JP5468013B2 - ポリエーテルアルコール類の製造方法 - Google Patents
ポリエーテルアルコール類の製造方法 Download PDFInfo
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- JP5468013B2 JP5468013B2 JP2010538639A JP2010538639A JP5468013B2 JP 5468013 B2 JP5468013 B2 JP 5468013B2 JP 2010538639 A JP2010538639 A JP 2010538639A JP 2010538639 A JP2010538639 A JP 2010538639A JP 5468013 B2 JP5468013 B2 JP 5468013B2
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- 239000004721 Polyphenylene oxide Substances 0.000 title claims description 26
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- 238000006243 chemical reaction Methods 0.000 claims description 51
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
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- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
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- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
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- 125000003158 alcohol group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
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- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
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- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
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Classifications
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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
- 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
- C08G65/2603—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 the other compounds containing oxygen
- C08G65/2606—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 the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—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 the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
-
- 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
- C08G65/2669—Non-metals or compounds thereof
- C08G65/2672—Nitrogen or compounds thereof
-
- 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
- C08G65/2696—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 process or apparatus used
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
生成物を固液分離にかけてもよい。この固液分離は、濾過であっても、クロスフロー濾過、あるいは重力除去、例えば液体サイクロンであってもよい。糖を含む液流は反応器に返送し、糖を含まない生成物流は、次の加工工程に流入させる。
ショ糖とグリセリンからなるペーストの連続生産
供給原料を連続的にリップ社のインライン剪断力ミキサー中に供給して、同ミキサー中でショ糖とグリセリン(比率:80:20)からなるペーストを調整した。得られたペーストを、偏心スクリューポンプで連続的に、加圧下(15bar)で反応容器中に投入した。粒度分布(PSD)は、レーザ回折により決定した。このために、このペーストをイソプロパノール中でスラリー化させ、超音波浴中で2分間処理した。次いで、一部を測定のために取り出し上記分析装置に移した。PSDでは、1〜1000μmの幅を示し、粒度分布曲線の極大は、約20〜50μmであった。ペーストに処理前の結晶状態の糖のPSDは、10〜2000μmであった。
ショ糖/グリセリン混合物とアルキレンオキシドとの連続反応
ショ糖とグリセリンの混合物(比率:80:20)を、逆回転エクストルーダー中で調整し、ピストンポンプにて、循環システムを有する水力的に満たされた連続攪拌槽(2.8l)に供給した。この反応容器は攪拌器を有していた。
ショ糖/グリセリン/ポリオール混合物の連続的アルキル化
ショ糖とグリセリンと実施例2のポリエーテルオールの混合物(ショ糖:グリセリン:ポリエーテルオール重量比=60:20:20)を逆回転エクストルーダー中で連続的に混合してペーストとした。これを、実施例2に記載の連続攪拌槽へピストンポンプにより導いた。これ以外の反応方法は同じであり、定常状態運転からの反応生成物は実施例1に近い分析データを示した。OHN:485、粘度:25200mPas(25℃)、残留糖含量:200ppm。また、連続反応から得られた最終生成物の一部を出発原料混合物に戻した。
ショ糖/グリセリン混合物の連続的アルキル化
実施例1に記載のようにして、ショ糖とグリセリンの混合物(比率:80:20)を逆回転エクストルーダー中で連続的に混合してペーストとし、実施例2に記載の連続攪拌槽にピストンポンプにより導いた。触媒のDMEOA(供給原料の総量に対して0.75重量%)とプロピレンオキシドとを、同様に、HPLCポンプにより連続的に反応容器(CSTR)に供給した。合計の流量は1378g/hであった。この混合物の一部を、第二の反応容器、容量が1.4lのCSTRに連続的に供給した。次いで、残留するプロピレンオキシドを除くため、この反応混合物を後反応器(1.1l)に供給した。未変換のプロピレンオキシドは、ストリッピング容器で連続的に除いた。CSTRと後反応器の反応温度はともに、110℃であった。後反応器の出口には圧力保持バルブがあり、このバルブにより反応器内容物を連続的に、減圧下(約50mbar)の生成物貯槽に放出した。この生成物は後処理をしなかった。定常状態運転(約5滞留時間)中に得られた反応生成物を分析した。ATR−IR検出端によれば、第一のCSTR中のプロピレンオキシド濃度は8.3%であり、第二のCSTRの同濃度は1.3%であった。得られた生成物のOH価は455mg・KOH/gであり、粘度は25℃で20150mPasであった。残留糖の含量は、生成物をシリル化後、ガスクロマトグラフィー分析で測定した。残留糖は検出されなかった。生成物の発泡性を分析したところ、相当する半回分式の生成物とほぼ同等の性質を示した。
Claims (17)
- アルキレンオキシドをH官能性出発物質に付加して、反応容器中でポリエーテルアルコールを製造する方法であって、
これらの出発成分は、上記反応容器中に連続的に供給され、
前記H官能性出発物質の内、少なくとも一種が室温で固体であり、
前記固体出発物質からペーストが調製され、及び該ペーストが前記反応容器に連続的に供給され、
前記ペーストは、前記固体出発物質を室温で液体の化合物と混合して製造され、及び
前記室温で液体の化合物がグリセリンであることを特徴とする方法。 - 逆混合反応器で実施される請求項1に記載の方法。
- 連続的に実施される請求項1に記載の方法。
- 半連続的に実施される請求項1に記載の方法。
- 前記反応容器が逆混合反応器であり、前記逆混合反応器が攪拌槽反応器である請求項1に記載の方法。
- 前記反応容器が逆混合反応器であり、前記逆混合反応器が攪拌槽バッテリーである請求項1に記載の方法。
- 前記反応容器が逆混合反応器であり、前記逆混合反応器がジェットループ反応器である請求項1に記載の方法。
- 前記反応容器が管状反応器である請求項3に記載の方法。
- 前記反応容器が連続逆混合反応器であり、前記連続逆混合反応器の下流に他の連続反応器が連続する請求項3に記載の方法。
- 前記他の連続反応器が栓流の反応器である請求項9に記載の方法。
- 前記他の連続反応器が管状反応器である請求項9に記載の方法。
- 固体出発物質として用いられる化合物が少なくとも4官能性である請求項1に記載の方法。
- 用いる固体出発物質が炭水化物を含む請求項1に記載の方法。
- 前記炭水化物が、ペンタエリスリトール、ソルビトール、ショ糖、セルロース、澱粉および澱粉加水分解物からなる群から選ばれる請求項13に記載の方法。
- 用いる固体出発物質が、少なくとも一個の窒素原子を含む化合物を含む請求項1に記載の方法。
- 前記少なくとも一個の窒素原子を含む固体出発物質として用いられる化合物が、トリレンジアミン、ジフェニルメタンジアミン、尿素、メラミン、これらのH官能性誘導体、およびアミンとイソシアネートの反応生成物とからなる群から選ばれる請求項15に記載の方法。
- 前記ペーストが前記固体出発物質と室温で液体の化合物とを剪断力ミキサー中で混合して製造される請求項1に記載の方法。
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US20130030074A1 (en) * | 2011-07-26 | 2013-01-31 | Basf Se | Process for the continuous production of polyetherols |
EP2551289A1 (en) | 2011-07-26 | 2013-01-30 | Basf Se | Process for the continuous production of polyetherols |
US9156761B2 (en) * | 2012-03-26 | 2015-10-13 | Basf Se | Process for preparing polyether polyols |
US9056945B2 (en) | 2012-03-26 | 2015-06-16 | Basf Se | Process for organocatalytic ring-opening polymerization |
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US20130261206A1 (en) * | 2012-04-03 | 2013-10-03 | Basf Se | Process for the continuous production of polyetherols |
CN106164130B (zh) | 2014-04-09 | 2020-07-31 | 巴斯夫欧洲公司 | 连续生产聚醚多元醇的方法 |
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