CA3139043C - Device and method of obtaining diols and other chemicals using decarboxylation - Google Patents
Device and method of obtaining diols and other chemicals using decarboxylation Download PDFInfo
- Publication number
- CA3139043C CA3139043C CA3139043A CA3139043A CA3139043C CA 3139043 C CA3139043 C CA 3139043C CA 3139043 A CA3139043 A CA 3139043A CA 3139043 A CA3139043 A CA 3139043A CA 3139043 C CA3139043 C CA 3139043C
- Authority
- CA
- Canada
- Prior art keywords
- carboxylic acid
- anolyte
- alkali metal
- decarboxylation
- solvent
- 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.)
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- 238000000034 method Methods 0.000 title claims abstract description 66
- 238000006114 decarboxylation reaction Methods 0.000 title claims description 44
- 150000002009 diols Chemical class 0.000 title abstract description 30
- 239000000126 substance Substances 0.000 title abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 33
- 239000002028 Biomass Substances 0.000 claims abstract description 25
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 53
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
- -1 alkali metal salt Chemical class 0.000 claims description 42
- 125000000524 functional group Chemical group 0.000 claims description 26
- 229910052783 alkali metal Inorganic materials 0.000 claims description 20
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 20
- 159000000000 sodium salts Chemical class 0.000 claims description 15
- 238000007254 oxidation reaction Methods 0.000 claims description 14
- 230000003647 oxidation Effects 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 11
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical group CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 claims description 10
- 229940116333 ethyl lactate Drugs 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical group CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 6
- 239000003495 polar organic solvent Substances 0.000 claims description 6
- GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 claims description 5
- 239000002608 ionic liquid Substances 0.000 claims description 5
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 4
- 238000005935 nucleophilic addition reaction Methods 0.000 claims description 4
- 239000001540 sodium lactate Substances 0.000 claims description 4
- 235000011088 sodium lactate Nutrition 0.000 claims description 4
- 229940005581 sodium lactate Drugs 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
- 230000000911 decarboxylating effect Effects 0.000 claims 1
- 238000002848 electrochemical method Methods 0.000 claims 1
- 150000001993 dienes Chemical class 0.000 abstract description 36
- 238000005868 electrolysis reaction Methods 0.000 abstract description 33
- 230000008569 process Effects 0.000 abstract description 27
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 17
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 15
- 239000001301 oxygen Substances 0.000 abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 abstract description 15
- 229930195733 hydrocarbon Natural products 0.000 abstract description 14
- 239000000463 material Substances 0.000 abstract description 9
- 150000001447 alkali salts Chemical class 0.000 abstract description 8
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 53
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 33
- 239000000047 product Substances 0.000 description 29
- 239000012528 membrane Substances 0.000 description 26
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 24
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 20
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
- 239000000178 monomer Substances 0.000 description 18
- 229910002092 carbon dioxide Inorganic materials 0.000 description 17
- 150000002500 ions Chemical class 0.000 description 16
- 230000000670 limiting effect Effects 0.000 description 16
- 239000003513 alkali Substances 0.000 description 15
- 125000001424 substituent group Chemical group 0.000 description 15
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000003792 electrolyte Substances 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 11
- 238000000855 fermentation Methods 0.000 description 11
- 230000004151 fermentation Effects 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 150000007942 carboxylates Chemical class 0.000 description 10
- 239000013013 elastic material Substances 0.000 description 10
- NGSFWBMYFKHRBD-DKWTVANSSA-M sodium;(2s)-2-hydroxypropanoate Chemical compound [Na+].C[C@H](O)C([O-])=O NGSFWBMYFKHRBD-DKWTVANSSA-M 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 9
- 238000004817 gas chromatography Methods 0.000 description 9
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000006576 Kolbe electrolysis reaction Methods 0.000 description 7
- 239000004310 lactic acid Substances 0.000 description 7
- 235000014655 lactic acid Nutrition 0.000 description 7
- 230000037361 pathway Effects 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 230000018044 dehydration Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 238000007127 saponification reaction Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 4
- 238000011088 calibration curve Methods 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 235000013373 food additive Nutrition 0.000 description 4
- 239000002778 food additive Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 229910001415 sodium ion Inorganic materials 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 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 3
- 239000006227 byproduct Substances 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 238000006880 cross-coupling reaction Methods 0.000 description 3
- 238000006356 dehydrogenation reaction Methods 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 235000001727 glucose Nutrition 0.000 description 3
- 238000009815 homocoupling reaction Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000003115 supporting electrolyte Substances 0.000 description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 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 2
- 229930006000 Sucrose Natural products 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MKJXYGKVIBWPFZ-UHFFFAOYSA-L calcium lactate Chemical compound [Ca+2].CC(O)C([O-])=O.CC(O)C([O-])=O MKJXYGKVIBWPFZ-UHFFFAOYSA-L 0.000 description 2
- 239000001527 calcium lactate Substances 0.000 description 2
- 235000011086 calcium lactate Nutrition 0.000 description 2
- 229960002401 calcium lactate Drugs 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000007867 post-reaction treatment Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 2
- AVXDKPABPXSLIZ-UHFFFAOYSA-M sodium;3-hydroxypropanoate Chemical compound [Na+].OCCC([O-])=O AVXDKPABPXSLIZ-UHFFFAOYSA-M 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
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- 239000010936 titanium Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- NWYLBGYCSAJFCB-UHFFFAOYSA-N 6-chloro-1h-pyrazolo[3,4-b]pyridine Chemical compound ClC1=CC=C2C=NNC2=N1 NWYLBGYCSAJFCB-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 229910001030 Iron–nickel alloy Inorganic materials 0.000 description 1
- 238000006612 Kolbe reaction Methods 0.000 description 1
- 238000007065 Kolbe-Schmitt synthesis reaction Methods 0.000 description 1
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- 125000003158 alcohol group Chemical group 0.000 description 1
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- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
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- 229920005610 lignin Polymers 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- WXBOMIKEWRRKBB-UHFFFAOYSA-N rhenium(iv) oxide Chemical compound O=[Re]=O WXBOMIKEWRRKBB-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- PBCFLUZVCVVTBY-UHFFFAOYSA-N tantalum pentoxide Inorganic materials O=[Ta](=O)O[Ta](=O)=O PBCFLUZVCVVTBY-UHFFFAOYSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- WGHUNMFFLAMBJD-UHFFFAOYSA-M tetraethylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CC[N+](CC)(CC)CC WGHUNMFFLAMBJD-UHFFFAOYSA-M 0.000 description 1
- ZCWKIFAQRXNZCH-UHFFFAOYSA-M tetramethylazanium;perchlorate Chemical compound C[N+](C)(C)C.[O-]Cl(=O)(=O)=O ZCWKIFAQRXNZCH-UHFFFAOYSA-M 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B13/00—Diaphragms; Spacing elements
- C25B13/02—Diaphragms; Spacing elements characterised by shape or form
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B1/00—Electrolytic production of inorganic compounds or non-metals
- C25B1/01—Products
- C25B1/02—Hydrogen or oxygen
- C25B1/04—Hydrogen or oxygen by electrolysis of water
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/23—Oxidation
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/29—Coupling reactions
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B9/00—Cells or assemblies of cells; Constructional parts of cells; Assemblies of constructional parts, e.g. electrode-diaphragm assemblies; Process-related cell features
- C25B9/17—Cells comprising dimensionally-stable non-movable electrodes; Assemblies of constructional parts thereof
- C25B9/19—Cells comprising dimensionally-stable non-movable electrodes; Assemblies of constructional parts thereof with diaphragms
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B9/00—Cells or assemblies of cells; Constructional parts of cells; Assemblies of constructional parts, e.g. electrode-diaphragm assemblies; Process-related cell features
- C25B9/70—Assemblies comprising two or more cells
- C25B9/73—Assemblies comprising two or more cells of the filter-press type
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/36—Hydrogen production from non-carbon containing sources, e.g. by water electrolysis
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Metallurgy (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/790,744 | 2013-03-08 | ||
| US13/790,744 US9957622B2 (en) | 2009-07-23 | 2013-03-08 | Device and method of obtaining diols and other chemicals using decarboxylation |
| CA2902997A CA2902997C (en) | 2013-03-08 | 2014-03-07 | Device and method of obtaining diols and other chemicals using decarboxylation |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2902997A Division CA2902997C (en) | 2013-03-08 | 2014-03-07 | Device and method of obtaining diols and other chemicals using decarboxylation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA3139043A1 CA3139043A1 (en) | 2014-09-12 |
| CA3139043C true CA3139043C (en) | 2023-09-19 |
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3139043A Active CA3139043C (en) | 2013-03-08 | 2014-03-07 | Device and method of obtaining diols and other chemicals using decarboxylation |
| CA2902997A Active CA2902997C (en) | 2013-03-08 | 2014-03-07 | Device and method of obtaining diols and other chemicals using decarboxylation |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2902997A Active CA2902997C (en) | 2013-03-08 | 2014-03-07 | Device and method of obtaining diols and other chemicals using decarboxylation |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP2964814B1 (enExample) |
| JP (2) | JP6618805B2 (enExample) |
| KR (1) | KR102311198B1 (enExample) |
| CA (2) | CA3139043C (enExample) |
| WO (1) | WO2014138631A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3139043C (en) * | 2013-03-08 | 2023-09-19 | Enlighten Innovations Inc. | Device and method of obtaining diols and other chemicals using decarboxylation |
| EP3155143B1 (en) * | 2014-06-13 | 2019-12-11 | Enlighten Innovations Inc. | Conversion of carboxylic acids to alpha-olefins |
| CN110016686B (zh) * | 2019-04-08 | 2021-01-15 | 天津大学 | 由混合羧酸电解制备烃类物质的方法 |
| US11826698B2 (en) * | 2019-12-30 | 2023-11-28 | Ffi Ionix Ip, Inc. | Environmental control system utilizing an anion conducting membrane |
| JPWO2022185975A1 (enExample) * | 2021-03-05 | 2022-09-09 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992471A (en) | 1974-08-12 | 1976-11-16 | Uop Inc. | Process for the separation of 1,3-butadiene by selective adsorption on a zeolite adsorbent |
| US4617090A (en) * | 1984-12-20 | 1986-10-14 | The United States Of America As Represented By The United States Department Of Energy | Process for producing peracids from aliphatic hydroxy carboxylic acids |
| JPH0788594B2 (ja) * | 1986-07-31 | 1995-09-27 | 日本メクトロン株式会社 | ヘキサフルオロアセトン水和物の製造法 |
| DE3828848A1 (de) * | 1988-08-25 | 1990-03-01 | Hoechst Ag | Verfahren zur elektrolytischen decarboxylierung von perfluorcarbonsaeuren oder deren loeslichen salzen und anschliessende dimerisierung der dabei entstehenden radikale |
| US5084146A (en) * | 1990-04-09 | 1992-01-28 | E. I. Du Pont De Nemours And Company | Method for preparing perfluoropolyethers |
| GB9519975D0 (en) * | 1995-09-28 | 1995-11-29 | Davy Process Techn Ltd | Process |
| JP5314246B2 (ja) * | 2003-12-11 | 2013-10-16 | アメリカン パシフィック コーポレイション | イオン伝導性セラミックの固体膜を用いたアルカリアルコラートを生成するための電気分解による方法 |
| US7955489B2 (en) * | 2006-02-08 | 2011-06-07 | Dynamic Food Ingredients Corporation | Methods for the electrolytic production of erythrose or erythritol |
| TW201100355A (en) * | 2009-02-23 | 2011-01-01 | Maria Flytzani-Stephanopoulos | Converting biomass to gaseous fuel hydrocarbons |
| US8518680B2 (en) * | 2009-04-17 | 2013-08-27 | The United States Of America, As Represented By The Secretary Of Agriculture | Biological/electrolytic conversion of biomass to hydrocarbons |
| WO2011011537A2 (en) * | 2009-07-23 | 2011-01-27 | Ceramatec, Inc. | Method of producing coupled radical products from biomass |
| US9051656B2 (en) * | 2009-07-23 | 2015-06-09 | Ceramatec, Inc. | Electrochemical synthesis of aryl-alkyl surfacant precursor |
| EP2561123B1 (en) * | 2010-04-23 | 2018-09-12 | Field Upgrading Limited | Electrochemical synthesis of aryl-alkyl surfactant precursor |
| ES2685783T3 (es) * | 2010-08-05 | 2018-10-11 | Field Upgrading Limited | Método y dispositivo para la producción de ácido carboxílico |
| JP5897039B2 (ja) * | 2011-01-25 | 2016-03-30 | セラマテック・インク | バイオマスから誘導された化学物質からの燃料の製造 |
| CN102719844A (zh) * | 2012-07-03 | 2012-10-10 | 北京化工大学 | 一种苯甲醇氧化制苯甲醛的方法 |
| CA3139043C (en) * | 2013-03-08 | 2023-09-19 | Enlighten Innovations Inc. | Device and method of obtaining diols and other chemicals using decarboxylation |
-
2014
- 2014-03-07 CA CA3139043A patent/CA3139043C/en active Active
- 2014-03-07 JP JP2015561725A patent/JP6618805B2/ja not_active Expired - Fee Related
- 2014-03-07 KR KR1020157027472A patent/KR102311198B1/ko active Active
- 2014-03-07 CA CA2902997A patent/CA2902997C/en active Active
- 2014-03-07 EP EP14760889.7A patent/EP2964814B1/en active Active
- 2014-03-07 WO PCT/US2014/021927 patent/WO2014138631A1/en not_active Ceased
-
2019
- 2019-11-12 JP JP2019204799A patent/JP6894487B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2964814A1 (en) | 2016-01-13 |
| CA2902997C (en) | 2022-01-04 |
| KR20150126902A (ko) | 2015-11-13 |
| EP2964814B1 (en) | 2020-08-19 |
| CA3139043A1 (en) | 2014-09-12 |
| JP2016516128A (ja) | 2016-06-02 |
| CA2902997A1 (en) | 2014-09-12 |
| JP6894487B2 (ja) | 2021-06-30 |
| EP2964814A4 (en) | 2016-10-19 |
| JP2020023578A (ja) | 2020-02-13 |
| JP6618805B2 (ja) | 2019-12-11 |
| KR102311198B1 (ko) | 2021-10-13 |
| WO2014138631A1 (en) | 2014-09-12 |
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