CN101343227A - Catalyst and technique for synthesis of dialkyl carbonates and aliphatic polyester with coupling method - Google Patents
Catalyst and technique for synthesis of dialkyl carbonates and aliphatic polyester with coupling method Download PDFInfo
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- CN101343227A CN101343227A CNA2008101445257A CN200810144525A CN101343227A CN 101343227 A CN101343227 A CN 101343227A CN A2008101445257 A CNA2008101445257 A CN A2008101445257A CN 200810144525 A CN200810144525 A CN 200810144525A CN 101343227 A CN101343227 A CN 101343227A
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- Prior art keywords
- dimethyl
- aliphatic polyester
- cyclic carbonate
- acetylacetonate
- acid ester
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- 229920003232 aliphatic polyester Polymers 0.000 title claims abstract description 11
- 150000004649 carbonic acid derivatives Chemical class 0.000 title claims abstract description 6
- 230000015572 biosynthetic process Effects 0.000 title claims description 6
- 238000003786 synthesis reaction Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title abstract description 9
- 239000003054 catalyst Substances 0.000 title abstract description 4
- 238000010168 coupling process Methods 0.000 title 1
- 150000005676 cyclic carbonates Chemical class 0.000 claims abstract description 10
- -1 lanthanide metals Chemical class 0.000 claims abstract description 8
- 238000005859 coupling reaction Methods 0.000 claims abstract description 6
- 229910052751 metal Inorganic materials 0.000 claims abstract description 5
- 239000002184 metal Substances 0.000 claims abstract description 5
- 239000010936 titanium Substances 0.000 claims abstract description 4
- 229910052684 Cerium Inorganic materials 0.000 claims abstract description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 3
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052747 lanthanoid Inorganic materials 0.000 claims abstract description 3
- 229910052746 lanthanum Inorganic materials 0.000 claims abstract description 3
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 3
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 3
- 150000003624 transition metals Chemical class 0.000 claims abstract description 3
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 3
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 12
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical class C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 6
- 229940014772 dimethyl sebacate Drugs 0.000 claims description 6
- 238000005516 engineering process Methods 0.000 claims description 5
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052735 hafnium Inorganic materials 0.000 claims description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- IBMRTYCHDPMBFN-UHFFFAOYSA-N Mono-Me ester-Pentanedioic acid Natural products COC(=O)CCCC(O)=O IBMRTYCHDPMBFN-UHFFFAOYSA-N 0.000 claims 2
- RGCVYEOTYJCNOS-UHFFFAOYSA-N (4-cyano-2-methylphenyl)boronic acid Chemical compound CC1=CC(C#N)=CC=C1B(O)O RGCVYEOTYJCNOS-UHFFFAOYSA-N 0.000 claims 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims 1
- MTRYLAXNDGUFAK-UHFFFAOYSA-N 9-ethoxy-9-oxononanoic acid Chemical compound CCOC(=O)CCCCCCCC(O)=O MTRYLAXNDGUFAK-UHFFFAOYSA-N 0.000 claims 1
- ONKUXPIBXRRIDU-UHFFFAOYSA-N Diethyl decanedioate Chemical compound CCOC(=O)CCCCCCCCC(=O)OCC ONKUXPIBXRRIDU-UHFFFAOYSA-N 0.000 claims 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 claims 1
- LNLCRJXCNQABMV-UHFFFAOYSA-N Dimethyl suberate Chemical compound COC(=O)CCCCCCC(=O)OC LNLCRJXCNQABMV-UHFFFAOYSA-N 0.000 claims 1
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 claims 1
- DRUKNYVQGHETPO-UHFFFAOYSA-N Nonanedioic acid dimethyl ester Natural products COC(=O)CCCCCCCC(=O)OC DRUKNYVQGHETPO-UHFFFAOYSA-N 0.000 claims 1
- OUWSNHWQZPEFEX-UHFFFAOYSA-N diethyl glutarate Chemical compound CCOC(=O)CCCC(=O)OCC OUWSNHWQZPEFEX-UHFFFAOYSA-N 0.000 claims 1
- LKKOGZVQGQUVHF-UHFFFAOYSA-N diethyl heptanedioate Chemical compound CCOC(=O)CCCCCC(=O)OCC LKKOGZVQGQUVHF-UHFFFAOYSA-N 0.000 claims 1
- PEUGOJXLBSIJQS-UHFFFAOYSA-N diethyl octanedioate Chemical compound CCOC(=O)CCCCCCC(=O)OCC PEUGOJXLBSIJQS-UHFFFAOYSA-N 0.000 claims 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 claims 1
- SHWINQXIGSEZAP-UHFFFAOYSA-N dimethyl heptanedioate Chemical compound COC(=O)CCCCCC(=O)OC SHWINQXIGSEZAP-UHFFFAOYSA-N 0.000 claims 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 claims 1
- XHEDLZYGAQSNTR-UHFFFAOYSA-N ethene;hexanedioic acid Chemical compound C=C.C=C.OC(=O)CCCCC(O)=O XHEDLZYGAQSNTR-UHFFFAOYSA-N 0.000 claims 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 abstract description 2
- 150000005690 diesters Chemical class 0.000 abstract 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical class CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 8
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 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 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- GYUPBLLGIHQRGT-UHFFFAOYSA-N pentane-2,4-dione;titanium Chemical compound [Ti].CC(=O)CC(C)=O GYUPBLLGIHQRGT-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229940116351 sebacate Drugs 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 240000000146 Agaricus augustus Species 0.000 description 1
- HMWVNKJRYWXJGS-UHFFFAOYSA-N C(C)(=O)OC=C.[C] Chemical compound C(C)(=O)OC=C.[C] HMWVNKJRYWXJGS-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 150000007520 diprotic acids Chemical class 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- AHBPBADERZDJKT-UHFFFAOYSA-N pentane-2,3-dione zirconium Chemical compound [Zr].C(C)C(=O)C(=O)C AHBPBADERZDJKT-UHFFFAOYSA-N 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003606 tin 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
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for synthesizing dialkyl carbonates and aliphatic polyesters by coupled reaction between cyclic carbonate and organic diester. The method uses transition metals such as titanium and zirconium as well as acetylacetone compounds of lanthanide metals such as lanthanum and cerium. The cyclic carbonate and organic diester are present in a molar ratio of 1-5:5-1, a catalyst and a reaction mixture are in a mass ratio of 0.01 to 10 percent, and the decomposition temperature is between 200 and 290DEG C.
Description
Technical field
What the present invention relates to is to be used for the acetylacetonate compound catalyzer that cyclic carbonate and organic dibasic acid ester coupling reaction prepare dialkyl carbonate and aliphatic polyester.
Background technology
Being applied to cyclic carbonate and organic dibasic acid ester by method involved in the present invention, to prepare the reaction expression of dialkyl carbonate and aliphatic polyester as follows:
R wherein
1Represent hydrogen atom and methyl; R
2Represent C
1-C
18Alkyl; R
3Representative-(CH
2)
m-, m=0,1 ... 18.
Reaction with NSC 11801 and dimethyl sebacate is an example.In recent years, many plastic refuses all are to be directly exposed in the environment, and can not degrade for a long time, have caused more and more serious environmental pollution.Aliphatic polyester has biodegradable, and as the substitute of conventional plastic, its synthetic method has obtained extensive studies.At present, the method for chemosynthesis polyester mainly comprises ring-opening polymerization, diprotic acid and diol reaction polymerization, dicarboxylic esters and the polymerization of binary alcohol esters permutoid reaction.The operational path of a while Synthesis of dimethyl carbonate and poly-dimethyl sebacate has been opened up in the reaction of NSC 11801 and dimethyl sebacate, sees reaction formula (3), has improved atom utilization.To this route research is in order to seek green chemical process and novel degradable high polymer material.
At present; some transesterification reaction reports about NSC 11801 and aromatic dicarboxylic acid esters are arranged; people such as Corrado Berti are catalyzer with the tetrabutyl titanate; studied NSC 11801 and dimethyl terephthalate (DMT) reaction (.Macromolecular chemistry and physics[J such as Corrado Berti]; 2002; 203:845-853); JP2000143585 is 1.5 moles in NSC 11801; it is catalyzer with tetrabutyl titanate that dimethyl terephthalate (DMT) is 0.5 mole; nitrogen protection, temperature of reaction are 250 ℃, and the reaction times is under 2 hours the condition; the yield of methylcarbonate is 53%, also reports Al
2O
3, TiO
2, Sb
2O
3,, Ni (OAc)
2.4H
2O, Ti (OCH
3)
4, nBu
2Sn (OCH
3)
2, nBu
2The SnO catalyzer (princes and dukes should for Du Zhiping, Yao Jie. catalysis journal [J], and 2005,26 (8): 637-638), and wherein, nBu
2The effect of SnO is best; the yield of methylcarbonate is 68.4%; also reported a series of metal acetate be catalyzer (Zhang Dan etc. Chinese chemical wall bulletin [J]; 2006; 17 (12): 1607-1610 and Zhang Dan etc. institution of higher education's chemical research [J], 2007,23 (2): 173-175; wherein the effect of Lithium Acetate is best, and the yield of methylcarbonate is 79.1%.In addition; JP09176093 is 190 ℃ in temperature; tetrabutyl titanate is a catalyzer, and nitrogen protection was reacted 3 hours; studied the reaction of NSC 11801 and phenol benzoate, phenylacetate respectively; the yield of diphenyl carbonate is respectively 9.1%, 2.6%, and JP200063331 is 1: 2 in the mol ratio of NSC 11801 and ethyl acetate; 140 ℃ of temperature of reaction, Gd
2O
3Be catalyzer, nitrogen protection was reacted 4 hours, and the transformation efficiency of NSC 11801 is 65%, and the yield of diethyl carbonate is 29%.
Mainly contain titan-alkoxide with the used catalyzer of produced in conventional processes aliphatic polyester, as tetrabutyl titanate, titanium isopropylate etc. (V.Tserki et al.Polymer Degradation and Stability[J], 2006,91:367-376, JP2004307690) but hydrolysis takes place such catalyzer easily, need strict control reaction conditions, also have zinc compounds (KR20030097237), tin compound (JP2000273165) rare earth class catalyzer (US2002082363) and metal oxide-type catalyzer (US2006293492).
Summary of the invention
What the present invention relates to is the novel method for preparing dialkyl carbonate and aliphatic polyester with cyclic carbonate and organic dibasic acid ester coupling reaction, carbonic acid gas is important carbon resource, the material carbon vinyl acetate that is adopted in present method can add by oxyethane and carbonic acid gas and is pressed into, help solving the problem of carbon resource waste, avoid again bringing " Greenhouse effect " to the whole world.And first with the acetylacetonate compound of transition metal such as titanium, zirconium, hafnium and lanthanide series metal such as lanthanum, cerium etc. as this catalyst for reaction, these acetylacetonate compounds use separately or two kinds of acetylacetonate compounds are mixed use, and ratio was 1～10: 10～1 when any two kinds of acetylacetonate compounds mixing was used.The processing condition that catalyst system therefor is fit to are, the mol ratio of cyclic carbonate and organic dibasic acid ester is 1～5: 5～1, and the mass ratio of catalyzer and reaction mixture is 0.01～10%, and temperature of reaction is 200～290 ℃.The product dialkyl carbonate is in time isolated reaction system with rectifying tower, analyzes with vapor-phase chromatography then.
Embodiment
Following example is further explained the present invention.
[example 1] adds the 0.15mol NSC 11801 successively in the there-necked flask of being furnished with thermometer, nitrogen conduit and fractional column, 0.05mol dimethyl sebacate, 0.0002mol titanium acetylacetone, temperature of reaction is 493K～523K, reaction times is 3 hours, the yield of methylcarbonate is 47.1%, and obtains the polyethylene glycol sebacate of oligomeric attitude.
[example 2] 0.05mol NSC 11801, the 0.05mol dimethyl sebacate, 0.0002mol methyl ethyl diketone zirconium is a catalyzer, and other condition is with example 1, and the yield of methylcarbonate is 14.4%, and obtains the polyethylene glycol sebacate of oligomeric attitude.
[example 3] 0.15mol NSC 11801, the 0.05mol dimethyl adipate, the 0.0002mol titanium acetylacetone, other condition is with example 1,, the yield of methylcarbonate is 30.5%, and obtains the polyethylene glycol adipate of oligomeric attitude.
Claims (3)
1. the technology of a cyclic carbonate and organic dibasic acid ester coupling reaction synthesis of dialkyl carbonates and aliphatic polyester, it is characterized in that adopting acetylacetonate compound is catalyzer.
2. the technology of a kind of cyclic carbonate according to claim 1 and organic dibasic acid ester coupling reaction synthesis of dialkyl carbonates and aliphatic polyester, it is characterized in that acetylacetonate compound wherein is meant the acetylacetonate compound of transition metal such as titanium, zirconium, hafnium and lanthanide series metal such as lanthanum, cerium etc., these acetylacetonate compounds use separately or two kinds of acetylacetonate compounds are mixed use, and ratio was 1～10: 10～1 when any two kinds of acetylacetonate compounds mixing was used.
3. the technology of a kind of cyclic carbonate according to claim 1 and organic dibasic acid ester coupling reaction synthesis of dialkyl carbonates and aliphatic polyester, it is characterized in that cyclic carbonate is a NSC 11801, propylene carbonate, the organic dibasic acid ester is meant ethylene dimethyl, diethyl oxalate, dimethyl malonate, diethyl malonate, dimethyl succinate and diethyl succinate, Methyl glutarate, ethyl glutarate, dimethyl adipate, diethylene adipate, NSC 52563, the pimelic acid diethyl ester, the suberic acid dimethyl ester, the suberic acid diethyl ester, dimethyl azelate, ethylazelaate, dimethyl sebacate, a kind of and relevant di-carboxylic acid ester derivative in the ethyl sebacate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008101445257A CN101343227A (en) | 2007-07-23 | 2008-07-23 | Catalyst and technique for synthesis of dialkyl carbonates and aliphatic polyester with coupling method |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200710049588 | 2007-07-23 | ||
| CN200710049588.X | 2007-07-23 | ||
| CNA2008101445257A CN101343227A (en) | 2007-07-23 | 2008-07-23 | Catalyst and technique for synthesis of dialkyl carbonates and aliphatic polyester with coupling method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101343227A true CN101343227A (en) | 2009-01-14 |
Family
ID=40245365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2008101445257A Pending CN101343227A (en) | 2007-07-23 | 2008-07-23 | Catalyst and technique for synthesis of dialkyl carbonates and aliphatic polyester with coupling method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101343227A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103183811A (en) * | 2011-12-29 | 2013-07-03 | 中国科学院成都有机化学有限公司 | Method for synthesizing aliphatic polyester and dialkyl carbonate using dibasic ester and cyclic carbonate |
| CN113698582A (en) * | 2021-09-03 | 2021-11-26 | 中国科学院长春应用化学研究所 | Preparation method of polyester material |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1746195A (en) * | 2004-09-04 | 2006-03-15 | 拜尔材料科学股份公司 | Metal acetylacetonates as transesterification catalysts |
| CN1907565A (en) * | 2006-07-28 | 2007-02-07 | 中国科学院成都有机化学有限公司 | Catalyst for coupling reaction of annular carbonic acid esters and organic dibasic acid ester |
-
2008
- 2008-07-23 CN CNA2008101445257A patent/CN101343227A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1746195A (en) * | 2004-09-04 | 2006-03-15 | 拜尔材料科学股份公司 | Metal acetylacetonates as transesterification catalysts |
| CN1907565A (en) * | 2006-07-28 | 2007-02-07 | 中国科学院成都有机化学有限公司 | Catalyst for coupling reaction of annular carbonic acid esters and organic dibasic acid ester |
Non-Patent Citations (1)
| Title |
|---|
| 张丹等: "金属－乙酰丙酮化合物催化合成PTT聚酯", 《第十一届全国青年催化会议论文集》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103183811A (en) * | 2011-12-29 | 2013-07-03 | 中国科学院成都有机化学有限公司 | Method for synthesizing aliphatic polyester and dialkyl carbonate using dibasic ester and cyclic carbonate |
| CN113698582A (en) * | 2021-09-03 | 2021-11-26 | 中国科学院长春应用化学研究所 | Preparation method of polyester material |
| CN113698582B (en) * | 2021-09-03 | 2022-09-06 | 中国科学院长春应用化学研究所 | Preparation method of polyester material |
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Application publication date: 20090114 |