DK2812304T3 - Carboxylatsyrning - Google Patents
Carboxylatsyrning Download PDFInfo
- Publication number
- DK2812304T3 DK2812304T3 DK13705419.3T DK13705419T DK2812304T3 DK 2812304 T3 DK2812304 T3 DK 2812304T3 DK 13705419 T DK13705419 T DK 13705419T DK 2812304 T3 DK2812304 T3 DK 2812304T3
- Authority
- DK
- Denmark
- Prior art keywords
- magnesium
- carboxylic acid
- carboxylate
- liquid
- solution
- Prior art date
Links
- 150000007942 carboxylates Chemical class 0.000 title claims abstract description 34
- 239000002253 acid Substances 0.000 title description 17
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims abstract description 267
- 229910001629 magnesium chloride Inorganic materials 0.000 claims abstract description 133
- 239000007788 liquid Substances 0.000 claims abstract description 126
- 238000000034 method Methods 0.000 claims abstract description 105
- 239000007789 gas Substances 0.000 claims abstract description 104
- -1 carboxylate salt Chemical class 0.000 claims abstract description 72
- 239000011777 magnesium Substances 0.000 claims abstract description 72
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 71
- 230000020477 pH reduction Effects 0.000 claims abstract description 56
- 238000005979 thermal decomposition reaction Methods 0.000 claims abstract description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 37
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 35
- 239000000395 magnesium oxide Substances 0.000 claims abstract description 30
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims abstract description 30
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000007787 solid Substances 0.000 claims abstract description 19
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 138
- 229910001868 water Inorganic materials 0.000 claims description 135
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 134
- 238000001556 precipitation Methods 0.000 claims description 80
- 238000000855 fermentation Methods 0.000 claims description 68
- 230000004151 fermentation Effects 0.000 claims description 66
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 24
- 239000000347 magnesium hydroxide Substances 0.000 claims description 24
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 21
- 238000000926 separation method Methods 0.000 claims description 19
- 239000000725 suspension Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000000605 extraction Methods 0.000 claims description 13
- 230000003472 neutralizing effect Effects 0.000 claims description 13
- 239000011261 inert gas Substances 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 11
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 244000005700 microbiome Species 0.000 claims description 9
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 5
- ALRHLSYJTWAHJZ-UHFFFAOYSA-M 3-hydroxypropionate Chemical compound OCCC([O-])=O ALRHLSYJTWAHJZ-UHFFFAOYSA-M 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 claims description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 3
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 3
- 239000001095 magnesium carbonate Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims description 2
- SJZRECIVHVDYJC-UHFFFAOYSA-M 4-hydroxybutyrate Chemical compound OCCCC([O-])=O SJZRECIVHVDYJC-UHFFFAOYSA-M 0.000 claims description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-M 4-oxopentanoate Chemical compound CC(=O)CCC([O-])=O JOOXCMJARBKPKM-UHFFFAOYSA-M 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 claims description 2
- 150000003841 chloride salts Chemical class 0.000 claims description 2
- 229940058352 levulinate Drugs 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- DNXDYHALMANNEJ-UHFFFAOYSA-N furan-2,3-dicarboxylic acid Chemical compound OC(=O)C=1C=COC=1C(O)=O DNXDYHALMANNEJ-UHFFFAOYSA-N 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 6
- 239000000243 solution Substances 0.000 description 139
- 229940091250 magnesium supplement Drugs 0.000 description 65
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 32
- 238000010521 absorption reaction Methods 0.000 description 23
- 235000012254 magnesium hydroxide Nutrition 0.000 description 20
- 238000001179 sorption measurement Methods 0.000 description 18
- 230000001965 increasing effect Effects 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 16
- OKUCEQDKBKYEJY-UHFFFAOYSA-N tert-butyl 3-(methylamino)pyrrolidine-1-carboxylate Chemical compound CNC1CCN(C(=O)OC(C)(C)C)C1 OKUCEQDKBKYEJY-UHFFFAOYSA-N 0.000 description 16
- 238000001704 evaporation Methods 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 12
- 239000001384 succinic acid Substances 0.000 description 12
- 235000011044 succinic acid Nutrition 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 150000002576 ketones Chemical class 0.000 description 11
- 230000008020 evaporation Effects 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 8
- 239000004310 lactic acid Substances 0.000 description 8
- 235000014655 lactic acid Nutrition 0.000 description 8
- 238000005185 salting out Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 159000000003 magnesium salts Chemical class 0.000 description 6
- 230000001376 precipitating effect Effects 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000002028 Biomass Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- OVGXLJDWSLQDRT-UHFFFAOYSA-L magnesium lactate Chemical compound [Mg+2].CC(O)C([O-])=O.CC(O)C([O-])=O OVGXLJDWSLQDRT-UHFFFAOYSA-L 0.000 description 5
- 239000000626 magnesium lactate Substances 0.000 description 5
- 235000015229 magnesium lactate Nutrition 0.000 description 5
- 229960004658 magnesium lactate Drugs 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 238000010899 nucleation Methods 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-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
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000012296 anti-solvent Substances 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
- 235000014633 carbohydrates Nutrition 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000012527 feed solution Substances 0.000 description 4
- 230000006911 nucleation Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000356 contaminant Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- AOHAPDDBNAPPIN-UHFFFAOYSA-N 3-Methoxy-4,5-methylenedioxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC2=C1OCO2 AOHAPDDBNAPPIN-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910017974 NH40H Inorganic materials 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 239000004063 acid-resistant material Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 1
- 239000002370 magnesium bicarbonate Substances 0.000 description 1
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 description 1
- 235000014824 magnesium bicarbonate Nutrition 0.000 description 1
- 229960005336 magnesium citrate Drugs 0.000 description 1
- 239000004337 magnesium citrate Substances 0.000 description 1
- 235000002538 magnesium citrate Nutrition 0.000 description 1
- QUIOHQITLKCGNW-TYYBGVCCSA-L magnesium;(e)-but-2-enedioate Chemical compound [Mg+2].[O-]C(=O)\C=C\C([O-])=O QUIOHQITLKCGNW-TYYBGVCCSA-L 0.000 description 1
- KMGUUVHVXYFYQN-UHFFFAOYSA-L magnesium;2-methylidenebutanedioate Chemical compound [Mg+2].[O-]C(=O)CC(=C)C([O-])=O KMGUUVHVXYFYQN-UHFFFAOYSA-L 0.000 description 1
- QXNFATVALXHNRJ-UHFFFAOYSA-L magnesium;hexanedioate Chemical compound [Mg+2].[O-]C(=O)CCCCC([O-])=O QXNFATVALXHNRJ-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003890 succinate salts Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- PLSARIKBYIPYPF-UHFFFAOYSA-H trimagnesium dicitrate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O PLSARIKBYIPYPF-UHFFFAOYSA-H 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/122—Propionic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/10—Succinic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/14—Adipic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C07C57/04—Acrylic acid; Methacrylic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/08—Lactic acid
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- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/56—Lactic acid
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- 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
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Claims (13)
1. Fremgangsmåde til fremstilling af en carboxylsyre ved syrning af en flydende tilførsel omfattende et carboxylatsalt, hvilken fremgangsmåde omfatter trinnene at - tilvejebringe en flydende tilførsel omfattende magnesiumcarboxylat, den flydende tilførsel har en temperatur på 60-120°C; - tilvejebringe en gastilførsel omfattende gasformig hydrogenchlorid ved at underkaste en vandig væske omfattende magnesiumchlorid for et termisk sønderdelingstrin hvor den vandige væske omfattende magnesiumchlorid underkastes til en temperatur på mindst 300°C, derved sønderdele magnesiumchlorid til magnesiumoxid og hydrogenchlorid, derved opnås et faststof omfattende magnesiumoxid og en gas omfattende gasformig hydrogenchlorid, gastilførslen har et hydrogenchlorid til vand vægtforhold på mellem 1:10 og 1:4; og - syrning af carboxylat til carboxylsyre ved at bringe den flydende tilførsel i kontakt med gastilførslen, derved danne en flydende udstrømning omfattende carboxylsyre og magnesiumchlorid, fremgangsmåden omfatter yderligere et separationstrin, hvor carboxylsyren og chloridsaltet til stede i den flydende udstrømning skilles fra hinanden, derved opnås en carboxylsyreproduktstrøm og en magnesiumchloridopløsning eller -suspension, hvor magnesiumchloridopløsningen eller -suspensionen tilvejebringes som væske omfattende magnesiumchlorid til det termiske sønderdelingstrin.
2. Fremgangsmåde ifølge krav 1, hvor hydrogenchloridet til vand vægtforholdet i gastilførslen er mellem 1:5 og 1:4.
3. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, hvor separationstrinnet omfatter et ekstraktionstrin eller et udfældningstrin.
4. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, hvor den flydende tilførsel har en temperatur på 80-120°C under atmosfærisk tryk.
5. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, hvor temperaturen af den flydende tilførsel er 1-50°C, fortrinsvis 3-25°C højere end temperaturen af gastilførslen.
6. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, hvor gastilførslen yderligere omfatter mindst 25 vægtprocent inert gas, fortrinsvis en inert gas valgt fra gruppen bestående af N2, O2, CO2 og blandinger deraf.
7. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, hvor gastilførslen omfatter mindst 2 vægtprocent hydrogenchlorid.
8. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, hvor carboxylat er valgt fra gruppen bestående af lactat, succinat, propionat, 3-hydroxypropionat, hydroxybutyrat, citrat, fumarat, itaconat, adipat, acrylat, levulinat, maleat, 2,5-furandicarboxylat, fedtacylat og lactylat og/eller blandinger deraf, fortrinsvis fra gruppen bestående af lactat, succinat, propionat, 2,5-furandicarboxylat og 3-hydroxypropionat, især fra gruppen af lactat og succinat.
9. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, hvor fremgangsmåden yderligere omfatter trinnet at fremstille den flydende tilførsel ved et fermentationstrin.
10. Fremgangsmåde ifølge krav 9, hvor et koncentrationstrin udføres efter fermentationstrinnet og før syrningstrinnet, resulterer i en flydende tilførsel med en temperatur på mindst 60°C.
11. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, hvor magnesiumoxid stammende fra det termiske sønderdelingstrin hydreres med vand for at danne en magnesiumhydroxidsuspension, hvor magnesiumhydroxidet tilvejebringes som neutraliseringsmiddel til en fermentation, eventuelt efter omdannelse til magnesiumcarbonat.
12. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, der er en integreret fremgangsmåde omfattende trinnene at - underkaste en carbonkilde for et fermentationstrin for at danne carboxylsyre, hvilket fermentationstrin omfatter trinnene til fermentering af en carbonkilde ved hjælp af en mikroorganisme i fermentationsbouillon for at danne carboxylsyre og neutralisere mindst del af carboxylsyren ved tilsætning afen magnesiumbase valgt fra magnesiumoxid og magnesiumhydroxid, derved opnås en magnesiumcarboxylat, - underkaste magnesiumcarboxylatet for et syrningstrin hvor magnesiumcarboxylatet bringes i kontakt med en gasstrøm omfattende gasformig HCI for at danne en flydende udstrømning omfattende carboxylsyre og magnesiumchlorid, - underkaste den flydende udstrømning omfattende carboxylsyre og magnesiumchlorid for et separationstrin for at give en carboxylsyre og en væske omfattende magnesiumchlorid, - underkaste den vandige væske omfattende magnesiumchlorid for en temperatur på mindst 300 °C, derved sønderdele magnesiumchlorid til magnesiumoxid og hydrogenchlorid, derved opnås et faststof omfattende magnesiumoxid og en gas omfattende gasformig hydrogenchlorid, hvilken gas tilvejebringes til syrningstrinnet, - tilvejebringe magnesiumoxidet som neutraliseringsmiddel til fermentationstrinnet, enten som sådan eller efter omdannelse til magnesiumhydroxid.
13. Fremgangsmåde ifølge krav 12, hvor et koncentrationstrin udføres efter fermentationstrinnet og før syrningstrinnet, resulterer i en flydende tilførsel med en temperatur på mindst 60°C.
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| EP12154534 | 2012-02-08 | ||
| PCT/EP2013/052525 WO2013117687A1 (en) | 2012-02-08 | 2013-02-08 | Carboxylate acidification |
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| DK2812304T3 true DK2812304T3 (da) | 2018-06-25 |
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| JP (2) | JP2015508758A (da) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| PL2744747T3 (pl) | 2011-08-16 | 2021-06-28 | Purac Biochem B.V. | Odzyskiwanie kwasu karboksylowego z ich soli magnezowych poprzez wytrącanie z zastosowaniem kwasu chlorowodorowego, do zastosowania w pracy z bulionem fermentacyjnym |
| GB201315929D0 (en) * | 2013-09-06 | 2013-10-23 | Plaxica Ltd | Lactate production process |
| HUE063358T2 (hu) * | 2014-04-01 | 2024-01-28 | Purac Biochem Bv | Magnézium-klorid hõbontása |
| FI3174988T3 (fi) | 2014-07-28 | 2022-12-15 | Menetelmä maitohapon valmistamiseksi | |
| WO2016016235A1 (en) * | 2014-07-28 | 2016-02-04 | Purac Biochem Bv | Preparation of lactic acid and/or a lactate salt from lignocellulosic material by separate saccharification and fermentation steps |
| US10093551B2 (en) * | 2014-09-23 | 2018-10-09 | Basf Se | Process and plant for treatment of secondary components obtained in acrolein and/or (meth)acrylic acid production |
| ES2898857T3 (es) * | 2015-03-17 | 2022-03-09 | Purac Biochem Bv | Procedimiento de fabricación del ácido furan-2,5-dicarboxílico (FDCA) a partir de una solución salina |
| EP3124434A1 (en) | 2015-07-31 | 2017-02-01 | PURAC Biochem BV | Method for providing a succinic acid solution |
| JP6667646B2 (ja) * | 2016-01-19 | 2020-03-18 | ピュラック バイオケム ビー． ブイ． | 塩化マグネシウム溶液の改良処理方法及びカルボン酸の製造方法 |
| ES2963382T3 (es) | 2019-06-12 | 2024-03-26 | Nouryon Chemicals Int Bv | Proceso para la producción de peróxidos de diacilo |
| CN113924282B (zh) * | 2019-06-12 | 2023-09-12 | 诺力昂化学品国际有限公司 | 用于从含水侧流中分离羧酸的方法 |
| WO2020249690A1 (en) | 2019-06-12 | 2020-12-17 | Nouryon Chemicals International B.V. | Process for the production of diacyl peroxides |
| HUE063678T2 (hu) | 2019-06-12 | 2024-01-28 | Nouryon Chemicals Int Bv | Eljárás peroxiészterek elõállítására |
| US11976035B2 (en) | 2019-06-12 | 2024-05-07 | Nouryon Chemicals International B.V. | Process for the production of diacyl peroxides |
| ES2963356T3 (es) * | 2019-06-12 | 2024-03-26 | Nouryon Chemicals Int Bv | Método para aislar ácido carboxílico a partir de una corriente lateral acuosa |
| BR112022013750A2 (pt) * | 2020-01-15 | 2022-10-11 | Purac Biochem Bv | Método para purificação de soluções de cloreto de magnésio |
| CN112457184A (zh) * | 2020-12-23 | 2021-03-09 | 河南瑞贝佳生物科技有限公司 | 一种富马酸镁的制备方法 |
| CN114906812B (zh) * | 2022-06-01 | 2023-06-23 | 湖南吴赣药业有限公司 | 一种有机混酸分离纯化方法 |
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| US4137258A (en) * | 1978-04-07 | 1979-01-30 | The Dow Chemical Company | Process for making pure salicylic acid |
| JPS58177986A (ja) * | 1982-04-09 | 1983-10-18 | Shionogi & Co Ltd | Ｌ−アスコルビン酸の製造方法 |
| JP3976832B2 (ja) * | 1996-04-30 | 2007-09-19 | ディーエスエム アイピー アセッツ ビー．ブイ． | ２−ケト−ｌ−グロン酸の単離方法 |
| IL126264A0 (en) | 1998-09-17 | 1999-05-09 | Tami Inst For Research & Dev L | Process for preparing lactic acid |
| CN101748161B (zh) * | 2010-01-19 | 2012-06-06 | 南京工业大学 | 一种厌氧发酵纯化丁二酸的工艺 |
| PL2744747T3 (pl) * | 2011-08-16 | 2021-06-28 | Purac Biochem B.V. | Odzyskiwanie kwasu karboksylowego z ich soli magnezowych poprzez wytrącanie z zastosowaniem kwasu chlorowodorowego, do zastosowania w pracy z bulionem fermentacyjnym |
| CN104640834B (zh) * | 2011-12-23 | 2017-02-22 | 普拉克生化公司 | 多羧酸萃取 |
| EP2735559A1 (en) * | 2012-11-22 | 2014-05-28 | PURAC Biochem BV | Method for preparing a liquid carboxylic acid |
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| Publication number | Publication date |
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| AU2013217968B2 (en) | 2015-12-17 |
| KR20160123392A (ko) | 2016-10-25 |
| EP2812304B1 (en) | 2018-04-11 |
| UA112462C2 (uk) | 2016-09-12 |
| JP2017052772A (ja) | 2017-03-16 |
| EA026029B1 (ru) | 2017-02-28 |
| US9090548B2 (en) | 2015-07-28 |
| CN104093691B (zh) | 2016-09-28 |
| AU2013217968A1 (en) | 2014-09-18 |
| CA2863737C (en) | 2016-11-08 |
| KR20140123998A (ko) | 2014-10-23 |
| MY169054A (en) | 2019-02-11 |
| KR101900256B1 (ko) | 2018-09-20 |
| CA2863737A1 (en) | 2013-08-15 |
| WO2013117687A1 (en) | 2013-08-15 |
| US20150044741A1 (en) | 2015-02-12 |
| JP6367891B2 (ja) | 2018-08-01 |
| HUE039256T2 (hu) | 2018-12-28 |
| CN104093691A (zh) | 2014-10-08 |
| PL2812304T3 (pl) | 2018-10-31 |
| EP2812304A1 (en) | 2014-12-17 |
| ES2675157T3 (es) | 2018-07-09 |
| EA201491396A1 (ru) | 2014-12-30 |
| JP2015508758A (ja) | 2015-03-23 |
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