): or a salt thereof and hydrogen in the presence of a transition metal catalyst, without using hydrogen cyanide.

Reactive Extraction of Free Organic Acids from the Ammonium Salts Thereof

The invention relates to a process for converting ammonium salts of organic acids to the particular free organic acid, wherein an aqueous solution of the ammonium salt is contacted with an organic extractant and the salt is dissociated at temperatures and pressures at which the aqueous solution and the extractant are in the liquid state, and a stripping medium or entraining gas is introduced in order to remove NH3 from the aqueous solution and transfer at least a portion of the free organic acid formed to the organic extractant. The invention described here thus provides an improved process for releasing an organic acid, preferably a carboxylic, sulphonic or phosphonic acid, especially an alpha-hydroxycarboxylic acid or beta-hydroxycarboxylic acid, from the ammonium salt thereof by release and removal of ammonia and simultaneous extraction of the acid released with a suitable extractant from the aqueous phase. This process corresponds to a reactive extraction. The reactive extraction of an organic acid from the aqueous ammonium salt solution thereof can be improved significantly by the use of a stripping medium or entraining gas, for example nitrogen, air, steam or inert gases, for example argon. The ammonia released is removed from the aqueous solution by the continuous gas stream and can be fed back into a production process. The free acid can be obtained from the extractant by a process such as distillation, rectification, crystallization, re-extraction, chromatography, adsorption, or by a membrane process.