AU2010331946A1 - Purification of isoprene from renewable resources - Google Patents
Purification of isoprene from renewable resources Download PDFInfo
- Publication number
- AU2010331946A1 AU2010331946A1 AU2010331946A AU2010331946A AU2010331946A1 AU 2010331946 A1 AU2010331946 A1 AU 2010331946A1 AU 2010331946 A AU2010331946 A AU 2010331946A AU 2010331946 A AU2010331946 A AU 2010331946A AU 2010331946 A1 AU2010331946 A1 AU 2010331946A1
- Authority
- AU
- Australia
- Prior art keywords
- isoprene
- solvent
- gas
- methyl
- column
- 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.)
- Abandoned
Links
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 title claims abstract description 904
- 238000000746 purification Methods 0.000 title abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 226
- 239000002904 solvent Substances 0.000 claims abstract description 215
- 239000012535 impurity Substances 0.000 claims abstract description 188
- 239000000203 mixture Substances 0.000 claims abstract description 166
- 239000006227 byproduct Substances 0.000 claims description 119
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 61
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 60
- 238000001179 sorption measurement Methods 0.000 claims description 56
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 48
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 47
- 229930195733 hydrocarbon Natural products 0.000 claims description 38
- 150000002430 hydrocarbons Chemical class 0.000 claims description 38
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 claims description 34
- 239000000377 silicon dioxide Substances 0.000 claims description 31
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 claims description 30
- 238000006116 polymerization reaction Methods 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 26
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 24
- 229910001868 water Inorganic materials 0.000 claims description 24
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 claims description 22
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 claims description 20
- 238000009835 boiling Methods 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- KJRRQXYWFQKJIP-UHFFFAOYSA-N 3-methylfuran Chemical compound CC=1C=COC=1 KJRRQXYWFQKJIP-UHFFFAOYSA-N 0.000 claims description 18
- MNDSSKADVGDFDF-UHFFFAOYSA-N 2,4,5-trimethylpyridine Chemical compound CC1=CC(C)=C(C)C=N1 MNDSSKADVGDFDF-UHFFFAOYSA-N 0.000 claims description 16
- HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 claims description 16
- SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 claims description 16
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 16
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 claims description 16
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims description 16
- 238000004821 distillation Methods 0.000 claims description 16
- WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 claims description 16
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 16
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims description 16
- UHEPJGULSIKKTP-UHFFFAOYSA-N sulcatone Chemical compound CC(C)=CCCC(C)=O UHEPJGULSIKKTP-UHFFFAOYSA-N 0.000 claims description 16
- IAEGWXHKWJGQAZ-UHFFFAOYSA-N trimethylpyrazine Chemical compound CC1=CN=C(C)C(C)=N1 IAEGWXHKWJGQAZ-UHFFFAOYSA-N 0.000 claims description 16
- IHPKGUQCSIINRJ-UHFFFAOYSA-N β-ocimene Natural products CC(C)=CCC=C(C)C=C IHPKGUQCSIINRJ-UHFFFAOYSA-N 0.000 claims description 16
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 15
- 239000003112 inhibitor Substances 0.000 claims description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 14
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
- OCUAPVNNQFAQSM-UHFFFAOYSA-N 3-Methyl-3-butenyl acetate Chemical compound CC(=C)CCOC(C)=O OCUAPVNNQFAQSM-UHFFFAOYSA-N 0.000 claims description 12
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 12
- XXIKYCPRDXIMQM-UHFFFAOYSA-N Isopentenyl acetate Chemical compound CC(C)=CCOC(C)=O XXIKYCPRDXIMQM-UHFFFAOYSA-N 0.000 claims description 12
- -1 Selexsorb@ Chemical compound 0.000 claims description 12
- 239000012188 paraffin wax Substances 0.000 claims description 12
- 238000002955 isolation Methods 0.000 claims description 11
- BOGRNZQRTNVZCZ-AATRIKPKSA-N (3e)-3-methylpenta-1,3-diene Chemical compound C\C=C(/C)C=C BOGRNZQRTNVZCZ-AATRIKPKSA-N 0.000 claims description 10
- BOGRNZQRTNVZCZ-WAYWQWQTSA-N (3z)-3-methylpenta-1,3-diene Chemical compound C\C=C(\C)C=C BOGRNZQRTNVZCZ-WAYWQWQTSA-N 0.000 claims description 10
- FVCDMHWSPLRYAB-UHFFFAOYSA-N 2-ethenyl-2-methyloxirane Chemical compound C=CC1(C)CO1 FVCDMHWSPLRYAB-UHFFFAOYSA-N 0.000 claims description 10
- NSPPRYXGGYQMPY-UHFFFAOYSA-N 3-Methylbuten-2-ol-1 Natural products CC(C)C(O)=C NSPPRYXGGYQMPY-UHFFFAOYSA-N 0.000 claims description 10
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 10
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 10
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- IHPKGUQCSIINRJ-CSKARUKUSA-N (E)-beta-ocimene Chemical compound CC(C)=CC\C=C(/C)C=C IHPKGUQCSIINRJ-CSKARUKUSA-N 0.000 claims description 8
- IHPKGUQCSIINRJ-NTMALXAHSA-N (Z)-beta-ocimene Chemical compound CC(C)=CC\C=C(\C)C=C IHPKGUQCSIINRJ-NTMALXAHSA-N 0.000 claims description 8
- BZAZNULYLRVMSW-UHFFFAOYSA-N 2-Methyl-2-buten-3-ol Natural products CC(C)=C(C)O BZAZNULYLRVMSW-UHFFFAOYSA-N 0.000 claims description 8
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims description 8
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 claims description 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 8
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims description 8
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 8
- ACWQBUSCFPJUPN-UHFFFAOYSA-N Tiglaldehyde Natural products CC=C(C)C=O ACWQBUSCFPJUPN-UHFFFAOYSA-N 0.000 claims description 8
- 235000000983 citronellal Nutrition 0.000 claims description 8
- 229930003633 citronellal Natural products 0.000 claims description 8
- 235000000484 citronellol Nutrition 0.000 claims description 8
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 claims description 8
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 8
- 238000000622 liquid--liquid extraction Methods 0.000 claims description 8
- 238000000638 solvent extraction Methods 0.000 claims description 8
- OHEFFKYYKJVVOX-UHFFFAOYSA-N sulcatol Natural products CC(O)CCC=C(C)C OHEFFKYYKJVVOX-UHFFFAOYSA-N 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 6
- UFLHIIWVXFIJGU-ONEGZZNKSA-N (E)-3-Hexenol Natural products CC\C=C\CCO UFLHIIWVXFIJGU-ONEGZZNKSA-N 0.000 claims description 4
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims description 4
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 claims description 4
- 239000000267 (Z)-hex-3-en-1-ol Substances 0.000 claims description 4
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 claims description 4
- 239000005792 Geraniol Substances 0.000 claims description 4
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 claims description 4
- 229940113087 geraniol Drugs 0.000 claims description 4
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 235000001510 limonene Nutrition 0.000 claims description 4
- 229940087305 limonene Drugs 0.000 claims description 4
- 239000002808 molecular sieve Substances 0.000 claims description 4
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 claims description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 4
- 150000003505 terpenes Chemical class 0.000 claims description 4
- 235000007586 terpenes Nutrition 0.000 claims description 4
- NPFVOOAXDOBMCE-PLNGDYQASA-N (3Z)-hex-3-en-1-yl acetate Chemical compound CC\C=C/CCOC(C)=O NPFVOOAXDOBMCE-PLNGDYQASA-N 0.000 claims description 3
- JSNRRGGBADWTMC-UHFFFAOYSA-N (6E)-7,11-dimethyl-3-methylene-1,6,10-dodecatriene Chemical compound CC(C)=CCCC(C)=CCCC(=C)C=C JSNRRGGBADWTMC-UHFFFAOYSA-N 0.000 claims description 3
- CXENHBSYCFFKJS-VDQVFBMKSA-N (E,E)-alpha-farnesene Chemical compound CC(C)=CCC\C(C)=C\C\C=C(/C)C=C CXENHBSYCFFKJS-VDQVFBMKSA-N 0.000 claims description 3
- ZJVWGOLNVKJRDF-UHFFFAOYSA-N 2-methylbut-3-en-2-yl acetate Chemical compound CC(=O)OC(C)(C)C=C ZJVWGOLNVKJRDF-UHFFFAOYSA-N 0.000 claims description 3
- GGFZWCZYTMEWNP-UHFFFAOYSA-N 3-methylbut-1-en-2-yl acetate Chemical compound CC(C)C(=C)OC(C)=O GGFZWCZYTMEWNP-UHFFFAOYSA-N 0.000 claims description 3
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- SXPLGYBFGPYAHS-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 SXPLGYBFGPYAHS-UHFFFAOYSA-N 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
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- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010907 stover Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- JREYOWJEWZVAOR-UHFFFAOYSA-N triazanium;[3-methylbut-3-enoxy(oxido)phosphoryl] phosphate Chemical compound [NH4+].[NH4+].[NH4+].CC(=C)CCOP([O-])(=O)OP([O-])([O-])=O JREYOWJEWZVAOR-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000005253 yeast cell Anatomy 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/12—Alkadienes
- C07C11/173—Alkadienes with five carbon atoms
- C07C11/18—Isoprene
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0426—Counter-current multistage extraction towers in a vertical or sloping position
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0492—Applications, solvents used
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28814209P | 2009-12-18 | 2009-12-18 | |
| US61/288,142 | 2009-12-18 | ||
| PCT/US2010/060552 WO2011075534A2 (en) | 2009-12-18 | 2010-12-15 | Purification of isoprene from renewable resources |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2010331946A1 true AU2010331946A1 (en) | 2012-06-28 |
| AU2010331946A2 AU2010331946A2 (en) | 2012-07-19 |
Family
ID=44167932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2010331946A Abandoned AU2010331946A1 (en) | 2009-12-18 | 2010-12-15 | Purification of isoprene from renewable resources |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US8569562B2 (OSRAM) |
| EP (1) | EP2513021A2 (OSRAM) |
| JP (3) | JP5643838B2 (OSRAM) |
| CN (1) | CN102884028B (OSRAM) |
| AR (1) | AR079560A1 (OSRAM) |
| AU (1) | AU2010331946A1 (OSRAM) |
| BR (1) | BR112012014736B1 (OSRAM) |
| CA (1) | CA2783976A1 (OSRAM) |
| IN (1) | IN2012DN05187A (OSRAM) |
| SG (1) | SG181605A1 (OSRAM) |
| TW (1) | TWI481594B (OSRAM) |
| WO (1) | WO2011075534A2 (OSRAM) |
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| TWI434921B (zh) * | 2009-06-17 | 2014-04-21 | Danisco Us Inc | 從生物異戊二烯組合物製造燃料成分之方法及系統 |
| TW201412988A (zh) * | 2009-06-17 | 2014-04-01 | Danisco Us Inc | 使用ｄｘｐ及ｍｖａ途徑之改良之異戊二烯製造 |
| CN102884028B (zh) | 2009-12-18 | 2015-08-19 | 丹尼斯科美国公司 | 从可再生资源中纯化异戊二烯 |
| US8778647B2 (en) * | 2009-12-22 | 2014-07-15 | Danisco Us Inc. | Methods of producing isoprene comprising a membrane bioreactor |
| EP2582649A1 (en) | 2010-06-17 | 2013-04-24 | Danisco US Inc. | Fuel compositions comprising isoprene derivatives |
| US20120045812A1 (en) | 2010-08-06 | 2012-02-23 | Danisco Us Inc. | PRODUCTION OF ISOPRENE UNDER NEUTRAL pH CONDITIONS |
| CA2816306A1 (en) | 2010-10-27 | 2012-05-03 | Danisco Us Inc. | Isoprene synthase variants for improved production of isoprene |
| EP2655597A1 (en) | 2010-12-22 | 2013-10-30 | Danisco US Inc. | Biological production of pentose sugars using recombinant cells |
| EP2655606A1 (en) | 2010-12-22 | 2013-10-30 | Danisco US Inc. | Compositions and methods for improved isoprene production using two types of ispg enzymes |
| US8889383B2 (en) | 2011-04-29 | 2014-11-18 | Danisco Us Inc. | Production of mevalonate, isoprene, and isoprenoids using genes encoding polypeptides having thiolase, HMG-CoA synthase and HMG-CoA reductase enzymatic activities |
| AU2012249320A1 (en) | 2011-04-29 | 2013-11-14 | Danisco Us Inc. | Recombinant microorganisms for enhanced production of mevalonate, isoprene, and isoprenoids |
| US8951764B2 (en) | 2011-08-05 | 2015-02-10 | Danisco Us Inc. | Production of isoprenoids under neutral pH conditions |
| US8993305B2 (en) | 2011-10-07 | 2015-03-31 | Danisco Us Inc. | Utilization of phosphoketolase in the production of mevalonate, isoprenoid precursors, and isoprene |
| HK1201554A1 (en) | 2011-10-27 | 2015-09-04 | Danisco Us Inc. | Isoprene synthase variants with improved solubility for production of isoprene |
| JP2015510392A (ja) | 2011-12-23 | 2015-04-09 | ダニスコ・ユーエス・インク | 低減したｉｓｐａ活性を有する宿主細胞を用いるイソプレン産生増強法 |
| US9315831B2 (en) | 2012-03-30 | 2016-04-19 | Danisco Us Inc. | Direct starch to fermentable sugar as feedstock for the production of isoprene, isoprenoid precursor molecules, and/or isoprenoids |
| US20130295627A1 (en) * | 2012-04-09 | 2013-11-07 | Robert J. Hanchar | Process for producing methyl butenol (2-methyl-3-buten-2-ol) |
| US9163263B2 (en) | 2012-05-02 | 2015-10-20 | The Goodyear Tire & Rubber Company | Identification of isoprene synthase variants with improved properties for the production of isoprene |
| US8895277B2 (en) | 2012-05-02 | 2014-11-25 | Danisco Us Inc. | Legume isoprene synthase for production of isoprene |
| JP6010343B2 (ja) * | 2012-05-21 | 2016-10-19 | 株式会社ブリヂストン | イソプレン−ブタジエン共重合体、イソプレン−ブタジエン共重合体の製造方法、ゴム組成物及びタイヤ |
| JP6010342B2 (ja) * | 2012-05-21 | 2016-10-19 | 株式会社ブリヂストン | イソプレン−ブタジエン共重合体、イソプレン−ブタジエン共重合体の製造方法、ゴム組成物及びタイヤ |
| JP6074160B2 (ja) * | 2012-05-22 | 2017-02-01 | 株式会社ブリヂストン | ゴム組成物およびタイヤの製造方法 |
| JP6074161B2 (ja) * | 2012-05-22 | 2017-02-01 | 株式会社ブリヂストン | ゴム組成物およびタイヤの製造方法 |
| WO2013181647A2 (en) | 2012-06-01 | 2013-12-05 | Danisco Us Inc. | Compositions and methods of producing isoprene and/or industrrial bio-products using anaerobic microorganisms |
| EP2935364A2 (en) | 2012-12-21 | 2015-10-28 | Danisco US Inc. | Production of isoprene, isoprenoid, and isoprenoid precursors using an alternative lower mevalonate pathway |
| WO2014121357A1 (en) * | 2013-02-07 | 2014-08-14 | Braskem S.A. | Method of separating and purifying a conjugated diolefin produced by fermentation under anaerobic conditions |
| US9850512B2 (en) | 2013-03-15 | 2017-12-26 | The Research Foundation For The State University Of New York | Hydrolysis of cellulosic fines in primary clarified sludge of paper mills and the addition of a surfactant to increase the yield |
| WO2014156997A1 (ja) | 2013-03-29 | 2014-10-02 | 味の素株式会社 | 発酵ガス中のイソプレンの回収方法および精製イソプレンの製造方法 |
| CN105555952A (zh) | 2013-04-10 | 2016-05-04 | 丹尼斯科美国公司 | 用于乙酰辅酶a-衍生代谢物、异戊二烯、类异戊二烯前体和类异戊二烯的改善生产的磷酸解酮酶 |
| WO2014205355A2 (en) | 2013-06-21 | 2014-12-24 | Danisco Us Inc. | Compositions and methods for clostridial transformation |
| US10427996B2 (en) * | 2013-12-02 | 2019-10-01 | Braskem S.A. | Fermentation hydrocarbon gas products separation via membrane |
| US10648004B2 (en) | 2014-02-20 | 2020-05-12 | Danisco Us Inc. | Recombinant microorganisms for the enhanced production of mevalonate, isoprene, isoprenoid precursors, isoprenoids, and acetyl-CoA-derived products |
| WO2015127435A1 (en) * | 2014-02-24 | 2015-08-27 | Glycos Biotechnologies, Inc. | Recovery of isoprene from fermentation processes using mechanical compression and condensation |
| US9951363B2 (en) | 2014-03-14 | 2018-04-24 | The Research Foundation for the State University of New York College of Environmental Science and Forestry | Enzymatic hydrolysis of old corrugated cardboard (OCC) fines from recycled linerboard mill waste rejects |
| CN106866341B (zh) * | 2017-01-20 | 2019-08-06 | 中国科学院青岛生物能源与过程研究所 | 一种分离回收发酵尾气中低浓度异戊二烯的方法 |
| FI128295B (en) * | 2017-12-29 | 2020-02-28 | Neste Oyj | Renewable, highly isoparaffinic solvent-based distillate |
| CN110354644A (zh) * | 2018-04-10 | 2019-10-22 | 天津科技大学 | 一种高效的醋酸丁酯废气吸收与解吸装置 |
| CN111454114B (zh) * | 2020-05-11 | 2023-07-14 | 长沙贝塔医药科技有限公司 | 一种用13c2-香叶醇合成高纯度13c2-月桂烯的方法 |
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-
2010
- 2010-12-15 CN CN201080064167.4A patent/CN102884028B/zh not_active Expired - Fee Related
- 2010-12-15 CA CA2783976A patent/CA2783976A1/en not_active Abandoned
- 2010-12-15 WO PCT/US2010/060552 patent/WO2011075534A2/en not_active Ceased
- 2010-12-15 IN IN5187DEN2012 patent/IN2012DN05187A/en unknown
- 2010-12-15 EP EP10799184A patent/EP2513021A2/en not_active Withdrawn
- 2010-12-15 US US12/969,440 patent/US8569562B2/en active Active
- 2010-12-15 SG SG2012042511A patent/SG181605A1/en unknown
- 2010-12-15 AU AU2010331946A patent/AU2010331946A1/en not_active Abandoned
- 2010-12-15 JP JP2012544763A patent/JP5643838B2/ja not_active Expired - Fee Related
- 2010-12-15 BR BR112012014736A patent/BR112012014736B1/pt not_active IP Right Cessation
- 2010-12-17 TW TW099144617A patent/TWI481594B/zh active
- 2010-12-20 AR ARP100104783A patent/AR079560A1/es unknown
-
2013
- 2013-09-24 US US14/035,746 patent/US20140187839A1/en not_active Abandoned
-
2014
- 2014-09-10 JP JP2014184058A patent/JP6378013B2/ja not_active Expired - Fee Related
-
2015
- 2015-04-09 US US14/682,930 patent/US9751820B2/en active Active
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2016
- 2016-11-18 JP JP2016225310A patent/JP2017081924A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2017081924A (ja) | 2017-05-18 |
| US20110178261A1 (en) | 2011-07-21 |
| EP2513021A2 (en) | 2012-10-24 |
| WO2011075534A2 (en) | 2011-06-23 |
| SG181605A1 (en) | 2012-07-30 |
| IN2012DN05187A (OSRAM) | 2015-10-23 |
| US20140187839A1 (en) | 2014-07-03 |
| BR112012014736A2 (pt) | 2016-04-19 |
| BR112012014736B1 (pt) | 2018-09-18 |
| CN102884028A (zh) | 2013-01-16 |
| AR079560A1 (es) | 2012-02-01 |
| TWI481594B (zh) | 2015-04-21 |
| JP2015007119A (ja) | 2015-01-15 |
| CA2783976A1 (en) | 2011-06-23 |
| JP2013514375A (ja) | 2013-04-25 |
| US9751820B2 (en) | 2017-09-05 |
| AU2010331946A2 (en) | 2012-07-19 |
| JP5643838B2 (ja) | 2014-12-17 |
| TW201139367A (en) | 2011-11-16 |
| WO2011075534A3 (en) | 2012-04-12 |
| US8569562B2 (en) | 2013-10-29 |
| CN102884028B (zh) | 2015-08-19 |
| US20150274615A1 (en) | 2015-10-01 |
| JP6378013B2 (ja) | 2018-08-22 |
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