JP2020534394A - ポリエーテルポリオールを作製するための連続プロセス - Google Patents
ポリエーテルポリオールを作製するための連続プロセス Download PDFInfo
- Publication number
- JP2020534394A JP2020534394A JP2020514688A JP2020514688A JP2020534394A JP 2020534394 A JP2020534394 A JP 2020534394A JP 2020514688 A JP2020514688 A JP 2020514688A JP 2020514688 A JP2020514688 A JP 2020514688A JP 2020534394 A JP2020534394 A JP 2020534394A
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- Prior art keywords
- weight
- oxide
- mixture
- glycol
- alkylene oxide
- 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
- 229920000570 polyether Polymers 0.000 title claims description 24
- 239000004721 Polyphenylene oxide Substances 0.000 title claims description 21
- 238000010924 continuous production Methods 0.000 title claims description 9
- 229920005862 polyol Polymers 0.000 title abstract description 16
- 150000003077 polyols Chemical class 0.000 title abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 43
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 239000003999 initiator Substances 0.000 claims abstract description 33
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 31
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 25
- 229910052751 metal Inorganic materials 0.000 claims abstract description 16
- 239000002184 metal Substances 0.000 claims abstract description 16
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 27
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 23
- -1 compound cyanide Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- 150000002739 metals Chemical class 0.000 claims description 9
- 235000011187 glycerol Nutrition 0.000 claims description 8
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 239000010452 phosphate Substances 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 150000002602 lanthanoids Chemical class 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 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 claims description 3
- 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 claims description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 3
- 229930006000 Sucrose Natural products 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 3
- 235000011180 diphosphates Nutrition 0.000 claims description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 125000005374 siloxide group Chemical group 0.000 claims description 3
- 239000000600 sorbitol Substances 0.000 claims description 3
- 239000005720 sucrose Substances 0.000 claims description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000006353 oxyethylene group Chemical group 0.000 abstract description 4
- 239000002685 polymerization catalyst Substances 0.000 abstract description 2
- 238000010586 diagram Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 38
- 230000003197 catalytic effect Effects 0.000 description 11
- 239000006260 foam Substances 0.000 description 7
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920005604 random copolymer Polymers 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 229920005830 Polyurethane Foam Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 239000011496 polyurethane foam Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- AZMMSEASPQHHTC-UHFFFAOYSA-N 2-[1,1-bis(2-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=CC=C(O)C=1C(C=1C(=CC=CC=1)O)(C)C1=CC=CC=C1O AZMMSEASPQHHTC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010021639 Incontinence Diseases 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000007373 indentation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- JOLPFRQHFARWCF-UHFFFAOYSA-N propane-1,2,3-triol;prop-1-ene Chemical compound CC=C.OCC(O)CO JOLPFRQHFARWCF-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- YOIAWAIKYVEKMF-UHFFFAOYSA-N trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F.OS(=O)(=O)C(F)(F)F YOIAWAIKYVEKMF-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 239000003190 viscoelastic substance Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G65/04—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 only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
- C08G65/12—Saturated oxiranes characterised by the catalysts used containing organo-metallic compounds or metal hydrides
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- 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
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- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2045—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings
- C08G18/2063—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having two nitrogen atoms in the condensed ring system
-
- 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
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- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
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- 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
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- C08G18/4816—Two or more polyethers of different physical or chemical nature mixtures of two or more polyetherpolyols having at least three hydroxy groups
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- 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
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- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C—CHEMISTRY; METALLURGY
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
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- 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
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- 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
- C08G65/2663—Metal cyanide catalysts, i.e. DMC's
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Abstract
Description
a)連続反応器において、A)複金属シアン化物触媒と、B)プロピレンオキシドおよびアルキレンオキシドの重量に基づいて少なくとも60重量%のエチレンオキシドとを含有するアルキレンオキシド混合物と、C)少なくとも1つのヒドロキシル基およびポリエーテル生成物のヒドロキシル当量よりも低い70〜200のヒドロキシル当量を有する少なくとも1つのアルコキシ化開始剤化合物と、D)開始剤化合物よりも大きく、ポリエーテル生成物の分子量以下の分子量を有するアルコキシ化種からなる重合体と、の混合物を形成することと、
b)追加の触媒と、プロピレンオキシドおよびアルキレンオキシドの重量に基づいて少なくとも60重量%のエチレンオキシドを含有する追加のアルキレンオキシド混合物と、追加の開始剤化合物と、を重合条件下で連続反応器に連続的に添加し、連続反応器からポリエーテル生成物を含有する生成物ストリームを連続的に取り出すことと、を含み、
式中、
i)ステップa)およびb)は、マグネシウム、少なくとも1つのアルコキシド、アリールオキシ、カルボキシレート、アシル、ピロホスフェート、ホスフェート、チオホスフェート、ジチオホスフェート、リン酸エステル、チオリン酸エステル、アミド、シロキシド、水素化物、カルバメートまたは炭化水素アニオンと結合し、かつハロゲン化物アニオンを有しない第3族〜第15族金属、またはランタニド系金属が実質的に存在しない状態で実行され、
ii)ポリエーテル生成物は、50〜90重量%の重合エチレンオキシドを含有する、連続プロセスである。
Mb[M1(CN)r(X)t]c[M2(X)6]d・nM3 xAy
式中、MおよびM3はそれぞれ金属であり、M1はMとは異なる遷移金属であり、各XはM1イオンと配位するシアン化物以外の基を表し、M2は遷移金属であり、Aはアニオンを表し、b、c、およびdは静電気的に中性の錯体をもたらす数であり、rは4〜6であり、tは0〜2であり、xおよびyは金属塩M3 xAyの電荷を調整する整数であり、nはゼロまたは正の整数である。前述の式は、多くの場合にDMC触媒錯体内に存在するt−ブタノールなどの中性錯化剤の存在は反映していない。
加熱した外部再循環ループおよび内部冷却コイルを備えた500mL Autoclave Engineers連続攪拌タンク反応器で連続重合を実行する。再循環ループは、反応器の内容物を再循環させるためのギアポンプによって駆動される。この反応器にはさらに、近赤外線分析装置のフローセルと、開始剤、触媒スラリー、および酸化アルキレン用の注入ポートが装備されている。反応器には出口ポートを有し、反応器の内容物が反応器から加熱された出口ラインを通ってサンプル収集システムに流れ込むようにさせる。反応器圧力は、出口ラインの圧力制御バルブによって制御される。
ポリオールAは、168個のヒドロキシル価(333当量、分子量1000)、三官能性ランダムコポリマーまたはプロピレンオキシドとエチレンオキシドである。ポリオールAは、60重量%のオキシエチレン単位を含有する。1kgのポリオールAを、外部ジャケットを介して加熱された1LBuchi反応器に満たす。反応器には、反応物を導入するための注入ポートと、生成物ストリームを除去するための取り出しポートが装備されている。圧力制御は、取り出しポートに取り付けられた出口ラインの圧力制御バルブを介して維持される。生成物ストリーム中の未反応の酸化物含有量を測定するために、反応器の出口に近赤外線セルが設置されている。
流量を次のように変更して、実施例1を繰り返す:(1)ポリオールA中の触媒混合物−15.9g/時、260g/molの分子量を有するプロポキシ化グリセリン開始剤−38g/時、エチレンオキシド/プロピレンオキシド混合物−114g/時、生成物ストリーム−167.9g/時。これらの流量により、反応器内および生成物ストリーム内に95ppmのDMC触媒濃度が生成される。これらの条件は、15時間、および生成物が収集されるさらに24時間維持され、その後、実験は任意に中止される。生成物ストリーム中の未反応の酸化物含有量は、全体の試験中に1重量%未満であり、これもDMC活性の損失がないことを示している。この生成物は、168のヒドロキシル価(333当量、1000分子量)を有し、60重量%のオキシエチレン単位を含有する。
Claims (14)
- 200〜2000のヒドロキシル当量を有するポリエーテル生成物を生成するための連続プロセスであって、
a)連続反応器において、複金属シアン化物触媒と、プロピレンオキシドおよびアルキレンオキシドの重量に基づいて少なくとも60重量%のエチレンオキシドを含有する前記アルキレンオキシドの混合物と、少なくとも1つのヒドロキシル基および70〜200であるが、前記ポリエーテル生成物のヒドロキシル当量よりも低いヒドロキシル当量を有する少なくとも1つのアルコキシ化開始剤化合物と、前記開始剤化合物よりも大きく、前記ポリエーテル生成物の分子量以下の分子量を有するアルコキシ化種からなる重合物と、の混合物を形成することと、
b)追加の触媒と、プロピレンオキシドおよびアルキレンオキシドの重量に基づいて少なくとも60重量%のエチレンオキシドを含有する追加の前記アルキレンオキシドの混合物と、追加の開始剤化合物と、を重合条件下で前記連続反応器に連続的に添加し、前記連続反応器から前記ポリエーテル生成物を含有する生成物ストリームを連続的に取り出すことと、を含み、
式中、
i)ステップa)およびb)は、マグネシウム、少なくとも1つのアルコキシド、アリールオキシ、カルボキシレート、アシル、ピロホスフェート、ホスフェート、チオホスフェート、ジチオホスフェート、リン酸エステル、チオリン酸エステル、アミド、シロキシド、水素化物、酸化物、カルバメートまたは炭化水素アニオンと結合し、かつハロゲン化物アニオンを有しない第3族〜第15族金属、またはランタニド系金属が実質的に存在しない状態で実行され、
ii)前記ポリエーテル生成物が、50〜90重量%の重合エチレンオキシドを含有する、連続プロセス。 - ステップb)の前に、前記複金属シアン化物触媒、前記アルキレンオキシド混合物および前記開始剤化合物の定常状態濃度が重合条件下で前記連続反応器内で確立され、そのような定常状態濃度がステップb)の間、維持される、請求項1に記載の連続プロセス。
- 前記開始剤化合物が、70〜150のヒドロキシル当量を有する、請求項1または請求項2に記載の方法。
- 前記開始剤化合物が、エチレングリコール、ジエチレングリコール、トリエチレングリコール、プロピレングリコール、ジプロピレングリコール、トリプロピレングリコール、グリセリン、トリメチロールプロパン、ペンタエリスリトール、スクロースおよびソルビトールのうちの1つ以上の70〜150当量のアルコキシレートである、請求項3に記載の方法。
- 前記開始剤化合物が、エチレングリコール、ジエチレングリコール、トリエチレングリコール、プロピレングリコール、ジプロピレングリコール、トリプロピレングリコール、グリセリン、トリメチロールプロパン、ペンタエリスリトール、スクロースおよびソルビトールの1つ以上のうちの70〜150当量のアルコキシレートである、請求項4に記載の方法。
- 前記開始剤化合物が、グリセリンまたはトリメチロールプロパンの70〜125当量のプロポキシレートである、請求項5に記載の方法。
- 前記ポリエーテル生成物が、200〜1750のヒドロキシル当量を有する、請求項1〜6のいずれか1項に記載の方法。
- 前記ポリエーテル生成物が、200〜700のヒドロキシル当量を有する、請求項1〜7のいずれか1項に記載の方法。
- 前記ポリエーテル生成物が、275〜400のヒドロキシル当量を有する、請求項1〜8のいずれか1項に記載の方法。
- ステップa)およびb)における前記アルキレンオキシド混合物が、65〜90重量%のエチレンオキシドおよび対応して35〜10重量%のプロピレンオキシドを含有する、請求項1〜9のいずれか1項に記載の方法。
- ステップa)およびb)における前記アルキレンオキシド混合物が、70〜85重量%のエチレンオキシドおよび対応して30〜15重量%のプロピレンオキシドを含有する、請求項10に記載の方法。
- ステップa)およびb)における前記アルキレンオキシド混合物が、75〜85重量%のエチレンオキシドおよび対応して25〜15重量%のプロピレンオキシドを含有する、請求項11に記載の方法。
- 前記複金属シアン化物触媒が、亜鉛ヘキサシアノコバルテート触媒錯体である、請求項1〜12のいずれか1項に記載の方法。
- 前記複金属シアン化物触媒の量が、ステップb)において25〜100重量ppmの濃度で存在する、請求項1〜13のいずれか1項に記載の方法。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002543228A (ja) * | 1999-04-24 | 2002-12-17 | バイエル アクチェンゲゼルシャフト | 第1級oh基高含有長鎖ポリエーテルポリオール |
JP2007204680A (ja) * | 2006-02-03 | 2007-08-16 | Asahi Glass Co Ltd | ポリエーテルポリオールの製造方法 |
JP2013522407A (ja) * | 2010-03-17 | 2013-06-13 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 高いエチレンオキシド含有量を有するポリエーテルポリオールの製造方法 |
JP2015533915A (ja) * | 2012-11-09 | 2015-11-26 | バイエル・マテリアルサイエンス・アクチェンゲゼルシャフトBayer MaterialScience AG | ポリエーテルカーボナートポリオールの製造方法 |
JP2018517821A (ja) * | 2015-06-20 | 2018-07-05 | ダウ グローバル テクノロジーズ エルエルシー | 二重金属シアニド触媒錯体、及びマグネシウム、3族−15族金属またはランタニド系列金属化合物を使用して、高含量の重合エチレンオキシドを有するポリエーテルポリオールを作製するための連続プロセス |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3427335A (en) | 1963-02-14 | 1969-02-11 | Gen Tire & Rubber Co | Double metal cyanides complexed with an acyclic aliphatic saturated monoether,an ester and a cyclic ether and methods for making the same |
GB1063525A (en) | 1963-02-14 | 1967-03-30 | Gen Tire & Rubber Co | Organic cyclic oxide polymers, their preparation and tires prepared therefrom |
US3427334A (en) | 1963-02-14 | 1969-02-11 | Gen Tire & Rubber Co | Double metal cyanides complexed with an alcohol aldehyde or ketone to increase catalytic activity |
US3278458A (en) | 1963-02-14 | 1966-10-11 | Gen Tire & Rubber Co | Method of making a polyether using a double metal cyanide complex compound |
US3278457A (en) | 1963-02-14 | 1966-10-11 | Gen Tire & Rubber Co | Method of making a polyether using a double metal cyanide complex compound |
US3278459A (en) | 1963-02-14 | 1966-10-11 | Gen Tire & Rubber Co | Method of making a polyether using a double metal cyanide complex compound |
US3427256A (en) | 1963-02-14 | 1969-02-11 | Gen Tire & Rubber Co | Double metal cyanide complex compounds |
US5470813A (en) | 1993-11-23 | 1995-11-28 | Arco Chemical Technology, L.P. | Double metal cyanide complex catalysts |
US6077978A (en) | 1997-09-17 | 2000-06-20 | Arco Chemical Technology L.P. | Direct polyoxyalkylation of glycerine with double metal cyanide catalysis |
US6884826B2 (en) | 2003-06-09 | 2005-04-26 | Bayer Antwerp, N.V. | Process for preparing double metal cyanide catalyzed polyols |
US20050209438A1 (en) | 2004-03-19 | 2005-09-22 | Browne Edward P | Starter feed stream acidification in DMC-catalyzed process |
EP2513192B1 (en) * | 2009-12-14 | 2014-01-22 | Dow Global Technologies LLC | Method for continuously producing low equivalent weight polyols using double metal cyanide catalysts |
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002543228A (ja) * | 1999-04-24 | 2002-12-17 | バイエル アクチェンゲゼルシャフト | 第1級oh基高含有長鎖ポリエーテルポリオール |
JP2007204680A (ja) * | 2006-02-03 | 2007-08-16 | Asahi Glass Co Ltd | ポリエーテルポリオールの製造方法 |
JP2013522407A (ja) * | 2010-03-17 | 2013-06-13 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 高いエチレンオキシド含有量を有するポリエーテルポリオールの製造方法 |
JP2015533915A (ja) * | 2012-11-09 | 2015-11-26 | バイエル・マテリアルサイエンス・アクチェンゲゼルシャフトBayer MaterialScience AG | ポリエーテルカーボナートポリオールの製造方法 |
JP2018517821A (ja) * | 2015-06-20 | 2018-07-05 | ダウ グローバル テクノロジーズ エルエルシー | 二重金属シアニド触媒錯体、及びマグネシウム、3族−15族金属またはランタニド系列金属化合物を使用して、高含量の重合エチレンオキシドを有するポリエーテルポリオールを作製するための連続プロセス |
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