FR2536069A1 - Procede de preparation de produits d'addition d'epoxydes et de composes hydroxyles - Google Patents
Procede de preparation de produits d'addition d'epoxydes et de composes hydroxyles Download PDFInfo
- Publication number
- FR2536069A1 FR2536069A1 FR8219231A FR8219231A FR2536069A1 FR 2536069 A1 FR2536069 A1 FR 2536069A1 FR 8219231 A FR8219231 A FR 8219231A FR 8219231 A FR8219231 A FR 8219231A FR 2536069 A1 FR2536069 A1 FR 2536069A1
- Authority
- FR
- France
- Prior art keywords
- reaction
- ppm
- examples
- triflate
- epoxide
- 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.)
- Granted
Links
- -1 HYDROXYL COMPOUNDS Chemical class 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 11
- 150000002118 epoxides Chemical class 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- 239000003054 catalyst Substances 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000007791 liquid phase Substances 0.000 claims abstract description 4
- 150000002924 oxiranes Chemical class 0.000 claims description 15
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 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 15
- 235000011056 potassium acetate Nutrition 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 12
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 239000011701 zinc Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 7
- 230000003197 catalytic effect Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
- 150000008648 triflates Chemical class 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 210000000952 spleen Anatomy 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- WRIYPTGFYKBSFU-UHFFFAOYSA-N ()-Conen Chemical compound CCCCOP(=O)(SCC)SCC1=CC=CC=C1 WRIYPTGFYKBSFU-UHFFFAOYSA-N 0.000 description 1
- XVYAXLVMQFDGTK-UHFFFAOYSA-N 1-butoxybutane;ethane-1,2-diol Chemical compound OCCO.CCCCOCCCC XVYAXLVMQFDGTK-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 241001331845 Equus asinus x caballus Species 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
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- QACCCIVMWADWMN-UHFFFAOYSA-N ethane-1,2-diol;methoxymethane Chemical compound COC.OCCO QACCCIVMWADWMN-UHFFFAOYSA-N 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009434 installation 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
- 239000011572 manganese Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- CITILBVTAYEWKR-UHFFFAOYSA-L zinc trifluoromethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F CITILBVTAYEWKR-UHFFFAOYSA-L 0.000 description 1
- RXBXBWBHKPGHIB-UHFFFAOYSA-L zinc;diperchlorate Chemical compound [Zn+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O RXBXBWBHKPGHIB-UHFFFAOYSA-L 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)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8219231A FR2536069A1 (fr) | 1982-11-17 | 1982-11-17 | Procede de preparation de produits d'addition d'epoxydes et de composes hydroxyles |
| DE8383402091T DE3361806D1 (en) | 1982-11-17 | 1983-10-27 | Process for the preparation of addition products of epoxides and hydroxy compounds |
| EP83402091A EP0110749B1 (fr) | 1982-11-17 | 1983-10-27 | Procédé de préparation de produits d'addition d'époxydes et de composés hydroxyles |
| US06/549,571 US4543430A (en) | 1982-11-17 | 1983-11-07 | Process for the preparation of addition products of epoxides and hydroxylated compounds |
| CA000441325A CA1242220A (en) | 1982-11-17 | 1983-11-16 | Process for the preparation of addition products of epoxides and hydroxylated compounds |
| ES527322A ES8406410A1 (es) | 1982-11-17 | 1983-11-16 | Procedimiento para la preparacion de productos de adicion a base de epoxidos y de compuestos hidroxilados |
| JP58217065A 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 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8219231A FR2536069A1 (fr) | 1982-11-17 | 1982-11-17 | Procede de preparation de produits d'addition d'epoxydes et de composes hydroxyles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2536069A1 true FR2536069A1 (fr) | 1984-05-18 |
| FR2536069B1 FR2536069B1 (cg-RX-API-DMAC7.html) | 1985-03-08 |
Family
ID=9279255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8219231A Granted FR2536069A1 (fr) | 1982-11-17 | 1982-11-17 | Procede de preparation de produits d'addition d'epoxydes et de composes hydroxyles |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4543430A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0110749B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS59104334A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1242220A (cg-RX-API-DMAC7.html) |
| DE (1) | DE3361806D1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES8406410A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2536069A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (31)
| 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 |
| US4825009A (en) * | 1985-12-23 | 1989-04-25 | Shell Oil Company | Preparation of nonionic surfactants |
| US4721816A (en) * | 1985-12-23 | 1988-01-26 | Shell Oil Company | Preparation of nonionic surfactants |
| GB9027448D0 (en) * | 1990-12-18 | 1991-02-06 | Ciba Geigy Ag | Production of glycidyl compounds |
| GB9027406D0 (en) * | 1990-12-18 | 1991-02-06 | Ciba Geigy Ag | Production of compounds |
| US5117010A (en) * | 1991-08-15 | 1992-05-26 | Ciba-Geigy Corporation | Process for the preparation of addition products of epoxides and alcohols |
| TW224108B (cg-RX-API-DMAC7.html) * | 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 |
| KR960706519A (ko) * | 1993-12-21 | 1996-12-09 | 스티븐 에스. 그레이스 | 에폭시드 함유 화합물과 지방족 알콜을 반응시키는 방법(Process to react epoxide-containing compounds and aliphatic alcohols) |
| DE19702787A1 (de) * | 1997-01-27 | 1998-07-30 | Bayer Ag | Verfahren zur Herstellung von Polyetherpolyolen |
| US6207845B1 (en) * | 1997-05-01 | 2001-03-27 | Kao Corporation | Aluminum compounds and use thereof |
| 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 |
| EP2403914A1 (en) | 2009-03-05 | 2012-01-11 | Akzo Nobel Coatings International B.V. | 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 |
| SG193502A1 (en) | 2011-03-31 | 2013-10-30 | Dow Global Technologies Llc | Method for producing short-chain polyfunctional polyether polyols utilizing superacid and double-metal cyanide catalysis |
| MX2014004563A (es) | 2011-10-14 | 2014-08-01 | Dow Global Technologies Llc | Polioles de poliester-polieter hibridos para la expansion de desmoldeo mejorada en espumas rigidas de poliuretano. |
| BR112014014094B1 (pt) | 2011-12-21 | 2020-12-01 | Akzo Nobel Coatings International B.V. | composição de revestimento e substrato |
| ES2599253T3 (es) | 2011-12-21 | 2017-01-31 | Akzo Nobel Coatings International B.V. | Composiciones de revestimiento basadas en disolvente |
| 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 |
| KR102011170B1 (ko) | 2012-03-30 | 2019-08-14 | 우베 고산 가부시키가이샤 | 히드록시알킬화 폴리로탁산의 제조 방법 |
| 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 |
| 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2917085A1 (de) * | 1978-05-10 | 1979-11-22 | Varen Technology | Verfahren zum oxalkylieren einer hydroxylverbindung |
| EP0013026A1 (de) * | 1979-01-02 | 1980-07-09 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung von Etheralkoholen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4409403A (en) * | 1976-02-23 | 1983-10-11 | Varen Technology | Oxyalkylation process |
| JPS56166136A (en) * | 1980-05-27 | 1981-12-21 | Nisso Yuka Kogyo Kk | Preparation of diether |
-
1982
- 1982-11-17 FR FR8219231A patent/FR2536069A1/fr active Granted
-
1983
- 1983-10-27 EP EP83402091A patent/EP0110749B1/fr not_active Expired
- 1983-10-27 DE DE8383402091T patent/DE3361806D1/de 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 (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2917085A1 (de) * | 1978-05-10 | 1979-11-22 | Varen Technology | Verfahren zum oxalkylieren einer hydroxylverbindung |
| EP0013026A1 (de) * | 1979-01-02 | 1980-07-09 | Henkel Kommanditgesellschaft auf Aktien | Verfahren zur Herstellung von Etheralkoholen |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0110749B1 (fr) | 1986-01-08 |
| FR2536069B1 (cg-RX-API-DMAC7.html) | 1985-03-08 |
| ES527322A0 (es) | 1984-08-01 |
| US4543430A (en) | 1985-09-24 |
| DE3361806D1 (en) | 1986-02-20 |
| CA1242220A (en) | 1988-09-20 |
| EP0110749A1 (fr) | 1984-06-13 |
| ES8406410A1 (es) | 1984-08-01 |
| JPS59104334A (ja) | 1984-06-16 |
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Legal Events
| Date | Code | Title | Description |
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| ST | Notification of lapse |