CN101407448B - Method for continuously preparing 1, 3-propylene glycol by one-step conversion of glycerol - Google Patents
Method for continuously preparing 1, 3-propylene glycol by one-step conversion of glycerol Download PDFInfo
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- CN101407448B CN101407448B CN2008101952181A CN200810195218A CN101407448B CN 101407448 B CN101407448 B CN 101407448B CN 2008101952181 A CN2008101952181 A CN 2008101952181A CN 200810195218 A CN200810195218 A CN 200810195218A CN 101407448 B CN101407448 B CN 101407448B
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- ammediol
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims abstract description 231
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 title claims abstract description 30
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 title abstract 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 25
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 16
- 229910052751 metal Inorganic materials 0.000 claims abstract description 16
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 11
- 239000000047 product Substances 0.000 claims abstract description 11
- 239000011973 solid acid Substances 0.000 claims abstract description 10
- 239000006227 byproduct Substances 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 239000002184 metal Substances 0.000 claims abstract description 9
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 6
- 238000000926 separation method Methods 0.000 claims abstract description 6
- 239000002131 composite material Substances 0.000 claims abstract description 5
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910001930 tungsten oxide Inorganic materials 0.000 claims abstract description 5
- 239000007791 liquid phase Substances 0.000 claims abstract description 4
- 235000011187 glycerol Nutrition 0.000 claims description 92
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 claims description 71
- 239000002994 raw material Substances 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 12
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 7
- 230000009467 reduction Effects 0.000 claims description 6
- 230000004913 activation Effects 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 3
- 238000005194 fractionation Methods 0.000 claims description 3
- 239000012495 reaction gas Substances 0.000 claims description 2
- 239000007789 gas Substances 0.000 abstract description 5
- 238000000746 purification Methods 0.000 abstract description 4
- 238000010924 continuous production Methods 0.000 abstract description 3
- 150000002431 hydrogen Chemical class 0.000 abstract description 2
- 239000007864 aqueous solution Substances 0.000 abstract 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 abstract 2
- 229940035437 1,3-propanediol Drugs 0.000 abstract 2
- 230000001588 bifunctional effect Effects 0.000 abstract 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 abstract 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical group [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 abstract 1
- 229910001928 zirconium oxide Inorganic materials 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 11
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 9
- 229910052721 tungsten Inorganic materials 0.000 description 9
- 239000010937 tungsten Substances 0.000 description 9
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 8
- AKXKFZDCRYJKTF-UHFFFAOYSA-N 3-Hydroxypropionaldehyde Chemical compound OCCC=O AKXKFZDCRYJKTF-UHFFFAOYSA-N 0.000 description 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 229910052726 zirconium Inorganic materials 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 4
- 238000000855 fermentation Methods 0.000 description 4
- 230000004151 fermentation Effects 0.000 description 4
- 230000036571 hydration Effects 0.000 description 4
- 238000006703 hydration reaction Methods 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 238000007037 hydroformylation reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000002283 diesel fuel Substances 0.000 description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- -1 terepthaloyl moietie Chemical compound 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- 239000003225 biodiesel Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 229940106580 ginkgo biloba leaf extract Drugs 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN2008101952181A CN101407448B (en) | 2008-11-07 | 2008-11-07 | Method for continuously preparing 1, 3-propylene glycol by one-step conversion of glycerol |
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CN2008101952181A CN101407448B (en) | 2008-11-07 | 2008-11-07 | Method for continuously preparing 1, 3-propylene glycol by one-step conversion of glycerol |
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Publication Number | Publication Date |
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CN101407448A CN101407448A (en) | 2009-04-15 |
CN101407448B true CN101407448B (en) | 2012-05-30 |
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CN2008101952181A Active CN101407448B (en) | 2008-11-07 | 2008-11-07 | Method for continuously preparing 1, 3-propylene glycol by one-step conversion of glycerol |
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Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013024055A1 (en) * | 2011-08-17 | 2013-02-21 | Solvay Sa | Process for the manufacture of propanediol |
CN102344341B (en) * | 2011-09-30 | 2014-03-12 | 东南大学 | Method for preparing 1,3-propylene glycol by utilizing glycerol one-step hydrogenolysis method |
JP5886678B2 (en) * | 2012-04-19 | 2016-03-16 | 株式会社ダイセル | Process for producing 1,3-propanediol and catalyst for hydrogenation reaction of glycerin |
CN102942448A (en) * | 2012-12-10 | 2013-02-27 | 南京工业大学 | Method for continuously preparing 1, 5-pentanediol from tetrahydrofurfuryl alcohol |
CN103524302A (en) * | 2013-09-30 | 2014-01-22 | 南京工业大学 | Process method for preparing 1, 3-propylene glycol by glycerol hydrogenation |
CN103922893B (en) * | 2014-04-19 | 2015-11-25 | 青岛科技大学 | A kind of composite catalyst hydrogenolysis catalysis of glycerin prepares the method for 1,2-PD |
CN107096564B (en) * | 2017-06-05 | 2019-11-01 | 扬州大学 | A kind of SAPO-34 supporting Pt and the catalyst of WOx and preparation method thereof |
CN111039756B (en) * | 2018-10-15 | 2023-10-10 | 中国石油化工股份有限公司 | Method and system for preparing 1, 3-propanediol |
CN112169795B (en) * | 2019-07-02 | 2022-05-06 | 中国科学院大连化学物理研究所 | Optimized polyol hydrogenolysis catalyst activation process |
CN110746269A (en) * | 2019-11-06 | 2020-02-04 | 山西中医药大学 | Synthesis method of 1, 3-propylene glycol |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007129560A1 (en) * | 2006-05-09 | 2007-11-15 | Kao Corporation | Process for producing product of hydrogenolysis of polyhydric alcohol |
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2008
- 2008-11-07 CN CN2008101952181A patent/CN101407448B/en active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007129560A1 (en) * | 2006-05-09 | 2007-11-15 | Kao Corporation | Process for producing product of hydrogenolysis of polyhydric alcohol |
Non-Patent Citations (2)
Title |
---|
tadahiro kurosaka et al..production of 1,3-propanediol by hydrogenolysis of glycerol catalyzed by Pt/WO3/Zro2.《catalysis communications》.2008,第9卷(第6期),1360-1362. * |
tadahirokurosakaetal..productionof1 3-propanediol by hydrogenolysis of glycerol catalyzed by Pt/WO3/Zro2.《catalysis communications》.2008 |
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CN101407448A (en) | 2009-04-15 |
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GR01 | Patent grant | ||
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Application publication date: 20090415 Assignee: Zhangjiagang Meijing Rong Chemical Industry Co.,Ltd. Assignor: Nanjing Tech University Contract record no.: 2015320000112 Denomination of invention: Method of continuous and high-yield separating and extracting 1,3-dihydroxypropane from fermentation liquid Granted publication date: 20120530 License type: Exclusive License Record date: 20150330 |
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LICC | Enforcement, change and cancellation of record of contracts on the licence for exploitation of a patent or utility model | ||
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TR01 | Transfer of patent right |
Effective date of registration: 20171121 Address after: 215600 Zhangjiagang City, Suzhou, Jiangsu, Jiangsu Yangzi River International Chemical Industrial Park, Tian Ba Road No. 95 Patentee after: Zhangjiagang Meijing Rong Chemical Industry Co.,Ltd. Address before: 210009 Nanjing City, Jiangsu Province, the new model road No. 5 Patentee before: Nanjing Tech University |
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PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Method of continuous and high-yield separating and extracting 1,3-dihydroxypropane from fermentation liquid Effective date of registration: 20180228 Granted publication date: 20120530 Pledgee: Jiangsu Xinhai Company Development Group Ltd. Pledgor: Zhangjiagang Meijing Rong Chemical Industry Co.,Ltd. Registration number: 2018320000023 |
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PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20230908 Granted publication date: 20120530 Pledgee: Jiangsu Xinhai Company Development Group Ltd. Pledgor: Zhangjiagang Meijing Rong Chemical Industry Co.,Ltd. Registration number: 2018320000023 |