CA2921625C - Production of partially refined waste glycerol - Google Patents
Production of partially refined waste glycerol Download PDFInfo
- Publication number
- CA2921625C CA2921625C CA2921625A CA2921625A CA2921625C CA 2921625 C CA2921625 C CA 2921625C CA 2921625 A CA2921625 A CA 2921625A CA 2921625 A CA2921625 A CA 2921625A CA 2921625 C CA2921625 C CA 2921625C
- Authority
- CA
- Canada
- Prior art keywords
- glycerol
- salt
- percent
- polar solvent
- crude
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims abstract description 2586
- 239000002699 waste material Substances 0.000 title claims abstract description 132
- 238000004519 manufacturing process Methods 0.000 title description 37
- 238000000034 method Methods 0.000 claims abstract description 234
- 238000000855 fermentation Methods 0.000 claims abstract description 142
- 230000004151 fermentation Effects 0.000 claims abstract description 142
- 238000011033 desalting Methods 0.000 claims abstract description 43
- 150000003839 salts Chemical class 0.000 claims description 302
- 230000008569 process Effects 0.000 claims description 196
- 239000002798 polar solvent Substances 0.000 claims description 170
- 239000002904 solvent Substances 0.000 claims description 158
- 230000002209 hydrophobic effect Effects 0.000 claims description 141
- 239000012535 impurity Substances 0.000 claims description 124
- 239000000203 mixture Substances 0.000 claims description 123
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 111
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 109
- 238000001704 evaporation Methods 0.000 claims description 77
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 72
- 230000008020 evaporation Effects 0.000 claims description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 45
- 238000001035 drying Methods 0.000 claims description 43
- 150000003626 triacylglycerols Chemical class 0.000 claims description 41
- -1 fatty acid alcohol ester Chemical class 0.000 claims description 40
- 239000011780 sodium chloride Substances 0.000 claims description 36
- 238000000926 separation method Methods 0.000 claims description 26
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 24
- 238000007670 refining Methods 0.000 claims description 24
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 22
- 239000000194 fatty acid Substances 0.000 claims description 22
- 229930195729 fatty acid Natural products 0.000 claims description 22
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 19
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 17
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical group CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 15
- 230000001376 precipitating effect Effects 0.000 claims description 15
- 150000001336 alkenes Chemical class 0.000 claims description 13
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 13
- 239000008158 vegetable oil Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 12
- 230000005484 gravity Effects 0.000 claims description 9
- 238000010908 decantation Methods 0.000 claims description 7
- 125000003158 alcohol group Chemical group 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000000746 purification Methods 0.000 abstract description 9
- 239000012264 purified product Substances 0.000 abstract 1
- 235000011187 glycerol Nutrition 0.000 description 781
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 238000000638 solvent extraction Methods 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 239000003225 biodiesel Substances 0.000 description 30
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 30
- 239000000047 product Substances 0.000 description 29
- 235000010633 broth Nutrition 0.000 description 21
- 230000000813 microbial effect Effects 0.000 description 20
- 238000001556 precipitation Methods 0.000 description 19
- 238000000622 liquid--liquid extraction Methods 0.000 description 18
- 239000012528 membrane Substances 0.000 description 18
- 239000000356 contaminant Substances 0.000 description 17
- 244000005700 microbiome Species 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000009835 boiling Methods 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 239000006227 byproduct Substances 0.000 description 14
- 238000000605 extraction Methods 0.000 description 14
- 238000004508 fractional distillation Methods 0.000 description 14
- 229910052938 sodium sulfate Inorganic materials 0.000 description 14
- 235000011152 sodium sulphate Nutrition 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 238000010586 diagram Methods 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 12
- 229910052939 potassium sulfate Inorganic materials 0.000 description 12
- 238000000935 solvent evaporation Methods 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 239000007832 Na2SO4 Substances 0.000 description 11
- 108091006629 SLC13A2 Proteins 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 238000011084 recovery Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 230000008901 benefit Effects 0.000 description 9
- 238000005516 engineering process Methods 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 8
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 239000003925 fat Substances 0.000 description 7
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- 241000588724 Escherichia coli Species 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000000446 fuel Substances 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 238000009834 vaporization Methods 0.000 description 6
- 230000008016 vaporization Effects 0.000 description 6
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 235000008504 concentrate Nutrition 0.000 description 5
- 239000002285 corn oil Substances 0.000 description 5
- 235000019197 fats Nutrition 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 235000011007 phosphoric acid Nutrition 0.000 description 5
- 231100000331 toxic Toxicity 0.000 description 5
- 230000002588 toxic effect Effects 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- 241000193830 Bacillus <bacterium> Species 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 150000001242 acetic acid derivatives Chemical class 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 235000015165 citric acid Nutrition 0.000 description 4
- 235000005687 corn oil Nutrition 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 229910001385 heavy metal Inorganic materials 0.000 description 4
- 230000015784 hyperosmotic salinity response Effects 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- CMDGQTVYVAKDNA-UHFFFAOYSA-N propane-1,2,3-triol;hydrate Chemical compound O.OCC(O)CO CMDGQTVYVAKDNA-UHFFFAOYSA-N 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 4
- 235000019254 sodium formate Nutrition 0.000 description 4
- 235000010344 sodium nitrate Nutrition 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- 241000228212 Aspergillus Species 0.000 description 3
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 238000000909 electrodialysis Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000000174 gluconic acid Substances 0.000 description 3
- 235000012208 gluconic acid Nutrition 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 239000012466 permeate Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 235000011151 potassium sulphates Nutrition 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- AEQDJSLRWYMAQI-UHFFFAOYSA-N 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 description 2
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 241000159506 Cyanothece Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 241000588722 Escherichia Species 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 241000235395 Mucor Species 0.000 description 2
- KKCBUQHMOMHUOY-UHFFFAOYSA-N Na2O Inorganic materials [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 2
- HLCFGWHYROZGBI-JJKGCWMISA-M Potassium gluconate Chemical compound [K+].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O HLCFGWHYROZGBI-JJKGCWMISA-M 0.000 description 2
- 241000316848 Rhodococcus <scale insect> Species 0.000 description 2
- 239000004280 Sodium formate Substances 0.000 description 2
- 241000192560 Synechococcus sp. Species 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 241000223259 Trichoderma Species 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 2
- 239000002551 biofuel Substances 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
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- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- MVDYEFQVZNBPPH-UHFFFAOYSA-N pentane-2,3,4-trione Chemical compound CC(=O)C(=O)C(C)=O MVDYEFQVZNBPPH-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 125000005575 polycyclic aromatic hydrocarbon group Polymers 0.000 description 2
- 239000001508 potassium citrate Substances 0.000 description 2
- 229960002635 potassium citrate Drugs 0.000 description 2
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 2
- 235000011082 potassium citrates Nutrition 0.000 description 2
- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 2
- 239000004224 potassium gluconate Substances 0.000 description 2
- 235000013926 potassium gluconate Nutrition 0.000 description 2
- 229960003189 potassium gluconate Drugs 0.000 description 2
- PHZLMBHDXVLRIX-UHFFFAOYSA-M potassium lactate Chemical compound [K+].CC(O)C([O-])=O PHZLMBHDXVLRIX-UHFFFAOYSA-M 0.000 description 2
- 235000011085 potassium lactate Nutrition 0.000 description 2
- 239000001521 potassium lactate Substances 0.000 description 2
- 229960001304 potassium lactate Drugs 0.000 description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000011027 product recovery Methods 0.000 description 2
- YNZOICUNEVJUEJ-UHFFFAOYSA-N propane-1,2,3-triol Chemical compound OCC(O)CO.OCC(O)CO.OCC(O)CO YNZOICUNEVJUEJ-UHFFFAOYSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
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- 239000000176 sodium gluconate Substances 0.000 description 2
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- 235000019871 vegetable fat Nutrition 0.000 description 2
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- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
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- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
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- 201000011510 cancer Diseases 0.000 description 1
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- CEDDGDWODCGBFQ-UHFFFAOYSA-N carbamimidoylazanium;hydron;phosphate Chemical compound NC(N)=N.OP(O)(O)=O CEDDGDWODCGBFQ-UHFFFAOYSA-N 0.000 description 1
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- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
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- CZPDZQLCDXNFKZ-UHFFFAOYSA-N guanidine;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound NC(N)=N.OC(=O)CC(O)(C(O)=O)CC(O)=O CZPDZQLCDXNFKZ-UHFFFAOYSA-N 0.000 description 1
- FFKLEXGOVSZWEV-UHFFFAOYSA-N guanidine;methanesulfonic acid Chemical compound NC(N)=N.CS(O)(=O)=O.CS(O)(=O)=O FFKLEXGOVSZWEV-UHFFFAOYSA-N 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
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- 239000002480 mineral oil Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
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- 238000005498 polishing Methods 0.000 description 1
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- XWIJIXWOZCRYEL-UHFFFAOYSA-M potassium;methanesulfonate Chemical compound [K+].CS([O-])(=O)=O XWIJIXWOZCRYEL-UHFFFAOYSA-M 0.000 description 1
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- 239000013535 sea water Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- KKVTYAVXTDIPAP-UHFFFAOYSA-M sodium;methanesulfonate Chemical compound [Na+].CS([O-])(=O)=O KKVTYAVXTDIPAP-UHFFFAOYSA-M 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
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- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
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- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
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- 239000010891 toxic waste Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/86—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/94—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/22—Trihydroxylic alcohols, e.g. glycerol
- C07C31/225—Glycerol
-
- 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
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361867473P | 2013-08-19 | 2013-08-19 | |
| US61/867,473 | 2013-08-19 | ||
| PCT/US2014/051757 WO2015026870A1 (en) | 2013-08-19 | 2014-08-19 | Production of partially refined waste glycerol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2921625A1 CA2921625A1 (en) | 2015-02-26 |
| CA2921625C true CA2921625C (en) | 2020-05-26 |
Family
ID=51541286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2921625A Expired - Fee Related CA2921625C (en) | 2013-08-19 | 2014-08-19 | Production of partially refined waste glycerol |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9868682B2 (enExample) |
| EP (1) | EP3019461A1 (enExample) |
| JP (2) | JP2016529259A (enExample) |
| KR (2) | KR20160060643A (enExample) |
| CN (1) | CN105579426A (enExample) |
| AU (1) | AU2014308977B2 (enExample) |
| CA (1) | CA2921625C (enExample) |
| MX (1) | MX357722B (enExample) |
| WO (1) | WO2015026870A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2017143194A2 (en) * | 2016-02-19 | 2017-08-24 | Invista North America S.A.R.L | Biocatalytic processes and materials for enhanced carbon utilization |
| CN106831344A (zh) * | 2016-12-15 | 2017-06-13 | 天长市康宁甘油科技有限公司 | 一种粗甘油的吸附纯化工艺 |
| CN106518617A (zh) * | 2016-12-15 | 2017-03-22 | 天长市康宁甘油科技有限公司 | 一种粗甘油的精制回收工艺 |
| CN107324577A (zh) * | 2017-08-17 | 2017-11-07 | 长兴上拓环境科技有限公司 | 一种环氧树脂生产废水资源化处理工艺 |
| US11873271B1 (en) * | 2018-05-31 | 2024-01-16 | Donald Lee Bush | Glycerin separation system and method of use |
| KR102105605B1 (ko) * | 2018-10-30 | 2020-04-28 | 한국생산기술연구원 | 용매추출에 의한 글리세롤 정제장치 |
| WO2022155778A1 (zh) * | 2021-01-19 | 2022-07-28 | 汇智工程科技股份有限公司 | 用于甘油精制生产工艺的自动分油装置 |
| CN113716781A (zh) * | 2021-09-07 | 2021-11-30 | 南京齐超环保科技有限公司 | 一种环氧树脂废水中甘油及氯化钠的回收方法 |
| CN115612559A (zh) * | 2022-08-24 | 2023-01-17 | 东莞市新东欣环保投资有限公司 | 一种甘油残渣的处理方法 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE698642C (de) * | 1937-04-11 | 1940-11-14 | I G Farbenindustrie Akt Ges | Verfahren zur Trennung von Gemischen mehrwertiger Alkohole |
| US2461220A (en) * | 1947-03-14 | 1949-02-08 | Hercules Powder Co Ltd | Separation of polyhydric alcohols |
| JPS51136607A (en) * | 1975-05-22 | 1976-11-26 | Kao Corp | Process for purification of aqueous glycerine solution |
| US4164507A (en) | 1978-07-13 | 1979-08-14 | Shell Oil Company | Process for separation of salt from heavy ends wastes of glycerine manufacture |
| US4560812A (en) | 1984-12-10 | 1985-12-24 | Shell Oil Company | Recovery of glycerine from saline waters |
| US4683347A (en) * | 1986-06-23 | 1987-07-28 | Shell Oil Company | Glycerine purification process |
| CA2093429A1 (en) * | 1990-10-09 | 1992-04-10 | Shieh-Shung T. Chen | Process for biophosphorylating organic compounds |
| JP3041443B2 (ja) * | 1992-12-15 | 2000-05-15 | 花王株式会社 | グリセリンの製造方法 |
| JP2005350630A (ja) * | 2004-06-14 | 2005-12-22 | Electric Power Dev Co Ltd | 低排出型バイオディーゼル燃料製造技術 |
| US8110670B2 (en) | 2006-05-19 | 2012-02-07 | Ls9, Inc. | Enhanced production of fatty acid derivatives |
| CA2654717A1 (en) * | 2006-06-14 | 2007-12-21 | Solvay (Societe Anonyme) | Crude glycerol-based product, process for its purification and its use in the manufacture of dichloropropanol |
| US8110093B2 (en) | 2007-03-14 | 2012-02-07 | Ls9, Inc. | Process for producing low molecular weight hydrocarbons from renewable resources |
| BRPI0704952A2 (pt) | 2007-04-04 | 2008-11-18 | Rohm & Haas | mÉtodo para a purificaÇço de glicerol |
| US7534923B2 (en) * | 2007-08-15 | 2009-05-19 | Rohm And Haas Company | Method for purification of glycerol from biodiesel production |
| CA2692266C (en) | 2007-09-27 | 2019-04-16 | Ls9, Inc. | Reduction of the toxic effect of impurities from raw materials by extractive fermentation |
| US7718833B2 (en) | 2007-11-02 | 2010-05-18 | Johann Haltermann, Ltd. | Purification of glycerin obtained as a bioproduct from the transesterification of triglycerides in the synthesis of biofuel |
| FR2925045B1 (fr) | 2007-12-17 | 2012-02-24 | Solvay | Produit a base de glycerol, procede pour son obtention et son utilisation dans la fabrication de dichloropropanol |
| WO2009085278A1 (en) | 2007-12-21 | 2009-07-09 | Ls9, Inc. | Methods and compositions for producing olefins |
| JP2011520455A (ja) | 2008-05-16 | 2011-07-21 | エルエス９・インコーポレイテッド | 炭化水素を製造するための方法および組成物 |
| EP2159212B1 (en) * | 2008-09-01 | 2010-06-02 | Rohm and Haas Company | Method for purification of glycerol from biodiesel production |
| MX2011003597A (es) | 2008-10-07 | 2011-06-20 | Ls9 Inc | Metodos y composiciones para producir aldehidos grasos. |
| EP2248904A1 (en) * | 2009-05-05 | 2010-11-10 | Metabolic Explorer | Continuous culture for 1,3-propanediol production using high glycerine concentration |
| US8372610B2 (en) | 2010-09-15 | 2013-02-12 | Ls9, Inc. | Production of odd chain fatty acid derivatives in recombinant microbial cells |
-
2014
- 2014-08-19 JP JP2016536390A patent/JP2016529259A/ja active Pending
- 2014-08-19 US US14/912,104 patent/US9868682B2/en not_active Expired - Fee Related
- 2014-08-19 KR KR1020167007133A patent/KR20160060643A/ko not_active Ceased
- 2014-08-19 MX MX2016002009A patent/MX357722B/es active IP Right Grant
- 2014-08-19 CA CA2921625A patent/CA2921625C/en not_active Expired - Fee Related
- 2014-08-19 KR KR1020197004188A patent/KR20190017074A/ko not_active Ceased
- 2014-08-19 EP EP14766256.3A patent/EP3019461A1/en not_active Withdrawn
- 2014-08-19 CN CN201480053627.1A patent/CN105579426A/zh active Pending
- 2014-08-19 AU AU2014308977A patent/AU2014308977B2/en not_active Ceased
- 2014-08-19 WO PCT/US2014/051757 patent/WO2015026870A1/en not_active Ceased
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2019
- 2019-05-21 JP JP2019094953A patent/JP2019151659A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2019151659A (ja) | 2019-09-12 |
| AU2014308977B2 (en) | 2017-03-02 |
| MX357722B (es) | 2018-07-20 |
| US9868682B2 (en) | 2018-01-16 |
| KR20190017074A (ko) | 2019-02-19 |
| AU2014308977A1 (en) | 2016-03-03 |
| CN105579426A (zh) | 2016-05-11 |
| US20160200652A1 (en) | 2016-07-14 |
| KR20160060643A (ko) | 2016-05-30 |
| WO2015026870A1 (en) | 2015-02-26 |
| JP2016529259A (ja) | 2016-09-23 |
| EP3019461A1 (en) | 2016-05-18 |
| CA2921625A1 (en) | 2015-02-26 |
| MX2016002009A (es) | 2016-05-18 |
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