JP2016535029A5 - - Google Patents
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- Publication number
- JP2016535029A5 JP2016535029A5 JP2016526303A JP2016526303A JP2016535029A5 JP 2016535029 A5 JP2016535029 A5 JP 2016535029A5 JP 2016526303 A JP2016526303 A JP 2016526303A JP 2016526303 A JP2016526303 A JP 2016526303A JP 2016535029 A5 JP2016535029 A5 JP 2016535029A5
- Authority
- JP
- Japan
- Prior art keywords
- tetra
- tin
- orthozirconate
- orthotitanate
- boric acid
- 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 aliphatic monocarboxylic acids Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 229940071182 stannate Drugs 0.000 description 5
- 125000005402 stannate group Chemical group 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 2
- BMASLOOHTMQIGP-ZOKJKDLISA-H (z)-but-2-enedioate;butyltin(3+) Chemical compound CCCC[Sn+3].CCCC[Sn+3].[O-]C(=O)\C=C/C([O-])=O.[O-]C(=O)\C=C/C([O-])=O.[O-]C(=O)\C=C/C([O-])=O BMASLOOHTMQIGP-ZOKJKDLISA-H 0.000 description 1
- OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 description 1
- GDKAXSGMPFSRJY-UHFFFAOYSA-J 2-ethylhexanoate;titanium(4+) Chemical compound [Ti+4].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O GDKAXSGMPFSRJY-UHFFFAOYSA-J 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- IMFVDBUUZFZPOI-UHFFFAOYSA-J C(C)(=O)[O-].O[Ti+3].C(C)(=O)[O-].C(C)(=O)[O-] Chemical compound C(C)(=O)[O-].O[Ti+3].C(C)(=O)[O-].C(C)(=O)[O-] IMFVDBUUZFZPOI-UHFFFAOYSA-J 0.000 description 1
- SENWYOSJEOOKBX-UHFFFAOYSA-J C(CCC)(=O)[O-].O[Ti+3].C(CCC)(=O)[O-].C(CCC)(=O)[O-] Chemical compound C(CCC)(=O)[O-].O[Ti+3].C(CCC)(=O)[O-].C(CCC)(=O)[O-] SENWYOSJEOOKBX-UHFFFAOYSA-J 0.000 description 1
- BMMFMORLUFVBHA-UHFFFAOYSA-J C(CCCC)(=O)[O-].O[Ti+3].C(CCCC)(=O)[O-].C(CCCC)(=O)[O-] Chemical compound C(CCCC)(=O)[O-].O[Ti+3].C(CCCC)(=O)[O-].C(CCCC)(=O)[O-] BMMFMORLUFVBHA-UHFFFAOYSA-J 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QVHMSMOUDQXMRS-UHFFFAOYSA-N PPG n4 Chemical compound CC(O)COC(C)COC(C)COC(C)CO QVHMSMOUDQXMRS-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- BNVBVPNCFXAQEJ-UHFFFAOYSA-J [Ti+4].CCC([O-])=O.CCC([O-])=O.CCC([O-])=O.CCC([O-])=O Chemical compound [Ti+4].CCC([O-])=O.CCC([O-])=O.CCC([O-])=O.CCC([O-])=O BNVBVPNCFXAQEJ-UHFFFAOYSA-J 0.000 description 1
- CLWKTGYOENLRGS-UHFFFAOYSA-J [Ti+4].CCCCC([O-])=O.CCCCC([O-])=O.CCCCC([O-])=O.CCCCC([O-])=O Chemical compound [Ti+4].CCCCC([O-])=O.CCCCC([O-])=O.CCCCC([O-])=O.CCCCC([O-])=O CLWKTGYOENLRGS-UHFFFAOYSA-J 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- ZRHOFLXFAAEXEE-UHFFFAOYSA-J butanoate;titanium(4+) Chemical compound [Ti+4].CCCC([O-])=O.CCCC([O-])=O.CCCC([O-])=O.CCCC([O-])=O ZRHOFLXFAAEXEE-UHFFFAOYSA-J 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 150000002363 hafnium compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical compound [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- GPMKKHIGAJLBMZ-UHFFFAOYSA-J titanium(4+);tetraacetate Chemical compound [Ti+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O GPMKKHIGAJLBMZ-UHFFFAOYSA-J 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
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 1
- LHJSLDBKUGXPMI-UHFFFAOYSA-N tris(2-methylpropyl) borate Chemical compound CC(C)COB(OCC(C)C)OCC(C)C LHJSLDBKUGXPMI-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102013018456.8 | 2013-11-02 | ||
| DE102013018456.8A DE102013018456B4 (de) | 2013-11-02 | 2013-11-02 | Verfahren zur Gewinnung von mit Polyolestern angereicherten Produktströmen aus den Nebenströmen der Polyolesterherstellung |
| PCT/EP2014/002737 WO2015062700A1 (de) | 2013-11-02 | 2014-10-09 | Verfahren zur gewinnung von mit polyolestern angereicherten produktströmen aus den nebenströmen der polyolesterherstellung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016535029A JP2016535029A (ja) | 2016-11-10 |
| JP2016535029A5 true JP2016535029A5 (https=) | 2017-11-02 |
| JP6470277B2 JP6470277B2 (ja) | 2019-02-13 |
Family
ID=51844660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016526303A Active JP6470277B2 (ja) | 2013-11-02 | 2014-10-09 | ポリオールエステル製造における副流から、ポリオールエステルが富化された生成物流を得るための方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9840454B2 (https=) |
| EP (1) | EP3063121B1 (https=) |
| JP (1) | JP6470277B2 (https=) |
| KR (1) | KR102309656B1 (https=) |
| CN (1) | CN105555750B (https=) |
| DE (1) | DE102013018456B4 (https=) |
| WO (1) | WO2015062700A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105330543B (zh) * | 2015-10-19 | 2017-09-26 | 中国石油化工股份有限公司 | 一种多元醇酯的精制处理方法 |
| KR102570952B1 (ko) * | 2016-06-16 | 2023-08-28 | 주식회사 엘지생활건강 | 색상 물성이 우수한 다가 알코올 에스테르의 합성 |
| DE102016008559A1 (de) * | 2016-07-12 | 2018-01-18 | Staedtler Mars Gmbh & Co. Kg | Radierer |
| CN120623042B (zh) * | 2025-08-14 | 2025-12-05 | 山东旺林新材料有限公司 | 一种三甘醇二异辛酸酯的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2628249A (en) | 1951-01-03 | 1953-02-10 | Pittsburgh Coke & Chemical Co | Esterification process |
| DE3737759A1 (de) | 1987-11-06 | 1989-05-18 | Henkel Kgaa | Verfahren zur herstellung von estern der monochloressigsaeure mit c(pfeil abwaerts)1(pfeil abwaerts)-c(pfeil abwaerts)4(pfeil abwaerts)-alkanolen |
| US5324853A (en) | 1993-01-19 | 1994-06-28 | Exxon Chemical Patents Inc. | Process for the production of plasticizer and polyolesters |
| DE102009048774A1 (de) * | 2009-10-08 | 2011-04-28 | Oxea Deutschland Gmbh | Verfahren zur Farbaufhellung von Polyolestern |
| DE102009048771A1 (de) | 2009-10-08 | 2011-04-21 | Oxea Deutschland Gmbh | Verfahren zur Herstellung von Polyolestern |
| DE102009048772A1 (de) | 2009-10-08 | 2011-04-21 | Oxea Deutschland Gmbh | Verfahren zur Herstellung von Polyolestern |
| DE102009048773A1 (de) * | 2009-10-08 | 2011-04-21 | Oxea Deutschland Gmbh | Verfahren zur Farbaufhellung von Polyolestern |
| DE102009048775A1 (de) | 2009-10-08 | 2011-04-21 | Oxea Deutschland Gmbh | Verfahren zur Herstellung von Polyolestern |
| JP2011218321A (ja) * | 2010-04-13 | 2011-11-04 | Hitachi Plant Technologies Ltd | 揮発性有機物の蒸留装置および蒸留方法 |
| DE102010027458A1 (de) * | 2010-07-17 | 2012-01-19 | Oxea Gmbh | Verfahren zur Nachbehandlung von Polyolestern |
-
2013
- 2013-11-02 DE DE102013018456.8A patent/DE102013018456B4/de not_active Expired - Fee Related
-
2014
- 2014-10-09 KR KR1020167011641A patent/KR102309656B1/ko active Active
- 2014-10-09 US US14/915,915 patent/US9840454B2/en active Active
- 2014-10-09 WO PCT/EP2014/002737 patent/WO2015062700A1/de not_active Ceased
- 2014-10-09 CN CN201480050930.6A patent/CN105555750B/zh active Active
- 2014-10-09 EP EP14792386.6A patent/EP3063121B1/de active Active
- 2014-10-09 JP JP2016526303A patent/JP6470277B2/ja active Active
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