DE2144316C3 - Verfahren zur Herstellung von 1,4-Butandiol - Google Patents
Verfahren zur Herstellung von 1,4-ButandiolInfo
- Publication number
- DE2144316C3 DE2144316C3 DE2144316A DE2144316DA DE2144316C3 DE 2144316 C3 DE2144316 C3 DE 2144316C3 DE 2144316 A DE2144316 A DE 2144316A DE 2144316D A DE2144316D A DE 2144316DA DE 2144316 C3 DE2144316 C3 DE 2144316C3
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- thorium
- nickel
- cobalt
- metallic
- 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
- 238000000034 method Methods 0.000 title claims description 25
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 230000008569 process Effects 0.000 title description 11
- 239000003054 catalyst Substances 0.000 claims description 38
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 239000010941 cobalt Substances 0.000 claims description 11
- 229910017052 cobalt Inorganic materials 0.000 claims description 10
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 10
- ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 claims description 10
- 239000012876 carrier material Substances 0.000 claims description 8
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 5
- 229910003452 thorium oxide Inorganic materials 0.000 claims description 5
- 150000001869 cobalt compounds Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 150000002816 nickel compounds Chemical class 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 230000002195 synergetic effect Effects 0.000 claims 1
- 150000003586 thorium compounds Chemical class 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229910052776 Thorium Inorganic materials 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000000975 co-precipitation Methods 0.000 description 3
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 3
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VGBPIHVLVSGJGR-UHFFFAOYSA-N thorium(4+);tetranitrate Chemical compound [Th+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VGBPIHVLVSGJGR-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- SFKTYEXKZXBQRQ-UHFFFAOYSA-J thorium(4+);tetrahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[Th+4] SFKTYEXKZXBQRQ-UHFFFAOYSA-J 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45077667A JPS4831084B1 (OSRAM) | 1970-09-04 | 1970-09-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2144316B2 DE2144316B2 (de) | 1973-10-25 |
| DE2144316C3 true DE2144316C3 (de) | 1974-07-04 |
Family
ID=13640217
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2144316A Expired DE2144316C3 (de) | 1970-09-04 | 1971-09-03 | Verfahren zur Herstellung von 1,4-Butandiol |
| DE19712144316 Granted DE2144316A1 (de) | 1970-09-04 | 1971-09-03 | Verfahren zur Herstellung von Tetra methylenglykol |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712144316 Granted DE2144316A1 (de) | 1970-09-04 | 1971-09-03 | Verfahren zur Herstellung von Tetra methylenglykol |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3772395A (OSRAM) |
| JP (1) | JPS4831084B1 (OSRAM) |
| CA (1) | CA933174A (OSRAM) |
| DE (2) | DE2144316C3 (OSRAM) |
| FR (1) | FR2107091A5 (OSRAM) |
| GB (1) | GB1314126A (OSRAM) |
| NL (1) | NL7112128A (OSRAM) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5494092U (OSRAM) * | 1977-12-16 | 1979-07-03 | ||
| US4203870A (en) * | 1978-04-17 | 1980-05-20 | Ppg Industries, Inc. | Catalyst for hydrogenation of glycolic acid |
| US4141930A (en) * | 1978-04-17 | 1979-02-27 | Ppg Industries, Inc. | Hydrogenation of glycolic acid |
| DE2845905C3 (de) * | 1978-10-21 | 1983-05-26 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur kontinuierlichen Herstellung von Butandiol-1,4 |
| GB8514002D0 (en) * | 1985-06-04 | 1985-07-10 | Davy Mckee Ltd | Process |
| US4652685A (en) * | 1985-11-15 | 1987-03-24 | General Electric Company | Hydrogenation of lactones to glycols |
| BE1012342A6 (fr) | 1998-01-08 | 2000-10-03 | Pantochim Sa | Procede de production de butanediol par hydrogenation en phase liquide. |
| US20070010696A1 (en) * | 2005-07-08 | 2007-01-11 | Ramazanova Elmira M | Method of preparation of methyl-benzyl-ketone |
| WO2008091627A2 (en) | 2007-01-22 | 2008-07-31 | Genomatica, Inc. | Methods and organisms for growth-coupled production of 3-hydroxypropionic acid |
| WO2008115840A2 (en) | 2007-03-16 | 2008-09-25 | Genomatica, Inc. | Compositions and methods for the biosynthesis of 1,4-butanediol and its precursors |
| US7947483B2 (en) | 2007-08-10 | 2011-05-24 | Genomatica, Inc. | Methods and organisms for the growth-coupled production of 1,4-butanediol |
| CA2696018A1 (en) | 2007-08-10 | 2009-04-09 | Genomatica, Inc. | Methods for the synthesis of olefins and derivatives |
| US7803589B2 (en) | 2008-01-22 | 2010-09-28 | Genomatica, Inc. | Methods and organisms for utilizing synthesis gas or other gaseous carbon sources and methanol |
| WO2009111672A1 (en) | 2008-03-05 | 2009-09-11 | Genomatica, Inc. | Primary alcohol producing organisms |
| WO2009151728A2 (en) | 2008-03-27 | 2009-12-17 | Genomatica, Inc. | Microorganisms for the production of adipic acid and other compounds |
| AU2009242615A1 (en) | 2008-05-01 | 2009-11-05 | Genomatica, Inc. | Microorganisms for the production of methacrylic acid |
| WO2009155382A1 (en) | 2008-06-17 | 2009-12-23 | Genomatica, Inc. | Microorganisms and methods for the biosynthesis of fumarate, malate, and acrylate |
| EP2334800B1 (en) | 2008-09-10 | 2018-12-26 | Genomatica, Inc. | Microorganisms for the production of 1,4-butanediol |
| AU2009327490A1 (en) | 2008-12-16 | 2011-07-28 | Genomatica, Inc. | Microorganisms and methods for conversion of syngas and other carbon sources to useful products |
| US9017983B2 (en) | 2009-04-30 | 2015-04-28 | Genomatica, Inc. | Organisms for the production of 1,3-butanediol |
| BRPI1013505A2 (pt) | 2009-04-30 | 2018-02-14 | Genomatica Inc | organismos para a produção de isopropanol, n-butanol, e isobutanol |
| SI2427544T1 (sl) | 2009-05-07 | 2019-11-29 | Genomatica Inc | Mikroorganizmi in metode za biosintezo adipata, heksametilendiamina in 6-aminokaprojske kisline |
| KR20120036851A (ko) | 2009-05-15 | 2012-04-18 | 게노마티카 인코포레이티드 | 사이클로헥사논의 제조를 위한 유기체 |
| CN113528417A (zh) | 2009-06-04 | 2021-10-22 | 基因组股份公司 | 生产1,4-丁二醇的微生物和相关方法 |
| PL3199511T3 (pl) | 2009-06-04 | 2020-05-18 | Genomatica, Inc. | Sposób oddzielania składników brzeczki fermentacyjnej |
| US8420375B2 (en) | 2009-06-10 | 2013-04-16 | Genomatica, Inc. | Microorganisms and methods for carbon-efficient biosynthesis of MEK and 2-butanol |
| BR112012002643A2 (pt) | 2009-08-05 | 2018-08-28 | Genomatica Inc | ácido tereftalático semissintético por meio de micro-organismos que produzem ácido mucônico |
| SG179048A1 (en) | 2009-09-09 | 2012-04-27 | Genomatica Inc | Microorganisms and methods for the co-production of isopropanol with primary alcohols, diols and acids |
| KR20120083908A (ko) | 2009-10-13 | 2012-07-26 | 게노마티카 인코포레이티드 | 1,4-부탄다이올, 4-하이드록시부탄알, 4-하이드록시부티릴-ｃｏａ, 푸트레신 및 관련 화합물의 제조를 위한 미생물 및 관련 방법 |
| BR112012009332A2 (pt) | 2009-10-23 | 2015-09-15 | Genomatica Inc | micro-organismo para a produção de anilina |
| US8530210B2 (en) | 2009-11-25 | 2013-09-10 | Genomatica, Inc. | Microorganisms and methods for the coproduction 1,4-butanediol and gamma-butyrolactone |
| BR112012014062A2 (pt) | 2009-12-10 | 2017-04-04 | Genomatica Inc | organismo microbiano que não ocorre naturalmente e método para produzir 1,3 bdo |
| PH12012501526A1 (en) | 2010-01-29 | 2018-03-21 | Genomatica Inc | Microorganisms and methods for the biosynthesis of p-toluate and terephthalate |
| US8637286B2 (en) | 2010-02-23 | 2014-01-28 | Genomatica, Inc. | Methods for increasing product yields |
| US8048661B2 (en) | 2010-02-23 | 2011-11-01 | Genomatica, Inc. | Microbial organisms comprising exogenous nucleic acids encoding reductive TCA pathway enzymes |
| US9023636B2 (en) | 2010-04-30 | 2015-05-05 | Genomatica, Inc. | Microorganisms and methods for the biosynthesis of propylene |
| WO2011140171A2 (en) | 2010-05-05 | 2011-11-10 | Genomatica, Inc. | Microorganisms and methods for the biosynthesis of butadiene |
| MX2013001071A (es) | 2010-07-26 | 2013-06-28 | Genomatica Inc | Microorganismos y metodos para la biosintesis de aromaticos, 2, 4-pentadienoato y 1, 3-butadieno. |
| CN111705028A (zh) | 2012-06-04 | 2020-09-25 | 基因组股份公司 | 制造4-羟基丁酸酯、1，4-丁二醇和相关化合物的微生物和方法 |
| WO2014176514A2 (en) | 2013-04-26 | 2014-10-30 | Genomatica, Inc. | Microorganisms and methods for production of 4-hydroxybutyrate, 1,4-butanediol and related compounds |
-
1970
- 1970-09-04 JP JP45077667A patent/JPS4831084B1/ja active Pending
-
1971
- 1971-08-26 US US00175359A patent/US3772395A/en not_active Expired - Lifetime
- 1971-09-01 FR FR7131571A patent/FR2107091A5/fr not_active Expired
- 1971-09-02 GB GB4102271A patent/GB1314126A/en not_active Expired
- 1971-09-03 DE DE2144316A patent/DE2144316C3/de not_active Expired
- 1971-09-03 DE DE19712144316 patent/DE2144316A1/de active Granted
- 1971-09-03 CA CA122102A patent/CA933174A/en not_active Expired
- 1971-09-03 NL NL7112128A patent/NL7112128A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7112128A (OSRAM) | 1972-03-07 |
| CA933174A (en) | 1973-09-04 |
| US3772395A (en) | 1973-11-13 |
| JPS4831084B1 (OSRAM) | 1973-09-26 |
| DE2144316B2 (de) | 1973-10-25 |
| GB1314126A (en) | 1973-04-18 |
| DE2144316A1 (de) | 1972-03-16 |
| FR2107091A5 (OSRAM) | 1972-05-05 |
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