JPH0325417B2 - - Google Patents
Info
- Publication number
- JPH0325417B2 JPH0325417B2 JP57019873A JP1987382A JPH0325417B2 JP H0325417 B2 JPH0325417 B2 JP H0325417B2 JP 57019873 A JP57019873 A JP 57019873A JP 1987382 A JP1987382 A JP 1987382A JP H0325417 B2 JPH0325417 B2 JP H0325417B2
- Authority
- JP
- Japan
- Prior art keywords
- methionine
- sodium
- aqueous solution
- hydantoin
- methylmercaptoethyl
- 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 - Lifetime
Links
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 21
- IREPZTZSVPKCAR-WCCKRBBISA-M sodium;(2s)-2-amino-4-methylsulfanylbutanoate Chemical compound [Na+].CSCC[C@H](N)C([O-])=O IREPZTZSVPKCAR-WCCKRBBISA-M 0.000 claims description 19
- 239000007864 aqueous solution Substances 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 14
- 238000007127 saponification reaction Methods 0.000 claims description 13
- SBKRXUMXMKBCLD-UHFFFAOYSA-N 5-(2-methylsulfanylethyl)imidazolidine-2,4-dione Chemical compound CSCCC1NC(=O)NC1=O SBKRXUMXMKBCLD-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000292 calcium oxide Substances 0.000 claims description 8
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 5
- 239000000920 calcium hydroxide Substances 0.000 claims description 5
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 229940091173 hydantoin Drugs 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229940088417 precipitated calcium carbonate Drugs 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- -1 methylmercaptoethyl Chemical group 0.000 claims 1
- 235000006109 methionine Nutrition 0.000 description 23
- 229930182817 methionine Natural products 0.000 description 23
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 4
- 239000001099 ammonium carbonate Substances 0.000 description 4
- 235000012501 ammonium carbonate Nutrition 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 239000003674 animal food additive Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-IGMARMGPSA-N Calcium-40 Chemical compound [40Ca] OYPRJOBELJOOCE-IGMARMGPSA-N 0.000 description 1
- 239000004470 DL Methionine Substances 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 1
- 150000002741 methionine derivatives Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/142—Amino acids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】
本発明は５−（β−メチルメルカプトエチル）−
ヒダントインを110〜180℃でアルカリ性鹸化し、
実際には異種塩不含のナトリウムメチオニネート
水溶液の製法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention provides 5-(β-methylmercaptoethyl)-
Hydantoin is alkaline saponified at 110-180℃,
It actually relates to a method for producing an aqueous sodium methioninate solution that is free of foreign salts.
従来、必須アミノ酸メチオニンは多量に合成さ
れ、飼料添加物として、特に鳥類、豚及びその他
の農業用蓄のための工業的に製造した混合資料中
に使用される。しかしながらメチオニンの貯蔵及
び加工の際に問題が生じる。結晶状で存在するメ
チオニンはもとより流動性ではなく、かつ好適な
費用のかかる結晶条件により回避しなければ貯蔵
の際にくつついて塊になつてしまう。場合により
流動性を保持する薬剤の添加下に、メチオニンが
粉末状で存在する場合、すべての粉末状物質にお
いて生じる粉塵の問題が取り扱う際に生じる。 Traditionally, the essential amino acid methionine is synthesized in large quantities and used as a feed additive, especially in industrially produced mixed materials for poultry, pigs and other agricultural stocks. However, problems arise during storage and processing of methionine. Methionine, which is present in crystalline form, is naturally not fluid and will clump up into clumps during storage, unless this is avoided by suitable and expensive crystallization conditions. If methionine is present in powder form, optionally with the addition of agents to maintain fluidity, the dust problems that occur with all powdered materials arise during handling.
もう１つの点は混合飼料中への固体メチオニン
の正確な配量及び均質な分配である。混合飼料へ
のメチオニンの補充は約0.01〜1.0重量％の低い
濃度で使用される。均質な分配を達成するために
は、特別にメチオニンを相応して高濃度に含有す
る予混合物の製造は回避できない。 Another point is the precise dosing and homogeneous distribution of solid methionine into the mixed feed. Supplementation of methionine to mixed feeds is used at low concentrations of about 0.01-1.0% by weight. In order to achieve a homogeneous distribution, it is unavoidable to produce a premix with a correspondingly high concentration of methionine.
固体メチオニンのかわりに有利に液状組成物を
使用することもできる。液体は正確に配量するこ
ともできるし、噴霧により他の所望の最終濃度の
混合成分と均質に混合することもできる。 Instead of solid methionine, it is also advantageous to use liquid compositions. The liquid can be precisely metered or homogeneously mixed with the other mixture components at the desired final concentration by spraying.
遊離メチオニンは水中に僅少量のみ溶解性であ
るので、水に易容性塩、特にナトリウムメチオニ
ネートが実際の需要に好適である。自体公知のし
ばしば使用されているDL−メチオニンの製法に
おいて５−（β−メチルメルカプトエチル）−ヒダ
ントインの水溶液を水酸化ナトリウム及び／又は
炭酸カルシウム1.1〜６当量で鹸化する場合、ナ
トリウムメチオニネートの水溶液が必然的に生じ
る。しかし、この粗加水分解混合物は同様に必然
的に多かれ少なかれ多量の炭酸カルシウム、一般
にナトリウムメチオニネート１モル当り0.5〜１
モルを含有する。この炭酸カルシウムは混合飼料
の製造において異種の塩として不所望である。 Since free methionine is only slightly soluble in water, water-soluble salts, especially sodium methioninate, are suitable for practical needs. In the per se known and often used process for the preparation of DL-methionine, when an aqueous solution of 5-(β-methylmercaptoethyl)-hydantoin is saponified with 1.1 to 6 equivalents of sodium hydroxide and/or calcium carbonate, the An aqueous solution inevitably results. However, this crude hydrolysis mixture also necessarily contains more or less large amounts of calcium carbonate, generally from 0.5 to 1 per mole of sodium methioninate.
Contains moles. This calcium carbonate is undesirable as a foreign salt in the production of mixed feeds.
更に長期間の貯蔵において部分的に晶出する傾
向があり、粗加水分解混合物は貯蔵安定性ではな
い。粗加水分解混合物から自体公知法でメチオニ
ンを単離し、次いでこれを水酸化ナトリウム水溶
液中にあとから溶かし、異種塩不含のナトリウム
メチオニネート溶液とすることも、もちろん可能
である。しかし、５−（β−メチルメルカプトエ
チル）−ヒダントインの鹸化において直種異種塩
不含のナトリウムメチオニネート溶液とすること
ができるならば、より容易であり、特に費用がか
からない。 Furthermore, there is a tendency to partially crystallize on long-term storage, and the crude hydrolysis mixture is not storage stable. It is, of course, also possible to isolate methionine from the crude hydrolysis mixture in a manner known per se and then dissolve it afterwards in an aqueous sodium hydroxide solution to give a sodium methioninate solution free of foreign salts. However, if saponification of 5-(β-methylmercaptoethyl)-hydantoin can be made into a sodium methioninate solution free of direct dissimilar salts, it will be easier and particularly less expensive.
本発明による方法は、それぞれ使用した５−
（β−メチルメルカプトエチル）−ヒダントインに
対し、水酸化ナトリウム１当量及び酸化カルシウ
ム又は水酸化カルシウム２当量からなる混合物を
鹸化剤として使用し、鹸化の終了後析出した炭酸
カルシウムを分離し、残つたナトリウムメチオニ
ネート水溶液を濃縮し、含有されるアンモニアを
除去することを特徴とする。 The method according to the invention involves the use of 5-
(β-Methylmercaptoethyl)-hydantoin, a mixture consisting of 1 equivalent of sodium hydroxide and 2 equivalents of calcium oxide or calcium hydroxide was used as a saponifying agent, and after the saponification was completed, precipitated calcium carbonate was separated and the remaining It is characterized by concentrating the sodium methioninate aqueous solution and removing the ammonia contained therein.
分離した炭酸カルシウムはメチオニン及びメチ
オニン塩を実質的に不含であり、残つた水溶液が
鹸化の際に予想されるメチオニンを高収率でナト
リウムメチオニネートの形で含有することは意外
である。本発明方法の付加的な利点は、析出する
炭酸カルシウムが一定の副生物を吸着しているよ
うに思われる事である。いずれにせよ、残つた水
溶液は、その他は同じ条件下にしか水酸化ナトリ
ウム（３当量）のみで製造した鹸化混合物より明
らかに淡色である。 It is surprising that the separated calcium carbonate is substantially free of methionine and methionine salts, and that the remaining aqueous solution contains the expected methionine upon saponification in high yield in the form of sodium methioninate. An additional advantage of the process of the invention is that the precipitated calcium carbonate appears to adsorb certain by-products. In any case, the remaining aqueous solution is clearly lighter in color than the saponification mixture prepared only with sodium hydroxide (3 equivalents) under otherwise identical conditions.
鹸化剤の選択以外は５−（β−メチルメルカプ
トエチル）−ヒダントインの鹸化は公知法で行な
う。５−（β−メチルメルカプトエチル）−ヒダン
トインの10〜45重量％水溶液から出発するのが有
利である。鹸化は110〜180℃、有利に120〜150℃
で、かつ最も簡単な場合には選択した鹸化温度で
必然的に生じる圧力で行なう。 Saponification of 5-(β-methylmercaptoethyl)-hydantoin is carried out by known methods except for the selection of the saponifying agent. It is advantageous to start from a 10 to 45% strength by weight aqueous solution of 5-(β-methylmercaptoethyl)-hydantoin. Saponification at 110-180℃, preferably 120-150℃
and, in the simplest case, at the pressure necessarily occurring at the selected saponification temperature.
水酸化ナトリウム１当量及び酸化カルシウム又
は水酸化カルシウム２当量の使用すべき量は正確
に５−（β−メチルメルカプトエチル）−ヒダント
インの鹸化に必要な量である。合成工程に起因す
る過剰の炭酸アンモニウムを含有する、粗ヒダン
トイン水溶液を使用するならば、鹸化反応の前に
この炭酸アンモニウムを水蒸気での処理により除
去するか、又は更に簡単に炭酸イオン含量に当量
の酸化カルシウム又は水酸化カルシウムを付加的
に添加する。 The amounts to be used of 1 equivalent of sodium hydroxide and 2 equivalents of calcium oxide or calcium hydroxide are exactly those required for saponification of 5-(β-methylmercaptoethyl)-hydantoin. If a crude aqueous hydantoin solution containing excess ammonium carbonate resulting from the synthesis process is used, this ammonium carbonate can be removed by treatment with steam before the saponification reaction, or even more simply by adding an amount equivalent to the carbonate ion content. Calcium oxide or calcium hydroxide is additionally added.
鹸化及び加水分解混合物の冷却の終了後、生じ
た炭酸カルシウムを濾過又は遠心分離により分離
する。これを常法で燃焼させることにより再び酸
化カルシウムとし、これを新たに鹸化の際に使用
する。 After the saponification and cooling of the hydrolysis mixture has ended, the calcium carbonate formed is separated by filtration or centrifugation. By burning this in a conventional manner, it is converted into calcium oxide again, which is then used for saponification.
炭酸カルシウムの分離後、残る水溶液はヒダン
トインの鹸化において遊離するアンモニアを含有
しており、これは単に濃縮することにより除去す
ることができる。ナトリウムメチオニネートが含
量が40〜65重量％となるまで水溶液を濃縮するの
が有利である。ナトリウムメチオニネートのその
つど含量は容易にブロミド／ブロメートでの滴定
により測定される。 After separation of the calcium carbonate, the remaining aqueous solution contains ammonia, which is liberated in the saponification of the hydantoin, and can be removed simply by concentrating. It is advantageous to concentrate the aqueous solution to a sodium methioninate content of 40 to 65% by weight. The respective content of sodium methioninate is easily determined by titration with bromide/bromate.
本発明の方法により製造したナトリウムメチオ
ニネートの水溶液は、飼料添加物としてこれを使
用する際、固体メチオニンと同じメチオニン作用
を有するので、これと当モル量で使用する。 When the aqueous solution of sodium methioninate produced by the method of the present invention is used as a feed additive, it is used in an equimolar amount since it has the same methionine effect as solid methionine.
液状組成物としてこれはメチオニンでの混合飼
料の補充の際、特別にメチオニンを相応して高濃
度に含有する予混合物の製造を必要としない。す
でに所望の濃度の他の混合飼料成分の入つた混合
ガマ中にこれを直接噴霧することにより予定した
濃度に均質に混合することができる。 As a liquid composition, this does not require the preparation of a special premix containing a correspondingly high concentration of methionine when supplementing mixed feeds with methionine. By directly spraying this into a mixing pot containing other mixed feed ingredients already at the desired concentration, it can be homogeneously mixed to the predetermined concentration.
次の実施例により、本発明方法を詳細に説明す
る。他に記載のないかぎり、すべての「％」は
「重量％」を表わす。 The following examples illustrate the method of the invention in detail. Unless otherwise specified, all "%" represent "% by weight".
例 １
水400ml中の５−（β−メチルメルカプトエチ
ル）−ヒダントイン174ｇ（１モル）を水酸化カル
シウム74ｇ（１モル）及び水酸化ナトリウム40ｇ
（１モル）と窒素雰囲気下に４時間140℃で、自己
圧下に撹拌する。100℃より低い冷却した後、な
お熱時濾過する。濾過残分とし残る炭酸カルシウ
ムを熱湯で後洗浄する。濾液と洗浄水を合併し、
常圧で350mlに濃縮する。この溶液のナトリウム
メチオニネート含量は38％である（＝160ｇ、メ
チオニン収率は理論値の93％に相応する）。Example 1 174 g (1 mol) of 5-(β-methylmercaptoethyl)-hydantoin in 400 ml of water was mixed with 74 g (1 mol) of calcium hydroxide and 40 g of sodium hydroxide.
(1 mol) and stirred under autogenous pressure at 140° C. for 4 hours under nitrogen atmosphere. After cooling to below 100°C, filter while still hot. The calcium carbonate remaining as a filter residue is then washed with boiling water. Combine the filtrate and wash water,
Concentrate to 350ml at normal pressure. The sodium methioninate content of this solution is 38% (=160 g, methionine yield corresponds to 93% of theory).
例 ２
例１を繰り返すが、保護ガス雰囲気を使用しな
い。得られた溶液はなおナトリウムメチオニネー
ト159ｇを含有し、これは理論値の93％に相応す
る。Example 2 Repeat Example 1, but without using a protective gas atmosphere. The solution obtained still contains 159 g of sodium methioninate, which corresponds to 93% of theory.
例 ３
例１を繰り返すが、保護ガス雰囲気を使用せ
ず、炭酸カルシウムの分離後減圧（50ミリバー
ル）下に298mlに濃縮する。この溶液のナトリウ
ムメチオニネート含量は46％である（＝164ｇ、
これは理論値の96％のメチオニン収率に相応す
る）。Example 3 Example 1 is repeated, but without the protective gas atmosphere and after separation of the calcium carbonate is concentrated under reduced pressure (50 mbar) to 298 ml. The sodium methioninate content of this solution is 46% (=164g,
This corresponds to a methionine yield of 96% of theory).
例 ４
５−（β−メチル−メルカプトエチル）−ヒダン
トインの20％水溶液870ml、酸化カルシウム56ｇ
（１モル）及び50％水酸化ナトリウム溶液80ｇを
３時間160℃で自己圧下に撹拌する。20℃に冷却
後、濾過する。この濾滓をそれぞれ水20mlで２回
後洗浄する。濾液及び洗浄水を合併し、減圧（80
ミリバール）下に350mlに濃縮する。この溶液の
ナトリウムメチオニネート含量は39％である（＝
164ｇ、メチオニン収率は理論値の96％に相応す
る）。Example 4 870 ml of 20% aqueous solution of 5-(β-methyl-mercaptoethyl)-hydantoin, 56 g of calcium oxide
(1 mol) and 80 g of 50% sodium hydroxide solution are stirred for 3 hours at 160° C. under autogenous pressure. After cooling to 20°C, filter. The filter cake is rewashed twice with 20 ml of water each time. Combine the filtrate and wash water and reduce pressure (80
mbar) to 350 ml. The sodium methioninate content of this solution is 39% (=
164 g, methionine yield corresponding to 96% of theory).
例 ５
炭酸アンモニウムの形で炭酸0.8モルをなお含
有する５−（β−メチルメルカプトエチルヒダン
トイン）の30％水溶液580ｇを酸化カルシウム101
ｇ（1.8モル）及び50％水酸化ナトリウム溶液80
ｇと混合し、140℃で４時間自己圧下に撹拌する。
50℃に冷却後濾過する。濾滓を２回それぞれ熱湯
40mlで後洗浄する。濾液及び洗浄水を合併し、
300ｇに濃縮する。この溶液のナトリウムメチオ
ニネート含量は54.7％である（＝160ｇ、メチオ
ニン収率は理論値の94％である）。Example 5 580 g of a 30% aqueous solution of 5-(β-methylmercaptoethylhydantoin), which still contains 0.8 mol of carbonate in the form of ammonium carbonate, is mixed with 101 g of calcium oxide.
g (1.8 mol) and 50% sodium hydroxide solution 80
g and stirred under autogenous pressure at 140°C for 4 hours.
Cool to 50°C and filter. Rinse the filter cake twice with boiling water.
Post-wash with 40ml. Combine the filtrate and wash water,
Concentrate to 300g. The sodium methioninate content of this solution is 54.7% (=160 g, methionine yield 94% of theory).
例 ６
例５と同様に行なう炭酸を炭酸アンモニウムの
形でわずか0.2モルのみを含有する５−（β−メチ
ルメルカプトエチル）−ヒダントインの30％水溶
液を使用する。それに相応して酸化カルシウムを
わずか67ｇ（1.2モル）添加する。メチオニン含
量55％の溶液300ｇ（＝161ｇ、メチオニン収率は
理論値の94.6％に相応する）を含有する。Example 6 The procedure is as in Example 5, using a 30% aqueous solution of 5-(β-methylmercaptoethyl)-hydantoin containing only 0.2 mol of carbonic acid in the form of ammonium carbonate. Correspondingly, only 67 g (1.2 mol) of calcium oxide are added. It contains 300 g of a solution with a methionine content of 55% (=161 g, methionine yield corresponding to 94.6% of theory).
Claims (1)
トインを110〜180℃でアルカリ性鹸化し、実際に
は異種塩不含のナトリウムメチオニネート水溶液
を製造するために、それぞれ使用した５−（β−
メチルメルカプトエチル）−ヒダントインに対し、
水酸化ナトリウム１当量及び酸化カルシウム又は
水酸化カルシウム２当量からなる混合物を鹸化剤
として使用し、鹸化の終了後析出した炭酸カルシ
ウムを分離し、残つたナトリウムメチオニネート
水溶液を濃縮して含有されるアンモニアを除去す
ることを特徴とするナトリウムメチオニネート水
溶液の製法。 ２ 炭酸カルシウムの分離後残つた水溶液を、ナ
トリウムメチオニネート含量が40〜65重量％にな
るまで濃縮する特許請求の範囲第１項記載の方
法。[Scope of Claims] 1 5-(β-Methylmercaptoethyl)-hydantoin was alkaline saponified at 110 to 180°C and used to produce an aqueous sodium methioninate solution that was actually free of foreign salts. 5-(β-
For methylmercaptoethyl)-hydantoin,
A mixture consisting of 1 equivalent of sodium hydroxide and 2 equivalents of calcium oxide or calcium hydroxide is used as a saponifying agent, and after saponification, precipitated calcium carbonate is separated, and the remaining sodium methioninate aqueous solution is concentrated and contained. A method for producing a sodium methioninate aqueous solution characterized by removing ammonia. 2. The method according to claim 1, wherein the aqueous solution remaining after separation of calcium carbonate is concentrated until the sodium methioninate content is 40 to 65% by weight.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813105006 DE3105006A1 (en) | 1981-02-12 | 1981-02-12 | Process for the preparation of aqueous sodium methioninate solutions (C) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57150659A JPS57150659A (en) | 1982-09-17 |
| JPH0325417B2 true JPH0325417B2 (en) | 1991-04-05 |
Family
ID=6124648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57019873A Granted JPS57150659A (en) | 1981-02-12 | 1982-02-12 | Manufacture of sodium methioninate aqueous solution |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS57150659A (en) |
| DE (1) | DE3105006A1 (en) |
| FR (1) | FR2499565B1 (en) |
| MX (1) | MX6995E (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2343707A2 (en) | 2010-01-06 | 2011-07-13 | Funai Electric Co., Ltd. | Optical disc reproduction apparatus |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI410413B (en) * | 2006-04-26 | 2013-10-01 | Sumitomo Seika Chemicals | Preparation method of methylene disulfonate compound |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2527366A (en) * | 1946-11-07 | 1950-10-24 | Dow Chemical Co | Production of amino acids |
| DE2906934A1 (en) * | 1979-02-22 | 1980-09-04 | Metzeler Kautschuk | RUBBER PROFILE FRAME |
| US4272631A (en) * | 1980-02-25 | 1981-06-09 | Diamond Shamrock Corporation | Hydrolysis of 5-(beta-methylmercaptoethyl)-hydantoin |
-
1981
- 1981-02-12 DE DE19813105006 patent/DE3105006A1/en active Granted
-
1982
- 1982-02-08 FR FR8202000A patent/FR2499565B1/en not_active Expired
- 1982-02-11 MX MX829915U patent/MX6995E/en unknown
- 1982-02-12 JP JP57019873A patent/JPS57150659A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2343707A2 (en) | 2010-01-06 | 2011-07-13 | Funai Electric Co., Ltd. | Optical disc reproduction apparatus |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57150659A (en) | 1982-09-17 |
| FR2499565B1 (en) | 1985-05-31 |
| MX6995E (en) | 1987-01-27 |
| DE3105006A1 (en) | 1982-08-19 |
| FR2499565A1 (en) | 1982-08-13 |
| DE3105006C2 (en) | 1991-04-11 |
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