SA04250057B1 - تنقية 1، 3- بروبان دايول 1,3-propanediol بواسطة التقطير - Google Patents
تنقية 1، 3- بروبان دايول 1,3-propanediol بواسطة التقطير Download PDFInfo
- Publication number
- SA04250057B1 SA04250057B1 SA4250057A SA04250057A SA04250057B1 SA 04250057 B1 SA04250057 B1 SA 04250057B1 SA 4250057 A SA4250057 A SA 4250057A SA 04250057 A SA04250057 A SA 04250057A SA 04250057 B1 SA04250057 B1 SA 04250057B1
- Authority
- SA
- Saudi Arabia
- Prior art keywords
- distillation
- propanediol
- components
- pdo
- stream
- Prior art date
Links
- 238000004821 distillation Methods 0.000 title claims abstract description 144
- 238000000746 purification Methods 0.000 title abstract description 13
- YRVCHYUHISNKSG-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO.OCCCO YRVCHYUHISNKSG-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 40
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims abstract description 33
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims abstract description 32
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 25
- 238000000926 separation method Methods 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 23
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000470 constituent Substances 0.000 claims description 4
- YHLBDCUXFZRLFT-UHFFFAOYSA-N propane-1,1-diol;propane-1,3-diol Chemical compound CCC(O)O.OCCCO YHLBDCUXFZRLFT-UHFFFAOYSA-N 0.000 claims description 4
- 150000002009 diols Chemical class 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 8
- 239000001294 propane Substances 0.000 claims 4
- 230000018044 dehydration Effects 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 13
- 229940035437 1,3-propanediol Drugs 0.000 abstract 11
- 230000002829 reductive effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 27
- 239000012535 impurity Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 15
- 239000002253 acid Substances 0.000 description 12
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
- 238000000605 extraction Methods 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- 238000007037 hydroformylation reaction Methods 0.000 description 6
- 150000002148 esters Chemical class 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
- 239000003637 basic solution Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 3
- 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
- 239000012736 aqueous medium Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- -1 polytrimethylene terephthalate Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 241000894007 species Species 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
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001944 continuous distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940117927 ethylene oxide Drugs 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 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
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction 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
- 239000000945 filler Substances 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000005339 levitation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 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
- 230000000306 recurrent effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000007306 turnover Effects 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 |
|---|---|
| SA04250057B1 true SA04250057B1 (ar) | 2008-06-09 |
Family
ID=32925336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SA4250057A SA04250057B1 (ar) | 2003-02-24 | 2004-03-30 | تنقية 1، 3- بروبان دايول 1,3-propanediol بواسطة التقطير |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1597221A1 (de) |
| JP (1) | JP2006514087A (de) |
| CN (1) | CN1321959C (de) |
| AR (1) | AR043228A1 (de) |
| AU (1) | AU2003219872B2 (de) |
| BR (1) | BR0318130A (de) |
| CA (1) | CA2516639A1 (de) |
| MX (1) | MXPA05008920A (de) |
| MY (1) | MY135900A (de) |
| SA (1) | SA04250057B1 (de) |
| TW (1) | TW200502201A (de) |
| WO (1) | WO2004076392A1 (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0410685B8 (pt) * | 2003-05-06 | 2017-05-30 | Du Pont | processos de purificação do 1,3-propanodiol e composição |
| 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 |
| 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 |
| 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 |
| EP1201633B1 (de) * | 2000-10-25 | 2004-06-23 | E.I. Dupont De Nemours And Company | Verfahren zur Herstellung von 1,3-Propandiol |
-
2003
- 2003-02-24 CN CNB038260271A patent/CN1321959C/zh not_active Expired - Fee Related
- 2003-02-24 CA CA002516639A patent/CA2516639A1/en not_active Abandoned
- 2003-02-24 WO PCT/US2003/005606 patent/WO2004076392A1/en active IP Right Grant
- 2003-02-24 EP EP03716155A patent/EP1597221A1/de not_active Withdrawn
- 2003-02-24 BR BR0318130-8A patent/BR0318130A/pt not_active IP Right Cessation
- 2003-02-24 JP JP2004568836A patent/JP2006514087A/ja active Pending
- 2003-02-24 AU AU2003219872A patent/AU2003219872B2/en not_active Ceased
- 2003-02-24 MX MXPA05008920A patent/MXPA05008920A/es active IP Right Grant
-
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 |
|---|---|
| AU2003219872B2 (en) | 2007-06-28 |
| MY135900A (en) | 2008-07-31 |
| BR0318130A (pt) | 2006-02-07 |
| JP2006514087A (ja) | 2006-04-27 |
| MXPA05008920A (es) | 2005-10-05 |
| CN1321959C (zh) | 2007-06-20 |
| EP1597221A1 (de) | 2005-11-23 |
| WO2004076392A1 (en) | 2004-09-10 |
| CN1745052A (zh) | 2006-03-08 |
| AR043228A1 (es) | 2005-07-20 |
| CA2516639A1 (en) | 2004-09-10 |
| TW200502201A (en) | 2005-01-16 |
| AU2003219872A1 (en) | 2004-09-17 |
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