NO780351L - PROCEDURE FOR PREPARING ACETON AND BUTANOL FROM CELLULOSE MATERIAL - Google Patents
PROCEDURE FOR PREPARING ACETON AND BUTANOL FROM CELLULOSE MATERIALInfo
- Publication number
- NO780351L NO780351L NO780351A NO780351A NO780351L NO 780351 L NO780351 L NO 780351L NO 780351 A NO780351 A NO 780351A NO 780351 A NO780351 A NO 780351A NO 780351 L NO780351 L NO 780351L
- Authority
- NO
- Norway
- Prior art keywords
- butanol
- acetone
- cellulase
- cellulose
- glucose
- Prior art date
Links
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 title claims abstract description 24
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 239000000463 material Substances 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 13
- 239000001913 cellulose Substances 0.000 title claims description 17
- 229920002678 cellulose Polymers 0.000 title claims description 17
- 108010059892 Cellulase Proteins 0.000 claims description 21
- 229940106157 cellulase Drugs 0.000 claims description 21
- DNZWLJIKNWYXJP-UHFFFAOYSA-N butan-1-ol;propan-2-one Chemical compound CC(C)=O.CCCCO DNZWLJIKNWYXJP-UHFFFAOYSA-N 0.000 claims description 14
- 244000005700 microbiome Species 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 abstract description 2
- 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 12
- 239000008103 glucose Substances 0.000 description 12
- 238000000855 fermentation Methods 0.000 description 9
- 230000004151 fermentation Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000193401 Clostridium acetobutylicum Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241000223261 Trichoderma viride Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000009630 liquid culture Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 241000193403 Clostridium Species 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
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000013028 medium composition Substances 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000010893 paper waste Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 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
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
- C12P7/26—Ketones
- C12P7/28—Acetone-containing products
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
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)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Fremgangsmåte til fremstilling av aceton og butanol fra et celluloseholdig materiale.Process for the preparation of acetone and butanol from a cellulosic material.
Description
Foreliggende oppfinnelse vedrører en fremgangsmåte til fremstilling av aceton og butanol fra et celluloseholdig materiale. The present invention relates to a method for producing acetone and butanol from a cellulose-containing material.
Cellulose eller celluloseholdige stoffer forekommer i naturen i meget stort omfang og anvendes som råmateriale på forskjellige områder innen industrien. Som et middel for ut-nyttelse av disse materialer, er det rapportert forskjellige forslag angående fremstilling av etanol, melkesyre, aceton, butanol og lignende, ved å hydrolysere materialene til glukose, som er en bestanddel i cellulose, og anvende den fremstilte glukose som et råmateriale for fermenteringsproduktene. Til forskjell fra de tilfeller hvor molasse anvendes som råmateriale, har imidlertid den nevnte metode den ulempe at cellulosen eller det celluloseholdige materiale som er utgangssubstratet, Cellulose or cellulose-containing substances occur in nature in very large quantities and are used as raw material in various areas within industry. As a means of utilizing these materials, various proposals have been reported regarding the production of ethanol, lactic acid, acetone, butanol, and the like, by hydrolyzing the materials into glucose, which is a component of cellulose, and using the produced glucose as a raw material for the fermentation products. However, in contrast to the cases where molasses is used as raw material, the mentioned method has the disadvantage that the cellulose or the cellulose-containing material which is the starting substrate,
først må hydrolyseres til glukpse, og dermed er det nødvendig med minst to trinn, dvs. hydrolyse og fermentering. Siden" • celluloseholdige materialer er vanskelig å dekomponere, har den oppnådde glukose lav konsentrasjon, hvilket resulterer i en lav konsentrasjon av "^fermenter ingsprodukter. Når konsentra-sjonen av en fremstilt aceton-butanolblanding er lav, blir således spesielt separering og rensing av blandingen vanskelig. Denne to-trinnsmetode er følgelig upraktisk. must first be hydrolysed to glucose, and thus at least two steps are necessary, i.e. hydrolysis and fermentation. Since cellulosic materials are difficult to decompose, the glucose obtained has a low concentration, resulting in a low concentration of fermentation products. When the concentration of a prepared acetone-butanol mixture is low, separation and purification of the mixture thus becomes especially difficult. This two-step method is therefore impractical.
Det er nå funnet at større konsentrasjon av en aceton-butanolblanding kan oppnås fra et celluloseholdig materiale ved hjelp av en en-trinnsprosess når det celluloseholdige materiale samtidig innvirkes på av en cellulase og en aceton-butanolproduserende mikroorganisme. Foreliggende oppfinnelse angår derfor en metode hvorved aceton og butanol med fordel kan fremstilles fra et celluloseholdig materiale ved hjelp av en en-trinnsprosess. It has now been found that greater concentration of an acetone-butanol mixture can be obtained from a cellulosic material by means of a one-step process when the cellulosic material is simultaneously acted upon by a cellulase and an acetone-butanol-producing microorganism. The present invention therefore relates to a method by which acetone and butanol can be advantageously produced from a cellulose-containing material by means of a one-step process.
"Celluloseholdige materialer" som anvendes som utgangs-materialer i foreliggende oppfinnelse, omfatter cellulose "Cellulosic materials" used as starting materials in the present invention include cellulose
eller stoffer sammensatt hovedsakelig av cellulose, hvilket omfatter tre, risstrå, risskall, maisstengel, maiskolber og papiravfall, slik som avispapir, korrugert papir, tidsskrift-papir, korte fibre fra papirfabrikker og fiberavfall fra byer og industrier. For at disse stoffer skal kunne anvendes på effektiv måte som substrater, er det ønskelig at de pulveri-seres eller disintegreres. or substances composed mainly of cellulose, which includes wood, rice straw, rice husks, corn stalks, corn cobs and paper waste, such as newsprint, corrugated paper, magazine paper, short fibers from paper mills and fiber waste from cities and industries. In order for these substances to be used effectively as substrates, it is desirable that they be pulverized or disintegrated.
For forsukring av disse cellulosesubstrater, er det tilstrekkelig å benytte en kommersielt tilgjengelig cellulase, slik som "Cellulase Onozuka". Et væskeformig enzymatisk prepa-rat, slik som et flytende kulturfiltrat eller fast kultur-ekstrakt fra en cellulaseproduserende mikroorganisme, slik som T. viride, kan anvendes. En flytende kultur eller fast kultur For saccharification of these cellulose substrates, it is sufficient to use a commercially available cellulase, such as "Cellulase Onozuka". A liquid enzymatic preparation, such as a liquid culture filtrate or solid culture extract from a cellulase-producing microorganism, such as T. viride, can be used. A liquid culture or solid culture
av selve mikroorganismen T. viride, kan også anvendes som enof the microorganism T. viride itself, can also be used as a
rå hel kulturblanding uten separering, ekstrahering eller rensing. raw whole culture mixture without separation, extraction or purification.
Som aceton-butanolproduserende mikroorganisme for samtidig bruk med cellulasen, kan man f.eks. benytte den vel-kjente organisme Clostridium acetobutylicum og Clostridium saccharoacetobutylicum. As an acetone-butanol-producing microorganism for simultaneous use with the cellulase, one can e.g. using the well-known organisms Clostridium acetobutylicum and Clostridium saccharoacetobutylicum.
For at det celluloseholdige substrat samtidig skalIn order for the cellulose-containing substrate to simultaneously
kunne utsettes for en cellulase og en aceton-butanolproduserende mikroorganisme, fremstilles en vandig suspensjon inneholdende 1-50 vekt-% celluloseholdig materiale, passende mengder av en nitrogenkilde, uorganiske salter og andre næringsstoffer, og steriliseres på konvensjonell måte for å kunne tjene som substrat. En cellulase (eller cellulaseholdig væske) tilsettes til substratet og samtidig tilsettes en aceton-butanolproduserende mikroorganisme som er dyrket på forhånd, slik at fermenteringen vil forløpe. could be exposed to a cellulase and an acetone-butanol-producing microorganism, an aqueous suspension containing 1-50% by weight of cellulosic material, suitable amounts of a nitrogen source, inorganic salts and other nutrients is prepared and sterilized in a conventional manner to serve as a substrate. A cellulase (or cellulase-containing liquid) is added to the substrate and at the same time an acetone-butanol-producing microorganism that has been cultured in advance is added, so that the fermentation will proceed.
Temperatur- og pH-betingelser avhenger av mikroorganismen og den cellulasetype som anvendes, men det er generelt ønskelig å ha optimale forhold i området 30-55°C og pH 4-6. Fermenteringstidene er også forskjellige avhengig av .typen av celluloseholdig materiale, aceton-butanolproduserende mikroorganisme og cellulaseaktivitet, men den ønskede mengde aceton-butanol produseres vanligvis iløpet av 48 timer. Temperature and pH conditions depend on the microorganism and the type of cellulase used, but it is generally desirable to have optimal conditions in the range 30-55°C and pH 4-6. Fermentation times also differ depending on the type of cellulosic material, acetone-butanol-producing microorganism and cellulase activity, but the desired amount of acetone-butanol is usually produced within 48 hours.
Som det fremgår fra nedenstående eksempel, representerer foreliggen.de oppfinnelse ikke bare en forenkling av produksjonen, men også en reduksjon av glukoseinhiberingen av cellulasereak-sjonen, samt av den aceton-butanolproduserende mikroorganisme, sammenlignet med den konvensjonelle metode som består av en to-trinnsprosess, dvs. forsukring og fermentering, fordi i foreliggende oppfinnelse holdes sukkerkonsentrasjonen i mediet lav gjennom hele fermenteringsprosessen. Som et resultat får man en betydelig utbytteøkning av aceton-butanol fra cellulosen. As can be seen from the example below, the present invention represents not only a simplification of the production, but also a reduction of the glucose inhibition of the cellulase reaction, as well as of the acetone-butanol-producing microorganism, compared to the conventional method which consists of a two-step process , i.e. saccharification and fermentation, because in the present invention the sugar concentration in the medium is kept low throughout the entire fermentation process. As a result, a significant yield increase of acetone-butanol from the cellulose is obtained.
Ifølge oppfinnelsen er det således tilveiebragt en fremgangsmåte for økonomisk og fordelaktig fremstilling i et trinn av aceton og butanol fra et celluloseholdig materiale. According to the invention, a method has thus been provided for the economic and advantageous production in one step of acetone and butanol from a cellulose-containing material.
Oppfinnelsen skal i det følgende beskrives under hen-visning .til foretrukne utførelser. The invention will be described below with reference to preferred embodiments.
EksempelExample
Fremstillin2_av_kimkulturProduction of 2_of_germ culture
Clostridium acetobutylicum, IFO 3854, aceton-butanolproduserende mikroorganisme, ble inokkulert i 10 ml av et sterilisert medium bestående av nedenstående komponenter og dyrket anaerobt ved 37°C i 3 dager. Clostridium acetobutylicum, IFO 3854, acetone-butanol-producing microorganism, was inoculated into 10 ml of a sterilized medium consisting of the components below and grown anaerobically at 37°C for 3 days.
Mediumsammensetning:Medium composition:
Av et medium bestående av de ovenfor angitte komponenter, ble 50 ml anbragt i en 100 ml<1>s kolbe og 5 ml av ovennevnte kulturoppløsning ble tilsatt til dette medium for anaerob dyrkning ved 37°C i 3 dager. Dette ble gjort til en kimkultur. Of a medium consisting of the above components, 50 ml was placed in a 100 ml<1>s flask and 5 ml of the above culture solution was added to this medium for anaerobic cultivation at 37°C for 3 days. This was made into a germ culture.
( 1) Medium A( 1) Medium A
Et medium med samme sammensetning som ovenfor med unntagelse av 60 g glukose isteden for 20 g. A medium with the same composition as above with the exception of 60 g of glucose instead of 20 g.
( 2) Medium B( 2) Medium B
Et medium med samme sammensetning som angitt ovenfor, med unntagelse av 100 g cellulosepulver (under 100 mesh) isteden for glukose. A medium with the same composition as stated above, with the exception of 100 g of cellulose powder (below 100 mesh) instead of glucose.
Cellulase og dens aktivitetCellulase and its activity
Kommersielt tilgjengelig cellulase ble utsaltet med ammoniumsulfat og avsaltet, og deretter liofilisert.for opp-nåelse av en ren cellulase. Commercially available cellulase was salted out with ammonium sulfate and desalted, and then lyophilized to obtain a pure cellulase.
Ett gram av denne cellulase ble oppløst i 100 ml vann med pH regulert til 4,5 og 10 g cellulosepulver (under 100 mesh) ble tilsatt. Deretter ble forsukring utført ved 45°C i 48 timer. Når forsukringen var ferdig, ble reaksjonsoppløsningen analysert ved væskekromatografi og 3,2 g glukose ble funnet. Denne cellulase hadde,med andre ord, den ovenfor nevnte aktivitet. One gram of this cellulase was dissolved in 100 ml of water with pH adjusted to 4.5 and 10 g of cellulose powder (below 100 mesh) was added. Saccharification was then carried out at 45°C for 48 hours. When saccharification was complete, the reaction solution was analyzed by liquid chromatography and 3.2 g of glucose was found. In other words, this cellulase had the above-mentioned activity.
FermenteringsprosessFermentation process
Ett gram av den ovenfor angitte cellulase og 5 ml av kimkulturen fremstilt på angitt måte, ble tilsatt til 100 ml av godt omrørt medium B. Blandingen ble innstilt til pH 6,5 og fikk deretter fermenteres anaerobt ved 37°C i 48 timer, mens pH-verdien ble regulert slik at den ikke falt under 4,5. Sammenligningseksempel One gram of the above-mentioned cellulase and 5 ml of the germ culture prepared as indicated were added to 100 ml of well-stirred medium B. The mixture was adjusted to pH 6.5 and then allowed to ferment anaerobically at 37°C for 48 hours, while The pH value was regulated so that it did not fall below 4.5. Comparative example
(1) Det ovenfor angitte medium B ble omrørt grundig og til 100 ml av dette medium ble det tilsatt 3 g av nevnte cellulase. Blandingen ble regulert til pH 4,5 og fikk forsukres ved 45°C i 48 timer. Når den resulterende sukkeroppløsning ble analysert, fant man at 6,3 g glukose var fremstilt. Sukker-oppløsningen (glukoseinnhold 6,3 g) ble varmesterilisert og 5 ml av kimkulturen fremstilt som tidligere beskrevet, ble tilsatt. Deretter ble en aceton-butanolfermentering utført anaerobt ved 3 7°C i 48 timer. (2) 5 ml av kimkulturen fremstilt som angitt ovenfor, ble inokkulert i 100 ml av nevnte medium A som hadde blitt varmesterilisert. Blandingen ble regulert til pH 6,5 og fikk reagere anaerobt ved 37°C i 48 timer under regulering av pH-verdien, slik at den ikke falt under 4,5. De oppnådde resul-tater er angitt i nedenstående tabell. Produktene ble analysert ved gasskromatografi. (1) The above-mentioned medium B was thoroughly stirred and 3 g of said cellulase were added to 100 ml of this medium. The mixture was adjusted to pH 4.5 and allowed to saccharify at 45°C for 48 hours. When the resulting sugar solution was analyzed, it was found that 6.3 g of glucose had been produced. The sugar solution (glucose content 6.3 g) was heat sterilized and 5 ml of the germ culture prepared as previously described was added. Then an acetone-butanol fermentation was carried out anaerobically at 37°C for 48 hours. (2) 5 ml of the germ culture prepared as indicated above was inoculated into 100 ml of said medium A which had been heat sterilized. The mixture was adjusted to pH 6.5 and allowed to react anaerobically at 37°C for 48 hours while adjusting the pH so that it did not fall below 4.5. The results obtained are indicated in the table below. The products were analyzed by gas chromatography.
Som det fremgår fra tabellen, oppnår man med foreliggende fremgangsmåte 1,4 ganger så mye aceton og butanol som det oppnås ved den konvensjonelle metode hvorved cellulose på forhånd hydrolysres til glukose for anvendelse som substrat (eksempel 1) eller glukose anvendes i seg selv som substrat (eksempel 2). Foreliggende oppfinnelse har følgelig den fordel at aceton og butanol fremstilles ved hjelp av en enkel en-trinnsprosess, at utbyttene av de ønskede produkter er sterkt forbedret og at forbruket av cellulase er mindre sammenlignet med de konvensjonelle metoder. As can be seen from the table, with the present method 1.4 times as much acetone and butanol is obtained as is obtained with the conventional method whereby cellulose is first hydrolysed to glucose for use as a substrate (example 1) or glucose is used in itself as a substrate (example 2). The present invention consequently has the advantage that acetone and butanol are produced using a simple one-step process, that the yields of the desired products are greatly improved and that the consumption of cellulase is less compared to the conventional methods.
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4940177A JPS53136585A (en) | 1977-04-28 | 1977-04-28 | Production of acetone and butanol from cellulosic substance |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO780351L true NO780351L (en) | 1978-10-31 |
Family
ID=12830011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO780351A NO780351L (en) | 1977-04-28 | 1978-02-01 | PROCEDURE FOR PREPARING ACETON AND BUTANOL FROM CELLULOSE MATERIAL |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS53136585A (en) |
| BE (1) | BE863677A (en) |
| CA (1) | CA1093487A (en) |
| DE (1) | DE2754650A1 (en) |
| DK (1) | DK183578A (en) |
| FI (1) | FI780341A (en) |
| FR (1) | FR2388883A1 (en) |
| GB (1) | GB1552207A (en) |
| IT (1) | IT1089324B (en) |
| NL (1) | NL7800106A (en) |
| NO (1) | NO780351L (en) |
| SE (1) | SE438868B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2483944B1 (en) * | 1980-06-09 | 1986-05-02 | Inst Francais Du Petrole | NEW FUELS BASED ON BUTYL ALCOHOL AND ACETONE |
| FR2493863A1 (en) * | 1980-11-07 | 1982-05-14 | Inst Francais Du Petrole | NEW FUEL BASED ON FUEL CONTAINING ETHANOL HYDRATE AND AN ADDITIVE |
| KR100481692B1 (en) * | 2001-11-23 | 2005-04-07 | 배진호 | Valve activity apparatus for engine |
| JP2011529345A (en) | 2008-07-28 | 2011-12-08 | ユニバーシティ オブ マサチューセッツ | Methods and compositions for improving production of products in microorganisms |
| GB2468558A (en) * | 2009-03-09 | 2010-09-15 | Qteros Inc | Fermentation process comprising microorganism and external source of enzymes such as cellulase |
-
1977
- 1977-04-28 JP JP4940177A patent/JPS53136585A/en active Granted
- 1977-12-08 DE DE19772754650 patent/DE2754650A1/en not_active Withdrawn
- 1977-12-21 GB GB53337/77A patent/GB1552207A/en not_active Expired
- 1977-12-22 CA CA293,799A patent/CA1093487A/en not_active Expired
- 1977-12-30 IT IT31511/77A patent/IT1089324B/en active
-
1978
- 1978-01-04 NL NL7800106A patent/NL7800106A/en not_active Application Discontinuation
- 1978-02-01 NO NO780351A patent/NO780351L/en unknown
- 1978-02-02 FI FI780341A patent/FI780341A/en not_active Application Discontinuation
- 1978-02-02 SE SE7801262A patent/SE438868B/en not_active IP Right Cessation
- 1978-02-06 BE BE184924A patent/BE863677A/en not_active IP Right Cessation
- 1978-02-06 FR FR7803245A patent/FR2388883A1/en active Granted
- 1978-04-27 DK DK183578A patent/DK183578A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7800106A (en) | 1978-10-31 |
| JPS5710719B2 (en) | 1982-02-27 |
| IT1089324B (en) | 1985-06-18 |
| SE438868B (en) | 1985-05-13 |
| SE7801262L (en) | 1978-10-29 |
| DE2754650A1 (en) | 1978-11-09 |
| BE863677A (en) | 1978-08-07 |
| JPS53136585A (en) | 1978-11-29 |
| FR2388883B3 (en) | 1980-10-10 |
| FI780341A (en) | 1978-10-29 |
| DK183578A (en) | 1978-10-29 |
| CA1093487A (en) | 1981-01-13 |
| GB1552207A (en) | 1979-09-12 |
| FR2388883A1 (en) | 1978-11-24 |
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