DE2059051C2 - Polymethyläther und deren Verwendung - Google Patents
Polymethyläther und deren VerwendungInfo
- Publication number
- DE2059051C2 DE2059051C2 DE2059051A DE2059051A DE2059051C2 DE 2059051 C2 DE2059051 C2 DE 2059051C2 DE 2059051 A DE2059051 A DE 2059051A DE 2059051 A DE2059051 A DE 2059051A DE 2059051 C2 DE2059051 C2 DE 2059051C2
- Authority
- DE
- Germany
- Prior art keywords
- groups
- ether
- product
- pressure
- molecular weight
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 14
- 229920005862 polyol Polymers 0.000 claims description 23
- 150000003077 polyols Chemical class 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 13
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000007789 gas Substances 0.000 description 32
- 239000002904 solvent Substances 0.000 description 30
- 239000000047 product Substances 0.000 description 27
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 20
- 230000002378 acidificating effect Effects 0.000 description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- -1 alkane hydrocarbons Chemical class 0.000 description 14
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 14
- 229920000570 polyether Polymers 0.000 description 14
- 239000004721 Polyphenylene oxide Substances 0.000 description 13
- 229910002092 carbon dioxide Inorganic materials 0.000 description 12
- 239000003345 natural gas Substances 0.000 description 10
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 8
- 239000002202 Polyethylene glycol Substances 0.000 description 8
- 239000001569 carbon dioxide Substances 0.000 description 8
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229940050176 methyl chloride Drugs 0.000 description 7
- CAYMIAFKNJGSOR-UHFFFAOYSA-N 1,2,3-trimethoxypropane Chemical compound COCC(OC)COC CAYMIAFKNJGSOR-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 6
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 150000005219 trimethyl ethers Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- 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 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 206010000210 abortion Diseases 0.000 description 2
- 231100000176 abortion Toxicity 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- RNDZFNZUJTYGES-UHFFFAOYSA-N 3-methoxy-2,2-bis(methoxymethyl)propan-1-ol Chemical class COCC(CO)(COC)COC RNDZFNZUJTYGES-UHFFFAOYSA-N 0.000 description 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 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
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B17/00—Sulfur; Compounds thereof
- C01B17/16—Hydrogen sulfides
- C01B17/167—Separation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/46—Removing components of defined structure
- B01D53/48—Sulfur compounds
- B01D53/52—Hydrogen sulfide
- B01D53/526—Mixtures of hydrogen sulfide and carbon dioxide
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Environmental & Geological Engineering (AREA)
- Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Inorganic Chemistry (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treating Waste Gases (AREA)
- Gas Separation By Absorption (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1100370A | 1970-02-12 | 1970-02-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2059051A1 DE2059051A1 (de) | 1971-08-19 |
| DE2059051C2 true DE2059051C2 (de) | 1982-10-28 |
Family
ID=21748437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2059051A Expired DE2059051C2 (de) | 1970-02-12 | 1970-12-01 | Polymethyläther und deren Verwendung |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3653183A (enExample) |
| CA (1) | CA953082A (enExample) |
| DE (1) | DE2059051C2 (enExample) |
| FR (1) | FR2080982B1 (enExample) |
| GB (1) | GB1312277A (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3915674A (en) * | 1973-12-26 | 1975-10-28 | Northern Natural Gas Co | Removal of sulfur from polyether solvents |
| US4581154A (en) * | 1983-12-19 | 1986-04-08 | Norton Company | Solvent composition for the removal of acid gas from gas mixtures at subfreezing temperatures |
| US5053554A (en) * | 1985-04-22 | 1991-10-01 | Diamond Shamrock Chemical Company | Radiation-hardenable diluents |
| DE3726121A1 (de) * | 1987-08-06 | 1989-02-16 | Basf Ag | Veretherung von polyoxyalkylenderivaten |
| DE19530388A1 (de) * | 1995-08-18 | 1997-02-20 | Bayer Ag | Geruchsarme, höhermolekulare Polyetherpolyole, ein Verfahren zu deren Herstellung sowie deren Verwendung für die Herstellung von auf Polyetherpolyolen aufbauenden Polymeren, Kosmetika und pharmazeutischen Produkten |
| US6585784B1 (en) * | 1999-12-13 | 2003-07-01 | Exxonmobil Chemical Patents Inc. | Method for utilizing gas reserves with low methane concentrations for fueling gas turbines |
| US6298652B1 (en) * | 1999-12-13 | 2001-10-09 | Exxon Mobil Chemical Patents Inc. | Method for utilizing gas reserves with low methane concentrations and high inert gas concentrations for fueling gas turbines |
| US7241813B2 (en) * | 2001-12-21 | 2007-07-10 | Isotis Orthobiologics, Inc. | End-capped polymers and compositions containing such compounds |
| US7205337B2 (en) * | 2001-12-21 | 2007-04-17 | Isotis Orthobiologics, Inc. | End-capped polymers and compositions containing such compounds |
| DE102004053167A1 (de) * | 2004-11-01 | 2006-05-04 | Degussa Ag | Polymere Absorptionsmittel für die Gasabsorption und Absorptionsprozess |
| US7964170B2 (en) * | 2007-10-19 | 2011-06-21 | Fluegen, Inc. | Method and apparatus for the removal of carbon dioxide from a gas stream |
| US20100074828A1 (en) * | 2008-01-28 | 2010-03-25 | Fluegen, Inc. | Method and Apparatus for the Removal of Carbon Dioxide from a Gas Stream |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2552528A (en) * | 1949-07-14 | 1951-05-15 | Petrolite Corp | Process for breaking petroleum emulsions |
| US2649166A (en) * | 1950-05-02 | 1953-08-18 | Allied Chem & Dye Corp | Absorption of carbon dioxide from gases containing the same |
| US2733272A (en) * | 1950-10-27 | 1956-01-31 | Trihydroxy polyoxyalkylene ethers | |
| US2781863A (en) * | 1953-12-30 | 1957-02-19 | Universal Oil Prod Co | Gas purification process |
| US2951094A (en) * | 1954-05-28 | 1960-08-30 | Dow Chemical Co | Triethers of glycerol |
| US3362133A (en) * | 1965-10-25 | 1968-01-09 | Allied Chem | Process for hydrogen sulfide removal from gas mixtures containing h2s and co2 |
-
1970
- 1970-02-12 US US11003A patent/US3653183A/en not_active Expired - Lifetime
- 1970-11-09 CA CA097,740A patent/CA953082A/en not_active Expired
- 1970-11-11 GB GB5366570A patent/GB1312277A/en not_active Expired
- 1970-12-01 DE DE2059051A patent/DE2059051C2/de not_active Expired
-
1971
- 1971-02-10 FR FR717104409A patent/FR2080982B1/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2080982A1 (enExample) | 1971-11-26 |
| FR2080982B1 (enExample) | 1973-06-08 |
| CA953082A (en) | 1974-08-20 |
| GB1312277A (en) | 1973-04-04 |
| US3653183A (en) | 1972-04-04 |
| DE2059051A1 (de) | 1971-08-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8128 | New person/name/address of the agent |
Representative=s name: SCHOENWALD, K., DR.-ING. FUES, J., DIPL.-CHEM. DR. |
|
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |