GB1386393A - Enzymic oxidation of hydrocarbons alcohols and aldehydes - Google Patents
Enzymic oxidation of hydrocarbons alcohols and aldehydesInfo
- Publication number
- GB1386393A GB1386393A GB1313471A GB1313471A GB1386393A GB 1386393 A GB1386393 A GB 1386393A GB 1313471 A GB1313471 A GB 1313471A GB 1313471 A GB1313471 A GB 1313471A GB 1386393 A GB1386393 A GB 1386393A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formamide
- oxidation
- substrate
- decane
- decanol
- 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
- 230000003647 oxidation Effects 0.000 title abstract 4
- 238000007254 oxidation reaction Methods 0.000 title abstract 4
- 229930195733 hydrocarbon Natural products 0.000 title abstract 2
- 150000001299 aldehydes Chemical class 0.000 title 1
- -1 hydrocarbons alcohols Chemical class 0.000 title 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 6
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 abstract 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 abstract 4
- 150000001408 amides Chemical class 0.000 abstract 3
- 239000000758 substrate Substances 0.000 abstract 3
- YJCJVMMDTBEITC-UHFFFAOYSA-N 10-hydroxycapric acid Chemical compound OCCCCCCCCCC(O)=O YJCJVMMDTBEITC-UHFFFAOYSA-N 0.000 abstract 2
- 102000004190 Enzymes Human genes 0.000 abstract 2
- 108090000790 Enzymes Proteins 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 abstract 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 abstract 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000005968 1-Decanol Substances 0.000 abstract 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 abstract 1
- 241000222178 Candida tropicalis Species 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 abstract 1
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 abstract 1
- XJLXINKUBYWONI-NNYOXOHSSA-N NADP zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-NNYOXOHSSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 239000012062 aqueous buffer Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 abstract 1
- 229950006238 nadide Drugs 0.000 abstract 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
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
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Enzymes And Modification Thereof (AREA)
Abstract
1386393 Enzymic oxidation BRITISH PETROLEUM CO Ltd 27 April 1972 [5 May 1971] 13134/71 Heading C2C An alcohol, aldehyde or acid is prepared by the enzymic oxidation of a substrate of a waterimmiscible or insoluble hydrocarbon, alcohol or aldehyde dissolved in an amide of formula where R 1 , R 2 or R 3 represent hydrogen or a C 1 to C 5 aliphatic group, dispersed in an aqueous buffer with a pH 6-5 to 9À5, to give a mixture of from a trace to 50% by volume of the substrate in the amide, and maintained at 20-38‹ C. in the presence of oxygen. Substrate with at least 6 to 20 carbon atoms, e.g. n-decane, n-hexadecane, 1-decanol, 1-tetradecanol, 1-10-decandiol, and 1-10-hexadecandiol is preferred. Single enzymes or enzyme complexes may be used and co-enzymes such as nicotinamide adenine dinucleotide or nicotinamide adenine dinucleotide phosphate may be included. Suitable amides are N,N-dimethyl formamide, formamide, N,N-diethyl formamide, N-ethyl formamide and N-methyl formamide. Examples describe the oxidation of decane to decanol and decanoic acid, and 1-10-decane diol to 10- hydroxy decanoic acid using Candida tropicalis with dimethyl formamide.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1313471A GB1386393A (en) | 1971-05-05 | 1971-05-05 | Enzymic oxidation of hydrocarbons alcohols and aldehydes |
| DE19722221534 DE2221534A1 (en) | 1971-05-05 | 1972-05-03 | Process for the oxidation of hydrocarbons, alcohols and aldehydes |
| FR7216226A FR2135345B1 (en) | 1971-05-05 | 1972-05-05 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1313471A GB1386393A (en) | 1971-05-05 | 1971-05-05 | Enzymic oxidation of hydrocarbons alcohols and aldehydes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1386393A true GB1386393A (en) | 1975-03-05 |
Family
ID=10017449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1313471A Expired GB1386393A (en) | 1971-05-05 | 1971-05-05 | Enzymic oxidation of hydrocarbons alcohols and aldehydes |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE2221534A1 (en) |
| FR (1) | FR2135345B1 (en) |
| GB (1) | GB1386393A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ221213A (en) * | 1986-08-11 | 1990-10-26 | Univ Texas | Microbial enzymatic transformations of chrysanthemol, lavandulol and analagous alcohols to acids |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1252686B (en) * | 1964-12-17 | 1967-10-26 | Shell Internationale Research Maatschappij N.V., Den Haag | Process for the microbiological oxidation of organic compounds |
-
1971
- 1971-05-05 GB GB1313471A patent/GB1386393A/en not_active Expired
-
1972
- 1972-05-03 DE DE19722221534 patent/DE2221534A1/en active Pending
- 1972-05-05 FR FR7216226A patent/FR2135345B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2135345B1 (en) | 1977-04-01 |
| FR2135345A1 (en) | 1972-12-15 |
| DE2221534A1 (en) | 1972-11-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |