CN100398509C - 酯取代的二芳基碳酸酯的无溶剂制备方法 - Google Patents
酯取代的二芳基碳酸酯的无溶剂制备方法 Download PDFInfo
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- CN100398509C CN100398509C CNB028186974A CN02818697A CN100398509C CN 100398509 C CN100398509 C CN 100398509C CN B028186974 A CNB028186974 A CN B028186974A CN 02818697 A CN02818697 A CN 02818697A CN 100398509 C CN100398509 C CN 100398509C
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- Prior art keywords
- ester
- phosgene
- phenol
- radical
- alkyl
- 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.)
- Expired - Fee Related
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- -1 diaryl carbonates Chemical class 0.000 title claims abstract description 100
- 238000002360 preparation method Methods 0.000 title claims description 10
- 238000000034 method Methods 0.000 claims abstract description 82
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 62
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 12
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 150000002148 esters Chemical class 0.000 claims description 90
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 51
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 239000011541 reaction mixture Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 21
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 17
- 239000009637 wintergreen oil Substances 0.000 claims description 17
- 150000003512 tertiary amines Chemical group 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 8
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 8
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 5
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000001449 anionic compounds Chemical class 0.000 claims description 4
- 229910001412 inorganic anion Inorganic materials 0.000 claims description 4
- 150000002891 organic anions Chemical class 0.000 claims description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 4
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- LZFIOSVZIQOVFW-UHFFFAOYSA-N propyl 2-hydroxybenzoate Chemical compound CCCOC(=O)C1=CC=CC=C1O LZFIOSVZIQOVFW-UHFFFAOYSA-N 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 3
- RQTVIKMRXYJTDX-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-4-phenylpiperidine-4-carbonitrile Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CCC(C=2C=CC=CC=2)(C#N)CC1 RQTVIKMRXYJTDX-UHFFFAOYSA-N 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- GYCKQBWUSACYIF-UHFFFAOYSA-N Ethyl salicylate Chemical compound CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- ZSZGLSAHRNYXPR-UHFFFAOYSA-N bis(diethylamino)methylidene-diethylazanium Chemical compound CCN(CC)C(N(CC)CC)=[N+](CC)CC ZSZGLSAHRNYXPR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- HXWGXXDEYMNGCT-UHFFFAOYSA-M decyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)C HXWGXXDEYMNGCT-UHFFFAOYSA-M 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 31
- 239000002904 solvent Substances 0.000 abstract description 16
- 150000002989 phenols Chemical class 0.000 abstract description 6
- 239000007787 solid Substances 0.000 abstract description 4
- 239000012970 tertiary amine catalyst Substances 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- SBCZJQDTHTUBRP-UHFFFAOYSA-N (2-hydroxyphenyl)methyl methyl carbonate Chemical compound COC(=O)OCC1=CC=CC=C1O SBCZJQDTHTUBRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000006561 solvent free reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 37
- 230000009466 transformation Effects 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 10
- 210000004271 bone marrow stromal cell Anatomy 0.000 description 8
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 8
- 229920000515 polycarbonate Polymers 0.000 description 7
- 239000004417 polycarbonate Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000003125 aqueous solvent Substances 0.000 description 5
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 5
- TZSMWSKOPZEMAJ-UHFFFAOYSA-N bis[(2-methoxyphenyl)methyl] carbonate Chemical compound COC1=CC=CC=C1COC(=O)OCC1=CC=CC=C1OC TZSMWSKOPZEMAJ-UHFFFAOYSA-N 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000008676 import Effects 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GVGVUNDFQUSHDM-UHFFFAOYSA-N 1-benzyl-2h-pyridine Chemical group C=1C=CC=CC=1CN1CC=CC=C1 GVGVUNDFQUSHDM-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- XUNCVWQATLFOFE-UHFFFAOYSA-N butylphosphanium;acetate Chemical group CC([O-])=O.CCCC[PH3+] XUNCVWQATLFOFE-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- BMOAQMNPJSPXIU-UHFFFAOYSA-N ethyl 2-(3-fluoro-4-nitrophenyl)propanoate Chemical compound CCOC(=O)C(C)C1=CC=C([N+]([O-])=O)C(F)=C1 BMOAQMNPJSPXIU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical class [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical group C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
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)
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
实施例 | 催化剂 | 催化剂水平 | ℃ | pH | %转化率 | %选择性 |
1 | Et<sub>3</sub>N | 1% | r.t.-48 | 10.3 | 48.65 | 96.8% |
2 | Et<sub>3</sub>N | 1% | <15 | 10.3 | 46.2% | 99.5% |
3 | MTBA | 1% | r.t.-48 | 10.3 | 61.4% | 91.7% |
4 | MTBA | 1% | <15 | 10.3 | 69.4% | 98.1% |
实施例 | 催化剂 | 催化剂水平 | ℃ | pH | %转化率 | %选择性 |
5 | MTBA | 1% | r.t.-48 | 8.3 | 28.8% | 95.8% |
6 | Et<sub>3</sub>N | 1% | r.t.-48 | 8.3 | 29.6% | 99.3% |
7 | MTBA | 1% | r.t.-48 | 9.3 | 42.8% | 99.2% |
8 | MTBA | 1% | r.t.-48 | 10.3 | 47.1% | 97.0% |
实施例 | 催化剂 | 催化剂水平 | ℃ | pH | %转化率 | %选择性 |
9 | MTBA | 1% | <15 | 10.3 | 69.4% | 98.1% |
10 | Et<sub>3</sub>N | 1% | <15 | 8.3 | 48.6% | 96.9% |
11 | MTBA | 0.5% | <15 | 10.3 | 70.8% | 98.5% |
12 | MTBA | 0.25% | <15 | 10.3 | 69.9% | 99.0% |
实施例 | 催化剂 | 催化剂水平 | ℃ | pH | %转化率 | %选择性 |
13 | MTBA | 0.5% | r.t.-48 | 10.3 | 67.0% | 91.2% |
14 | MTBA | 0.5% | <35 | 10.3 | 64.6% | 97.9% |
15 | MTBA | 0.5% | <15 | 10.3 | 70.8% | 98.5% |
实施例 | 催化剂 | 催化剂水平 | 理论转化率 | 理论的% | %选择性 |
16 | MTBA | 0.5% | 50% | 100% | 98.9% |
17 | MTBA | 0.5% | 60% | 100% | 98.6% |
18 | MTBA | 0.5% | 70% | 100% | 98.5% |
19 | MTBA | 0.5% | 80% | 100% | 98.9% |
20 | MTBA | 0.5% | 100% | 89% | 98.3% |
实施例 | 催化剂 | ℃ | 理论转化率 | %转化率 | %选择性 |
21 | MTBA-Et<sub>3</sub>N | r.t.-48 | 70% | 56% | 93.6% |
22 | MTBA-Et<sub>3</sub>N | <15 | 70% | 61.9% | 98.7% |
Claims (36)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/911,527 | 2001-07-24 | ||
US09/911,527 US6469192B1 (en) | 2001-07-24 | 2001-07-24 | Solventless preparation of ester-substituted diaryl carbonates |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1558892A CN1558892A (zh) | 2004-12-29 |
CN100398509C true CN100398509C (zh) | 2008-07-02 |
Family
ID=25430396
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB028186974A Expired - Fee Related CN100398509C (zh) | 2001-07-24 | 2002-07-01 | 酯取代的二芳基碳酸酯的无溶剂制备方法 |
Country Status (7)
Country | Link |
---|---|
US (2) | US6469192B1 (zh) |
EP (1) | EP1414779B1 (zh) |
JP (1) | JP2004536865A (zh) |
KR (1) | KR20040018498A (zh) |
CN (1) | CN100398509C (zh) |
TW (1) | TWI224095B (zh) |
WO (1) | WO2003010123A1 (zh) |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6469192B1 (en) * | 2001-07-24 | 2002-10-22 | General Electric Company | Solventless preparation of ester-substituted diaryl carbonates |
US6548623B2 (en) * | 2001-07-24 | 2003-04-15 | General Electric Company | Method of polycarbonate preparation |
US6870025B2 (en) * | 2001-07-24 | 2005-03-22 | General Electric Company | Method of polycarbonate preparation |
US7151189B2 (en) * | 2003-06-19 | 2006-12-19 | General Electric Company | Method and apparatus for waste stream recovery |
US7057004B2 (en) * | 2004-01-29 | 2006-06-06 | General Electric Company | Process for the production of copolycarbonates with reduced color |
US7041775B2 (en) * | 2004-04-20 | 2006-05-09 | General Electric Company | Method for preparing a polycarbonate oligomer mixture at low temperature for manufacturing polycarbonate |
US7312352B2 (en) | 2004-08-02 | 2007-12-25 | Paul William Buckley | Method of preparing ester-substituted diaryl carbonates |
US7105626B2 (en) * | 2004-09-10 | 2006-09-12 | General Electric Company | Method for incorporating alkyl ester endgroups to improve the release properties of melt polycarbonate |
US7132498B2 (en) * | 2004-09-27 | 2006-11-07 | General Electric Company | Process to make polycarbonate from bismethylsalicylcarbonate (BMSC) |
US7230066B2 (en) * | 2004-12-16 | 2007-06-12 | General Electric Company | Polycarbonate—ultem block copolymers |
US7365149B2 (en) * | 2005-12-12 | 2008-04-29 | Hans-Peter Brack | Equipment cleaning in the manufacture of polycarbonates |
US7485695B2 (en) * | 2005-12-21 | 2009-02-03 | Sabic Innovative Plastics Ip B.V | Polycarbonates containing low levels of methyl salicylate prepared by a melt polymerization in a reactive extruder |
US7485694B2 (en) * | 2005-12-21 | 2009-02-03 | Sabic Innovative Plastics Ip B.V. | Polycarbonates containing low levels of methyl salicylate prepared by a melt polymerization in a reactive extruder |
US7498399B2 (en) * | 2006-05-31 | 2009-03-03 | Sabic Innovative Plastics Ip B.V. | Method of preparing ester-substituted diaryl carbonates |
US7495064B2 (en) * | 2006-06-26 | 2009-02-24 | Sabic Innovative Plastics Ip Bv | Manufacture of polycarbonates |
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US7671165B2 (en) * | 2008-05-16 | 2010-03-02 | Sabic Innovative Plastics Ip B.V. | Method of forming polycarbonate |
US7674872B2 (en) * | 2008-06-17 | 2010-03-09 | Sabic Innovative Plastics Ip B.V. | Method of producing high molecular weight polymer |
US7547799B1 (en) | 2008-06-20 | 2009-06-16 | Sabic Innovative Plastics Ip B.V. | Method for producing phenolic compound |
US8343608B2 (en) | 2010-08-31 | 2013-01-01 | General Electric Company | Use of appended dyes in optical data storage media |
CN108727193B (zh) * | 2017-04-24 | 2021-03-16 | 中国石油化工股份有限公司 | 碳酸二苯酯类化合物的制备方法 |
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US6300459B1 (en) * | 1998-03-17 | 2001-10-09 | Teijin Limited | Process for producing aromatic polycarbonate |
JPH11302228A (ja) | 1998-04-20 | 1999-11-02 | Teijin Ltd | サリチル酸エステル誘導体およびその製造方法 |
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US6469192B1 (en) * | 2001-07-24 | 2002-10-22 | General Electric Company | Solventless preparation of ester-substituted diaryl carbonates |
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- 2001-07-24 US US09/911,527 patent/US6469192B1/en not_active Expired - Lifetime
-
2002
- 2002-07-01 JP JP2003515485A patent/JP2004536865A/ja active Pending
- 2002-07-01 EP EP02742382.1A patent/EP1414779B1/en not_active Expired - Lifetime
- 2002-07-01 CN CNB028186974A patent/CN100398509C/zh not_active Expired - Fee Related
- 2002-07-01 KR KR10-2004-7000979A patent/KR20040018498A/ko not_active Application Discontinuation
- 2002-07-01 WO PCT/US2002/020941 patent/WO2003010123A1/en active Application Filing
- 2002-07-12 TW TW091115566A patent/TWI224095B/zh active
- 2002-08-12 US US10/216,512 patent/US6891015B2/en not_active Expired - Lifetime
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US2837555A (en) * | 1956-09-20 | 1958-06-03 | Dow Chemical Co | Preparation of carbonate esters |
US4016190A (en) * | 1975-03-01 | 1977-04-05 | Bayer Aktiengesellschaft | Process for the preparation of diarylcarbonates |
US6175017B1 (en) * | 1991-10-22 | 2001-01-16 | Bayer Aktiengesellschaft | Process for the production of aryl carbonates |
WO1998045246A1 (fr) * | 1997-04-04 | 1998-10-15 | Teijin Limited | Derives d'esters salicyliques et leur procede de preparation |
Also Published As
Publication number | Publication date |
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US20030060649A1 (en) | 2003-03-27 |
US6469192B1 (en) | 2002-10-22 |
JP2004536865A (ja) | 2004-12-09 |
EP1414779B1 (en) | 2015-05-27 |
US6891015B2 (en) | 2005-05-10 |
KR20040018498A (ko) | 2004-03-03 |
CN1558892A (zh) | 2004-12-29 |
EP1414779A1 (en) | 2004-05-06 |
WO2003010123A1 (en) | 2003-02-06 |
TWI224095B (en) | 2004-11-21 |
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