JPS59104334A - エポキシドとヒドロキシル化化合物との付加生成物の製造法 - Google Patents
エポキシドとヒドロキシル化化合物との付加生成物の製造法Info
- Publication number
- JPS59104334A JPS59104334A JP58217065A JP21706583A JPS59104334A JP S59104334 A JPS59104334 A JP S59104334A JP 58217065 A JP58217065 A JP 58217065A JP 21706583 A JP21706583 A JP 21706583A JP S59104334 A JPS59104334 A JP S59104334A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- epoxide
- ppm
- aluminum
- hydroxylated compound
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 23
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 150000002118 epoxides Chemical class 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims description 40
- 239000003054 catalyst Substances 0.000 claims description 27
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 16
- 150000002924 oxiranes Chemical class 0.000 claims description 14
- -1 alkylene glycol monoalkyl ether Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- CITILBVTAYEWKR-UHFFFAOYSA-L zinc trifluoromethanesulfonate Substances [Zn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F CITILBVTAYEWKR-UHFFFAOYSA-L 0.000 claims description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- CMWINYFJZCARON-UHFFFAOYSA-N 6-chloro-2-(4-iodophenyl)imidazo[1,2-b]pyridazine Chemical compound C=1N2N=C(Cl)C=CC2=NC=1C1=CC=C(I)C=C1 CMWINYFJZCARON-UHFFFAOYSA-N 0.000 claims 1
- ZMLPZCGHASSGEA-UHFFFAOYSA-M zinc trifluoromethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C(F)(F)F ZMLPZCGHASSGEA-UHFFFAOYSA-M 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 18
- 230000000694 effects Effects 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- FKOASGGZYSYPBI-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)alumanyl trifluoromethanesulfonate Chemical compound [Al+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F FKOASGGZYSYPBI-UHFFFAOYSA-K 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 235000011056 potassium acetate Nutrition 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000011701 zinc Substances 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- 238000007259 addition reaction Methods 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 4
- RXBXBWBHKPGHIB-UHFFFAOYSA-L zinc;diperchlorate Chemical class [Zn+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O RXBXBWBHKPGHIB-UHFFFAOYSA-L 0.000 description 4
- MPCRDALPQLDDFX-UHFFFAOYSA-L Magnesium perchlorate Chemical compound [Mg+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O MPCRDALPQLDDFX-UHFFFAOYSA-L 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- QPLNUHHRGZVCLQ-UHFFFAOYSA-K aluminum;[oxido(phosphonooxy)phosphoryl] phosphate Chemical compound [Al+3].OP([O-])(=O)OP([O-])(=O)OP(O)([O-])=O QPLNUHHRGZVCLQ-UHFFFAOYSA-K 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 150000008648 triflates Chemical class 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical group CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- IRYBKFGKUNZRSI-UHFFFAOYSA-N Pyrene-1,2-oxide Chemical compound C1=C2C3OC3C=C(C=C3)C2=C2C3=CC=CC2=C1 IRYBKFGKUNZRSI-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910001914 chlorine tetroxide Inorganic materials 0.000 description 1
- RDLMYNHWUFIVQE-UHFFFAOYSA-L cobalt(2+);trifluoromethanesulfonate Chemical compound [Co+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F RDLMYNHWUFIVQE-UHFFFAOYSA-L 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ICQJNCNVUCTBHZ-UHFFFAOYSA-N dec-1-en-1-ol Chemical compound CCCCCCCCC=CO ICQJNCNVUCTBHZ-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- GWVOFXBLSFFSEG-UHFFFAOYSA-N furan-2-carboxylic acid;hydrate Chemical compound O.OC(=O)C1=CC=CO1 GWVOFXBLSFFSEG-UHFFFAOYSA-N 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 229960002050 hydrofluoric acid Drugs 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- BZQRBEVTLZHKEA-UHFFFAOYSA-L magnesium;trifluoromethanesulfonate Chemical compound [Mg+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F BZQRBEVTLZHKEA-UHFFFAOYSA-L 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8219231 | 1982-11-17 | ||
| FR8219231A FR2536069A1 (fr) | 1982-11-17 | 1982-11-17 | Procede de preparation de produits d'addition d'epoxydes et de composes hydroxyles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS59104334A true JPS59104334A (ja) | 1984-06-16 |
Family
ID=9279255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58217065A Pending JPS59104334A (ja) | 1982-11-17 | 1983-11-17 | エポキシドとヒドロキシル化化合物との付加生成物の製造法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4543430A (en:Method) |
| EP (1) | EP0110749B1 (en:Method) |
| JP (1) | JPS59104334A (en:Method) |
| CA (1) | CA1242220A (en:Method) |
| DE (1) | DE3361806D1 (en:Method) |
| ES (1) | ES8406410A1 (en:Method) |
| FR (1) | FR2536069A1 (en:Method) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998050389A1 (en) * | 1997-05-01 | 1998-11-12 | Kao Corporation | Aluminum compounds and use thereof |
| WO2013147300A1 (ja) | 2012-03-30 | 2013-10-03 | 宇部興産株式会社 | ヒドロキシアルキル化ポリロタキサンの製造方法 |
| JP2014530282A (ja) * | 2011-10-14 | 2014-11-17 | ダウ グローバル テクノロジーズ エルエルシー | ポリウレタン硬質発泡体における向上した離型膨張のためのハイブリッドポリエステル−ポリエーテルポリオール |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8415806D0 (en) * | 1984-06-21 | 1984-07-25 | Bp Chem Int Ltd | Alkanolamines |
| FR2573067B1 (fr) * | 1984-11-13 | 1987-10-02 | Bp Chimie Sa | Procede de preparation de produits d'addition d'epoxydes et de composes organiques comprenant un atome d'hydrogene actif |
| GB8517188D0 (en) * | 1985-07-06 | 1985-08-14 | Bp Chem Int Ltd | Metal perfluorosulphonic acid polymer catalyst |
| US4721816A (en) * | 1985-12-23 | 1988-01-26 | Shell Oil Company | Preparation of nonionic surfactants |
| US4825009A (en) * | 1985-12-23 | 1989-04-25 | Shell Oil Company | Preparation of nonionic surfactants |
| GB9027406D0 (en) * | 1990-12-18 | 1991-02-06 | Ciba Geigy Ag | Production of compounds |
| GB9027448D0 (en) * | 1990-12-18 | 1991-02-06 | Ciba Geigy Ag | Production of glycidyl compounds |
| US5117010A (en) * | 1991-08-15 | 1992-05-26 | Ciba-Geigy Corporation | Process for the preparation of addition products of epoxides and alcohols |
| TW224108B (en:Method) * | 1992-05-06 | 1994-05-21 | Ciba Geigy | |
| US5239093A (en) * | 1992-06-12 | 1993-08-24 | Ciba-Geigy Corporation | Process for the preparation of addition products of epoxides and alcohols |
| US5250743A (en) * | 1992-12-31 | 1993-10-05 | Eastman Kodak Company | Method of intercoversion of enantiomers of acyclic 1,2-dihydroxy-3-alkenes |
| WO1995017445A1 (en) * | 1993-12-21 | 1995-06-29 | The Dow Chemical Company | Process to react epoxide-containing compounds and aliphatic alcohols |
| DE19702787A1 (de) * | 1997-01-27 | 1998-07-30 | Bayer Ag | Verfahren zur Herstellung von Polyetherpolyolen |
| US6492565B2 (en) | 1998-10-07 | 2002-12-10 | Bayer Aktiengesellschaft | Process for the preparation of polyether polyols |
| WO2001000552A1 (en) * | 1999-06-30 | 2001-01-04 | Union Carbide Chemicals & Plastics Technology Corporation | Selective alkanol alkoxylations process |
| US6455459B1 (en) | 1999-11-18 | 2002-09-24 | Union Carbide Chemicals & Plastics Technology Corporation | Antimony catalyst compositions |
| US20040116733A1 (en) * | 2000-07-13 | 2004-06-17 | Jacques Dubac | Composition and compound based on salt (s) of metals and of acid exhibiting a sulfonyl group carried by a perhalogenated carbon and their use as lewis acid |
| US6593500B2 (en) | 2001-01-19 | 2003-07-15 | Rhodia, Inc. | Process for alkoxylation with a boron-containing catalyst |
| US6916963B2 (en) * | 2003-07-14 | 2005-07-12 | Saudi Basic Industries Corporation | Process using water tolerant Lewis acids in catalytic hydration of alkylene oxides to alkylene glycols |
| GB0809439D0 (en) * | 2008-05-23 | 2008-07-30 | Qinetiq Ltd | Novel curing method |
| US20120022186A1 (en) | 2009-05-14 | 2012-01-26 | Craun Gary P | Hydroxyl functional oil polyols and coating compositions prepared from hydroxyl functional oil polyols |
| JP5986070B2 (ja) | 2010-04-29 | 2016-09-06 | ダウ グローバル テクノロジーズ エルエルシー | 混成ポリエステル−ポリエーテルポリオール |
| ES2539235T3 (es) | 2011-03-31 | 2015-06-29 | Dow Global Technologies Llc | Método para producir polioles de poliéter polifuncionales de cadena corta usando catálisis de superácido y cianuro de metal doble |
| EP2794704B1 (en) | 2011-12-21 | 2017-04-05 | Akzo Nobel Coatings International B.V. | Water-based coating compositions |
| BR112014014107B1 (pt) | 2011-12-21 | 2020-12-08 | Akzo Nobel Coatings International B.V | método de preparação de uma composição de revestimento e substrato revestido |
| WO2013092680A1 (en) | 2011-12-22 | 2013-06-27 | Akzo Nobel Chemicals International B.V. | Catalyst used for the production of addition products of epoxides and compounds having active hydrogen atoms |
| CN111747828B (zh) * | 2020-07-23 | 2023-05-26 | 浙江皇马科技股份有限公司 | 一种乙二醇单丙基醚的制备方法及系统 |
| CN111675605A (zh) * | 2020-07-23 | 2020-09-18 | 浙江皇马科技股份有限公司 | 一种乙二醇单烯丙基醚的制备方法及系统 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56166136A (en) * | 1980-05-27 | 1981-12-21 | Nisso Yuka Kogyo Kk | Preparation of diether |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4409403A (en) * | 1976-02-23 | 1983-10-11 | Varen Technology | Oxyalkylation process |
| JPS54148705A (en) * | 1978-05-10 | 1979-11-21 | Varen Technology | Oxyalkylation process |
| EP0013026A1 (de) * | 1979-01-02 | 1980-07-09 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung von Etheralkoholen |
-
1982
- 1982-11-17 FR FR8219231A patent/FR2536069A1/fr active Granted
-
1983
- 1983-10-27 DE DE8383402091T patent/DE3361806D1/de not_active Expired
- 1983-10-27 EP EP83402091A patent/EP0110749B1/fr not_active Expired
- 1983-11-07 US US06/549,571 patent/US4543430A/en not_active Expired - Fee Related
- 1983-11-16 ES ES527322A patent/ES8406410A1/es not_active Expired
- 1983-11-16 CA CA000441325A patent/CA1242220A/en not_active Expired
- 1983-11-17 JP JP58217065A patent/JPS59104334A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56166136A (en) * | 1980-05-27 | 1981-12-21 | Nisso Yuka Kogyo Kk | Preparation of diether |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998050389A1 (en) * | 1997-05-01 | 1998-11-12 | Kao Corporation | Aluminum compounds and use thereof |
| JP2014530282A (ja) * | 2011-10-14 | 2014-11-17 | ダウ グローバル テクノロジーズ エルエルシー | ポリウレタン硬質発泡体における向上した離型膨張のためのハイブリッドポリエステル−ポリエーテルポリオール |
| WO2013147300A1 (ja) | 2012-03-30 | 2013-10-03 | 宇部興産株式会社 | ヒドロキシアルキル化ポリロタキサンの製造方法 |
| KR20150002688A (ko) | 2012-03-30 | 2015-01-07 | 우베 고산 가부시키가이샤 | 히드록시알킬화 폴리로탁산의 제조 방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2536069A1 (fr) | 1984-05-18 |
| US4543430A (en) | 1985-09-24 |
| ES527322A0 (es) | 1984-08-01 |
| ES8406410A1 (es) | 1984-08-01 |
| CA1242220A (en) | 1988-09-20 |
| DE3361806D1 (en) | 1986-02-20 |
| EP0110749A1 (fr) | 1984-06-13 |
| EP0110749B1 (fr) | 1986-01-08 |
| FR2536069B1 (en:Method) | 1985-03-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS59104334A (ja) | エポキシドとヒドロキシル化化合物との付加生成物の製造法 | |
| EP0055045B1 (en) | Production of ethers | |
| EP0212820B1 (en) | Metal perfluorosulphonic acid polymer catalyst | |
| WO2006025226A1 (ja) | ポリグリセリンモノエーテル及びその製造方法 | |
| EP0855417B1 (de) | Verfahren zur Herstellung von Polyetherpolyolen | |
| CN115636731B (zh) | 一种2,4-二枯基苯酚的合成方法 | |
| GB2037767A (en) | Preparation of methacrolein | |
| JPS59130231A (ja) | アルコ−ル混合物の製造方法 | |
| US2885385A (en) | Polyphenylol derivatives of olefinic aldehydes | |
| JPH03181448A (ja) | ポリオキシアルキレングリコールアミンの製法 | |
| JP2865165B2 (ja) | フエノール類のアルキルエーテルの製造方法及び該方法で使用される触媒 | |
| US3435077A (en) | Process for the production of asymmetrical formals | |
| KR101794370B1 (ko) | 에테르 카르복실레이트의 제조 방법 | |
| DE3121180A1 (de) | Verfahren zur herstellung von mono- oder poly-alkylen-glykol-diaethern | |
| EP1341607B1 (en) | Novel antimony catalyst compositions | |
| CN113336738A (zh) | 莽草酸醚类化合物及其制备方法 | |
| US6734327B2 (en) | Alkoxylation process using antimony catalyst | |
| CA2070056A1 (en) | Process for the preparation of alkoxylates having a narrow distribution of homologs using antimony pantahalide complexes as the catalyst | |
| JP3995750B2 (ja) | エーテル化合物の製造方法 | |
| JP3636570B2 (ja) | フェノ−ル類のエ−テル化方法 | |
| US2665292A (en) | Metal xanthates of the haloaryl polyalkylene glycol monoethers | |
| WO2001000552A1 (en) | Selective alkanol alkoxylations process | |
| EP0185554B1 (en) | Preparation of alkoxy halides | |
| JP3172079B2 (ja) | プロペニルエーテル化合物の製造方法 | |
| JPS6341434A (ja) | ３，４’−ジクロロジフエニルエ−テルの製造法 |