CN100464852C - Organic stannum sulfonate catalyst for exchange reaction of methyl carbonate and phenol ester - Google Patents
Organic stannum sulfonate catalyst for exchange reaction of methyl carbonate and phenol ester Download PDFInfo
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- CN100464852C CN100464852C CNB200610020953XA CN200610020953A CN100464852C CN 100464852 C CN100464852 C CN 100464852C CN B200610020953X A CNB200610020953X A CN B200610020953XA CN 200610020953 A CN200610020953 A CN 200610020953A CN 100464852 C CN100464852 C CN 100464852C
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- 239000003054 catalyst Substances 0.000 title claims abstract description 34
- -1 phenol ester Chemical class 0.000 title claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 title claims description 29
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 title claims description 9
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 title claims description 9
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 title 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000002148 esters Chemical group 0.000 claims abstract description 13
- 125000003944 tolyl group Chemical group 0.000 claims abstract description 6
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- NHZZUJIRMHDTKR-UHFFFAOYSA-N carbonic acid;toluene Chemical compound OC(O)=O.CC1=CC=CC=C1 NHZZUJIRMHDTKR-UHFFFAOYSA-N 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 240000005373 Panax quinquefolius Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 231100000004 severe toxicity Toxicity 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to an organic tin sulfonates catalyst used in ester exchange to compose the methyl phenyl carbonic ester and diphenyl carbonate. Wherein, said catalyst is trisubstitution organic tin sulfonates in following structure, while R1 and R2 are C1-C18 alkyl, and the substituted or non-substituted aryl. With said inventive catalyst, the total selectivity of methyl phenyl carbonic ester and diphenyl carbonate are higher than 99%.
Description
Technical field
The present invention relates to a kind of organic stannum sulfonate catalyst that is used for dimethyl carbonate and phenol ester exchange reaction synthesis of methyl phenyl carbonic ester, diphenyl carbonate.
Background technology
Diphenyl carbonate is nontoxic, pollution-free, is a kind of important " green " chemical products, can be used for synthetic many important organic compounds and macromolecular material, particularly can replace hypertoxic phosgene and bisphenol-a reaction to generate the Merlon of function admirable.The synthetic method of diphenyl carbonate has phosgenation, oxidation of phenol carbonyl process and ester-interchange method.Because the phosgene severe toxicity can cause serious environmental to pollute, and is just progressively eliminated; Though oxidation of phenol carbonyl process raw material is simple and easy to, atom utilization is also high, the catalyst costliness of its use, and catalytic efficiency is not high, make the use of this method be restricted; Ester-interchange method is that phenol and dimethyl carbonate are under catalyst action, reaction generates a kind of green synthetic route of diphenyl carbonate, the methyl alcohol of Sheng Chenging can be used as the raw material of green Synthesis of dimethyl carbonate again simultaneously, these two reacting phase combinations, can form the green building-up process of " zero-emission ", thereby ester-interchange method is considered to the most promising method of present diphenyl carbonate synthesis.The ester exchange reaction of dimethyl carbonate and phenol is the thermodynamics reversible reaction, and the equilibrium constant is very little (to be 3 * 10 during 453K
-4), be unfavorable for the generation of target product, make that the yield of diphenyl carbonate is low, reaction speed is also very slow, and the ester-interchange method diphenyl carbonate synthesis exists equilibrium yield low at present, has problems such as the catalyst price is more expensive, efficient is high inadequately now.Therefore, exploitation effective catalyst and suitable reaction process are very important.
JP 8188558, and EP 0780361, and JP 10032361 has introduced a class titanium, tin organic compound catalyst.As butyl titanate [Ti (OC
4H
9)
4], Dibutyltin oxide [n-Bu
2SnO], metatitanic acid four phenyl esters [Ti (OPh)
4] etc.Such catalyst performance height, target product productive rate can reach more than 50%, but catalyst and product separate difficulty of recovery.
Chinese patent CN 1411909 discloses a kind of composite catalyst that is used for ester exchange synthesis of methyl phenyl carbonic ester and preparation method thereof.This catalyst is to be formed by certain mol proportion is composite by organotin, organic titanium and organic amine.The mol ratio that is characterized in three kinds of components is: 1:0.2～2:0.001～0.5.Reaction temperature is 150～200 ℃, and reaction pressure is a normal pressure, and the time is 6～30 hours.Phenol conversion is 15～50%, the methyl benzol carbonate selectivity〉90%.This kind catalyst combines the advantage of organotin and organic titanium catalyst, adds organic amine on this basis, makes catalyst activity, selectivity higher.
Chinese patent CN1036951 has introduced a class organo-tin compound and a metal compound as catalyst.The organo-tin compound catalyst is XR
2SnOSnR
2(X and Y can be identical, also can be different for Y.They represent OH, SCN etc. separately); Metallic compound is the compound that is selected from any element in Sc, Cr, Mo, W, Mn, Au, Ga, In, Bi, Te and the blue lanthanide series.But these activity of such catalysts are low, and the total recovery of methyl benzol carbonate and diphenyl carbonate is lower than 20%.
US4554110 has reported a kind of tin compound of polymerization, and its molecular formula is as follows:
Wherein R, R1 represent alkyl.
When such catalyst is used for ester exchange reaction, only in long reaction time (≧ 24 hour) under the condition, could obtain high diphenyl carbonate yield.
US4552704 has reported RSn (O) OH catalyzed carbon acid dialkyl ester and aromatic hydroxy compound synthesizing aryl alkyl carbonate and diaryl carbonate.
Document (Lee H, Bae JY, Kwon O S, et al.[J] Journal of Organometallic Chemistry, 2004,689:1816-1820; Lee H, Kim S J, Ahn B S, et al.[J] Catalysis Today, 2003,87:139-144) reported [n-Bu respectively
2Sn (OH) (OSO
2CF
3)]
2, [n-Bu
2Sn (OCOCH
3) (OSO
2CF
3)]
2, and Dibutyltin oxide respectively with equimolar CF
3SO
3H, CH
3C
6H
4SO
3H, C
6H
4SO
3H, CH
3SO
3H mixed catalytic dimethyl carbonate and phenol are made the ester exchange reaction under the solvent condition at pressurization, benzene: the conversion ratio 57.5～60.9% of dimethyl carbonate, the yield 36.5～40.9% of methyl benzol carbonate, the yield 18.3～20.8% of diphenyl carbonate.
Summary of the invention
The organic stannum sulfonate catalyst that the purpose of this invention is to provide a kind of dimethyl carbonate and phenol ester exchange reaction synthesis of methyl phenyl carbonic ester, diphenyl carbonate.This organic stannum sulfonate catalyst is to have three of following array structure to replace organic stannum sulfonate.
R wherein
1Be C
1～C
18The aryl of alkyl, replacement or non-replacement etc.Substituent R
1Can be: methyl, ethyl, propyl group, isopropyl, butyl, isobutyl group, the tert-butyl group, amyl group, hexyl, heptyl, cyclopenta, cyclohexyl, dodecyl, phenyl, benzyl and single or many alkyl, halogen, phenyl that nitro replaces, in the benzyl any one.
R
2Be C
1～C
12Alkyl, the aryl of replacement or non-replacement etc., and R
2With R
1Can be identical, also can be different.Substituent R
2Can be: the alkyl that methyl, ethyl, propyl group, butyl, amyl group, hexyl, heptyl, cyclopenta, cyclohexyl, dodecyl, phenyl, benzyl, list or many halogens replace and single or many alkyl, halogen, phenyl that nitro replaces, in the benzyl any one.R
2Also can be the resin of sulfonic acid type.
The process conditions that catalyst system therefor of the present invention is fit to are: the mol ratio of dimethyl carbonate and phenol is 1:0.25～4, and the mol ratio of phenol and catalyst is 1:0.0005～0.03.120～260 ℃ of transesterification reaction temperature, ester exchange reaction pressure 0.1～1.5MPa.In the course of reaction, by-product methyl alcohol and dimethyl carbonate form azeotropic mixture, in time separate with rectifying column.The product gc analysis.
The specific embodiment
About method of the present invention, be illustrated with following example, but the present invention never is subjected to the restriction of these examples.
[embodiment 1] adds the p-CH of 0.3mol phenol and 0.00339mol in the 100ml reactor of being furnished with agitator, rectifying column, condenser, charge pump under nitrogen protection
3PhSO
3Sn (CH
2Ph)
3Catalyst.After reacting liquid temperature rises to 180 ℃, begin to add dimethyl carbonate.0.15mol dimethyl carbonate in 3h, add, continue reaction 5h then.The azeotropic mixture that timely separating by-products methyl alcohol of course of reaction and dimethyl carbonate form.The conversion ratio of dimethyl carbonate is 45.8%, and the productive rate of methyl benzol carbonate (MPC) is 38.4%, and the productive rate of diphenyl carbonate (DPC) is 7.4%.
Remove by equimolar CF [embodiment 2]
3SO
3Sn (CH
2Ph)
3Outside the catalyst in the catalyst replacement example 1, other reaction condition is with embodiment 1, and the result who records is: the conversion ratio of dimethyl carbonate is 57.5%, and the productive rate of methyl benzol carbonate (MPC) is 34.2%, the productive rate of diphenyl carbonate (DPC) is 16.2%, and the productive rate of methyl phenyl ethers anisole is 7.1%.
[embodiment 3] PhSO
3Sn (n-Bu)
3Catalyst consumption is 0.005mol, and other reaction condition is with embodiment 1, and the result who records is: the conversion ratio of dimethyl carbonate is 49.4%, and the productive rate of methyl benzol carbonate (MPC) is 36.1%, and the productive rate of diphenyl carbonate (DPC) is 13.3%.
[embodiment 4] add the RSO of 0.1mol phenol and 1g in the 100ml reactor of being furnished with agitator, rectifying column, condenser, charge pump under nitrogen protection
3Sn (CH
3)
3(R represents strongly acidic cation-exchange) catalyst.When reaction temperature reaches 160 ℃, begin slowly to add the 0.3mol dimethyl carbonate, finish reaction behind the 10h.The azeotropic mixture that timely separating by-products methyl alcohol of course of reaction and dimethyl carbonate form.The conversion ratio of phenol is 10.0%, and the productive rate of methyl benzol carbonate (MPC) is 8.4%, and the productive rate of diphenyl carbonate (DPC) is 1.6%.
Claims (1)
1. the method by dimethyl carbonate and phenol ester exchange reaction synthesis of methyl phenyl carbonic ester and diphenyl carbonate is characterized in that catalyst is an organic stannum sulfonate catalyst,
Organic stannum sulfonate catalyst is to have three of above structure to replace organic stannum sulfonate; Substituent R wherein
1In the phenyl that is methyl, ethyl, propyl group, isopropyl, butyl, isobutyl group, the tert-butyl group, amyl group, hexyl, heptyl, cyclopenta, cyclohexyl, dodecyl, phenyl, benzyl, replaces by single alkyl, many alkyl, halogen or nitro, the benzyl that replaces by single alkyl, many alkyl, halogen or nitro any one; Substituent R
2With R
1Can be identical, also can be different, substituent R
2In the phenyl that is the resin, list of methyl, ethyl, propyl group, butyl, amyl group, hexyl, heptyl, cyclopenta, cyclohexyl, dodecyl, phenyl, benzyl, sulfonic acid type or alkyl that many halogens replace, replaces by single alkyl, many alkyl, halogen or nitro, the benzyl that replaces by single alkyl, many alkyl, halogen or nitro any one.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB200610020953XA CN100464852C (en) | 2006-04-30 | 2006-04-30 | Organic stannum sulfonate catalyst for exchange reaction of methyl carbonate and phenol ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB200610020953XA CN100464852C (en) | 2006-04-30 | 2006-04-30 | Organic stannum sulfonate catalyst for exchange reaction of methyl carbonate and phenol ester |
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| Publication Number | Publication Date |
|---|---|
| CN1843627A CN1843627A (en) | 2006-10-11 |
| CN100464852C true CN100464852C (en) | 2009-03-04 |
Family
ID=37062615
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB200610020953XA Active CN100464852C (en) | 2006-04-30 | 2006-04-30 | Organic stannum sulfonate catalyst for exchange reaction of methyl carbonate and phenol ester |
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| Country | Link |
|---|---|
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Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104478711B (en) * | 2014-12-04 | 2016-04-06 | 陕西延长石油（集团）有限责任公司 | The method of microreactor continuous synthesis methyl benzol carbonate |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4552704A (en) * | 1983-12-27 | 1985-11-12 | General Electric Company | Process for the production of aromatic carbonates |
| CN1036951A (en) * | 1988-04-16 | 1989-11-08 | 三井石油化学工业株式会社 | The manufacture method of aromatic carbonate |
| KR20040061898A (en) * | 2002-12-31 | 2004-07-07 | 한국과학기술연구원 | Method for preparing of Diphenyl Carbonate |
| CN1736601A (en) * | 2005-07-28 | 2006-02-22 | 中国科学院成都有机化学有限公司 | Stannum contained compound catalyst for synthesizing aryl carbonate by ester exchange |
| CN1736600A (en) * | 2005-07-28 | 2006-02-22 | 中国科学院成都有机化学有限公司 | Dialkyl containing stannum compound catalyst for synthesizing aryl carbonate by ester exchange |
-
2006
- 2006-04-30 CN CNB200610020953XA patent/CN100464852C/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4552704A (en) * | 1983-12-27 | 1985-11-12 | General Electric Company | Process for the production of aromatic carbonates |
| CN1036951A (en) * | 1988-04-16 | 1989-11-08 | 三井石油化学工业株式会社 | The manufacture method of aromatic carbonate |
| KR20040061898A (en) * | 2002-12-31 | 2004-07-07 | 한국과학기술연구원 | Method for preparing of Diphenyl Carbonate |
| CN1736601A (en) * | 2005-07-28 | 2006-02-22 | 中国科学院成都有机化学有限公司 | Stannum contained compound catalyst for synthesizing aryl carbonate by ester exchange |
| CN1736600A (en) * | 2005-07-28 | 2006-02-22 | 中国科学院成都有机化学有限公司 | Dialkyl containing stannum compound catalyst for synthesizing aryl carbonate by ester exchange |
Non-Patent Citations (2)
| Title |
|---|
| 119Sn-NMR Spectroscopic Investigations of TributyltinDerivatives of Aromatic Sulfonic Acids. Frank Thunecke, et al.Journal f. prakt. Chemie,Vol.333 No.3. 1991 |
| 119Sn-NMR Spectroscopic Investigations of TributyltinDerivatives of Aromatic Sulfonic Acids. Frank Thunecke, et al.Journal f. prakt. Chemie,Vol.333 No.3. 1991 * |
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|---|---|
| CN1843627A (en) | 2006-10-11 |
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Owner name: AOKE CHEMICAL YANGZHOU CO., LTD. Effective date: 20130730 |
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Effective date of registration: 20130730 Address after: 610041 Chengdu hi tech Zone, East Road, high tech building Patentee after: Chengdu Organic Chemicals Co., Ltd., Chinese Academy of Sciences Patentee after: Oxiranchem (Yangzhou) Co., Ltd. Address before: 610041 Chengdu hi tech Zone, East Road, high tech building Patentee before: Chengdu Organic Chemicals Co., Ltd., Chinese Academy of Sciences |
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Address after: 610041 Chengdu hi tech Zone, East Road, high tech building Co-patentee after: Jiangsu oxiranchem Co., Ltd. Patentee after: Chengdu Organic Chemicals Co., Ltd., Chinese Academy of Sciences Address before: 610041 Chengdu hi tech Zone, East Road, high tech building Co-patentee before: Oxiranchem (Yangzhou) Co., Ltd. Patentee before: Chengdu Organic Chemicals Co., Ltd., Chinese Academy of Sciences |
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| CP01 | Change in the name or title of a patent holder |