JP2001506274A - 乳酸の精製法 - Google Patents
乳酸の精製法Info
- Publication number
- JP2001506274A JP2001506274A JP50115599A JP50115599A JP2001506274A JP 2001506274 A JP2001506274 A JP 2001506274A JP 50115599 A JP50115599 A JP 50115599A JP 50115599 A JP50115599 A JP 50115599A JP 2001506274 A JP2001506274 A JP 2001506274A
- Authority
- JP
- Japan
- Prior art keywords
- lactic acid
- distillation
- concentration
- weight
- solution
- 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.)
- Granted
Links
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 title claims abstract description 212
- 235000014655 lactic acid Nutrition 0.000 title claims abstract description 105
- 239000004310 lactic acid Substances 0.000 title claims abstract description 104
- 238000000034 method Methods 0.000 title claims abstract description 54
- 238000000746 purification Methods 0.000 title description 10
- 238000000855 fermentation Methods 0.000 claims abstract description 6
- 230000004151 fermentation Effects 0.000 claims abstract description 6
- 239000000243 solution Substances 0.000 claims description 39
- 238000004821 distillation Methods 0.000 claims description 30
- 238000010438 heat treatment Methods 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 239000010409 thin film Substances 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 125000002091 cationic group Chemical group 0.000 claims description 7
- 239000012535 impurity Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000000129 anionic group Chemical group 0.000 claims description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 238000006068 polycondensation reaction Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 abstract description 10
- 238000009833 condensation Methods 0.000 abstract description 9
- 238000005342 ion exchange Methods 0.000 abstract description 3
- 230000014759 maintenance of location Effects 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 description 13
- 230000000694 effects Effects 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000005388 borosilicate glass Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002479 acid--base titration Methods 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000006384 oligomerization reaction Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000002028 Biomass Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000005115 demineralization Methods 0.000 description 2
- 230000002328 demineralizing effect Effects 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000011552 falling film Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229940001447 lactate Drugs 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- OZZQHCBFUVFZGT-BKLSDQPFSA-N (2s)-2-(2-hydroxypropanoyloxy)propanoic acid Chemical group CC(O)C(=O)O[C@@H](C)C(O)=O OZZQHCBFUVFZGT-BKLSDQPFSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004251 Ammonium lactate Substances 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000007848 Bronsted acid Substances 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
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241001057690 Geococcus <mealybug> Species 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
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 1
- 241000194036 Lactococcus Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- 240000005384 Rhizopus oryzae Species 0.000 description 1
- 235000013752 Rhizopus oryzae Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000005862 Whey Substances 0.000 description 1
- 102000007544 Whey Proteins Human genes 0.000 description 1
- 108010046377 Whey Proteins Proteins 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229940059265 ammonium lactate Drugs 0.000 description 1
- 235000019286 ammonium lactate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- RZOBLYBZQXQGFY-HSHFZTNMSA-N azanium;(2r)-2-hydroxypropanoate Chemical compound [NH4+].C[C@@H](O)C([O-])=O RZOBLYBZQXQGFY-HSHFZTNMSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000000909 electrodialysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 235000019249 food preservative Nutrition 0.000 description 1
- 239000005452 food preservative Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000000423 heterosexual effect Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- -1 hydroxide ions Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.発酵媒体または他の任意の供給源から得られる乳酸の水溶液を回収、精製 する方法にして、乳酸の重縮合を触媒することができるイオン性物質を除去する 予備処理、乳酸が重縮合する危険を少なくする少なくとも1つの濃縮工程、およ び乳酸を選択的かつ本質的に、定量的に蒸留する少なくとも1つの工程を含んで 成ることを特徴とする、上記の方法。 2.乳酸を薄層原理に従って濃縮および蒸留する、請求の範囲第1項に記載の 方法。 3.乳酸の蒸留を内部または外部凝縮器を具える機械的振盪機付き薄膜型蒸発 装置を用いて行う、請求の範囲第1項に記載の方法。 4.乳酸を10-3〜10+2ミリバールの絶対圧下、110〜160℃の加熱表 面温度で蒸留する、請求の範囲第1〜3項のいずれか1項に記載の方法。 5.乳酸溶液に、蒸留前に、その重量に基づいて少なくとも1%で、かつ多く ても20%の不活性かつ非混和性の化合物を追加する、請求の範囲第1〜4項の いずれか1項に記載の方法。 6.乳酸の蒸留から出る残分を第二の蒸留に付し、それを再循環させる、請求 の範囲第1〜5項のいずれか1項に記載の方法。 7.蒸留残分に、蒸留前に、その重量に基づいて、少なくとも1%で、かつ多 くても20%の不活性かつ非混和性の化合物を追加する、請求の範囲第6項に記 載の方法。 8.乳酸を、乳酸濃度を50〜500ミリバール絶対圧条件下において50〜 90重量%に、次いで100重量%に連続的に到達させるために、2つの工程で 濃縮する、請求の範囲第1項または第2項に記載の方法。 9.第二濃縮工程を、内部または外部凝縮器を具える機械的振盪機付き薄膜型 蒸発装置中で、10〜500ミリバールの圧力下、50〜150℃の加熱表面温 度で行う、請求の範囲第8項に記載の方法。 10.予備処理を濃度が80重量%未満である乳酸の水溶液を出発原料として 用いて行う、請求の範囲第1〜9項のいずれかに記載の方法。 11.アニオン性およびカチオン性不純物を固体または液体イオン交換樹脂を 用いて除去する、請求の範囲第1項または第10項のいずれかに記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE9700489A BE1011197A3 (fr) | 1997-06-06 | 1997-06-06 | Procede de purification d'acide lactique. |
BE9700489 | 1997-06-06 | ||
PCT/BE1998/000080 WO1998055442A1 (fr) | 1997-06-06 | 1998-06-05 | Procede de purification d'acide lactique |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2001506274A true JP2001506274A (ja) | 2001-05-15 |
JP3782465B2 JP3782465B2 (ja) | 2006-06-07 |
Family
ID=3890555
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP50115599A Expired - Lifetime JP3782465B2 (ja) | 1997-06-06 | 1998-06-05 | 乳酸の精製法 |
Country Status (21)
Country | Link |
---|---|
US (1) | US6489508B1 (ja) |
EP (1) | EP0986532B2 (ja) |
JP (1) | JP3782465B2 (ja) |
KR (1) | KR100387909B1 (ja) |
AT (1) | ATE246166T1 (ja) |
AU (1) | AU737545B2 (ja) |
BE (1) | BE1011197A3 (ja) |
BR (1) | BR9809965B1 (ja) |
CA (1) | CA2301066C (ja) |
CZ (1) | CZ295759B6 (ja) |
DE (1) | DE69816815T3 (ja) |
DK (1) | DK0986532T4 (ja) |
ES (1) | ES2203959T5 (ja) |
HU (1) | HU227442B1 (ja) |
IL (1) | IL132598A (ja) |
NO (1) | NO309083B1 (ja) |
NZ (1) | NZ501465A (ja) |
PL (1) | PL193667B1 (ja) |
PT (1) | PT986532E (ja) |
SK (1) | SK285911B6 (ja) |
WO (1) | WO1998055442A1 (ja) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009004922A1 (ja) | 2007-06-29 | 2009-01-08 | Toray Industries, Inc. | 乳酸の製造方法 |
JP2009034030A (ja) * | 2007-08-01 | 2009-02-19 | Toray Ind Inc | 乳酸の製造方法および製造装置 |
JP2009142265A (ja) * | 2007-11-20 | 2009-07-02 | Toray Ind Inc | 乳酸の製造方法 |
WO2012081112A1 (ja) * | 2010-12-16 | 2012-06-21 | 株式会社日立プラントテクノロジー | 精製乳酸溶液の製造方法 |
JP2012532917A (ja) * | 2009-07-16 | 2012-12-20 | ピュラック バイオケム ビー.ブイ. | 液状乳酸組成物及びその調製方法 |
JP2013518865A (ja) * | 2010-02-08 | 2013-05-23 | ピュラック バイオケム ビー. ブイ. | 乳酸を製造する方法 |
JP2013199679A (ja) * | 2012-03-26 | 2013-10-03 | Nippon Steel & Sumikin Stainless Steel Corp | 耐高温乳酸腐食性に優れたステンレス鋼及びその使用方法 |
WO2013176101A1 (ja) | 2012-05-22 | 2013-11-28 | 東レ株式会社 | 乳酸の製造方法 |
EP3147275A1 (en) | 2008-12-26 | 2017-03-29 | Toray Industries, Inc. | Method for producing lactic acid and method for producing polylactic acid |
US10501399B2 (en) | 2014-03-31 | 2019-12-10 | Toray Industries, Inc. | Lactic acid manufacturing method |
JP7408225B2 (ja) | 2020-11-24 | 2024-01-05 | エルジー・ケム・リミテッド | アクリル酸の製造方法 |
Families Citing this family (50)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1294728B1 (it) * | 1997-09-12 | 1999-04-12 | Biopolo S C A R L | Ceppi di lievito per la riproduzione di acido lattico |
US20070031950A1 (en) * | 1998-09-11 | 2007-02-08 | Winkler Aaron A | Production of D-lactic acid with yeast |
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