TW434218B - Process for preparing ester plasticizers - Google Patents
Process for preparing ester plasticizers Download PDFInfo
- Publication number
- TW434218B TW434218B TW087107871A TW87107871A TW434218B TW 434218 B TW434218 B TW 434218B TW 087107871 A TW087107871 A TW 087107871A TW 87107871 A TW87107871 A TW 87107871A TW 434218 B TW434218 B TW 434218B
- Authority
- TW
- Taiwan
- Prior art keywords
- patent application
- hydroxide
- reaction
- alcohol
- osmium
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 23
- 150000002148 esters Chemical class 0.000 title claims abstract description 19
- 239000004014 plasticizer Substances 0.000 title claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000011541 reaction mixture Substances 0.000 claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract description 9
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 8
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000002500 ions Chemical class 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- -1 alkali metal rhenium hydroxide Chemical class 0.000 claims description 9
- 229910052719 titanium Inorganic materials 0.000 claims description 8
- 239000010936 titanium Substances 0.000 claims description 8
- 238000011049 filling Methods 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 238000006386 neutralization reaction Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000003463 adsorbent Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 3
- 150000004692 metal hydroxides Chemical class 0.000 claims description 3
- 230000002079 cooperative effect Effects 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- CDCFKVCOZYCTBR-UHFFFAOYSA-J osmium(4+);tetrahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[Os+4] CDCFKVCOZYCTBR-UHFFFAOYSA-J 0.000 claims 4
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims 2
- UMYPNPGPPBUKGC-UHFFFAOYSA-J [Os](O)(O)(O)O.[Os] Chemical compound [Os](O)(O)(O)O.[Os] UMYPNPGPPBUKGC-UHFFFAOYSA-J 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 claims 2
- WNNJOHWNSYNHPW-UHFFFAOYSA-N osmium Chemical compound [Os].[Os] WNNJOHWNSYNHPW-UHFFFAOYSA-N 0.000 claims 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
- 238000001256 steam distillation Methods 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 abstract description 7
- 150000007513 acids Chemical class 0.000 abstract description 4
- 238000001035 drying Methods 0.000 abstract description 3
- 238000001914 filtration Methods 0.000 abstract description 3
- 230000003472 neutralizing effect Effects 0.000 abstract description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 2
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 230000032050 esterification Effects 0.000 description 7
- 238000005886 esterification reaction Methods 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000010025 steaming Methods 0.000 description 4
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 235000015170 shellfish Nutrition 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- YXTDAZMTQFUZHK-UHFFFAOYSA-L 5,6-dihydroxy-1,3,2$l^{2}-dioxastannepane-4,7-dione Chemical compound [Sn+2].[O-]C(=O)C(O)C(O)C([O-])=O YXTDAZMTQFUZHK-UHFFFAOYSA-L 0.000 description 1
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 1
- 241000269420 Bufonidae Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- PGZSVAXKRVWAHV-UHFFFAOYSA-N [Re].[Os] Chemical compound [Re].[Os] PGZSVAXKRVWAHV-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- CMBZEFASPGWDEN-UHFFFAOYSA-N argon;hydrate Chemical compound O.[Ar] CMBZEFASPGWDEN-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 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
- 150000004820 halides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 125000005590 trimellitic acid group Chemical group 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19721347A DE19721347B9 (de) | 1997-05-22 | 1997-05-22 | Verfahren zur Herstellung von Esterweichmachern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW434218B true TW434218B (en) | 2001-05-16 |
Family
ID=7830133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW087107871A TW434218B (en) | 1997-05-22 | 1998-05-21 | Process for preparing ester plasticizers |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6310235B1 (enExample) |
| EP (1) | EP0984917B1 (enExample) |
| JP (1) | JP2001526672A (enExample) |
| KR (1) | KR20010012754A (enExample) |
| CN (1) | CN1190407C (enExample) |
| AT (1) | ATE253035T1 (enExample) |
| AU (1) | AU736462B2 (enExample) |
| BR (1) | BR9809662A (enExample) |
| CA (1) | CA2290663C (enExample) |
| DE (2) | DE19721347B9 (enExample) |
| DK (1) | DK0984917T3 (enExample) |
| ES (1) | ES2209150T3 (enExample) |
| ID (1) | ID20315A (enExample) |
| MX (1) | MX215587B (enExample) |
| PL (1) | PL194776B1 (enExample) |
| PT (1) | PT984917E (enExample) |
| RO (1) | RO120539B1 (enExample) |
| SA (1) | SA99200261B1 (enExample) |
| TW (1) | TW434218B (enExample) |
| WO (1) | WO1998052901A2 (enExample) |
| ZA (1) | ZA984271B (enExample) |
Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10043545A1 (de) | 2000-09-05 | 2002-03-14 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Carbonsäureestern |
| DE10236279A1 (de) | 2002-08-08 | 2004-02-19 | Basf Ag | Verfahren zur Abtrennung von Veresterungskatalysator |
| GB0320206D0 (en) * | 2003-08-29 | 2003-10-01 | Exxonmobil Chem Patents Inc | Improvements in or relating to plasticiser |
| US7291748B2 (en) * | 2005-07-28 | 2007-11-06 | Basf Corporation | C10/C7 ester mixtures based on 2-propylheptanol |
| US7276621B2 (en) * | 2005-08-12 | 2007-10-02 | Eastman Chemical Company | Production of di-(2-ethylhexyl) terephthalate |
| CN100537512C (zh) * | 2006-12-13 | 2009-09-09 | 井冈山学院 | 羧酸异丙基二乙基酯的制备方法及其应用 |
| CN100453521C (zh) * | 2006-12-13 | 2009-01-21 | 井冈山学院 | 羧酸乙基二异丙基酯的制备方法及其应用 |
| CN100480230C (zh) * | 2006-12-13 | 2009-04-22 | 井冈山学院 | 羧酸二乙基二异丙基酯的制备方法及其应用 |
| US20080183004A1 (en) * | 2007-01-30 | 2008-07-31 | Nan Ya Plastics Corporation | Method of preparing cyclohexanepolycarboxylic acid ester without phthalatic and plasticizer prepared by the same |
| DE602008002827D1 (de) * | 2007-03-13 | 2010-11-11 | Exxonmobil Chem Patents Inc | Verfahren zur herstellung von estern |
| EP2155654B1 (en) * | 2007-03-13 | 2012-02-22 | ExxonMobil Chemical Patents Inc. | Improvement in ester production |
| US20100300694A1 (en) * | 2007-11-20 | 2010-12-02 | Anja Vonderhagen | Method for producing an organic composition containing an n-nonyl ether |
| CN102256925B (zh) * | 2008-12-16 | 2014-01-22 | 巴斯夫欧洲公司 | 再生粗酯的方法 |
| CN101607905B (zh) * | 2009-07-24 | 2013-04-10 | 镇江联成化学工业有限公司 | 环烷烃类酸酐增塑剂的制备方法 |
| ES2464516T3 (es) | 2009-11-05 | 2014-06-03 | Basf Se | Adhesivos y sellantes que contienen éster a base de 2-propilheptanol |
| CN101875609B (zh) * | 2010-06-04 | 2013-04-10 | 镇江联成化学工业有限公司 | 用富马酸生产副产物与回收醇制备pvc增塑剂的方法 |
| CN101973884A (zh) * | 2010-09-26 | 2011-02-16 | 昆山合峰化工有限公司 | 偏苯三甲酸三异壬酯的制备方法 |
| EP2655511B1 (de) | 2010-12-23 | 2016-04-06 | INEOS Styrolution Europe GmbH | Thermoplastische elastomer-zusammensetzung und verfahren zu deren herstellung |
| WO2013025277A1 (en) | 2011-08-15 | 2013-02-21 | Exxonmobil Chemical Patents Inc. | Esters and their preparation and use |
| CN102766046B (zh) * | 2012-08-15 | 2015-03-04 | 张开益 | 环保型增塑剂dida的制备方法 |
| EP3077453B1 (de) | 2013-12-06 | 2018-03-28 | Basf Se | Weichmacher-zusammensetzung, die tetrahydrofuranderivate und 1,2-cyclohexandicarbonsäureester enthält |
| WO2015104309A1 (de) | 2014-01-09 | 2015-07-16 | Basf Se | Weichmacher-zusammensetzung, die furanderivate und 1,2-cyclohexandicarbonsäureester enthält |
| DE102015207291A1 (de) | 2014-04-24 | 2016-03-10 | Basf Se | Weichmacher-Zusammensetzung, die Furanderivate und 1,2-Cyclohexandicarbonsäureester enthält |
| TW201609628A (zh) | 2014-07-08 | 2016-03-16 | 巴斯夫歐洲公司 | 包含脂族二羧酸二酯及對苯二甲酸二烷基酯之塑化劑組成物 |
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| WO2019185409A1 (de) | 2018-03-29 | 2019-10-03 | Basf Se | Pvc-zusammensetzung, enthaltend wenigstens einen weichmacher der wenigstens eine carbonsäureestergruppe aufweist und wenigstens eine carbodiimidverbindung |
| EP3747860B1 (de) | 2019-06-04 | 2023-07-26 | Basf Se | Neue weichmacher auf cyclohexanon-basis |
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| EP4386020A1 (en) | 2022-12-12 | 2024-06-19 | Basf Se | Biodegradable graft polymers for dye transfer inhibition |
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| US3056818A (en) * | 1955-10-13 | 1962-10-02 | Goodrich Co B F | Titanium and zirconium esterification catalysts |
| DE1905095A1 (de) * | 1969-02-01 | 1970-08-13 | Dynamit Nobel Ag | Verfahren zur Herstellung von Phosphor enthaltenden Verbindungen |
| DE1945359B2 (de) * | 1969-09-08 | 1973-05-10 | Verfahren zur gewinnung von estern | |
| GB1426057A (en) | 1972-04-24 | 1976-02-25 | Ici Ltd | Production of esters |
| DE2612355C3 (de) * | 1976-03-24 | 1983-11-17 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Abtrennung von Katalysatoren aus rohen Weichmacherestern |
| JPS55130937A (en) * | 1979-03-29 | 1980-10-11 | Sekisui Chem Co Ltd | Preparation of ester |
| DE3935796A1 (de) * | 1989-10-27 | 1991-05-02 | Basf Ag | Di-decylphthalat-gemisch und seine verwendung als weichmacher |
| US5434294A (en) * | 1994-04-04 | 1995-07-18 | Aristech Chemical Corporation | Method of making plasticizers |
| SE514045C2 (sv) * | 1995-09-20 | 2000-12-18 | Bengt G Nilsson | Användning av en diester som hydrofileringsmedel i PVC, PVC- material, diestrar och framställning av diestrar |
-
1997
- 1997-05-22 DE DE19721347A patent/DE19721347B9/de not_active Expired - Fee Related
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1998
- 1998-05-07 ID IDP980677A patent/ID20315A/id unknown
- 1998-05-16 AU AU77661/98A patent/AU736462B2/en not_active Ceased
- 1998-05-16 EP EP98925609A patent/EP0984917B1/de not_active Revoked
- 1998-05-16 PT PT98925609T patent/PT984917E/pt unknown
- 1998-05-16 KR KR19997010715A patent/KR20010012754A/ko not_active Ceased
- 1998-05-16 US US09/424,124 patent/US6310235B1/en not_active Expired - Lifetime
- 1998-05-16 ES ES98925609T patent/ES2209150T3/es not_active Expired - Lifetime
- 1998-05-16 CN CNB988052695A patent/CN1190407C/zh not_active Expired - Fee Related
- 1998-05-16 BR BR9809662-1A patent/BR9809662A/pt not_active Application Discontinuation
- 1998-05-16 RO RO99-01213A patent/RO120539B1/ro unknown
- 1998-05-16 DE DE59810029T patent/DE59810029D1/de not_active Revoked
- 1998-05-16 PL PL337028A patent/PL194776B1/pl unknown
- 1998-05-16 CA CA002290663A patent/CA2290663C/en not_active Expired - Fee Related
- 1998-05-16 DK DK98925609T patent/DK0984917T3/da active
- 1998-05-16 WO PCT/EP1998/002899 patent/WO1998052901A2/de not_active Ceased
- 1998-05-16 AT AT98925609T patent/ATE253035T1/de not_active IP Right Cessation
- 1998-05-16 JP JP54993198A patent/JP2001526672A/ja not_active Ceased
- 1998-05-20 ZA ZA984271A patent/ZA984271B/xx unknown
- 1998-05-21 TW TW087107871A patent/TW434218B/zh not_active IP Right Cessation
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1999
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2001526672A (ja) | 2001-12-18 |
| MX9910734A (es) | 2000-04-30 |
| ID20315A (id) | 1998-11-26 |
| MX215587B (es) | 2003-08-04 |
| CA2290663C (en) | 2006-01-24 |
| EP0984917A2 (de) | 2000-03-15 |
| ATE253035T1 (de) | 2003-11-15 |
| KR20010012754A (ko) | 2001-02-26 |
| AU7766198A (en) | 1998-12-11 |
| DK0984917T3 (da) | 2003-12-01 |
| PT984917E (pt) | 2004-02-27 |
| CA2290663A1 (en) | 1998-11-26 |
| DE19721347C2 (de) | 2000-03-23 |
| PL337028A1 (en) | 2000-07-31 |
| PL194776B1 (pl) | 2007-07-31 |
| CN1257472A (zh) | 2000-06-21 |
| EP0984917B1 (de) | 2003-10-29 |
| ES2209150T3 (es) | 2004-06-16 |
| US6310235B1 (en) | 2001-10-30 |
| CN1190407C (zh) | 2005-02-23 |
| SA99200261B1 (ar) | 2006-05-13 |
| HK1027341A1 (en) | 2001-01-12 |
| WO1998052901A3 (de) | 1999-05-14 |
| DE59810029D1 (de) | 2003-12-04 |
| ZA984271B (en) | 1998-11-30 |
| BR9809662A (pt) | 2000-07-11 |
| AU736462B2 (en) | 2001-07-26 |
| DE19721347B9 (de) | 2005-09-29 |
| DE19721347A1 (de) | 1998-11-26 |
| RO120539B1 (ro) | 2006-03-30 |
| WO1998052901A2 (de) | 1998-11-26 |
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