NO134211B - - Google Patents
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- Publication number
- NO134211B NO134211B NO741930A NO741930A NO134211B NO 134211 B NO134211 B NO 134211B NO 741930 A NO741930 A NO 741930A NO 741930 A NO741930 A NO 741930A NO 134211 B NO134211 B NO 134211B
- Authority
- NO
- Norway
- Prior art keywords
- dioxane
- weighed
- ethylene oxide
- contained
- complexes
- Prior art date
Links
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 33
- 125000004122 cyclic group Chemical group 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 229920000570 polyether Polymers 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 238000006384 oligomerization reaction Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052723 transition metal Chemical class 0.000 claims description 5
- 150000003624 transition metals Chemical class 0.000 claims description 5
- 229910015900 BF3 Inorganic materials 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 48
- 235000002639 sodium chloride Nutrition 0.000 description 27
- 239000012071 phase Substances 0.000 description 25
- 238000009826 distribution Methods 0.000 description 23
- 239000000706 filtrate Substances 0.000 description 17
- 238000001704 evaporation Methods 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 150000001450 anions Chemical class 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 150000004292 cyclic ethers Chemical class 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910018597 Ni(BF4)2 Inorganic materials 0.000 description 2
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003426 co-catalyst Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- 229910014478 Ca(BF4)2 Inorganic materials 0.000 description 1
- 229910020026 CsBF4 Inorganic materials 0.000 description 1
- 229910017981 Cu(BF4)2 Inorganic materials 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
- 229910020261 KBF4 Inorganic materials 0.000 description 1
- 229910021135 KPF6 Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- -1 alkali metal salts Chemical class 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- DWYMPOCYEZONEA-UHFFFAOYSA-L fluoridophosphate Chemical class [O-]P([O-])(F)=O DWYMPOCYEZONEA-UHFFFAOYSA-L 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D323/00—Heterocyclic compounds containing more than two oxygen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO741930A NO134211C (pt) | 1974-05-28 | 1974-05-28 | |
| GB2265675A GB1456190A (en) | 1974-05-28 | 1975-05-23 | Process for selective preparation of macrocyclic polyethers |
| NL7506186A NL7506186A (nl) | 1974-05-28 | 1975-05-26 | Werkwijze voor de selektieve bereiding van macrocyclische polyethers. |
| IT49776/75A IT1035884B (it) | 1974-05-28 | 1975-05-26 | Procedimento per preparaze polieteri ciclici |
| FR7516523A FR2273004B2 (pt) | 1974-05-28 | 1975-05-27 | |
| JP50063415A JPS5927351B2 (ja) | 1974-05-28 | 1975-05-27 | 環状ポリエ−テルの製造方法 |
| US05/580,794 US3997563A (en) | 1974-05-28 | 1975-05-27 | Process for selective preparation of macrocyclic polyethers |
| SE7506050A SE426068B (sv) | 1974-05-28 | 1975-05-27 | Forfarande for framstellning av cykliska polyetrar |
| DK234575A DK234575A (da) | 1974-05-28 | 1975-05-27 | Fremgangsmade til selektiv fremstilling af makrocykliske polyetere |
| DE19752523542 DE2523542A1 (de) | 1974-05-28 | 1975-05-27 | Verfahren zur herstellung makrocyclischer polyaether |
| CA227,880A CA1039733A (en) | 1974-05-28 | 1975-05-27 | Process for selective preparation of macrocyclic polyethers |
| CH678675A CH601284A5 (pt) | 1974-05-28 | 1975-05-27 | |
| BE6045029A BE829563A (fr) | 1974-05-28 | 1975-05-27 | Procede de preparation de polyethers macrocycliques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO741930A NO134211C (pt) | 1974-05-28 | 1974-05-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO741930L NO741930L (pt) | 1975-12-01 |
| NO134211B true NO134211B (pt) | 1976-05-24 |
| NO134211C NO134211C (pt) | 1976-09-01 |
Family
ID=19881635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO741930A NO134211C (pt) | 1974-05-28 | 1974-05-28 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3997563A (pt) |
| JP (1) | JPS5927351B2 (pt) |
| BE (1) | BE829563A (pt) |
| CA (1) | CA1039733A (pt) |
| CH (1) | CH601284A5 (pt) |
| DE (1) | DE2523542A1 (pt) |
| DK (1) | DK234575A (pt) |
| FR (1) | FR2273004B2 (pt) |
| GB (1) | GB1456190A (pt) |
| IT (1) | IT1035884B (pt) |
| NL (1) | NL7506186A (pt) |
| NO (1) | NO134211C (pt) |
| SE (1) | SE426068B (pt) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4127513A (en) * | 1977-11-09 | 1978-11-28 | E. I. Du Pont De Nemours And Company | Method for preparing polyether glycols |
| US4257955A (en) * | 1978-10-06 | 1981-03-24 | Board Of Trustees, Michigan State University | Lanthanide rare earth series cryptate compounds and process for the preparation of metal cryptates in general |
| CA1131647A (en) * | 1978-11-10 | 1982-09-14 | Arie Van Zon | Macrocyclic polyether complexes and method for macrocyclic polyether isolation via said complexes |
| US4228272A (en) * | 1979-03-27 | 1980-10-14 | E. I. Du Pont De Nemours And Company | Method of catalytically preparing tetrahydrofuran/alkylene oxide polymerizates using a montmorillonite clay as the catalyst |
| US4329445A (en) * | 1979-04-30 | 1982-05-11 | E. I. Du Pont De Nemours And Company | Process for preparing a tetrahydrofuran-alkylene oxide copolymer with treated bentonite catalyst |
| US4392978A (en) * | 1979-12-26 | 1983-07-12 | Allied Corporation | Selective aromatic nitration |
| US4562272A (en) * | 1981-03-27 | 1985-12-31 | Union Carbide Corporation | Process for preparing cyclic polyethers |
| US4432904A (en) * | 1982-09-29 | 1984-02-21 | E. I. Du Pont De Nemours And Company | Phosphine azacrown ether compounds |
| GB8724662D0 (en) * | 1987-10-21 | 1987-11-25 | Ass Octel | Lewis base complexes of alkali metal salts |
| US5913446A (en) | 1994-06-21 | 1999-06-22 | Von Holdt, Sr.; John W. | Plastic bucket and lid |
| GB2303130A (en) * | 1995-07-10 | 1997-02-12 | Secr Defence | Cyclic oligomers of substituted cyclic ethers |
| DE19755415A1 (de) * | 1997-12-12 | 1999-06-17 | Basf Ag | Katalysator und Verfahren zur Herstellung von Polytetrahydrofuran |
| WO2001007156A1 (en) | 1999-07-21 | 2001-02-01 | Uab Research Foundation | Metallacrown ether catalysts for hydroformylation |
| DE102006057142A1 (de) | 2006-12-01 | 2008-06-05 | Henkel Kgaa | Metallverbindungen als Initiatoren |
| CN114702472B (zh) * | 2022-04-01 | 2024-03-22 | 浙江肯特催化材料科技有限公司 | 一种环氧乙烷低聚合成脂肪族冠醚的制备方法 |
| CN114605374B (zh) * | 2022-04-01 | 2023-06-09 | 浙江肯特催化材料科技有限公司 | 一种环氧乙烷连续低聚合成脂肪族冠醚的方法 |
-
1974
- 1974-05-28 NO NO741930A patent/NO134211C/no unknown
-
1975
- 1975-05-23 GB GB2265675A patent/GB1456190A/en not_active Expired
- 1975-05-26 NL NL7506186A patent/NL7506186A/xx not_active Application Discontinuation
- 1975-05-26 IT IT49776/75A patent/IT1035884B/it active
- 1975-05-27 JP JP50063415A patent/JPS5927351B2/ja not_active Expired
- 1975-05-27 CA CA227,880A patent/CA1039733A/en not_active Expired
- 1975-05-27 BE BE6045029A patent/BE829563A/xx not_active IP Right Cessation
- 1975-05-27 SE SE7506050A patent/SE426068B/xx unknown
- 1975-05-27 US US05/580,794 patent/US3997563A/en not_active Expired - Lifetime
- 1975-05-27 CH CH678675A patent/CH601284A5/xx not_active IP Right Cessation
- 1975-05-27 DE DE19752523542 patent/DE2523542A1/de not_active Ceased
- 1975-05-27 FR FR7516523A patent/FR2273004B2/fr not_active Expired
- 1975-05-27 DK DK234575A patent/DK234575A/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5927351B2 (ja) | 1984-07-05 |
| US3997563A (en) | 1976-12-14 |
| FR2273004A2 (pt) | 1975-12-26 |
| FR2273004B2 (pt) | 1979-05-18 |
| DE2523542A1 (de) | 1975-12-04 |
| DK234575A (da) | 1975-11-29 |
| BE829563A (fr) | 1975-09-15 |
| CH601284A5 (pt) | 1978-07-14 |
| CA1039733A (en) | 1978-10-03 |
| IT1035884B (it) | 1979-10-20 |
| SE7506050L (sv) | 1975-12-01 |
| NO741930L (pt) | 1975-12-01 |
| NO134211C (pt) | 1976-09-01 |
| GB1456190A (en) | 1976-11-17 |
| JPS5123283A (en) | 1976-02-24 |
| NL7506186A (nl) | 1975-12-02 |
| SE426068B (sv) | 1982-12-06 |
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