DE1942094A1 - Verfahren zur Reinigung von verunreinigten Glykolen - Google Patents
Verfahren zur Reinigung von verunreinigten GlykolenInfo
- Publication number
- DE1942094A1 DE1942094A1 DE19691942094 DE1942094A DE1942094A1 DE 1942094 A1 DE1942094 A1 DE 1942094A1 DE 19691942094 DE19691942094 DE 19691942094 DE 1942094 A DE1942094 A DE 1942094A DE 1942094 A1 DE1942094 A1 DE 1942094A1
- Authority
- DE
- Germany
- Prior art keywords
- glycol
- impurities
- water
- column
- glycols
- 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.)
- Pending
Links
- 150000002334 glycols Chemical class 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 28
- 238000004140 cleaning Methods 0.000 title description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 155
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 65
- 239000012535 impurity Substances 0.000 claims description 48
- 238000004821 distillation Methods 0.000 claims description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 33
- 239000000463 material Substances 0.000 claims description 13
- 239000000356 contaminant Substances 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000047 product Substances 0.000 description 22
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
- 239000007788 liquid Substances 0.000 description 18
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 11
- 239000002689 soil Substances 0.000 description 9
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 230000005540 biological transmission Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000007670 refining Methods 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 6
- 230000035699 permeability Effects 0.000 description 6
- CLBRCZAHAHECKY-UHFFFAOYSA-N [Co].[Pt] Chemical compound [Co].[Pt] CLBRCZAHAHECKY-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 150000004862 dioxolanes Chemical class 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical group CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- QVHMSMOUDQXMRS-UHFFFAOYSA-N PPG n4 Chemical compound CC(O)COC(C)COC(C)COC(C)CO QVHMSMOUDQXMRS-UHFFFAOYSA-N 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- -1 alcohol ester Chemical class 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- VIQSRHWJEKERKR-UHFFFAOYSA-L disodium;terephthalate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 VIQSRHWJEKERKR-UHFFFAOYSA-L 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000007380 fibre production Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 229920006264 polyurethane film Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 150000003503 terephthalic acid derivatives Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/10—Saturated ethers of polyhydroxy compounds
- C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75473668A | 1968-08-22 | 1968-08-22 | |
| BE746639 | 1970-02-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1942094A1 true DE1942094A1 (de) | 1970-02-26 |
Family
ID=25656797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691942094 Pending DE1942094A1 (de) | 1968-08-22 | 1969-08-19 | Verfahren zur Reinigung von verunreinigten Glykolen |
Country Status (5)
| Country | Link |
|---|---|
| BE (2) | BE737770A (enExample) |
| DE (1) | DE1942094A1 (enExample) |
| FR (1) | FR2017970A1 (enExample) |
| GB (1) | GB1257558A (enExample) |
| NL (1) | NL6912836A (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0310189A3 (en) * | 1987-09-29 | 1990-01-10 | Union Carbide Corporation | Process for refining ethylene glycol |
| US6514388B1 (en) | 1998-09-23 | 2003-02-04 | Basf Aktiengesellschaft | Method for producing highly pure monoethylene glycol |
| US6605192B1 (en) | 1998-09-23 | 2003-08-12 | Basf Aktiengesellschaft | Method for producing highly pure monoethylene glycol |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111727181B (zh) | 2018-02-21 | 2023-03-14 | 国际壳牌研究有限公司 | 通过蒸汽喷射稳定多元醇 |
-
1969
- 1969-08-19 DE DE19691942094 patent/DE1942094A1/de active Pending
- 1969-08-21 BE BE737770D patent/BE737770A/xx unknown
- 1969-08-21 GB GB1257558D patent/GB1257558A/en not_active Expired
- 1969-08-22 NL NL6912836A patent/NL6912836A/xx unknown
- 1969-08-22 FR FR6928965A patent/FR2017970A1/fr not_active Withdrawn
-
1970
- 1970-02-27 BE BE746639D patent/BE746639R/xx active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0310189A3 (en) * | 1987-09-29 | 1990-01-10 | Union Carbide Corporation | Process for refining ethylene glycol |
| US6514388B1 (en) | 1998-09-23 | 2003-02-04 | Basf Aktiengesellschaft | Method for producing highly pure monoethylene glycol |
| US6605192B1 (en) | 1998-09-23 | 2003-08-12 | Basf Aktiengesellschaft | Method for producing highly pure monoethylene glycol |
Also Published As
| Publication number | Publication date |
|---|---|
| BE737770A (enExample) | 1970-02-23 |
| BE746639R (fr) | 1970-08-27 |
| GB1257558A (enExample) | 1971-12-22 |
| FR2017970A1 (enExample) | 1970-05-29 |
| NL6912836A (enExample) | 1970-02-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60002950T2 (de) | Verfahren zur Herstellung von Carbonsäure und Alkohol | |
| DE19610356B4 (de) | Verfahren zum Reinigen von Essigsäure | |
| DE1568022B2 (de) | Verfahren zur abtrennung von acrylsaeure aus einem gemisch von acrylsaeure und essigsaeure | |
| DE60013814T2 (de) | Behandlung einer zusammensetzung enthaltend ein trimethylolalkan-bis-monolineares formal | |
| DE2415127B2 (de) | Alkalische waessrige zusammensetzung zur denaturierung von lacken oder farben und verfahren zur denaturierung von lacken und farben | |
| EP0463434B1 (de) | Verfahren zur Herstellung von monoethylenisch ungesättigten Carbonsäureestern | |
| DE102009048774A1 (de) | Verfahren zur Farbaufhellung von Polyolestern | |
| DE1493971C3 (de) | Verfahren zur Gewinnung einer Phenolfraktion mit vermindertem Gehalt an alpha Hydroxycarbonyl verbindungen | |
| DE1953856B2 (de) | Herstellung von reinem Propylenglycol | |
| DE1942094A1 (de) | Verfahren zur Reinigung von verunreinigten Glykolen | |
| DE69724297T2 (de) | Wasserfreie Zusammensetzungen aus Alkylpolyglykosiden und alkoxylierten Fettalkoholen | |
| DE2645281A1 (de) | Verfahren zur herstellung von isophoron | |
| DE1618331C3 (de) | Verfahren zur Herstellung von Isopren | |
| DE2641134A1 (de) | Verfahren zur reinigung von aethylenglycol oder propylenglycol | |
| DE1157208B (de) | Verfahren zur Reinigung von hoehermolekularen aliphatischen Alkoholen | |
| DE3013927A1 (de) | Verfahren zur herstellung von hydroxylgruppenhaltigen polmeren | |
| DE2554228A1 (de) | Verfahren zur reinigung von hydroxylgruppenhaltigen polyaethern | |
| EP0036406B1 (de) | Verfahren zur Extraktion von Essigsäure, Ameisensäure, gegebenenfalls Furfurol | |
| DE2824859A1 (de) | Verfahren zur gewinnung von ethylenglykol oder propylenglykol | |
| DE2428081C3 (de) | Kontinuierliches Verfahren zum Reinigen von Glyoxal | |
| DE1932420C3 (de) | Verfahren zur Reinigung von 2,2-Dimethyl-1,3-propandlol-mono-hydroxyplvalinsäureester | |
| DE2349226A1 (de) | Verfahren zur reinigung von aceton | |
| DE888688C (de) | Verfahren zur Herstellung von esterartigen Kondensationsprodukten | |
| DE869485C (de) | Verfahren zur Gewinnung von aliphatischen Alkoholen mit mehr als 2 Kohlenstoffatomen oder deren Schwefelsaeureestern | |
| DE2043689A1 (de) | Verfahren zum Entwässern von Essigsaure |