CN101223126B - 制备乳酸酯的方法 - Google Patents
制备乳酸酯的方法 Download PDFInfo
- Publication number
- CN101223126B CN101223126B CN2006800256276A CN200680025627A CN101223126B CN 101223126 B CN101223126 B CN 101223126B CN 2006800256276 A CN2006800256276 A CN 2006800256276A CN 200680025627 A CN200680025627 A CN 200680025627A CN 101223126 B CN101223126 B CN 101223126B
- Authority
- CN
- China
- Prior art keywords
- lactate
- lactic acid
- esterification
- reaction soln
- reaction
- 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 - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- 150000003903 lactic acid esters Chemical class 0.000 title abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 84
- 238000006243 chemical reaction Methods 0.000 claims abstract description 82
- 238000000034 method Methods 0.000 claims abstract description 48
- 238000005886 esterification reaction Methods 0.000 claims abstract description 47
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000000855 fermentation Methods 0.000 claims abstract description 21
- 230000004151 fermentation Effects 0.000 claims abstract description 21
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 56
- 230000032050 esterification Effects 0.000 claims description 43
- RZOBLYBZQXQGFY-UHFFFAOYSA-N ammonium lactate Chemical compound [NH4+].CC(O)C([O-])=O RZOBLYBZQXQGFY-UHFFFAOYSA-N 0.000 claims description 19
- 230000009466 transformation Effects 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 abstract description 7
- 239000004251 Ammonium lactate Substances 0.000 abstract description 3
- 229940059265 ammonium lactate Drugs 0.000 abstract description 3
- 235000019286 ammonium lactate Nutrition 0.000 abstract description 3
- RZOBLYBZQXQGFY-HSHFZTNMSA-N azanium;(2r)-2-hydroxypropanoate Chemical compound [NH4+].C[C@@H](O)C([O-])=O RZOBLYBZQXQGFY-HSHFZTNMSA-N 0.000 abstract description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 52
- 229940001447 lactate Drugs 0.000 description 51
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 35
- 229960000448 lactic acid Drugs 0.000 description 26
- 235000014655 lactic acid Nutrition 0.000 description 26
- 239000004310 lactic acid Substances 0.000 description 26
- 238000004821 distillation Methods 0.000 description 21
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 229940017144 n-butyl lactate Drugs 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000005516 engineering process Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 241000894006 Bacteria Species 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
- 241000228212 Aspergillus Species 0.000 description 2
- 241000235649 Kluyveromyces Species 0.000 description 2
- 241000186660 Lactobacillus Species 0.000 description 2
- 241000192001 Pediococcus Species 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 241000194017 Streptococcus Species 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229940039696 lactobacillus Drugs 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N methyl propyl carbinol Natural products CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
- 238000001471 micro-filtration Methods 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QPRQEDXDYOZYLA-YFKPBYRVSA-N (S)-2-methylbutan-1-ol Chemical compound CC[C@H](C)CO QPRQEDXDYOZYLA-YFKPBYRVSA-N 0.000 description 1
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methyl-1-butanol Substances CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 1
- 241001112741 Bacillaceae Species 0.000 description 1
- 241000192132 Leuconostoc Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000235527 Rhizopus Species 0.000 description 1
- 241000235070 Saccharomyces Species 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- DSBUAQPRJNCZAU-UHFFFAOYSA-N azane;butan-1-ol Chemical compound N.CCCCO DSBUAQPRJNCZAU-UHFFFAOYSA-N 0.000 description 1
- -1 butyl methyl Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
氨浓度 | 平衡转化率 |
0.3wt% | 73.3% |
0.6wt% | 68.5% |
0.9wt% | 61.9% |
1.2wt% | 57.1% |
1.4wt% | 50.0% |
1.9wt% | 40.7% |
3.0wt% | 23.5% |
时间(小时) | 蒸馏的量 | ||
0.3l/小时 | 0.6l/小时 | 0.9l/小时 | |
0 | 2.67% | 2.93% | 2.76% |
1 | 2.12% | 1.91% | 1.98% |
2 | 1.77% | 1.68% | 1.55% |
3 | 1.5% | 1.31% | 1.2% |
4 | 1.28% | 1.08% | 0.97% |
5 | 1.1% | 0.9% | 0.8% |
Claims (3)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005217749A JP4929639B2 (ja) | 2005-07-27 | 2005-07-27 | 乳酸エステルの製造方法 |
JP217749/2005 | 2005-07-27 | ||
PCT/JP2006/313177 WO2007013259A1 (en) | 2005-07-27 | 2006-06-27 | Method for producing lactic acid ester |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101223126A CN101223126A (zh) | 2008-07-16 |
CN101223126B true CN101223126B (zh) | 2011-10-12 |
Family
ID=37198452
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2006800256276A Expired - Fee Related CN101223126B (zh) | 2005-07-27 | 2006-06-27 | 制备乳酸酯的方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US7696375B2 (zh) |
JP (1) | JP4929639B2 (zh) |
CN (1) | CN101223126B (zh) |
AU (1) | AU2006273509B2 (zh) |
WO (1) | WO2007013259A1 (zh) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102010002065B4 (de) | 2010-02-17 | 2014-04-10 | Deutsches Institut Für Lebensmitteltechnik E.V. | Vorrichtung und integriertes Herstellungsverfahren für Ammoniumlactat |
BE1019555A3 (fr) * | 2010-10-28 | 2012-08-07 | Galactic Sa | Procede de production d'un ester lactique a partir d'un jus de fermentation contenant du lactate d'ammonium. |
BE1019554A3 (fr) * | 2010-10-28 | 2012-08-07 | Galactic Sa | Procede de production energetiquement efficient d'un ester lactique a partir d'un jus de fermentation contenant du lactate d'ammonium. |
RU2535680C2 (ru) * | 2012-04-24 | 2014-12-20 | Валерий Федорович Швец | Способ переработки лактата аммония в молочную кислоту и ее сложные эфиры |
CN102746149B (zh) * | 2012-07-19 | 2014-06-11 | 旭阳化学技术研究院有限公司 | 由丁二酸二铵酯化制备丁二酸单酯的方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2722541A (en) * | 1950-08-02 | 1955-11-01 | Henry E Schulz | Process of esterifying butyl lactate |
CN1104254A (zh) * | 1993-03-02 | 1995-06-28 | 株式会社武藏野化学研究所 | 乳酸和乳酸酯的生产方法 |
US20020132967A1 (en) * | 2001-01-31 | 2002-09-19 | Hitomi Ohara | Process for producing lactide and process for producing polylactic acid from fermented lactic acid employed as starting material |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US722541A (en) * | 1902-11-15 | 1903-03-10 | Defiance Machine Works | Wabble-saw. |
DE4341770A1 (de) * | 1993-12-08 | 1995-06-14 | Basf Ag | Verfahren zur Herstellung von Milchsäureestern |
JP3855359B2 (ja) | 1997-04-15 | 2006-12-06 | トヨタ自動車株式会社 | 乳酸アンモニウムからポリ乳酸を製造する方法 |
JP4048764B2 (ja) * | 2001-01-31 | 2008-02-20 | トヨタ自動車株式会社 | 発酵乳酸を原料とするラクチドの製造方法及びポリ乳酸の製造方法 |
JP4158396B2 (ja) | 2002-03-28 | 2008-10-01 | トヨタ自動車株式会社 | 乳酸エステルの製造方法および装置 |
JP2004208501A (ja) | 2002-12-26 | 2004-07-29 | Toyota Central Res & Dev Lab Inc | 乳酸含有溶液を用いた乳酸エステルの製造方法 |
-
2005
- 2005-07-27 JP JP2005217749A patent/JP4929639B2/ja not_active Expired - Fee Related
-
2006
- 2006-06-27 WO PCT/JP2006/313177 patent/WO2007013259A1/en active Application Filing
- 2006-06-27 US US11/995,864 patent/US7696375B2/en not_active Expired - Fee Related
- 2006-06-27 AU AU2006273509A patent/AU2006273509B2/en not_active Ceased
- 2006-06-27 CN CN2006800256276A patent/CN101223126B/zh not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2722541A (en) * | 1950-08-02 | 1955-11-01 | Henry E Schulz | Process of esterifying butyl lactate |
CN1104254A (zh) * | 1993-03-02 | 1995-06-28 | 株式会社武藏野化学研究所 | 乳酸和乳酸酯的生产方法 |
US20020132967A1 (en) * | 2001-01-31 | 2002-09-19 | Hitomi Ohara | Process for producing lactide and process for producing polylactic acid from fermented lactic acid employed as starting material |
Also Published As
Publication number | Publication date |
---|---|
US20090105501A1 (en) | 2009-04-23 |
JP2007031361A (ja) | 2007-02-08 |
WO2007013259A1 (en) | 2007-02-01 |
CN101223126A (zh) | 2008-07-16 |
AU2006273509B2 (en) | 2011-03-10 |
US7696375B2 (en) | 2010-04-13 |
AU2006273509A1 (en) | 2007-02-01 |
JP4929639B2 (ja) | 2012-05-09 |
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Legal Events
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C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: TEIJIN LIMITED Free format text: FORMER OWNER: TOYOTA MOTOR CORPORATION Effective date: 20121011 |
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C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20121011 Address after: Osaka Japan Patentee after: TEIJIN Ltd. Address before: Aichi Prefecture, Japan Patentee before: Toyota Motor Corp. |
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ASS | Succession or assignment of patent right |
Owner name: UNITIKA CORP Effective date: 20121030 |
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C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20121030 Address after: Osaka Japan Patentee after: TEIJIN Ltd. Patentee after: UNITIKA Ltd. Address before: Osaka Japan Patentee before: TEIJIN Ltd. |
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CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20111012 Termination date: 20160627 |
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CF01 | Termination of patent right due to non-payment of annual fee |