13253-44-6Relevant articles and documents
Comparison of the sustainability metrics of the petrochemical and biomass-based routes to methionine
Sanders, Johan P.M.,Sheldon, Roger A.
, p. 44 - 49 (2015)
Sustainability metrics, based on material efficiency, energy input, land use and costs, of three processesfor the manufacture of methionine are compared. The petrochemical process affords dl-methionine whilethe two biomass-based routes afford the l-enantiomer. From the point of view of the major application,in animal feed, either can be used. The first bio-based route, developed by CJ Cheil-Jedang, involves theproduction of an l-methionine precursor, O-succinyl homoserine by fermentation followed by enzymaticreaction of the latter with methyl mercaptan.The second bio-based route involves the isolation of l-methionine from grass protein. Based on thisconcise evaluation of the sustainability metrics we conclude that both bio-based processe are potentiallyattractive sustainable routes for the manufacture of methionine.
METHOD FOR PRODUCING METHIONINE
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Paragraph 0100-0105, (2021/03/13)
An object of the present invention to provide a method for producing methionine with consideration given to the environment. The production method of the present invention comprises a removal step of blowing an inert gas into a liquid containing 5-(2-methylmercaptoethyl)hydantoin and thereby diffusing ammonia remaining in the liquid to obtain an emission gas containing the ammonia, and a recovery step of bringing the emission gas into contact with a washing liquid to recover ammonia contained in the emission gas.
METHOD FOR MANUFACTURING METHIONINE
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Paragraph 0078, (2021/04/02)
An object of the present invention is to provide a method for manufacturing methionine capable of achieving an improvement in ammonia removal efficiency. The manufacturing method of the present invention comprises a removal step of supplying a liquid containing a methionine salt, which is obtained by reacting 3-methylmercaptopropionaldehyde and hydrocyanic acid, or a compound obtained by reacting 3-methylmercaptopropionaldehyde and hydrocyanic acid, with carbon dioxide and ammonia to obtain a liquid containing 5-(2-methylmercaptoethyl)hydantoin and then hydrolyzing the 5-(2-methylmercaptoethyl)hydantoin, to a diffusion tower from an upper portion thereof while supplying a stripping gas to the diffusion tower from a lower portion thereof to remove ammonia contained in the liquid through stripping, and the stripping gas contains a process gas generated in a process of manufacturing methionine.
METHOD FOR PREPARING METHIONINE
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Page/Page column 16; 17, (2018/07/29)
The present invention relates to a method for preparing methionine or methionine salts. In particular, the invention describes the step of preparing 2-hydroxy-4-(methylthio)butyronitrile (MMP-CN) from 3-methylthiopropanal (MMP) and hydrogen cyanide (HCN) in the presence of ammonia by bringing a gaseous mixture comprising HCN and ammonia into contact with MMP.
By coarse hydrocyanic acid gas preparation 5 - (2-methylthioamphetamine amido ethyl)-hydantoin method
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Paragraph 0052; 0053, (2017/03/08)
The invention relates to a method for preparing 5-(2-methylmercapto-ethyl)-hydantoin by utilizing crude hydrocyanic acid gas and relates to the field of chemical industry. The method disclosed by the invention comprises the following steps of: completely reacting hydrocyanic acid mixed gas made by adopting an Ann method with methylmercapto propionaldehyde to obtain a 2-hydroxyl-4-methylmercapto-butyronitrile reaction system under the catalytic action of organic alkali; and sufficiently reacting the 2-hydroxyl-4-methylmercapto-butyronitrile reaction system with ammonium bicarbonate in a water medium to obtain 5-(2-methylmercapto-ethyl)-hydantoin. Due to adoption of raw materials which are not rectified or purified, the method disclosed by the invention is short in production time, high in production efficiency and low in production cost; the prepared 2-hydroxyl-4-methylmercapto-butyronitrile reaction system is steady in property and can be stored for a long time; and 5-(2-methylmercapto-ethyl)-hydantoin with high purity and high yield can be obtained through simple separation and purification operations under the synergistic effect of other substances in reaction liquid.
Continuous combination a method for environmental protection cleaning process of methionine
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Paragraph 0029; 0056; 0057, (2016/10/07)
The present invention relates to an environment-friendly process method for continuous synthesis of methionine. With the present invention, a combination reactor is adopted to produce the methionine, a new process for continuous synthesis of the methionine is provided, wherein the new process has characteristics of high automation, high energy saving and high environmental protection. The process method is characterized in that: the method for synthesis of the methionine by adopting the combination reactor is provided; methylthiopropanal synthesized from acrolein and methylmercaptan is adopted as a raw material; the methylthiopropanal reacts with hydrogen cyanide to obtain an intermediate 2-hydroxy-4-methylthiobutyronitrile; the intermediate 2-hydroxy-4-methylthiobutyronitrile is subjected to the continuous reaction in a first reaction bed of the combination reactor in the presence of excess ammonia and carbon dioxide to obtain a hydantoin solution; the hydantoin solution flows from the first reaction bed, passes through a resolving tower, and releases the excess carbon dioxide and the ammonia; the resolved hydantoin solution flows into a second reaction bed of the combination reactor, and is hydrolyzed under the alkaline condition to obtain an aqueous solution of potassium methionine; the aqueous solution of the potassium methionine is neutralized by the carbon dioxide to obtain an aqueous solution of the methionine and potassium bicarbonate; the methionine is crystallized and separated from the aqueous solution, and the potassium bicarbonate is subjected to the subsequent treatment along with the mother liquor, and is recovered and recycled.
CLEAN METHOD FOR PREPARING D,L-METHIONINE
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Paragraph 0057, (2015/10/28)
The present invention discloses a clean method for preparing a D,L-methionine comprising the steps of: preparing a potassium cyanide solution using a crystallized mother solution containing potassium carbonate as an absorbing liquid to absorb hydrocyanic acid, then reacting the potassium cyanide solution with 3-methylthio propionaldehyde and an ammonium bicarbonate solution at 50-150° C. for 3-15 minutes so as to obtain a 5-(β-methylthioethyl)glycolyurea solution, then bring the 5-(β-methylthioethyl)glycolyurea solution to a temperature of 140-220° C. and subjecting to a saponification reaction for 2-5 minutes, after the completion of the saponification, reducing the temperature to 0-40° C., extracting with an organic solvent, neutralising the water phase with CO2 and crystallizing, then filtering, washing, and drying to obtain an acceptable D,L-methionine product; bring the crystallized D,L-methionine mother solution from filtration to a temperature to 110-160° C. to remove CO2, which are all then circulated and used as a hydrocyanic acid-absorbing liquid. The process route of the present invention is a route suitable for a continuous and clean production, substantially without producing waste water and waste gas.
DEVICE AND METHOD FOR PREPARING HYDANTOIN
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Paragraph 0018, (2014/08/06)
Disclosed is a device for preparing hydantoin. The device comprises three stages of static mixing reactors connected in series and a stripping column. A feed port of the stripping column is in communication with a discharge port of the third-stage static mixing reactor. Also disclosed is a method for preparing hydantoin by using the foregoing device. The method comprises: feeding 3-(methylthio)propionaldehyde, sodium cyanide, and an aqueous solution of excessive carbon dioxide and ammonia to the three stages of static mixing reactors connected in series to undergo a continuous three-stage reaction, the pressure in the three stages of static mixing reactors connected in series being controlled to be 1.4-2.6 MPa, the temperature in the first-stage reactor rising with a gradient from 40 °C to 80 °C, the temperature in the second-stage reactor rising with a gradient from 80 °C to 120 °C, and the temperature in the third-stage reactor rising with a gradient from 120 °C to 160 °C; and feeding the liquid flowing out from the discharge port of the third-stage reactor to the atmospheric pressure vapor stripping column, and separating and recycling un-reacted carbon dioxide and ammonia, the liquid flowing out from the bottom of the column being an aqueous solution of hydantoin, and mixed gas discharged from the top of the column being used for recycling and preparing an aqueous solution of carbon dioxide and ammonia. The device and method of the present invention not only can easily achieve gradient temperature rising, high-efficiency mixing, complete reaction, high reaction speed and a small quantity of by-products, but also can achieve convenient and efficient refinement of hydantoin, with a high quality and yield of hydantoin.
Method for manufacturing methylmercaptopropionaldehyde and methionine using renewable raw materials
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Page/Page column 16-17, (2014/06/10)
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.
METHOD OF PRODUCING METHIONINE
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Paragraph 0038-0039, (2014/06/23)
The invention provides the following method capable of producing methionine in a shorter time by making rapid progress of the hydrolysis of 5-(2-methylmercaptoethyl)hydantoin from an aqueous 5-(2-methylmercaptoethyl)hydantoin solution containing ammonia component. A method of producing methionine is the method comprising hydrolyzing 5-(2-methylmercaptoethyl)hydantoin in an aqueous 5-(2-methylmercaptoethyl)hydantoin solution containing ammonia component, wherein the hydrolysis is performed after the ammonia component is removed from the aqueous solution.
