CA1148488A - Epoxydation d'alpha-olefines inferieures - Google Patents
Epoxydation d'alpha-olefines inferieuresInfo
- Publication number
- CA1148488A CA1148488A CA000325440A CA325440A CA1148488A CA 1148488 A CA1148488 A CA 1148488A CA 000325440 A CA000325440 A CA 000325440A CA 325440 A CA325440 A CA 325440A CA 1148488 A CA1148488 A CA 1148488A
- Authority
- CA
- Canada
- Prior art keywords
- methylomonas
- methane
- epoxidation
- nrrl
- propylene
- 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
- 238000006735 epoxidation reaction Methods 0.000 title claims abstract description 63
- 239000004711 α-olefin Substances 0.000 title 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 194
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 64
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 54
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- 238000000034 method Methods 0.000 claims abstract description 39
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- 239000001301 oxygen Substances 0.000 claims abstract description 25
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 25
- 235000015097 nutrients Nutrition 0.000 claims abstract description 10
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- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 24
- 150000001336 alkenes Chemical class 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 17
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 claims description 16
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims description 16
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 14
- 241000589344 Methylomonas Species 0.000 claims description 14
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- 150000001993 dienes Chemical class 0.000 claims description 5
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- 230000000284 resting effect Effects 0.000 claims description 4
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- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 3
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- PLHSVCWOEHYSHO-UHFFFAOYSA-K tripotassium;2-[hydroxy-bis(4-sulfonatooxyphenyl)methyl]benzoate Chemical compound [K+].[K+].[K+].C=1C=C(OS([O-])(=O)=O)C=CC=1C(C=1C(=CC=CC=1)C([O-])=O)(O)C1=CC=C(OS([O-])(=O)=O)C=C1 PLHSVCWOEHYSHO-UHFFFAOYSA-K 0.000 claims description 3
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- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 2
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- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 210000004671 cell-free system Anatomy 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- GPUADMRJQVPIAS-QCVDVZFFSA-M cerivastatin sodium Chemical compound [Na+].COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 GPUADMRJQVPIAS-QCVDVZFFSA-M 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001879 copper Chemical class 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
- 238000012937 correction Methods 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- BZEVNDPHINRVAB-UHFFFAOYSA-N ethane ethanol Chemical compound CC.CCO.CCO.CCO BZEVNDPHINRVAB-UHFFFAOYSA-N 0.000 description 1
- CDCIMUZJPLJFTE-UHFFFAOYSA-N ethene;oxirane Chemical compound C=C.C1CO1 CDCIMUZJPLJFTE-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000640 hydroxylating effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 101150085091 lat-2 gene Proteins 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 235000015250 liver sausages Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000003956 methylamines Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- WTEVQBCEXWBHNA-YFHOEESVSA-N neral Chemical class CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- MDVPRIBCAFEROC-UHFFFAOYSA-N oct-1-en-1-ol Chemical compound CCCCCCC=CO MDVPRIBCAFEROC-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- QVGXLLKOCUKJST-AKLPVKDBSA-N oxygen-19 atom Chemical compound [19O] QVGXLLKOCUKJST-AKLPVKDBSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Inorganic materials [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 101150090934 terD gene Proteins 0.000 description 1
- QGVNJRROSLYGKF-UHFFFAOYSA-N thiobarbital Chemical compound CCC1(CC)C(=O)NC(=S)NC1=O QGVNJRROSLYGKF-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/0004—Oxidoreductases (1.)
- C12N9/0071—Oxidoreductases (1.) acting on paired donors with incorporation of molecular oxygen (1.14)
- C12N9/0073—Oxidoreductases (1.) acting on paired donors with incorporation of molecular oxygen (1.14) with NADH or NADPH as one donor, and incorporation of one atom of oxygen 1.14.13
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/06—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the liquid phase
-
- 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
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
-
- 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
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y114/00—Oxidoreductases acting on paired donors, with incorporation or reduction of molecular oxygen (1.14)
- C12Y114/13—Oxidoreductases acting on paired donors, with incorporation or reduction of molecular oxygen (1.14) with NADH or NADPH as one donor, and incorporation of one atom of oxygen (1.14.13)
- C12Y114/13025—Methane monooxygenase (1.14.13.25)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89646778A | 1978-04-14 | 1978-04-14 | |
| US896,467 | 1978-04-14 | ||
| US2122779A | 1979-03-16 | 1979-03-16 | |
| US21,227 | 1979-03-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1148488A true CA1148488A (fr) | 1983-06-21 |
Family
ID=26694443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000325440A Expired CA1148488A (fr) | 1978-04-14 | 1979-04-12 | Epoxydation d'alpha-olefines inferieures |
Country Status (9)
| Country | Link |
|---|---|
| CA (1) | CA1148488A (fr) |
| CH (1) | CH647805A5 (fr) |
| DE (1) | DE2915108C2 (fr) |
| DK (1) | DK154779A (fr) |
| FR (1) | FR2422652A1 (fr) |
| GB (1) | GB2019390B (fr) |
| IT (1) | IT1119721B (fr) |
| NL (1) | NL7902940A (fr) |
| SE (1) | SE7903291L (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5037551A (en) * | 1988-12-19 | 1991-08-06 | Weyerhaeuser Company | High-flow rate capacity aerobic biological dehalogenation reactor |
| US5057221A (en) * | 1988-12-19 | 1991-10-15 | Weyerhaeuser Company | Aerobic biological dehalogenation reactor |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5526806A (en) * | 1978-08-11 | 1980-02-26 | Baiorisaac Center:Kk | Preparation of epoxides by immobilized microorganism |
| EP0042306A3 (fr) * | 1980-06-17 | 1983-02-09 | Exxon Research And Engineering Company | Procédé continu à basse énergie pour accroítre l'état d'oxydation d'un substrat organique oxydable |
| US4348476A (en) * | 1981-01-22 | 1982-09-07 | Exxon Research And Engineering Co. | Production of epoxides such as propylene oxide using packed catalytic bed containing moist resting cells exhibiting oxygenase activity |
| EP0088602A3 (fr) * | 1982-03-08 | 1984-03-28 | Exxon Research And Engineering Company | Procédé microbiologique d'oxydation |
| NL8303082A (nl) * | 1983-09-05 | 1985-04-01 | Delft Tech Hogeschool | Methanol dehydrogenase enzym; werkwijze voor het kweken van micro-organismen; chemische produkten; door micro-organismen gekatalyseerde epoxydaties of hydroxyleringen; methylotrofe micro-organismen. |
| JPS6391078A (ja) * | 1986-10-03 | 1988-04-21 | Idemitsu Kosan Co Ltd | 新規微生物 |
| DE19753316A1 (de) | 1997-12-02 | 1999-06-10 | Clariant Gmbh | Wasch-, Reinigungs- und Desinfektionsmittel enthaltend Chlor-aktive Substanzen und Fettsäurealkylesterethoxylate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL291163A (fr) * | 1900-01-01 |
-
1979
- 1979-04-11 DK DK154779A patent/DK154779A/da not_active IP Right Cessation
- 1979-04-12 DE DE2915108A patent/DE2915108C2/de not_active Expired
- 1979-04-12 CH CH3543/79A patent/CH647805A5/de not_active IP Right Cessation
- 1979-04-12 NL NL7902940A patent/NL7902940A/xx not_active Application Discontinuation
- 1979-04-12 CA CA000325440A patent/CA1148488A/fr not_active Expired
- 1979-04-12 IT IT21833/79A patent/IT1119721B/it active
- 1979-04-12 GB GB7913064A patent/GB2019390B/en not_active Expired
- 1979-04-12 SE SE7903291A patent/SE7903291L/xx not_active Application Discontinuation
- 1979-04-13 FR FR7909512A patent/FR2422652A1/fr not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5037551A (en) * | 1988-12-19 | 1991-08-06 | Weyerhaeuser Company | High-flow rate capacity aerobic biological dehalogenation reactor |
| US5057221A (en) * | 1988-12-19 | 1991-10-15 | Weyerhaeuser Company | Aerobic biological dehalogenation reactor |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1119721B (it) | 1986-03-10 |
| SE7903291L (sv) | 1979-10-15 |
| GB2019390B (en) | 1982-07-07 |
| DE2915108C2 (de) | 1984-08-23 |
| NL7902940A (nl) | 1979-10-16 |
| DE2915108A1 (de) | 1979-10-25 |
| DK154779A (da) | 1979-10-15 |
| GB2019390A (en) | 1979-10-31 |
| FR2422652A1 (fr) | 1979-11-09 |
| CH647805A5 (de) | 1985-02-15 |
| IT7921833A0 (it) | 1979-04-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |