JPS62122597A - （ｒ）−３−ハロゲノ−１，２−プロパンジオ−ルの製造法 - Google Patents
（ｒ）−３−ハロゲノ−１，２−プロパンジオ−ルの製造法Info
- Publication number
- JPS62122597A JPS62122597A JP26456885A JP26456885A JPS62122597A JP S62122597 A JPS62122597 A JP S62122597A JP 26456885 A JP26456885 A JP 26456885A JP 26456885 A JP26456885 A JP 26456885A JP S62122597 A JPS62122597 A JP S62122597A
- Authority
- JP
- Japan
- Prior art keywords
- genus
- propanediol
- halogeno
- pseudomonas
- rhodosporidium
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 244000005700 microbiome Species 0.000 claims abstract description 12
- 241000223252 Rhodotorula Species 0.000 claims abstract description 9
- 241000235648 Pichia Species 0.000 claims abstract description 8
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims abstract description 7
- 241000235649 Kluyveromyces Species 0.000 claims abstract description 6
- 241000193596 Nadsonia Species 0.000 claims abstract description 6
- 241000222068 Sporobolomyces <Sporidiobolaceae> Species 0.000 claims abstract description 5
- 241000235070 Saccharomyces Species 0.000 claims abstract description 4
- 241000159512 Geotrichum Species 0.000 claims abstract description 3
- 241000235652 Pachysolen Species 0.000 claims abstract description 3
- 241000235346 Schizosaccharomyces Species 0.000 claims abstract description 3
- 241000228389 Sporidiobolus Species 0.000 claims abstract description 3
- 241000193620 Wickerhamia Species 0.000 claims abstract description 3
- 241000178951 Endomyces Species 0.000 claims abstract 2
- 229960004063 propylene glycol Drugs 0.000 claims description 15
- 241000187654 Nocardia Species 0.000 claims description 6
- 241000589236 Gluconobacter Species 0.000 claims description 5
- 241000586779 Protaminobacter Species 0.000 claims description 5
- 241000589516 Pseudomonas Species 0.000 claims description 5
- 241000607534 Aeromonas Species 0.000 claims description 3
- 241000722885 Brettanomyces Species 0.000 claims description 3
- 241000588914 Enterobacter Species 0.000 claims description 3
- 241000192041 Micrococcus Species 0.000 claims description 3
- 241000203720 Pimelobacter simplex Species 0.000 claims description 3
- 241000316848 Rhodococcus <scale insect> Species 0.000 claims description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 3
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims description 3
- 241000235347 Schizosaccharomyces pombe Species 0.000 claims description 3
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 2
- 241000193755 Bacillus cereus Species 0.000 claims description 2
- 241000588722 Escherichia Species 0.000 claims description 2
- 241000588731 Hafnia Species 0.000 claims description 2
- 241000588748 Klebsiella Species 0.000 claims description 2
- 241000588915 Klebsiella aerogenes Species 0.000 claims description 2
- 241000588747 Klebsiella pneumoniae Species 0.000 claims description 2
- 244000285963 Kluyveromyces fragilis Species 0.000 claims description 2
- 235000014663 Kluyveromyces fragilis Nutrition 0.000 claims description 2
- 241000191938 Micrococcus luteus Species 0.000 claims description 2
- 241000589538 Pseudomonas fragi Species 0.000 claims description 2
- 241000223254 Rhodotorula mucilaginosa Species 0.000 claims description 2
- 241000221523 Rhodotorula toruloides Species 0.000 claims description 2
- 241000228390 Sporobolomyces johnsonii Species 0.000 claims description 2
- 229940092559 enterobacter aerogenes Drugs 0.000 claims description 2
- CJNBYAVZURUTKZ-UHFFFAOYSA-N hafnium(IV) oxide Inorganic materials O=[Hf]=O CJNBYAVZURUTKZ-UHFFFAOYSA-N 0.000 claims description 2
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims description 2
- 241000607528 Aeromonas hydrophila Species 0.000 claims 2
- 241000187561 Rhodococcus erythropolis Species 0.000 claims 2
- 241000588849 Acidiphilium cryptum Species 0.000 claims 1
- 241000722883 Brettanomyces custersianus Species 0.000 claims 1
- 241000235646 Cyberlindnera jadinii Species 0.000 claims 1
- 244000168141 Geotrichum candidum Species 0.000 claims 1
- 235000017388 Geotrichum candidum Nutrition 0.000 claims 1
- 241000588729 Hafnia alvei Species 0.000 claims 1
- 244000286779 Hansenula anomala Species 0.000 claims 1
- 235000014683 Hansenula anomala Nutrition 0.000 claims 1
- 241000150860 Hyphopichia burtonii Species 0.000 claims 1
- 241000159580 Magnusiomyces magnusii Species 0.000 claims 1
- 241000187653 Nocardia globerula Species 0.000 claims 1
- 241000235647 Pachysolen tannophilus Species 0.000 claims 1
- 241000222050 Vanrija humicola Species 0.000 claims 1
- 241000193647 Wickerhamia fluorescens Species 0.000 claims 1
- 210000000436 anus Anatomy 0.000 claims 1
- 241001508815 Lodderomyces Species 0.000 abstract description 4
- 241000235003 Saccharomycopsis Species 0.000 abstract description 2
- 150000002009 diols Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000758 substrate Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229940041514 candida albicans extract Drugs 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 239000012138 yeast extract Substances 0.000 description 3
- 241000588853 Acidiphilium Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241000223198 Humicola Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SSZWWUDQMAHNAQ-VKHMYHEASA-N (R)-3-chloro-1,2-propanediol Chemical compound OC[C@@H](O)CCl SSZWWUDQMAHNAQ-VKHMYHEASA-N 0.000 description 1
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- -1 2-7' lopanediol Chemical class 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 206010022528 Interactions Diseases 0.000 description 1
- 201000008225 Klebsiella pneumonia Diseases 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 206010035717 Pneumonia klebsiella Diseases 0.000 description 1
- 241001646398 Pseudomonas chlororaphis Species 0.000 description 1
- 241001303076 Pseudomonas cruciviae Species 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
- 229930006000 Sucrose Natural products 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 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
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 230000009141 biological interaction Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229960004203 carnitine Drugs 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 1
- 235000019838 diammonium phosphate Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- QKGYJVXSKCDGOK-UHFFFAOYSA-N hexane;propan-2-ol Chemical compound CC(C)O.CCCCCC QKGYJVXSKCDGOK-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000013028 medium composition Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229940081969 saccharomyces cerevisiae Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910021654 trace metal Inorganic materials 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26456885A JPS62122597A (ja) | 1985-11-25 | 1985-11-25 | （ｒ）−３−ハロゲノ−１，２−プロパンジオ−ルの製造法 |
| CA000523224A CA1338723C (en) | 1985-11-25 | 1986-11-18 | Process for preparing 3-chloro-1,2-propanediol |
| US06/933,822 US5017484A (en) | 1985-11-25 | 1986-11-24 | Process for preparing 3-chloro-1,2-propanediol |
| EP86116371A EP0224246B1 (en) | 1985-11-25 | 1986-11-25 | Process for preparing 3-chloro-1, 2-propanediol |
| DE8686116371T DE3680187D1 (de) | 1985-11-25 | 1986-11-25 | Verfahren zur herstellung von 3-chlor-1,2-propandiol. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26456885A JPS62122597A (ja) | 1985-11-25 | 1985-11-25 | （ｒ）−３−ハロゲノ−１，２−プロパンジオ−ルの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62122597A true JPS62122597A (ja) | 1987-06-03 |
| JPH0520072B2 JPH0520072B2 (enrdf_load_stackoverflow) | 1993-03-18 |
Family
ID=17405095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26456885A Granted JPS62122597A (ja) | 1985-11-25 | 1985-11-25 | （ｒ）−３−ハロゲノ−１，２−プロパンジオ−ルの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62122597A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4996995A (en) * | 1988-06-27 | 1991-03-05 | Kobishi Electric Co., Ltd. | Ashtray |
| EP1166644A1 (en) * | 2000-06-29 | 2002-01-02 | Societe Des Produits Nestle S.A. | Enzymatic biodegradation of halogenated compounds |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5894398A (ja) * | 1981-11-28 | 1983-06-04 | Kyowa Hakko Kogyo Co Ltd | インタ−フエロンの濃縮，精製法 |
| JPS60108698A (ja) * | 1983-11-17 | 1985-06-14 | 黒岩 基 | クレ−射撃の射弾位置判定装置 |
-
1985
- 1985-11-25 JP JP26456885A patent/JPS62122597A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5894398A (ja) * | 1981-11-28 | 1983-06-04 | Kyowa Hakko Kogyo Co Ltd | インタ−フエロンの濃縮，精製法 |
| JPS60108698A (ja) * | 1983-11-17 | 1985-06-14 | 黒岩 基 | クレ−射撃の射弾位置判定装置 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4996995A (en) * | 1988-06-27 | 1991-03-05 | Kobishi Electric Co., Ltd. | Ashtray |
| EP1166644A1 (en) * | 2000-06-29 | 2002-01-02 | Societe Des Produits Nestle S.A. | Enzymatic biodegradation of halogenated compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0520072B2 (enrdf_load_stackoverflow) | 1993-03-18 |
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