ZA200509090B - Process for producing 1,3-propanediol - Google Patents
Process for producing 1,3-propanediol Download PDFInfo
- Publication number
- ZA200509090B ZA200509090B ZA200509090A ZA200509090A ZA200509090B ZA 200509090 B ZA200509090 B ZA 200509090B ZA 200509090 A ZA200509090 A ZA 200509090A ZA 200509090 A ZA200509090 A ZA 200509090A ZA 200509090 B ZA200509090 B ZA 200509090B
- Authority
- ZA
- South Africa
- Prior art keywords
- phase
- propanediol
- fermentation broth
- solvent
- solvent extractant
- Prior art date
Links
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 title claims description 110
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 title claims description 93
- 229920000166 polytrimethylene carbonate Polymers 0.000 title claims description 93
- 238000000034 method Methods 0.000 title claims description 81
- 230000008569 process Effects 0.000 title claims description 60
- 239000002904 solvent Substances 0.000 claims description 147
- 229940035437 1,3-propanediol Drugs 0.000 claims description 92
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 83
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 80
- 238000000855 fermentation Methods 0.000 claims description 73
- 230000004151 fermentation Effects 0.000 claims description 73
- 239000000203 mixture Substances 0.000 claims description 57
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 claims description 46
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 44
- 239000000356 contaminant Substances 0.000 claims description 42
- 230000002209 hydrophobic effect Effects 0.000 claims description 28
- 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 claims description 26
- 239000008103 glucose Substances 0.000 claims description 25
- 239000007787 solid Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000011084 recovery Methods 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 150000007524 organic acids Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 235000005985 organic acids Nutrition 0.000 claims description 8
- GTTSNKDQDACYLV-UHFFFAOYSA-N Trihydroxybutane Chemical compound CCCC(O)(O)O GTTSNKDQDACYLV-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
- 239000003623 enhancer Substances 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000004359 castor oil Substances 0.000 claims description 3
- 235000019438 castor oil Nutrition 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 3
- 229940011051 isopropyl acetate Drugs 0.000 claims description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 108090000623 proteins and genes Proteins 0.000 claims description 3
- 102000004169 proteins and genes Human genes 0.000 claims description 3
- 235000012424 soybean oil Nutrition 0.000 claims description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 150000001720 carbohydrates Chemical class 0.000 claims description 2
- 235000014633 carbohydrates Nutrition 0.000 claims description 2
- 229940055577 oleyl alcohol Drugs 0.000 claims description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 claims description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
- 239000008158 vegetable oil Substances 0.000 claims description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims 2
- 238000004064 recycling Methods 0.000 claims 2
- 235000021313 oleic acid Nutrition 0.000 claims 1
- 239000012071 phase Substances 0.000 description 184
- 238000000605 extraction Methods 0.000 description 62
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 55
- 229940093635 tributyl phosphate Drugs 0.000 description 44
- 238000000746 purification Methods 0.000 description 22
- 239000008346 aqueous phase Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000012535 impurity Substances 0.000 description 15
- 239000000284 extract Substances 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- 238000010586 diagram Methods 0.000 description 9
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 8
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 7
- 238000009826 distribution Methods 0.000 description 7
- 239000003350 kerosene Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 238000005119 centrifugation Methods 0.000 description 5
- 239000003292 glue Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 238000000638 solvent extraction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 235000000346 sugar Nutrition 0.000 description 5
- 150000008163 sugars Chemical class 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 229940040102 levulinic acid Drugs 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000622 liquid--liquid extraction Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- 101100238304 Mus musculus Morc1 gene Proteins 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 238000010936 aqueous wash Methods 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004581 coalescence Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- -1 levulinic acid Chemical class 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 102100024452 DNA-directed RNA polymerase III subunit RPC1 Human genes 0.000 description 1
- 101100180051 Danio rerio isl2a gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 101000689002 Homo sapiens DNA-directed RNA polymerase III subunit RPC1 Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101100126318 Rattus norvegicus Isl2 gene Proteins 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000011575 calcium Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000011591 potassium Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- YRVCHYUHISNKSG-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO.OCCCO YRVCHYUHISNKSG-UHFFFAOYSA-N 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
-
- 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
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0446—Juxtaposition of mixers-settlers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0488—Flow sheets
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0492—Applications, solvents used
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/26—Treatment of water, waste water, or sewage by extraction
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Extraction Or Liquid Replacement (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/430,498 US7056439B2 (en) | 2003-05-06 | 2003-05-06 | Process for producing 1, 3-propanediol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200509090B true ZA200509090B (en) | 2007-03-28 |
Family
ID=33416251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200509090A ZA200509090B (en) | 2003-05-06 | 2005-11-10 | Process for producing 1,3-propanediol |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US7056439B2 (no) |
| EP (3) | EP2327465B1 (no) |
| JP (1) | JP4808624B2 (no) |
| KR (1) | KR101094018B1 (no) |
| CN (1) | CN100430111C (no) |
| AU (1) | AU2004238804B2 (no) |
| BR (2) | BR122014002952B1 (no) |
| CA (1) | CA2524452C (no) |
| ES (3) | ES2505541T3 (no) |
| IL (1) | IL171693A (no) |
| MX (1) | MXPA05011894A (no) |
| NO (1) | NO20055383L (no) |
| NZ (1) | NZ543388A (no) |
| RU (1) | RU2323200C2 (no) |
| UA (1) | UA84289C2 (no) |
| WO (1) | WO2004101437A2 (no) |
| ZA (1) | ZA200509090B (no) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7056439B2 (en) * | 2003-05-06 | 2006-06-06 | Tate & Lyle Ingredidents Americas, Inc. | Process for producing 1, 3-propanediol |
| JP4837949B2 (ja) * | 2005-06-22 | 2011-12-14 | パナソニック電工株式会社 | グリコールの分離方法 |
| SE531424C2 (sv) * | 2007-06-18 | 2009-03-31 | Perstorp Specialty Chem Ab | Extraktionsförfarande i en process för framställning av di-, tri- och polyhydroxialkoholer |
| US8399716B2 (en) * | 2007-11-30 | 2013-03-19 | Metabolic Explorer | Method of purifying alcohol from a fermentation broth |
| AR072446A1 (es) * | 2008-03-02 | 2010-09-01 | Dow Global Technologies Inc | Proceso de hidrogenacion mejorado |
| US8084651B2 (en) * | 2008-03-10 | 2011-12-27 | Tate & Lyle Ingredients Americas Llc | Process for purification of glycerol |
| MX2011003558A (es) * | 2008-10-03 | 2011-05-02 | Metabolic Explorer Sa | Metodo para purificar un alcohol de un caldo de fermentacion usando un evaporador de pelicula descendente, un evaporador de pelicula enjuagada, un evaporador de pelicula delgada o un evaporador de trayectoria corta. |
| VN29235A1 (no) * | 2009-06-04 | 2012-03-26 | ||
| US8367877B2 (en) * | 2009-11-17 | 2013-02-05 | Alliant Techsystems Inc. | Methods of purifying 1,2,4-butanetriol |
| KR101134619B1 (ko) * | 2009-12-10 | 2012-04-09 | 한국과학기술연구원 | 1,3-프로판다이올의 분리 방법 |
| WO2011076690A1 (en) | 2009-12-22 | 2011-06-30 | Metabolic Explorer | Method for purifying 1,2-propanediol from a fermentation broth |
| CN102140480B (zh) * | 2010-06-09 | 2013-07-17 | 河南天冠企业集团有限公司 | 一种发酵生产1,3-丙二醇的方法 |
| CN101898935A (zh) * | 2010-07-09 | 2010-12-01 | 华东理工大学 | 从发酵液中萃取分离1,3-丙二醇的方法 |
| US8829248B2 (en) | 2010-08-18 | 2014-09-09 | Eastman Chemical Company | Method for recovery and recycle of ruthenium homogeneous catalysts |
| US9227896B2 (en) | 2010-08-18 | 2016-01-05 | Eastman Chemical Company | Process for the separation and purification of a mixed diol stream |
| US8466328B2 (en) | 2010-08-18 | 2013-06-18 | Eastman Chemical Company | Method for recovery and recycle of ruthenium homogeneous catalysts |
| US8709376B2 (en) | 2010-09-23 | 2014-04-29 | Eastman Chemical Company | Process for recovering and recycling an acid catalyst |
| US8785686B2 (en) | 2010-09-23 | 2014-07-22 | Eastman Chemical Company | Process for recovering and recycling an acid catalyst |
| WO2012130316A1 (en) | 2011-03-31 | 2012-10-04 | Metabolic Explorer | Method for purifying mpg (monopropylene glycol) from a fermentation broth |
| KR102001695B1 (ko) * | 2011-07-29 | 2019-10-04 | 사우디 아라비안 오일 컴퍼니 | 방향족 분리를 이용한 수소화처리 및 이성화 통합 공정 |
| US8829234B2 (en) | 2012-03-27 | 2014-09-09 | Eastman Chemical Company | Hydrocarboxylation of formaldehyde in the presence of a higher order carboxylic acid and heterogeneous catalyst |
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