DE1668052C3 - Verfahren zur Reinigung von Glykolen - Google Patents
Verfahren zur Reinigung von GlykolenInfo
- Publication number
- DE1668052C3 DE1668052C3 DE1668052A DE1668052A DE1668052C3 DE 1668052 C3 DE1668052 C3 DE 1668052C3 DE 1668052 A DE1668052 A DE 1668052A DE 1668052 A DE1668052 A DE 1668052A DE 1668052 C3 DE1668052 C3 DE 1668052C3
- Authority
- DE
- Germany
- Prior art keywords
- glycols
- glycol
- cation
- apha
- exchanger
- 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.)
- Expired
Links
- 150000002334 glycols Chemical class 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 17
- 150000002500 ions Chemical class 0.000 claims description 11
- 230000002378 acidificating effect Effects 0.000 claims description 10
- -1 phosphoric acid groups Cation Chemical class 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 55
- 150000001768 cations Chemical class 0.000 description 27
- 241001550224 Apha Species 0.000 description 20
- 235000011121 sodium hydroxide Nutrition 0.000 description 19
- 238000004821 distillation Methods 0.000 description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 238000005341 cation exchange Methods 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000012535 impurity Substances 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 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 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000003729 cation exchange resin Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 230000003247 decreasing effect Effects 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
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000001838 alkalimetric titration Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 150000001767 cationic compounds Chemical group 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- WSKZQEYNQOLWTF-UHFFFAOYSA-N ethane-1,2-diol;formaldehyde Chemical compound O=C.OCCO WSKZQEYNQOLWTF-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 238000005292 vacuum distillation 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/04—Processes using organic exchangers
- B01J39/05—Processes using organic exchangers in the strongly acidic form
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J47/00—Ion-exchange processes in general; Apparatus therefor
- B01J47/02—Column or bed processes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1668052A DE1668052C3 (de) | 1967-12-07 | 1967-12-07 | Verfahren zur Reinigung von Glykolen |
| NL6816816A NL6816816A (enExample) | 1967-12-07 | 1968-11-25 | |
| BE725140D BE725140A (enExample) | 1967-12-07 | 1968-12-09 | |
| FR1598362D FR1598362A (enExample) | 1967-12-07 | 1968-12-09 | |
| GB58418/68A GB1219018A (en) | 1967-12-07 | 1968-12-09 | Process for the purification of glycols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1668052A DE1668052C3 (de) | 1967-12-07 | 1967-12-07 | Verfahren zur Reinigung von Glykolen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1668052A1 DE1668052A1 (de) | 1971-06-09 |
| DE1668052B2 DE1668052B2 (enExample) | 1974-05-22 |
| DE1668052C3 true DE1668052C3 (de) | 1975-01-30 |
Family
ID=5686054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1668052A Expired DE1668052C3 (de) | 1967-12-07 | 1967-12-07 | Verfahren zur Reinigung von Glykolen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE725140A (enExample) |
| DE (1) | DE1668052C3 (enExample) |
| FR (1) | FR1598362A (enExample) |
| GB (1) | GB1219018A (enExample) |
| NL (1) | NL6816816A (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2295938A1 (fr) * | 1974-12-24 | 1976-07-23 | Naphtachimie Sa | Separation des glycols contenus dans des solutions residuaires |
| US6242655B1 (en) * | 2000-07-11 | 2001-06-05 | Scientific Design Company, Inc. | Glycol purification |
| US7182841B2 (en) * | 2003-04-23 | 2007-02-27 | Huntsman International Llc | Purification of solvents used for the purification of alkylene oxide |
| US9433875B2 (en) | 2012-08-24 | 2016-09-06 | Cameron International Corporation | Divalent cation removal from rich monoethylene glycol (MEG) feed streams by ion exchange |
| US9089790B2 (en) | 2012-08-24 | 2015-07-28 | Cameron International Corporation | Hydrocarbon and divalent cation removal from rich mono ethylene glycol (MEG) feed streams by regenerable filters |
| WO2014085065A2 (en) * | 2012-11-29 | 2014-06-05 | Dow Global Technologies Llc | Method for treating glycol-containing well streams |
| CN112441882B (zh) * | 2019-09-02 | 2023-04-07 | 中国石油化工股份有限公司 | 用于乙二醇精制的稳定剂及其制备方法 |
| US11708315B2 (en) | 2020-03-30 | 2023-07-25 | Sabic Global Technologies B.V. | Method of pretreating ion-exchange resin for removal of aldehyde impurities |
| WO2024251421A1 (de) | 2023-06-06 | 2024-12-12 | Zschimmer & Schwarz Chemie Gmbh | Verfahren zur mindestens teilweisen entfernung von aldehyden aus einer zusammensetzung enthaltend mindestens eine verbindung mit mindestens einer alkylenoxideinheit |
-
1967
- 1967-12-07 DE DE1668052A patent/DE1668052C3/de not_active Expired
-
1968
- 1968-11-25 NL NL6816816A patent/NL6816816A/xx unknown
- 1968-12-09 BE BE725140D patent/BE725140A/xx unknown
- 1968-12-09 GB GB58418/68A patent/GB1219018A/en not_active Expired
- 1968-12-09 FR FR1598362D patent/FR1598362A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE725140A (enExample) | 1969-06-09 |
| DE1668052A1 (de) | 1971-06-09 |
| DE1668052B2 (enExample) | 1974-05-22 |
| GB1219018A (en) | 1971-01-13 |
| NL6816816A (enExample) | 1969-06-10 |
| FR1598362A (enExample) | 1970-07-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |