TW588043B - Process for producing composite mixed ester - Google Patents
Process for producing composite mixed ester Download PDFInfo
- Publication number
- TW588043B TW588043B TW091116007A TW91116007A TW588043B TW 588043 B TW588043 B TW 588043B TW 091116007 A TW091116007 A TW 091116007A TW 91116007 A TW91116007 A TW 91116007A TW 588043 B TW588043 B TW 588043B
- Authority
- TW
- Taiwan
- Prior art keywords
- reaction
- stage
- manufacturing
- scope
- patent application
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title abstract description 30
- 239000002131 composite material Substances 0.000 title abstract description 10
- 230000008569 process Effects 0.000 title abstract description 4
- 239000002253 acid Substances 0.000 claims abstract description 54
- 239000000203 mixture Substances 0.000 claims abstract description 45
- 238000004519 manufacturing process Methods 0.000 claims abstract description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 39
- 150000002009 diols Chemical class 0.000 claims abstract description 32
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 15
- 150000007513 acids Chemical class 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims description 97
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 48
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 34
- 239000001361 adipic acid Substances 0.000 claims description 25
- 235000011037 adipic acid Nutrition 0.000 claims description 25
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 230000001588 bifunctional effect Effects 0.000 claims description 3
- 238000005516 engineering process Methods 0.000 claims description 3
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 3
- 150000005690 diesters Chemical class 0.000 abstract description 12
- 238000005886 esterification reaction Methods 0.000 abstract description 12
- 125000003158 alcohol group Chemical group 0.000 abstract description 11
- 229920000642 polymer Polymers 0.000 abstract description 11
- 239000004014 plasticizer Substances 0.000 abstract description 10
- 230000032050 esterification Effects 0.000 abstract description 4
- 239000000598 endocrine disruptor Substances 0.000 abstract 1
- 231100000049 endocrine disruptor Toxicity 0.000 abstract 1
- 230000001988 toxicity Effects 0.000 abstract 1
- 231100000419 toxicity Toxicity 0.000 abstract 1
- 239000000047 product Substances 0.000 description 50
- 235000019441 ethanol Nutrition 0.000 description 42
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 32
- -1 hetero compound esters Chemical class 0.000 description 21
- 239000006227 byproduct Substances 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 16
- 238000006297 dehydration reaction Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 11
- 235000013772 propylene glycol Nutrition 0.000 description 11
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 10
- 230000018044 dehydration Effects 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 235000021419 vinegar Nutrition 0.000 description 9
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 8
- 239000000052 vinegar Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 4
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 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
- 239000005556 hormone Substances 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000282994 Cervidae Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Natural products OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- AIJTTZAVMXIJGM-UHFFFAOYSA-N Grepafloxacin Chemical compound C1CNC(C)CN1C(C(=C1C)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 AIJTTZAVMXIJGM-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-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
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-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
- 238000004364 calculation method Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000002469 cyanolytic effect Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- DJDSLBVSSOQSLW-UHFFFAOYSA-N mono(2-ethylhexyl) phthalate Chemical group CCCCC(CC)COC(=O)C1=CC=CC=C1C(O)=O DJDSLBVSSOQSLW-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- 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)
- Polyesters Or Polycarbonates (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001391299A JP3907470B2 (ja) | 2001-12-25 | 2001-12-25 | 異種複合エステルの製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW588043B true TW588043B (en) | 2004-05-21 |
Family
ID=19188498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091116007A TW588043B (en) | 2001-12-25 | 2002-07-18 | Process for producing composite mixed ester |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP3907470B2 (enExample) |
| KR (1) | KR100619575B1 (enExample) |
| CN (1) | CN1285564C (enExample) |
| TW (1) | TW588043B (enExample) |
| WO (1) | WO2003055842A1 (enExample) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62234044A (ja) * | 1986-04-01 | 1987-10-14 | Satoru Matsumoto | 異種複合エステルの製造方法 |
| JP3409067B2 (ja) * | 1994-06-02 | 2003-05-19 | 哲 松本 | 異種複合エステル |
| JP3409068B2 (ja) * | 1994-12-01 | 2003-05-19 | 哲 松本 | ジオールジエステルならびにそれを使用して造られる複合エステルならびにポリエステル |
| US7030057B2 (en) * | 2000-05-19 | 2006-04-18 | Japan Science And Technology Agency | Catalyst for esterification and transesterification and process for producing ester |
-
2001
- 2001-12-25 JP JP2001391299A patent/JP3907470B2/ja not_active Expired - Fee Related
-
2002
- 2002-06-18 WO PCT/JP2002/006083 patent/WO2003055842A1/ja not_active Ceased
- 2002-06-18 KR KR1020047004380A patent/KR100619575B1/ko not_active Expired - Fee Related
- 2002-06-18 CN CNB028261569A patent/CN1285564C/zh not_active Expired - Fee Related
- 2002-07-18 TW TW091116007A patent/TW588043B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003055842A1 (fr) | 2003-07-10 |
| JP3907470B2 (ja) | 2007-04-18 |
| CN1285564C (zh) | 2006-11-22 |
| CN1608046A (zh) | 2005-04-20 |
| JP2003183372A (ja) | 2003-07-03 |
| KR100619575B1 (ko) | 2006-09-08 |
| KR20040058190A (ko) | 2004-07-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7030057B2 (en) | Catalyst for esterification and transesterification and process for producing ester | |
| CN112266471B (zh) | 一种聚己二酸-对苯二甲酸丁二醇酯的制备方法 | |
| CN102482405B (zh) | 制备聚醚-聚酯嵌段共聚物的方法 | |
| CN114835886B (zh) | 一种固态双金属钛系聚酯催化剂及其制备方法、应用 | |
| JPS59136325A (ja) | ポリエステルの製法 | |
| CN102105509B (zh) | 脂肪族聚酯树脂及其制备方法 | |
| KR20160023973A (ko) | 투명 생분해성 고분자 | |
| TW593245B (en) | Process for the production of 5-sulfo isophthalate bis-glycolate ester metal salts and oxysulfonated polyesters made therefrom | |
| CN109134832A (zh) | 一种新型生物基pbat合成方法及其应用 | |
| KR20090090695A (ko) | 락트산 공중합체 및 그 제조방법 | |
| CN111886275A (zh) | 官能化的双环呋喃及其合成 | |
| US4139525A (en) | Flexible glycolic acid terpolymers | |
| CN102140165B (zh) | 一种可生物降解的共聚酯及其制备方法 | |
| US6528579B2 (en) | Zero-heel polyester process | |
| CN100439466C (zh) | 聚酯热熔胶及其制备方法 | |
| TW200400987A (en) | Partially ester-exchanged SIPM and process therewith | |
| JP3480274B2 (ja) | 脂肪族ポリエステル共重合体の製造方法 | |
| JPH04169566A (ja) | ５―スルホイソフタル酸アルキレングリコールエステル金属塩を含むアルキレングリコール溶液の製造方法 | |
| TW201030050A (en) | Method for preparing polyester resin | |
| CN114524923B (zh) | 一种基于十二烷二酸和乙二醇的生物降解聚酯及其制备方法和应用 | |
| JP3647689B2 (ja) | 脂肪族ポリエステルの製造方法 | |
| JPH08259680A (ja) | 脂肪族ポリエステル共重合体の製造法 | |
| JP3079717B2 (ja) | 高分子量脂肪族ポリエステルの製造方法 | |
| JP3409068B2 (ja) | ジオールジエステルならびにそれを使用して造られる複合エステルならびにポリエステル | |
| KR100619575B1 (ko) | 이종복합 에스테르의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |