BR112012014736B1 - método para purificação de isopreno a partir de um efluente gasoso do fermentador e composição - Google Patents
método para purificação de isopreno a partir de um efluente gasoso do fermentador e composição Download PDFInfo
- Publication number
- BR112012014736B1 BR112012014736B1 BR112012014736A BR112012014736A BR112012014736B1 BR 112012014736 B1 BR112012014736 B1 BR 112012014736B1 BR 112012014736 A BR112012014736 A BR 112012014736A BR 112012014736 A BR112012014736 A BR 112012014736A BR 112012014736 B1 BR112012014736 B1 BR 112012014736B1
- Authority
- BR
- Brazil
- Prior art keywords
- isoprene
- solvent
- column
- weight
- gaseous effluent
- Prior art date
Links
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 title claims abstract description 907
- 238000000034 method Methods 0.000 title claims abstract description 168
- 239000000203 mixture Substances 0.000 title claims abstract description 152
- 238000000746 purification Methods 0.000 title claims abstract description 35
- 239000002904 solvent Substances 0.000 claims abstract description 182
- 239000012535 impurity Substances 0.000 claims abstract description 170
- 239000006227 byproduct Substances 0.000 claims description 111
- 238000001179 sorption measurement Methods 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 47
- 150000002430 hydrocarbons Chemical class 0.000 claims description 38
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 37
- 229930195733 hydrocarbon Natural products 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 238000006116 polymerization reaction Methods 0.000 claims description 26
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 21
- 229910001868 water Inorganic materials 0.000 claims description 21
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 15
- HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 claims description 14
- SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 claims description 14
- WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 claims description 14
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 14
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 14
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 14
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims description 14
- UHEPJGULSIKKTP-UHFFFAOYSA-N sulcatone Chemical compound CC(C)=CCCC(C)=O UHEPJGULSIKKTP-UHFFFAOYSA-N 0.000 claims description 14
- IAEGWXHKWJGQAZ-UHFFFAOYSA-N trimethylpyrazine Chemical compound CC1=CN=C(C)C(C)=N1 IAEGWXHKWJGQAZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000004821 distillation Methods 0.000 claims description 13
- 239000003112 inhibitor Substances 0.000 claims description 13
- IHPKGUQCSIINRJ-UHFFFAOYSA-N β-ocimene Natural products CC(C)=CCC=C(C)C=C IHPKGUQCSIINRJ-UHFFFAOYSA-N 0.000 claims description 13
- MNDSSKADVGDFDF-UHFFFAOYSA-N 2,4,5-trimethylpyridine Chemical compound CC1=CC(C)=C(C)C=N1 MNDSSKADVGDFDF-UHFFFAOYSA-N 0.000 claims description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 10
- IHPKGUQCSIINRJ-CSKARUKUSA-N (E)-beta-ocimene Chemical compound CC(C)=CC\C=C(/C)C=C IHPKGUQCSIINRJ-CSKARUKUSA-N 0.000 claims description 7
- BZAZNULYLRVMSW-UHFFFAOYSA-N 2-Methyl-2-buten-3-ol Natural products CC(C)=C(C)O BZAZNULYLRVMSW-UHFFFAOYSA-N 0.000 claims description 7
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims description 7
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 claims description 7
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 7
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 7
- ACWQBUSCFPJUPN-UHFFFAOYSA-N Tiglaldehyde Natural products CC=C(C)C=O ACWQBUSCFPJUPN-UHFFFAOYSA-N 0.000 claims description 7
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 7
- 238000000622 liquid--liquid extraction Methods 0.000 claims description 7
- 238000000638 solvent extraction Methods 0.000 claims description 7
- OHEFFKYYKJVVOX-UHFFFAOYSA-N sulcatol Natural products CC(O)CCC=C(C)C OHEFFKYYKJVVOX-UHFFFAOYSA-N 0.000 claims description 7
- IHPKGUQCSIINRJ-NTMALXAHSA-N (Z)-beta-ocimene Chemical compound CC(C)=CC\C=C(\C)C=C IHPKGUQCSIINRJ-NTMALXAHSA-N 0.000 claims description 6
- 238000012546 transfer Methods 0.000 claims description 6
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 claims description 4
- 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 2
- 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 2
- 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 2
- 235000000983 citronellal Nutrition 0.000 claims description 2
- 229930003633 citronellal Natural products 0.000 claims description 2
- 229940044613 1-propanol Drugs 0.000 claims 1
- BVCLXNHIJBDDTH-UHFFFAOYSA-N but-1-en-2-yl acetate Chemical compound CCC(=C)OC(C)=O BVCLXNHIJBDDTH-UHFFFAOYSA-N 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 21
- 239000000243 solution Substances 0.000 description 109
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
- 210000004027 cell Anatomy 0.000 description 59
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 53
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 51
- 239000007789 gas Substances 0.000 description 47
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 238000000855 fermentation Methods 0.000 description 37
- 230000004151 fermentation Effects 0.000 description 37
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 32
- 108090000765 processed proteins & peptides Proteins 0.000 description 32
- 102000039446 nucleic acids Human genes 0.000 description 31
- 108020004707 nucleic acids Proteins 0.000 description 31
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 30
- 150000007523 nucleic acids Chemical class 0.000 description 29
- 229920001184 polypeptide Polymers 0.000 description 29
- 102000004196 processed proteins & peptides Human genes 0.000 description 29
- 229910052799 carbon Inorganic materials 0.000 description 27
- 229910002091 carbon monoxide Inorganic materials 0.000 description 26
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 description 25
- 239000000377 silicon dioxide Substances 0.000 description 25
- 239000007788 liquid Substances 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 238000010521 absorption reaction Methods 0.000 description 21
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 20
- -1 isoprene Chemical class 0.000 description 20
- 108010075483 isoprene synthase Proteins 0.000 description 19
- 229910052760 oxygen Chemical group 0.000 description 19
- 238000009835 boiling Methods 0.000 description 18
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 18
- 239000012071 phase Substances 0.000 description 18
- 230000002829 reductive effect Effects 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- KJRRQXYWFQKJIP-UHFFFAOYSA-N 3-methylfuran Chemical compound CC=1C=COC=1 KJRRQXYWFQKJIP-UHFFFAOYSA-N 0.000 description 14
- 229910002092 carbon dioxide Inorganic materials 0.000 description 14
- 239000003463 adsorbent Substances 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- KJTLQQUUPVSXIM-ZCFIWIBFSA-N (R)-mevalonic acid Chemical compound OCC[C@](O)(C)CC(O)=O KJTLQQUUPVSXIM-ZCFIWIBFSA-N 0.000 description 12
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 12
- KJTLQQUUPVSXIM-UHFFFAOYSA-N DL-mevalonic acid Natural products OCCC(O)(C)CC(O)=O KJTLQQUUPVSXIM-UHFFFAOYSA-N 0.000 description 12
- 210000004748 cultured cell Anatomy 0.000 description 12
- 240000008042 Zea mays Species 0.000 description 11
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 11
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 11
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 11
- 239000001569 carbon dioxide Substances 0.000 description 11
- 235000005822 corn Nutrition 0.000 description 11
- 239000012454 non-polar solvent Substances 0.000 description 11
- 230000004044 response Effects 0.000 description 11
- 230000005526 G1 to G0 transition Effects 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000002609 medium Substances 0.000 description 10
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 9
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 9
- 239000003518 caustics Substances 0.000 description 9
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- 229910001873 dinitrogen Inorganic materials 0.000 description 9
- 238000002955 isolation Methods 0.000 description 9
- 239000007790 solid phase Substances 0.000 description 9
- NSPPRYXGGYQMPY-UHFFFAOYSA-N 3-Methylbuten-2-ol-1 Natural products CC(C)C(O)=C NSPPRYXGGYQMPY-UHFFFAOYSA-N 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 8
- XXIKYCPRDXIMQM-UHFFFAOYSA-N Isopentenyl acetate Chemical compound CC(C)=CCOC(C)=O XXIKYCPRDXIMQM-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000012188 paraffin wax Substances 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- 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 7
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 7
- 238000004113 cell culture Methods 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000008103 glucose Substances 0.000 description 7
- 230000001965 increasing effect Effects 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- GWNNEESLGDFXNP-UHFFFAOYSA-N 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-n-[2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]ethyl]acetamide Chemical compound CC1=C(CC(=O)NCCNS(=O)(=O)C=2C3=CC=CC(=C3C=CC=2)N(C)C)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 GWNNEESLGDFXNP-UHFFFAOYSA-N 0.000 description 6
- OCUAPVNNQFAQSM-UHFFFAOYSA-N 3-Methyl-3-butenyl acetate Chemical compound CC(=C)CCOC(C)=O OCUAPVNNQFAQSM-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 6
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 6
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 6
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 6
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- 239000001301 oxygen Chemical group 0.000 description 6
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 5
- 239000002028 Biomass Substances 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229940041514 candida albicans extract Drugs 0.000 description 5
- 235000011089 carbon dioxide Nutrition 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 230000000813 microbial effect Effects 0.000 description 5
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 5
- 229920001195 polyisoprene Polymers 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000012808 vapor phase Substances 0.000 description 5
- 235000013311 vegetables Nutrition 0.000 description 5
- 239000012138 yeast extract Substances 0.000 description 5
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 4
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 4
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-metylindole Natural products C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 4
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
- 244000043261 Hevea brasiliensis Species 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- 241001520808 Panicum virgatum Species 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 230000001580 bacterial effect Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 4
- 229920003052 natural elastomer Polymers 0.000 description 4
- 229920001194 natural rubber Polymers 0.000 description 4
- 230000036961 partial effect Effects 0.000 description 4
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 229920003051 synthetic elastomer Polymers 0.000 description 4
- 239000005061 synthetic rubber Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- BOGRNZQRTNVZCZ-AATRIKPKSA-N (3e)-3-methylpenta-1,3-diene Chemical compound C\C=C(/C)C=C BOGRNZQRTNVZCZ-AATRIKPKSA-N 0.000 description 3
- BOGRNZQRTNVZCZ-WAYWQWQTSA-N (3z)-3-methylpenta-1,3-diene Chemical compound C\C=C(\C)C=C BOGRNZQRTNVZCZ-WAYWQWQTSA-N 0.000 description 3
- UFLHIIWVXFIJGU-ONEGZZNKSA-N (E)-3-Hexenol Natural products CC\C=C\CCO UFLHIIWVXFIJGU-ONEGZZNKSA-N 0.000 description 3
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 3
- 239000000267 (Z)-hex-3-en-1-ol Substances 0.000 description 3
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 235000019737 Animal fat Nutrition 0.000 description 3
- 101100286286 Dictyostelium discoideum ipi gene Proteins 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- 239000005792 Geraniol Substances 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 240000000111 Saccharum officinarum Species 0.000 description 3
- 235000007201 Saccharum officinarum Nutrition 0.000 description 3
- 244000062793 Sorghum vulgare Species 0.000 description 3
- 150000005215 alkyl ethers Chemical group 0.000 description 3
- 230000003698 anagen phase Effects 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 239000012159 carrier gas Substances 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000000484 citronellol Nutrition 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- 108010060155 deoxyxylulose-5-phosphate synthase Proteins 0.000 description 3
- 229940120503 dihydroxyacetone Drugs 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 101150014423 fni gene Proteins 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 239000007792 gaseous phase Substances 0.000 description 3
- 229940113087 geraniol Drugs 0.000 description 3
- 150000002313 glycerolipids Chemical class 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 239000001307 helium Substances 0.000 description 3
- 229910052734 helium Inorganic materials 0.000 description 3
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 3
- 239000010903 husk Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 101150075592 idi gene Proteins 0.000 description 3
- 235000001510 limonene Nutrition 0.000 description 3
- 229940087305 limonene Drugs 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 239000003550 marker Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 150000003904 phospholipids Chemical class 0.000 description 3
- 239000013612 plasmid Substances 0.000 description 3
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 3
- CBIDRCWHNCKSTO-UHFFFAOYSA-N prenyl diphosphate Chemical compound CC(C)=CCO[P@](O)(=O)OP(O)(O)=O CBIDRCWHNCKSTO-UHFFFAOYSA-N 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 150000003505 terpenes Chemical class 0.000 description 3
- 235000007586 terpenes Nutrition 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- NPFVOOAXDOBMCE-PLNGDYQASA-N (3Z)-hex-3-en-1-yl acetate Chemical compound CC\C=C/CCOC(C)=O NPFVOOAXDOBMCE-PLNGDYQASA-N 0.000 description 2
- FVCDMHWSPLRYAB-UHFFFAOYSA-N 2-ethenyl-2-methyloxirane Chemical compound C=CC1(C)CO1 FVCDMHWSPLRYAB-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- GGFZWCZYTMEWNP-UHFFFAOYSA-N 3-methylbut-1-en-2-yl acetate Chemical compound CC(C)C(=C)OC(C)=O GGFZWCZYTMEWNP-UHFFFAOYSA-N 0.000 description 2
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 2
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical group CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- 241000609240 Ambelania acida Species 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- 241000194032 Enterococcus faecalis Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 240000003183 Manihot esculenta Species 0.000 description 2
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241000219780 Pueraria Species 0.000 description 2
- 241000235070 Saccharomyces Species 0.000 description 2
- 244000082988 Secale cereale Species 0.000 description 2
- 235000007238 Secale cereale Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 235000019714 Triticale Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- 239000010905 bagasse Substances 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 239000006143 cell culture medium Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 229940032049 enterococcus faecalis Drugs 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 238000005373 pervaporation Methods 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 238000002336 sorption--desorption measurement Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- 241000228158 x Triticosecale Species 0.000 description 2
- JEYLKNVLTAPJAF-UHFFFAOYSA-N xi-3-Methyl-3-buten-2-ol Chemical compound CC(O)C(C)=C JEYLKNVLTAPJAF-UHFFFAOYSA-N 0.000 description 2
- MJYQFWSXKFLTAY-OVEQLNGDSA-N (2r,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol;(2r,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O.C1=C(O)C(OC)=CC(C[C@@H](CO)[C@H](CO)CC=2C=C(OC)C(O)=CC=2)=C1 MJYQFWSXKFLTAY-OVEQLNGDSA-N 0.000 description 1
- PMJHHCWVYXUKFD-PLNGDYQASA-N (3z)-penta-1,3-diene Chemical compound C\C=C/C=C PMJHHCWVYXUKFD-PLNGDYQASA-N 0.000 description 1
- XAJOPMVSQIBJCW-SNAWJCMRSA-N (E)-3-penten-1-yne Chemical compound C\C=C\C#C XAJOPMVSQIBJCW-SNAWJCMRSA-N 0.000 description 1
- XIYUIMLQTKODPS-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;acetate Chemical compound CC([O-])=O.CC[N+]=1C=CN(C)C=1 XIYUIMLQTKODPS-UHFFFAOYSA-M 0.000 description 1
- JRZXASDTNSFJBR-UHFFFAOYSA-L 1-ethyl-3-methylimidazol-3-ium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCN1C=C[N+](C)=C1.CCN1C=C[N+](C)=C1 JRZXASDTNSFJBR-UHFFFAOYSA-L 0.000 description 1
- VASPYXGQVWPGAB-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;thiocyanate Chemical compound [S-]C#N.CCN1C=C[N+](C)=C1 VASPYXGQVWPGAB-UHFFFAOYSA-M 0.000 description 1
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 1
- NKRASMXHSQKLHA-UHFFFAOYSA-M 1-hexyl-3-methylimidazolium chloride Chemical compound [Cl-].CCCCCCN1C=C[N+](C)=C1 NKRASMXHSQKLHA-UHFFFAOYSA-M 0.000 description 1
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical group CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 description 1
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
- XAJOPMVSQIBJCW-UHFFFAOYSA-N 3-penten-1-yne Chemical compound CC=CC#C XAJOPMVSQIBJCW-UHFFFAOYSA-N 0.000 description 1
- 241001133760 Acoelorraphe Species 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 240000006439 Aspergillus oryzae Species 0.000 description 1
- 235000002247 Aspergillus oryzae Nutrition 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 244000188595 Brassica sinapistrum Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- 241000221089 Jatropha Species 0.000 description 1
- 240000005561 Musa balbisiana Species 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- SWMKPTYNDGTEMC-UHFFFAOYSA-N N1=CC=CC=C1.C1(CC=CCCC1)O Chemical compound N1=CC=CC=C1.C1(CC=CCCC1)O SWMKPTYNDGTEMC-UHFFFAOYSA-N 0.000 description 1
- 101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 241000520272 Pantoea Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 244000046146 Pueraria lobata Species 0.000 description 1
- 235000010575 Pueraria lobata Nutrition 0.000 description 1
- 229920005683 SIBR Polymers 0.000 description 1
- 102000012479 Serine Proteases Human genes 0.000 description 1
- 108010022999 Serine Proteases Proteins 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 244000040738 Sesamum orientale Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 238000010793 Steam injection (oil industry) Methods 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 241000187432 Streptomyces coelicolor Species 0.000 description 1
- 241000187392 Streptomyces griseus Species 0.000 description 1
- 241000187398 Streptomyces lividans Species 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 1
- 241000520244 Tatumella citrea Species 0.000 description 1
- 241000223259 Trichoderma Species 0.000 description 1
- 241000499912 Trichoderma reesei Species 0.000 description 1
- 239000005862 Whey Substances 0.000 description 1
- 102000007544 Whey Proteins Human genes 0.000 description 1
- 108010046377 Whey Proteins Proteins 0.000 description 1
- 241000235013 Yarrowia Species 0.000 description 1
- 241000235015 Yarrowia lipolytica Species 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 150000000475 acetylene derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 235000021015 bananas Nutrition 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- VLLYOYVKQDKAHN-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene Chemical compound C=CC=C.CC(=C)C=C VLLYOYVKQDKAHN-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012832 cell culture technique Methods 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 210000000349 chromosome Anatomy 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 238000012444 downstream purification process Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- IERUFDDEIBWFQJ-UHFFFAOYSA-N hexane methyl 2-methylpropanoate Chemical compound C(C(C)C)(=O)OC.CCCCCC IERUFDDEIBWFQJ-UHFFFAOYSA-N 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910001872 inorganic gas Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 229920003049 isoprene rubber Polymers 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- LKOBTUTURSPCEE-UHFFFAOYSA-N pent-1-en-4-yne Chemical compound C=CCC#C LKOBTUTURSPCEE-UHFFFAOYSA-N 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000001184 proton transfer reaction mass spectrometry Methods 0.000 description 1
- 230000005258 radioactive decay Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 230000009919 sequestration Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 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
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 238000004448 titration 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
- 239000003981 vehicle Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002916 wood waste Substances 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28814209P | 2009-12-18 | 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 |
|---|---|
| BR112012014736A2 BR112012014736A2 (pt) | 2016-04-19 |
| BR112012014736B1 true BR112012014736B1 (pt) | 2018-09-18 |
Family
ID=44167932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112012014736A BR112012014736B1 (pt) | 2009-12-18 | 2010-12-15 | método para purificação de isopreno a partir de um efluente gasoso do fermentador e composição |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US8569562B2 (enExample) |
| EP (1) | EP2513021A2 (enExample) |
| JP (3) | JP5643838B2 (enExample) |
| CN (1) | CN102884028B (enExample) |
| AR (1) | AR079560A1 (enExample) |
| AU (1) | AU2010331946A1 (enExample) |
| BR (1) | BR112012014736B1 (enExample) |
| CA (1) | CA2783976A1 (enExample) |
| IN (1) | IN2012DN05187A (enExample) |
| SG (1) | SG181605A1 (enExample) |
| TW (1) | TWI481594B (enExample) |
| WO (1) | WO2011075534A2 (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3406722A1 (en) | 2008-07-02 | 2018-11-28 | Danisco US Inc. | Methods for producing isoprene free of c5 hydrocarbons under decoupling conditions and/or safe operating ranges |
| US8324442B2 (en) | 2009-03-03 | 2012-12-04 | Amyris, Inc. | Microbial derived isoprene and methods for making the same |
| TWI427149B (zh) * | 2009-06-17 | 2014-02-21 | Danisco Us Inc | 使用ｄｘｐ及ｍｖａ途徑之改良之異戊二烯製造 |
| 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 |
| BR112012014736B1 (pt) | 2009-12-18 | 2018-09-18 | Danisco Us Inc | método para purificação de isopreno a partir de um efluente gasoso do fermentador e composição |
| JP5855576B2 (ja) * | 2009-12-22 | 2016-02-09 | ダニスコ・ユーエス・インク | イソプレンガスの生成量を増大させるための膜バイオリアクター |
| WO2011160081A1 (en) | 2010-06-17 | 2011-12-22 | Danisco Us Inc. | Fuel compositions comprising isoprene derivatives |
| WO2012019169A1 (en) | 2010-08-06 | 2012-02-09 | Danisco Us Inc. | Production of isoprene under neutral ph conditions |
| BR112013010551A8 (pt) | 2010-10-27 | 2018-07-03 | Danisco Us Inc | variantes de isopreno sintase para produção aprimorada de isopreno |
| US8691541B2 (en) | 2010-12-22 | 2014-04-08 | Danisco Us Inc. | Biological production of pentose sugars using recombinant cells |
| CN103476926A (zh) | 2010-12-22 | 2013-12-25 | 丹尼斯科美国公司 | 使用两种类型的ispg酶改善异戊二烯产量的组合物和方法 |
| BR112013027555A2 (pt) | 2011-04-29 | 2021-08-10 | Danisco Us Inc. | células recombinantes capazes de maior produção de isopreno, mevalonato e isoprenoides e método para produzir isopreno, mevalonato e isoprenoides |
| EP2702139A1 (en) | 2011-04-29 | 2014-03-05 | Danisco US Inc. | Production of mevalonate, isoprene, and isoprenoids using genes encoding polypeptides having thiolase, hmg-coa synthase and hmg-coa reductase enzymatic activities |
| WO2013022799A1 (en) | 2011-08-05 | 2013-02-14 | Danisco Us Inc. | PRODUCTION OF ISOPRENOIDS UNDER NEUTRAL pH CONDITIONS |
| JP6420147B2 (ja) | 2011-10-07 | 2018-11-07 | ダニスコ・ユーエス・インク | メバロン酸、イソプレノイド前駆体、及びイソプレンの産生におけるホスホケトラーゼの使用 |
| CA2853125A1 (en) | 2011-10-27 | 2013-05-02 | The Goodyear Tire & Rubber Company | 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) |
| US8895277B2 (en) | 2012-05-02 | 2014-11-25 | Danisco Us Inc. | Legume isoprene synthase for production of isoprene |
| 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 |
| 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 |
| US9914071B2 (en) * | 2013-02-07 | 2018-03-13 | Braskem S.A. | Systems and methods for separating and purifying butadiene |
| 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 |
| CN105102624B (zh) | 2013-03-29 | 2019-11-01 | 味之素株式会社 | 用于收集发酵气体中含有的异戊二烯的方法及用于生产纯化的异戊二烯的方法 |
| WO2014169144A2 (en) | 2013-04-10 | 2014-10-16 | Danisco Us Inc. | Phosphoketolases foe improved production of acetyl coenzyme a-derived metabolites, isoprene, isoprenoid precurosors, and isoprenoids |
| 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 |
| DK3107993T3 (da) | 2014-02-20 | 2020-11-23 | Danisco Us Inc | Rekombinante mikroorganismer til forbedret fremstilling af mevalonat, isopren, isoprenoide forløbere, isoprenoider og acetyl-coa-afledte produkter |
| 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 |
| US12350968B2 (en) | 2022-09-19 | 2025-07-08 | The Goodyear Tire & Rubber Company | Sustainable tire |
| WO2026010860A1 (en) | 2024-07-02 | 2026-01-08 | Bp Corporation North America Inc. | Recombinant microorganisms for isoprene production |
Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1344713A (en) | 1915-12-02 | 1920-06-29 | Westinghouse Electric & Mfg Co | Reactance-coil |
| GB819188A (en) * | 1956-05-03 | 1959-09-02 | Gulf Research Development Co | Purifying isoprene by distillation |
| US3146278A (en) * | 1958-04-29 | 1964-08-25 | British Hydrocarbon Chem Ltd | Production of conjugated diolefins |
| GB1025432A (en) | 1963-05-13 | 1966-04-06 | Rikagaku Kenkyusho | Process for producing isoprene |
| US3510405A (en) * | 1967-11-11 | 1970-05-05 | Nippon Zeon Co | Isoprene purification process |
| US3621072A (en) | 1967-12-23 | 1971-11-16 | Sumitomo Chemical Co | Process for producing isoprene |
| DE1793254A1 (de) | 1968-08-23 | 1971-12-16 | Bayer Ag | Verfahren zur Gewinnung von Cyclopenten,Isopren und einem Diolefinstrom aus C?-Crackbenzinschnitten |
| JPS493962B1 (enExample) | 1969-08-02 | 1974-01-29 | ||
| US3574780A (en) * | 1969-08-08 | 1971-04-13 | Sumitomo Chemical Co | Method for producing isoprene |
| US3972955A (en) | 1973-09-22 | 1976-08-03 | Bayer Aktiengesellschaft | Process for preparation of isoprene |
| NL7409855A (nl) | 1974-07-22 | 1976-01-26 | Stamicarbon | Werkwijze voor de bereiding van isopreen. |
| US4000209A (en) | 1975-11-05 | 1976-12-28 | Monsanto Company | Isoprene production and catalyst therefor |
| US4067923A (en) | 1976-01-21 | 1978-01-10 | Vladimir Alexandrovich Belyaev | Process for producing isoprene |
| JPS6021125B2 (ja) | 1976-12-20 | 1985-05-25 | ジェイエスアール株式会社 | イソプレンの精製法 |
| JPS58222037A (ja) * | 1982-06-18 | 1983-12-23 | Japan Synthetic Rubber Co Ltd | １，３−ブタジエンの回収方法 |
| US4511751A (en) * | 1982-10-14 | 1985-04-16 | Kuraray Company, Ltd. | Process for producing isoprene |
| DE3338269A1 (de) | 1983-10-21 | 1985-05-02 | Basf Ag, 6700 Ludwigshafen | Verfahren zur gewinnung von isopren aus einem c(pfeil abwaerts)5(pfeil abwaerts)-kohlenwasserstoffgemisch |
| GB8407828D0 (en) * | 1984-03-27 | 1984-05-02 | Ontario Research Foundation | In situ preparation |
| US4570029A (en) * | 1985-03-04 | 1986-02-11 | Uop Inc. | Process for separating isoprene |
| US5035794A (en) | 1985-12-27 | 1991-07-30 | Exxon Chemical Patents Inc. | Isoprene recovery in the butyl rubber process |
| US5177290A (en) | 1991-01-10 | 1993-01-05 | Exxon Chemical Patents Inc. | Isoprene process |
| US5849970A (en) * | 1995-06-23 | 1998-12-15 | The Regents Of The University Of Colorado | Materials and methods for the bacterial production of isoprene |
| EP0955363A3 (en) | 1998-05-06 | 2004-01-28 | F. Hoffmann-La Roche Ag | Dna sequences encoding enzymes involved in production of isoprenoids |
| TWI250210B (en) | 1998-05-06 | 2006-03-01 | Dsm Ip Assets Bv | An isolated DNA sequence coding for an enzyme involved in the mevalonate pathway or the pathway from isopentenyl pyrophosphate to farnesyl pyrophosphate |
| US6500970B1 (en) * | 2001-07-20 | 2002-12-31 | Eastman Chemical Company | Recovery and purification of 3,4-epoxy-1-butene using high-boiling solvents |
| CA2501574C (en) | 2002-10-04 | 2013-12-03 | E. I. Du Pont De Nemours And Company | Process for the biological production of 1,3-propanediol with high yield |
| FR2850101B1 (fr) | 2003-01-22 | 2007-03-02 | Michelin Soc Tech | Procede d'obtention d'une coupe c5 "fcc" enrichie en isoprene et polymerisation selective de l'isoprene a partir de cette coupe |
| EP1614671B1 (en) * | 2003-03-31 | 2015-08-19 | Kuraray Co., Ltd. | Process for producing isoprene |
| US6987152B1 (en) | 2005-01-11 | 2006-01-17 | Univation Technologies, Llc | Feed purification at ambient temperature |
| US7442233B2 (en) * | 2005-07-06 | 2008-10-28 | Basf Catalysts Llc | Integrated heavy hydrocarbon removal, amine treating and dehydration |
| CN100410230C (zh) | 2006-05-17 | 2008-08-13 | 绍兴文理学院 | 1-氯-2-甲基-4-烃酰氧基-2-丁烯制备方法 |
| US7659097B2 (en) | 2006-05-26 | 2010-02-09 | Amyris Biotechnologies, Inc. | Production of isoprenoids |
| US7947478B2 (en) * | 2006-06-29 | 2011-05-24 | The Regents Of The University Of California | Short chain volatile hydrocarbon production using genetically engineered microalgae, cyanobacteria or bacteria |
| CN101244976B (zh) * | 2007-02-15 | 2011-05-04 | 中国石油化工股份有限公司 | 一种制取聚合级异戊二烯的方法 |
| CN101104573B (zh) * | 2007-07-19 | 2010-10-06 | 中国石油化工集团公司 | 组合精馏分离异戊二烯的方法 |
| JP6049982B2 (ja) | 2007-12-13 | 2016-12-21 | ダニスコ・ユーエス・インク | イソプレンを産出する組成物及び方法 |
| SG167485A1 (en) * | 2008-06-30 | 2011-01-28 | Danisco Us Inc | Polymers of isoprene from renewable resources |
| EP3406722A1 (en) | 2008-07-02 | 2018-11-28 | Danisco US Inc. | Methods for producing isoprene free of c5 hydrocarbons under decoupling conditions and/or safe operating ranges |
| JP5787756B2 (ja) | 2008-07-04 | 2015-09-30 | フィリップ マルリエ | ３−ヒドロキシアルカン酸の酵素的脱炭酸によるアルケンの製造法 |
| US7909913B2 (en) | 2008-07-17 | 2011-03-22 | Air Products And Chemicals, Inc. | Gas purification by adsorption of hydrogen sulfide |
| WO2010031062A1 (en) * | 2008-09-15 | 2010-03-18 | Danisco Us Inc. | Increased isoprene production using the archaeal lower mevalonate pathway |
| US20100184178A1 (en) * | 2008-09-15 | 2010-07-22 | Zachary Quinn Beck | Increased isoprene production using mevalonate kinase and isoprene synthase |
| ZA201102109B (en) * | 2008-09-15 | 2013-10-30 | Goodyear Tire & Rubber | Conversion of prenyl derivatives to isoprene |
| EP2344629B1 (en) * | 2008-09-15 | 2018-01-24 | Danisco US Inc. | Systems using cell culture for production of isoprene |
| WO2010031068A1 (en) | 2008-09-15 | 2010-03-18 | Danisco Us Inc. | Reduction of carbon dioxide emission during isoprene production by fermentation |
| US20100099932A1 (en) * | 2008-10-21 | 2010-04-22 | Ecoprene Llc | Isoprene Compositions and Methods of Use |
| MY171270A (en) | 2008-12-30 | 2019-10-07 | Goodyear Tire & Rubber | Methods of producing isoprene and a co-product |
| BRPI1008287A2 (pt) * | 2009-02-24 | 2016-03-15 | Gevo Inc | métodos de preparação de butadieno e isopreno renováveis |
| US8324442B2 (en) | 2009-03-03 | 2012-12-04 | Amyris, Inc. | Microbial derived isoprene and methods for making the same |
| 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 |
| TWI427149B (zh) * | 2009-06-17 | 2014-02-21 | Danisco Us Inc | 使用ｄｘｐ及ｍｖａ途徑之改良之異戊二烯製造 |
| TW201120213A (en) * | 2009-06-17 | 2011-06-16 | Danisco Us Inc | Polymerization of isoprene from renewable resources |
| US8178736B2 (en) * | 2009-08-07 | 2012-05-15 | Lummus Technology Inc. | Process and system for the production of isoprene |
| BR112012014736B1 (pt) * | 2009-12-18 | 2018-09-18 | Danisco Us Inc | método para purificação de isopreno a partir de um efluente gasoso do fermentador e composição |
-
2010
- 2010-12-15 BR BR112012014736A patent/BR112012014736B1/pt not_active IP Right Cessation
- 2010-12-15 IN IN5187DEN2012 patent/IN2012DN05187A/en unknown
- 2010-12-15 WO PCT/US2010/060552 patent/WO2011075534A2/en not_active Ceased
- 2010-12-15 CN CN201080064167.4A patent/CN102884028B/zh not_active Expired - Fee Related
- 2010-12-15 AU AU2010331946A patent/AU2010331946A1/en not_active Abandoned
- 2010-12-15 SG SG2012042511A patent/SG181605A1/en unknown
- 2010-12-15 JP JP2012544763A patent/JP5643838B2/ja not_active Expired - Fee Related
- 2010-12-15 US US12/969,440 patent/US8569562B2/en active Active
- 2010-12-15 CA CA2783976A patent/CA2783976A1/en not_active Abandoned
- 2010-12-15 EP EP10799184A patent/EP2513021A2/en not_active Withdrawn
- 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
-
2016
- 2016-11-18 JP JP2016225310A patent/JP2017081924A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AR079560A1 (es) | 2012-02-01 |
| JP2015007119A (ja) | 2015-01-15 |
| IN2012DN05187A (enExample) | 2015-10-23 |
| AU2010331946A2 (en) | 2012-07-19 |
| CN102884028B (zh) | 2015-08-19 |
| US20150274615A1 (en) | 2015-10-01 |
| TW201139367A (en) | 2011-11-16 |
| US8569562B2 (en) | 2013-10-29 |
| CA2783976A1 (en) | 2011-06-23 |
| US20140187839A1 (en) | 2014-07-03 |
| US9751820B2 (en) | 2017-09-05 |
| JP2013514375A (ja) | 2013-04-25 |
| SG181605A1 (en) | 2012-07-30 |
| JP5643838B2 (ja) | 2014-12-17 |
| EP2513021A2 (en) | 2012-10-24 |
| WO2011075534A3 (en) | 2012-04-12 |
| CN102884028A (zh) | 2013-01-16 |
| WO2011075534A2 (en) | 2011-06-23 |
| JP2017081924A (ja) | 2017-05-18 |
| JP6378013B2 (ja) | 2018-08-22 |
| US20110178261A1 (en) | 2011-07-21 |
| AU2010331946A1 (en) | 2012-06-28 |
| BR112012014736A2 (pt) | 2016-04-19 |
| TWI481594B (zh) | 2015-04-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BR112012014736B1 (pt) | método para purificação de isopreno a partir de um efluente gasoso do fermentador e composição | |
| Offeman et al. | Extraction of ethanol with higher alcohol solvents and their toxicity to yeast | |
| Stoffers et al. | Continuous multi-stage extraction of n-butanol from aqueous solutions with 1-hexyl-3-methylimidazolium tetracyanoborate | |
| AU2011215977A1 (en) | Process to remove product alcohol from a fermentation by vaporization under vacuum | |
| MX2012000608A (es) | Recuperacion de butanol a partir de una mezcla de butanol, agua y un extractante organico. | |
| MX2012000616A (es) | Recuperacion de butanol a partir de una mezcla de butanol, agua y un extractante organico. | |
| US8658845B2 (en) | Process and adsorbent for separating ethanol and associated oxygenates from a biofermentation system | |
| US20150224420A1 (en) | Processes for the production of plural anhydrous alcohols | |
| CN101148390A (zh) | 变压吸附提取高纯度正己烷产品工艺 | |
| BRPI0711992A2 (pt) | processo para a fabricaÇço de pelo menos um dibutil Éter | |
| JP2018070465A (ja) | 有機組成物、有機組成物の製造方法および燃料 | |
| Qureshi et al. | Recovery of butanol from Clostridium beijerinckii P260 fermentation broth by supercritical CO2 extraction | |
| Pérez-Bibbins et al. | Hybrid in situ product recovery technique applied to (A) IBE fermentation | |
| CN112723976A (zh) | 一种金属有机骨架材料回收炼厂干气用作乙烯原料的方法和系统 | |
| CN103620044B (zh) | 包括通过异佛尔酮吸收产物的abe发酵方法 | |
| US9914071B2 (en) | Systems and methods for separating and purifying butadiene | |
| US20160289567A1 (en) | Processing Carbonaceous Materials | |
| JPWO2016080531A1 (ja) | ブタノールの濃縮脱水方法 | |
| US9713789B2 (en) | Treatment of alcohol compositions | |
| Machida et al. | Journal of Advanced Chemical Engineering | |
| WO2015193553A1 (en) | Method of recovering butanol | |
| Qureshia et al. | Recovery of butanol from Clostridium beijerinckii P260 fermentation broth by supercritical CO | |
| WO2015097082A1 (en) | Treatment of alcohol compositions |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B06A | Patent application procedure suspended [chapter 6.1 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 15/12/2010, OBSERVADAS AS CONDICOES LEGAIS. |
|
| B21F | Lapse acc. art. 78, item iv - on non-payment of the annual fees in time |
Free format text: REFERENTE A 11A ANUIDADE. |
|
| B24J | Lapse because of non-payment of annual fees (definitively: art 78 iv lpi, resolution 113/2013 art. 12) |
Free format text: EM VIRTUDE DA EXTINCAO PUBLICADA NA RPI 2649 DE 13-10-2021 E CONSIDERANDO AUSENCIA DE MANIFESTACAO DENTRO DOS PRAZOS LEGAIS, INFORMO QUE CABE SER MANTIDA A EXTINCAO DA PATENTE E SEUS CERTIFICADOS, CONFORME O DISPOSTO NO ARTIGO 12, DA RESOLUCAO 113/2013. |