JPH0357755B2 - - Google Patents
Info
- Publication number
- JPH0357755B2 JPH0357755B2 JP15480281A JP15480281A JPH0357755B2 JP H0357755 B2 JPH0357755 B2 JP H0357755B2 JP 15480281 A JP15480281 A JP 15480281A JP 15480281 A JP15480281 A JP 15480281A JP H0357755 B2 JPH0357755 B2 JP H0357755B2
- Authority
- JP
- Japan
- Prior art keywords
- lactic acid
- silicon dioxide
- fermentation liquid
- added
- carried out
- 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
Links
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 64
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 50
- 239000004310 lactic acid Substances 0.000 claims description 32
- 235000014655 lactic acid Nutrition 0.000 claims description 32
- 238000000855 fermentation Methods 0.000 claims description 24
- 230000004151 fermentation Effects 0.000 claims description 24
- 239000000377 silicon dioxide Substances 0.000 claims description 20
- 235000012239 silicon dioxide Nutrition 0.000 claims description 20
- 239000002270 dispersing agent Substances 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- 150000003903 lactic acid esters Chemical class 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000356 contaminant Substances 0.000 description 11
- 230000032050 esterification Effects 0.000 description 10
- 238000005886 esterification reaction Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 6
- 229910002012 Aerosil® Inorganic materials 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 235000000346 sugar Nutrition 0.000 description 4
- WWILHZQYNPQALT-UHFFFAOYSA-N 2-methyl-2-morpholin-4-ylpropanal Chemical compound O=CC(C)(C)N1CCOCC1 WWILHZQYNPQALT-UHFFFAOYSA-N 0.000 description 3
- 239000004251 Ammonium lactate Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001447 alkali salts Chemical class 0.000 description 3
- 229940059265 ammonium lactate Drugs 0.000 description 3
- 235000019286 ammonium lactate Nutrition 0.000 description 3
- RZOBLYBZQXQGFY-HSHFZTNMSA-N azanium;(2r)-2-hydroxypropanoate Chemical compound [NH4+].C[C@@H](O)C([O-])=O RZOBLYBZQXQGFY-HSHFZTNMSA-N 0.000 description 3
- 229910052814 silicon oxide Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 229940001447 lactate Drugs 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- -1 CaCO 3 Substances 0.000 description 1
- 229930182843 D-Lactic acid Natural products 0.000 description 1
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
【発明の詳細な説明】
有機酸醗酵のうち、乳酸醗酵は、次の様に行な
われる。まず、主原料として、グルコース、砂糖
又は廃糖蜜が使用される。副原料としては、各種
アミノ酸類、ビタミン類、塩基類を使用し、両者
の混合物に乳酸菌を添加して醗酵が進行し乳酸が
生成すると醗酵液中のPHが低下し、そのため乳酸
菌が死滅するので、アルカリ類例えばNH3、
NaOH、CaCO3、Ca（OH）2、等で中和しPHを調
節する。このような理由のため、乳酸はまず乳酸
アンモニウムのような乳酸のアルカリ塩等として
製造される。DETAILED DESCRIPTION OF THE INVENTION Among organic acid fermentations, lactic acid fermentation is carried out as follows. Firstly, glucose, sugar or blackstrap molasses is used as the main raw material. As auxiliary raw materials, various amino acids, vitamins, and bases are used, and lactic acid bacteria are added to a mixture of the two, and as fermentation progresses and lactic acid is produced, the pH in the fermentation liquid decreases, which kills the lactic acid bacteria. , alkalis such as NH 3 ,
Neutralize with NaOH, CaCO 3 , Ca(OH) 2 , etc. to adjust PH. For this reason, lactic acid is first produced as an alkali salt of lactic acid such as ammonium lactate.
CH3CHOHCOOH
乳酸＋
NH4OH
水酸化アルモニウム→
CH3CHOHCOONH4
乳酸アンモニウム＋
H2O
水 …(1)
醗酵が終了すると、合成された乳酸塩より乳酸
を回収するため硫酸を加える。この工程で乳酸の
アルカリ塩はフリーの乳酸となり、硫酸はアルカ
リ塩となる。CH 3 CHOHCOOH Lactic acid + NH 4 OH Almonium hydroxide → CH 3 CHOHCOOH 4 Ammonium lactate + H 2 O Water...(1) When fermentation is complete, sulfuric acid is added to recover lactic acid from the synthesized lactate. In this process, the alkali salt of lactic acid becomes free lactic acid, and the sulfuric acid becomes an alkali salt.
CH3CHOHCOONH4
乳酸アンモニウム＋1/2
H2SO4
硫酸→
CH3CHOHCOOH
乳酸＋1/2
（NH4）2SO4
硫酸
…(2)
次に、乳酸を硫酸の塩、副原料及び未反応の残
糖より分離するために、通常、イソプロピルエー
テル等の抽剤で乳酸を抽出する。抽出をしないで
直接乳酸をエステル化して分離する方法もある。CH 3 CHOHCOONH 4 ammonium lactate + 1/2 H 2 SO 4 sulfuric acid → CH 3 CHOHCOOH lactic acid + 1/2 (NH 4 ) 2 SO 4 sulfuric acid...(2) Next, lactic acid is combined with the sulfuric acid salt, auxiliary raw materials, and unreacted residue. To separate lactic acid from sugar, lactic acid is usually extracted with an extractant such as isopropyl ether. There is also a method of directly esterifying and separating lactic acid without extraction.
抽出で得た乳酸は、未だ種々の不純物を多く含
むため、食品添加物としての規格に適合しないの
で、通常、メタノール等で乳酸をエステル化して
例えば乳酸メチルを合成し、この乳酸エステルを
精留した後、加水分解して精製乳酸を得る。乳酸
を抽出しないで直接エステル化する場合も同様
に、エステル化で得られた乳酸エステルを精留
後、加水分解して精製乳酸を得る。 The lactic acid obtained through extraction still contains many various impurities and does not meet the standards as a food additive. Therefore, usually, lactic acid is esterified with methanol etc. to synthesize, for example, methyl lactate, and this lactic acid ester is rectified. After that, it is hydrolyzed to obtain purified lactic acid. When directly esterifying lactic acid without extracting it, similarly, the lactic acid ester obtained by esterification is rectified and then hydrolyzed to obtain purified lactic acid.
CH3CHOHCOOH＋CH3OH
メタノール→
CH3CHOHCOOCH3
乳酸メチル＋H2O …(3)
CH3CHOHCOOCH3＋H2O→
CH3CHOHCOOH＋CH3OH …(4)
この様にして醗酵で製造された乳酸は、長い精
製工程を経て製造されるわけであるが、特に反応
式(3)のエステル化工程において、醗酵液中の副原
料や未反応の残糖などがエステル化釜の壁や撹拌
翼へ付着及び固結してしまい、遂にはパイプ等の
閉塞を起すため、連続化は困難であつた。CH 3 CHOHCOOH＋CH 3 OH Methanol → CH 3 CHOHCOOCH 3Methyl lactate + H 2 O …(3) CH 3 CHOHCOOCH 3 +H 2 O→ CH 3 CHOHCOOH＋CH 3 OH …(4) Lactic acid produced by fermentation in this way has a long It is produced through a purification process, but especially in the esterification process of reaction formula (3), auxiliary raw materials and unreacted residual sugars in the fermentation liquid may adhere to and solidify on the walls of the esterification tank and stirring blades. Continuation was difficult because the pipes were tied together and eventually the pipes etc. were clogged.
本発明者等は、種々研究の結果、醗酵液に２酸
化ケイ素系の分散剤を添加することにより反応釜
壁や撹拌翼への付着及び固結を起すことなく、反
応液を均一層に保持し、従つてパイプ等の閉塞を
みることなしに、連続化が容易に出来ることを見
出し、本発明を完成した。 As a result of various studies, the present inventors have found that by adding a silicon dioxide-based dispersant to the fermentation liquid, the reaction liquid can be maintained in a uniform layer without adhesion or caking to the reaction vessel wall or stirring blade. However, the present invention was completed based on the discovery that continuity can be easily achieved without clogging pipes, etc.
２酸化ケイ素系分散剤の醗酵液への添加量は、
分散剤中の２酸化ケイ素の量が醗酵液中の混入物
（混入物とは、副原料や未反応の残糖類等の物質、
即ち、乳酸、水及び硫酸塩以外の物質をいう）に
対して0.3重量％以上、好ましくは0.5重量％以上
となるような量であることが望ましい。上限は特
にはないが、経済性の面から考慮すれば、添加量
が少ない方が望ましいのは当然である。 The amount of silicon dioxide-based dispersant added to the fermentation liquid is
The amount of silicon dioxide in the dispersant is due to contaminants in the fermentation liquid (contaminants include substances such as auxiliary raw materials and unreacted residual sugars,
That is, it is desirable that the amount is 0.3% by weight or more, preferably 0.5% by weight or more, based on substances other than lactic acid, water, and sulfates). There is no particular upper limit, but from an economic standpoint, it is natural that a smaller amount is desirable.
２酸化ケイ素系分散剤は、微粒子状の２酸化ケ
イ素であれば何でもよいが、市販品を例にあげれ
ば、カープレツクス（２酸化ケイ素含量90重量
％、塩野義製薬）、アエロジル（２酸化ケイ素含
量100重量％、日本アエロジル）、スノーテツクス
（２酸化ケイ素含量40重量％、日産化学）等があ
る。 Any silicon dioxide-based dispersant may be used as long as it is silicon dioxide in the form of fine particles, but examples of commercially available products include Carplex (silicon dioxide content: 90% by weight, Shionogi & Co., Ltd.), Aerosil (silicon dioxide content: 90% by weight), Examples include 100% by weight, Nippon Aerosil) and Snowtex (40% by weight silicon dioxide content, Nissan Chemical).
次に、実施例により本発明を具体的に説明す
る。パーセントは重量基準である。また、２酸化
ケイ素系分散剤の醗酵液への添加量は、分散剤中
の２酸化ケイ素の醗酵液中の混入物に対する割合
で示す。 Next, the present invention will be specifically explained with reference to Examples. Percentages are by weight. Further, the amount of silicon dioxide-based dispersant added to the fermentation liquid is expressed as a ratio of silicon dioxide in the dispersant to contaminants in the fermentation liquid.
実施例 １
乳酸30.0％、硫酸水素アンモニウム38.4％、水
37.6％及び混入物６％の組成を持つ乳酸醗酵液
に、２酸化ケイ素系分散剤（アエロジル、２酸化
ケイ素含量100％）を上記の混入物に対して0.3％
添加した。この分散剤を添加した醗酵液10Kgを
300mlの反応釜でメタノールを同時に供給して連
続的にエステル化を行なつた。反応温度は110〜
145℃であつた。その結果、釜及び撹拌翼等への
付着及び固結が殆んどみられず、連続的に反応を
行なうことが出来た。Example 1 Lactic acid 30.0%, ammonium hydrogen sulfate 38.4%, water
A silicon dioxide-based dispersant (Aerosil, silicon dioxide content 100%) was added to a lactic acid fermentation solution with a composition of 37.6% and 6% contaminants at 0.3% of the above contaminants.
Added. 10kg of fermentation liquid with this dispersant added
Esterification was carried out continuously by simultaneously supplying methanol in a 300 ml reaction vessel. Reaction temperature is 110~
It was 145℃. As a result, there was almost no adhesion or caking to the pot, stirring blades, etc., and the reaction could be carried out continuously.
実施例 ２
実施例１と同様な組成を持つ乳酸醗酵液に、２
酸化ケイ素系分散剤（アエロジル、２酸化ケイ素
含量100％）を上記の混入物に対して0.5％添加し
た。この分散剤を添加した醗酵液10Kgを実施例１
と同様な条件で連続的にエステル化を行なつたと
ころ、釜及び撹拌翼等への付着及び固結が全く見
られず、連続的に反応を行なうことが出来た。Example 2 Into a lactic acid fermentation solution having the same composition as in Example 1, 2
A silicon oxide dispersant (Aerosil, silicon dioxide content 100%) was added in an amount of 0.5% based on the above contaminants. Example 1: 10 kg of fermentation liquid to which this dispersant was added
When esterification was carried out continuously under the same conditions as above, no adhesion or caking was observed on the pot, stirring blades, etc., and the reaction could be carried out continuously.
実施例 ３
実施例１と同様な組成を持つ乳酸醗酵液に、２
酸化ケイ素系分散剤（カープレツクス、２酸化ケ
イ素含量90％）を上記の混入物に対して２酸化ケ
イ素として90％添加し、実施例１と同様に連続的
にエステル化を行なつたところ、付着及び固結が
全く見られず、連続的に反応を行なうことが出来
た。Example 3 Into a lactic acid fermentation solution having the same composition as in Example 1, 2
A silicon oxide-based dispersant (Carplex, silicon dioxide content: 90%) was added to the above-mentioned contaminants in an amount of 90% silicon dioxide, and esterification was carried out continuously in the same manner as in Example 1. No caking was observed, and the reaction could be carried out continuously.
実施例 ４
乳酸60.0％、硫酸水素アンモニウム10％、水15
％及び混入物15％の組成を持つ乳酸醗酵液に、２
酸化ケイ素系分散剤（スノーテツクス、２酸化ケ
イ素含量40％）を上記の混入物に対して２酸化ケ
イ素として0.4％添加した。実施例１と同様な条
件で連続的にエステル化を行なつたところ、付着
及び固結が全く見られず、連続的に反応を行なう
ことが出来た。Example 4 Lactic acid 60.0%, ammonium hydrogen sulfate 10%, water 15
% and a lactic acid fermentation solution with a composition of 15% contaminants, 2
A silicon oxide dispersant (Snowtex, silicon dioxide content: 40%) was added in an amount of 0.4% as silicon dioxide to the above-mentioned contaminants. When esterification was carried out continuously under the same conditions as in Example 1, no adhesion or caking was observed, and the reaction could be carried out continuously.
実施例 ５
乳酸40％、硫酸カルシウム３％、水55％及び混
入物２％の組成を持つ乳酸醗酵液に、２酸化ケイ
素系分散剤（アエロジル、２酸化ケイ素含量100
％）を上記の混入物に対して0.5％添加した。次
に、エステル化用触媒として、硫酸を乳酸醗酵液
に対して0.1％添加した。実施例１と同様な条件
で連続的にエステル化を行なつたところ、付着及
び固結が全く見られず、連続的に反応を行なうこ
とが出来た。Example 5 A silicon dioxide-based dispersant (Aerosil, silicon dioxide content: 100
%) was added at 0.5% relative to the above contaminants. Next, 0.1% of sulfuric acid was added to the lactic acid fermentation solution as an esterification catalyst. When esterification was carried out continuously under the same conditions as in Example 1, no adhesion or caking was observed, and the reaction could be carried out continuously.
比較例
乳酸30.0％、硫酸水素アンモニウム38.4％、水
37.6％及び混入物６％の組成を持つ乳酸醗酵液
を、そのままで使用して、実施例１の条件と同様
な条件下で連続的にエステル化を行なつたとこ
ろ、反応釜及び撹拌翼への付着及び固結が多くみ
られ、パイプ等の詰りが著しくて、連続反応は不
可能であつた。Comparative example: Lactic acid 30.0%, ammonium hydrogen sulfate 38.4%, water
When a lactic acid fermentation liquid having a composition of 37.6% and 6% contaminants was used as it was and esterification was carried out continuously under the same conditions as in Example 1, the reaction vessel and stirring blade were mixed. There was a lot of adhesion and caking, and the pipes were so clogged that continuous reaction was impossible.
Claims (1)
系外に加熱分離する際に２酸化ケイ素系分散剤を
醗酵液に添加することにより醗酵液の釜壁や撹拌
翼等への付着及び固結を防ぐことを特徴とする醗
酵液の付着及び固結防止法。1. When heating and separating lactic acid from the lactic acid fermentation liquid as a lactic acid ester out of the system, a silicon dioxide-based dispersant is added to the fermentation liquid to prevent the fermentation liquid from adhering to and solidifying on the pot walls, stirring blades, etc. A method for preventing adhesion and caking of fermentation liquid, characterized by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15480281A JPS5856690A (en) | 1981-10-01 | 1981-10-01 | Method for preventing adhesion and coagulation of organic acid fermentation liquid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15480281A JPS5856690A (en) | 1981-10-01 | 1981-10-01 | Method for preventing adhesion and coagulation of organic acid fermentation liquid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5856690A JPS5856690A (en) | 1983-04-04 |
| JPH0357755B2 true JPH0357755B2 (en) | 1991-09-03 |
Family
ID=15592204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15480281A Granted JPS5856690A (en) | 1981-10-01 | 1981-10-01 | Method for preventing adhesion and coagulation of organic acid fermentation liquid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5856690A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61293388A (en) * | 1985-06-21 | 1986-12-24 | Daicel Chem Ind Ltd | Production of d-lactic acid |
| JP2007186075A (en) * | 2006-01-13 | 2007-07-26 | Marui:Kk | Saddle for bicycle |
| DE102007045701B3 (en) * | 2007-09-24 | 2009-05-14 | Uhde Gmbh | Production of lactic acid by fermentation and extraction with amines |
| JP2012519498A (en) | 2009-03-09 | 2012-08-30 | ダウ コーニング コーポレーション | Method for removing vicinal diol from lactic acid fermentation broth |
-
1981
- 1981-10-01 JP JP15480281A patent/JPS5856690A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5856690A (en) | 1983-04-04 |
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