CA2516639A1 - Purification of 1,3-propanediol by distillation - Google Patents
Purification of 1,3-propanediol by distillation Download PDFInfo
- Publication number
- CA2516639A1 CA2516639A1 CA002516639A CA2516639A CA2516639A1 CA 2516639 A1 CA2516639 A1 CA 2516639A1 CA 002516639 A CA002516639 A CA 002516639A CA 2516639 A CA2516639 A CA 2516639A CA 2516639 A1 CA2516639 A1 CA 2516639A1
- Authority
- CA
- Canada
- Prior art keywords
- propanediol
- distillation
- stream
- pdo
- components
- 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.)
- Abandoned
Links
- 238000004821 distillation Methods 0.000 title claims abstract description 91
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 title claims abstract description 42
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 229920000166 polytrimethylene carbonate Polymers 0.000 title claims abstract description 42
- 238000000746 purification Methods 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 238000000926 separation method Methods 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 239000000047 product Substances 0.000 description 28
- 239000012535 impurity Substances 0.000 description 17
- 229940035437 1,3-propanediol Drugs 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000007037 hydroformylation reaction Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- -1 polytrimethylene terephthalate Polymers 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- AKXKFZDCRYJKTF-UHFFFAOYSA-N 3-Hydroxypropionaldehyde Chemical compound OCCC=O AKXKFZDCRYJKTF-UHFFFAOYSA-N 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 3
- 239000003637 basic solution Substances 0.000 description 3
- 238000000998 batch distillation Methods 0.000 description 3
- 238000001944 continuous distillation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 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 1
- LYTNHFVPHUPKGE-UHFFFAOYSA-N 2-(1,3-dioxan-2-yl)ethanol Chemical compound OCCC1OCCCO1 LYTNHFVPHUPKGE-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
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
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2003/005606 WO2004076392A1 (en) | 2003-02-24 | 2003-02-24 | Purification of 1,3-propanediol by distillation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2516639A1 true CA2516639A1 (en) | 2004-09-10 |
Family
ID=32925336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002516639A Abandoned CA2516639A1 (en) | 2003-02-24 | 2003-02-24 | Purification of 1,3-propanediol by distillation |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1597221A1 (enExample) |
| JP (1) | JP2006514087A (enExample) |
| CN (1) | CN1321959C (enExample) |
| AR (1) | AR043228A1 (enExample) |
| AU (1) | AU2003219872B2 (enExample) |
| BR (1) | BR0318130A (enExample) |
| CA (1) | CA2516639A1 (enExample) |
| MX (1) | MXPA05008920A (enExample) |
| MY (1) | MY135900A (enExample) |
| SA (1) | SA04250057B1 (enExample) |
| TW (1) | TW200502201A (enExample) |
| WO (1) | WO2004076392A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7323539B2 (en) | 2003-05-06 | 2008-01-29 | E. I. Du Pont De Nemours And Company | Polytrimethylene ether glycol and polytrimethylene ether ester with excellent quality |
| US7084311B2 (en) | 2003-05-06 | 2006-08-01 | E. I. Du Pont De Nemours And Company | Hydrogenation of chemically derived 1,3-propanediol |
| EP1625224B1 (en) * | 2003-05-06 | 2010-07-28 | E.I. Du Pont De Nemours And Company | Purification of biologically-produced 1,3-propanediol |
| JP2009013094A (ja) * | 2007-07-03 | 2009-01-22 | Teijin Fibers Ltd | グリコールの製造方法 |
| JP5755995B2 (ja) * | 2011-10-26 | 2015-07-29 | 株式会社日立製作所 | 超臨界水を用いた反応プロセス |
| FI20205345A1 (en) * | 2020-04-03 | 2021-10-04 | Upm Kymmene Corp | MONO-PROPYLENE GLYCOOL RECYCLING |
| CN112920020B (zh) * | 2021-01-29 | 2022-07-08 | 浙江恒逸石化研究院有限公司 | 一种1,3-丙二醇的精制生产线及方法 |
| CN115636730A (zh) * | 2021-07-20 | 2023-01-24 | 中国石油天然气股份有限公司 | 1,3-丙二醇粗品的提纯及脱色的方法 |
| JP7501778B2 (ja) * | 2022-01-20 | 2024-06-18 | 三菱ケミカル株式会社 | 多価アルコール類の製造方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4222708A1 (de) * | 1992-07-10 | 1994-01-13 | Degussa | Verfahren zur Herstellung von 1,3-Propandiol |
| ATE269841T1 (de) * | 2000-10-25 | 2004-07-15 | Du Pont | Verfahren zur herstellung von 1,3-propandiol |
-
2003
- 2003-02-24 CA CA002516639A patent/CA2516639A1/en not_active Abandoned
- 2003-02-24 WO PCT/US2003/005606 patent/WO2004076392A1/en not_active Ceased
- 2003-02-24 MX MXPA05008920A patent/MXPA05008920A/es active IP Right Grant
- 2003-02-24 EP EP03716155A patent/EP1597221A1/en not_active Withdrawn
- 2003-02-24 JP JP2004568836A patent/JP2006514087A/ja active Pending
- 2003-02-24 CN CNB038260271A patent/CN1321959C/zh not_active Expired - Fee Related
- 2003-02-24 BR BR0318130-8A patent/BR0318130A/pt not_active IP Right Cessation
- 2003-02-24 AU AU2003219872A patent/AU2003219872B2/en not_active Ceased
-
2004
- 2004-02-19 AR ARP040100514A patent/AR043228A1/es unknown
- 2004-02-20 TW TW093104183A patent/TW200502201A/zh unknown
- 2004-02-20 MY MYPI20040567A patent/MY135900A/en unknown
- 2004-03-30 SA SA4250057A patent/SA04250057B1/ar unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SA04250057B1 (ar) | 2008-06-09 |
| AU2003219872B2 (en) | 2007-06-28 |
| CN1321959C (zh) | 2007-06-20 |
| MY135900A (en) | 2008-07-31 |
| CN1745052A (zh) | 2006-03-08 |
| JP2006514087A (ja) | 2006-04-27 |
| BR0318130A (pt) | 2006-02-07 |
| AR043228A1 (es) | 2005-07-20 |
| EP1597221A1 (en) | 2005-11-23 |
| TW200502201A (en) | 2005-01-16 |
| AU2003219872A1 (en) | 2004-09-17 |
| MXPA05008920A (es) | 2005-10-05 |
| WO2004076392A1 (en) | 2004-09-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |