US4250259A
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US
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Microbiological production of ketones from C3 -C6 secondary alcohols
Assignee: ExxonMobil Technology and Engineering Co
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Filing: 1979-03-30
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Granted: 1981-02-10
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Expires: 1999-03-30
Abstract
Abstract A process is disclosed for the microbiological production of ketones from C3-C6 secondary alcohols by contacting C3-C6 secondary alcohols under aerobic conditions with resting microbial cells derived from a microorganism of enzyme preparation derived from said cells, wherein the microorganism has been previously grown under aerobic conditions in a nutrient medium containing a methyl-radical donating compound. Typical methyl-radical donating compounds are: methane, methanol, dimethyl ether, methylamine, methyl formate, methyl carbonate, ethanol, propanol, butanol, etc. Isolation and purification of a novel C3-C6 secondary alcohol dehydrogenase enzyme is also disclosed.
Inventors
- 👤 Ching-Tsang Hou
- 👤 Ramesh N. Patel
- 👤 Allen I. Laskin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 13:18
CPC Classifications
C; C12; C12N; C12N9/00; C12N9/0004; C12N9/0006; C12N1/00; C12N1/26; C12N1/28; C12N1/30; C12N1/32; C12P; C12P7/00; C12P7/02; C12P7/04; C12P7/24; C12P7/26; Y; Y10; Y10S; Y10S435/00; Y10S435/8215; Y10S435/822; Y10S435/824; Y10S435/832; Y10S435/84; Y10S435/858; Y10S435/874; Y10S435/909
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
127 words
A process for the microbiological conversion of a C 3 -C 6 liner secondary alcohol to the corresponding methyl ketone comprising oxidizing said alcohol by contacting a C 3 -C 6 linear secondary alcohol, under aerobic conditions, with microbial cell derived from a methylotrophic microorganism or an enzyme preparation derived from said microorganism, wherein said secondary alcohol is converted to the corresponding methyl ketone by said cells or enzyme preparation, wherein said microorganism has been previously grown under aerobic conditions in a nutrient medium containing a carbon-containing compound which provides the carbon and energy source for growth of the cells of the microorganism and induces C 3 -C 6 secondary alcohol dehydrogenase enzyme activity in said cells and wherein said methyl ketone is produced in insolable amounts.
Claim 2
Dependent Claim
127 words
A process for the microbiological conversion of a C 3 -C 6 liner secondary alcohol to the corresponding methyl ketone comprising oxidizing said alcohol by contacting a C 3 -C 6 linear secondary alcohol, under aerobic conditions, with microbial cell derived from a methylotrophic microorganism or an enzyme preparation derived from said microorganism, wherein said secondary alcohol is converted to the corresponding methyl ketone by said cells or enzyme preparation, wherein said microorganism has been previously grown under aerobic conditions in a nutrient medium containing a carbon-containing compound which provides the carbon and energy source for growth of the cells of the microorganism and induces C 3 -C 6 secondary alcohol dehydrogenase enzyme activity in said cells and wherein said methyl ketone is produced in insolable amounts.
Claim 3
Dependent Claim
20 words
The process of claim 1 wherein said microbial cells are derived from either a methane-utilizing or methanol-utilizing type methylotrophic microorganism.
Claim 4
Dependent Claim
14 words
The process of claim 2 wherein said methylotrophic microorganism is either obligate or facultative.
Claim 5
Dependent Claim
27 words
The process of claim 1 wherein said microorganisms are methane-utilizers belonging to the genera selected from the group consisting of: Methylosinus, Methylocystis, Methylomonas, Methylobacter, Methylococcus and Methylobacterium.
Claim 6
Dependent Claim
50 words
The process of claim 4 wherein said methane-utilizing microorganisms are species selected from the group consisting of: Methylosinus trichosporium, Methylosinus sporium, Methylocystis parvus, Methylomonas methanica, Methylomonas albus, Methylomonas streptobacterium, Methylomonas agile, Methylomonas rubrum, Methylomonas rosaceus, Methylobacter chrooccum, Methylobacter bovis, Methylobacter capsulatus, Methylobacter vinelandii, Methyloccus capsulatus, Methylococcus minimus and Methylobacterium organophilum.
Claim 7
Dependent Claim
80 words
The process of claim 5 wherein said methane-utilizing microorganisms are strains having the designations selected from the group consisting of: Methylosinus trichosporium OB3b (NRRL B-11,196); Methylosinus sporium 5 (NRRL B-11,197); Methylocystis parvus OBBP (NRRL B-11,198); Methylomonas methanica S 1 (NRRL B-11,199); Methylomonas albus BG8 (NRRL B-11,200); Methylobacter capsulatus Y (NRRL B-11,201); Methylococcus capsulatus (Texas) ATCC 19069; Methylobacterium organophilum sp. nov (ATCC 27,886); Methylomonas sp. AJ-3670 (FERM P-2400); Methylococcus 999 (NCIB Accession No. 11083); and Methlomonas SM3 (NCIB Accession No. 11084).
Claim 8
Dependent Claim
33 words
The process of claim 1 wherein said microorganisms are methano-utilizers belonging to the genera selected from the group consisting of: Methanomonas; Pseudomonas; Bacterium; Hyphomicrobium; Achromobacter; Protaminobacter; Vibro; Rhodopseudomonas; Bacillus; Brevibacterium; Candida; Hansenula; Pichia.
Claim 9
Dependent Claim
43 words
The process of claim 1 wherein said microorganisms are obligate methanol-utilizing methylotrophic microorganisms selected from the group consisting of: Methanomonas methylovora ATCC 21852; Pseudomonas sp. ATCC 21439; Pseudomonas w 1 ; Bacterium C 2 A 1 ; Bacterium 4B6; Hyphomicrobium sp.; Achromobacter sp.;
Claim 10
Dependent Claim
52 words
The process of claim 1 wherein said microorganisms are facultative methanol-utilizing methylotrophic microorganisms selected from the group consisting of: Pseudomonas sp. ATCC 21439; Pseudomonas AM 1 ; Hyphomicrobium sp.; Protaminobacter ruber; Vibrio extroquens; Rhodopseudomonas acidophila; Pseudomonas MS ATCC 25262; Achromobacter rufescens; Bacillus soraceus; Brevibacterium sp.; Pseudomonas M 27 ; and Pseudomonas C.
Claim 11
Dependent Claim
24 words
The process of claim 7 wherein the carbon-containing compound is selected from the group consisting of methanol, ethanol, n-propanol, n-butanol, methylamine and methyl formate.
Claim 12
Dependent Claim
40 words
The process of any of claims 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 wherein said enzyme preparation is derived from a cell-free extract of said microbial cells and additionally contains endogenous or exogeneous NAD + .
Claim 13
Dependent Claim
82 words
The process of any of claims 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 wherein said enzyme preparation comprises: (a) a dehydrogenase enzyme characterized as having a molecular weight of about 95,000±3,000 datlon as determined by Bio-gel column chromatography and two zinc atoms per molecule of protein and converting C 3 -C 6 secondary alcohols to methyl ketones, under aerobic conditions, in the presence of nicotinamide adenine dinucleotide (NAD + ) and (b) nicotinamide adenine dinucleotide (NAD + ).
Claim 14
Dependent Claim
79 words
A secondary alcohol dehydrogenase enzyme which converts C 3 -C 6 secondary alcohols to the corresponding methyl ketones under aerobic conditions and further characterized as being derived from cells of a methylotrophic microorganism which has been previously grown under aerobic conditions in a nutrient medium containing a carbon containing compound which provides the carbon and energy source for growth of the cells of the microorganism and induces C 3 -C 6 secondary alcohol dehydrogenase enzyme activity in said cells.
Claim 15
Dependent Claim
79 words
A secondary alcohol dehydrogenase enzyme which converts C 3 -C 6 secondary alcohols to the corresponding methyl ketones under aerobic conditions and further characterized as being derived from cells of a methylotrophic microorganism which has been previously grown under aerobic conditions in a nutrient medium containing a carbon containing compound which provides the carbon and energy source for growth of the cells of the microorganism and induces C 3 -C 6 secondary alcohol dehydrogenase enzyme activity in said cells.
Claim 16
Dependent Claim
34 words
The enzyme of claim 13 wherein the enzyme is derived from microorganisms selected from the group consisting of bacteria, fungi and yeast grown under aerobic conditions in the presence of methyl radical donating compounds.
Claim 17
Dependent Claim
27 words
The enzyme of claim 14 wherein the methyl radical donating compound is selected from the group consisting of methane, methanol, ethanol, n-propanol, n-butanol, methylamine and methyl formate.
Claim 18
Dependent Claim
22 words
The enzyme of claim 13 wherein the enzyme is in the form of a soluble extract of the cells of said microorganism.
Claim 19
Dependent Claim
13 words
The enzyme of claim 13 wherein the enzyme is in substantially purified form.
Claim 20
Dependent Claim
34 words
The enzyme of claim 13 wherein the enzyme is further characterized as having a molecular weight of about 95,000±3,000 dalton as determined by Bio-gel column chromatography and two zinc atoms per molecule of protein.
Claim 21
Dependent Claim
17 words
The enzyme of claims 16, 17 or 18 which additionally includes nicotinamide adenine dinucleotide (NAD + ).
Claim 22
Dependent Claim
89 words
A process for preparing a C 3 -C 6 secondary alcohol dehydrogenase enzyme, comprising: (a) cultivating, under aerobic conditions, an obligate or facultative methylotrophic microorganism in a nutrient medium containing a methyl radical donating compound in an amount sufficient to induce enzyme activity whereby microbial cells are obtained containing secondary alcohol dehydrogenase activity; (b) recovering and disrupting said cells; (c) removing the cellular debris and recovering the supernatant and isolating the enzyme containing the secondary alcohol dehydrogenase activity therefrom, said enzyme converting secondary alcohol to the corresponding methyl ketone.
Claim 23
Dependent Claim
89 words
A process for preparing a C 3 -C 6 secondary alcohol dehydrogenase enzyme, comprising: (a) cultivating, under aerobic conditions, an obligate or facultative methylotrophic microorganism in a nutrient medium containing a methyl radical donating compound in an amount sufficient to induce enzyme activity whereby microbial cells are obtained containing secondary alcohol dehydrogenase activity; (b) recovering and disrupting said cells; (c) removing the cellular debris and recovering the supernatant and isolating the enzyme containing the secondary alcohol dehydrogenase activity therefrom, said enzyme converting secondary alcohol to the corresponding methyl ketone.
Claim 24
Dependent Claim
47 words
A procee for converting C3-C6 secondary alcohols to the corresponding methyl ketones comprising: oxidizing said alcohols under aerobic conditions in the presence of nicotinamide adenine dinucleotide (NAD + ) and a cell-free enzyme preparation of C3-C6 secondary alcohol dehydrogenase and producing said methyl ketones in isolable amounts.
Claim 25
Dependent Claim
47 words
A procee for converting C3-C6 secondary alcohols to the corresponding methyl ketones comprising: oxidizing said alcohols under aerobic conditions in the presence of nicotinamide adenine dinucleotide (NAD + ) and a cell-free enzyme preparation of C3-C6 secondary alcohol dehydrogenase and producing said methyl ketones in isolable amounts.
Claim 26
Dependent Claim
34 words
The process of claim 21 wherein said dehydrogenase enzyme is characterized as having a molecular weight of about 95,000±3,000 dalton as determined by Bio-gel column chromatography and two zinc atoms per molecule of protein.
Claim 27
Dependent Claim
16 words
The process of claims 21 or 22 wherein the enzyme is in a substantially purified form.
Claim 28
Dependent Claim
37 words
The process of claims 21 or 22 wherein the conversion is carried out at a temperature ranging from about 5° to about 55° C. and at a pH in the range from about 4 to about 9.
Claim 29
Dependent Claim
22 words
The process of claims 21 or 22 wherein the conversion is carried out in a continuous manner and the enzyme is immobilized.
Claim 30
Dependent Claim
28 words
Secondary alcohol dehydrogenase enzyme characterized as having a molecular weight of about 95,000±3,000 dalton as determined by Bio-gel column chromatography and two zinc atoms per molecule of protein.
Claim 31
Dependent Claim
28 words
Secondary alcohol dehydrogenase enzyme characterized as having a molecular weight of about 95,000±3,000 dalton as determined by Bio-gel column chromatography and two zinc atoms per molecule of protein.
Claim 32
Dependent Claim
14 words
The enzyme of claim 26 which additionally includes nicotinamide adenine dinucleotide (NAD + ).
Claim 33
Dependent Claim
13 words
The enzyme of claim 26 wherein the enzyme is in substantially purified form.
Claim 34
Dependent Claim
9 words
The enzyme of claim 26 which has been immobilized.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-02-10 | 1984-08-11 | 1985-02-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-02-10 | 1988-08-11 | 1989-02-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-02-10 | 1992-08-11 | 1993-02-10 | $7700.00 | Window Closed / Lapsed |