CN108129379A - Oxo-bis-（N-Methyl-o-phthalimide）Synthetic method - Google Patents
Oxo-bis-（N-Methyl-o-phthalimide）Synthetic method Download PDFInfo
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- CN108129379A CN108129379A CN201810078559.4A CN201810078559A CN108129379A CN 108129379 A CN108129379 A CN 108129379A CN 201810078559 A CN201810078559 A CN 201810078559A CN 108129379 A CN108129379 A CN 108129379A
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- phthalimide
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- synthetic method
- oxo
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- 238000010189 synthetic method Methods 0.000 title claims abstract description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 239000012046 mixed solvent Substances 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims abstract description 6
- 239000002798 polar solvent Substances 0.000 claims abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 claims description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 claims description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 claims description 2
- 229940113088 dimethylacetamide Drugs 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 238000003912 environmental pollution Methods 0.000 abstract description 4
- 239000003444 phase transfer catalyst Substances 0.000 abstract description 4
- ABCGRFHYOYXEJV-UHFFFAOYSA-N 4-methylisoindole-1,3-dione Chemical class CC1=CC=CC2=C1C(=O)NC2=O ABCGRFHYOYXEJV-UHFFFAOYSA-N 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 4
- 239000004642 Polyimide Substances 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- -1 etherimide Polymers 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- 229920000784 Nomex Polymers 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 230000009970 fire resistant effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000004763 nomex Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003055 poly(ester-imide) Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
It is double the invention discloses a kind of oxo（N methyl phthalimides）Synthetic method, it is obtained in the presence of basic catalyst, in the mixed solvent, nucleo philic substitution reaction by 4 nitro N methyl phthalimides and 4 hydroxyl N methyl phthalimides.The mixed solvent is made of benzene kind solvent and aprotic polar solvent according to 1: 1~1: 5 volume ratio.The method of the present invention is without expensive self-control catalyst, without using the phase transfer catalyst polluted the environment, it is reacted only with conventional base catalysts in the mixed solvent, the operation is simple, and process safety is high, and production cost is relatively low, environmental pollution is smaller, especially reaction yield is higher, and product purity is high, so as to be suitble to industrialized production.
Description
Technical field
The invention belongs to technical field of fine, and in particular to a kind of oxo-bis-（N-Methyl-o-phthalimide）
Synthetic method.
Background technology
3,3 ', 4,4 '-diphenyl ether tetraformic dianhydride（Hereinafter referred to as ODPA）It is new special engineering plastics polyimides, poly-
The important monomer of the fire resistant resins such as etherimide, polyesterimide, polyamide-imide, poly maleimide, Nomex it
One.ODPA types polyimides has prominent mechanical performance, electrical property, radiation resistance, can be in the range of -269~250 DEG C
It is used for a long time.Since ODPA introduces flexible ether linkage in polyimides backbone structure, softening temperature is greatly reduced, belongs to heat
Plastic polyimide has good processing performance, is widely used for the aerospace and other high-tech sectors in China.
Oxo-bis-（N-Methyl-o-phthalimide）It is then the important intermediate for synthesizing ODPA, structure is as follows：
。
At present, oxo-bis-（N-Methyl-o-phthalimide）Synthetic method be by 4- nitros-N- methyl-neighbour's benzene
Dicarboximide is obtained through self-condensation reaction【Referring to 1~document of document 4】, synthetic route is as follows：
。
The deficiency of this method is：
（1）Using conventional base catalysts and phase transfer catalyst, yield is relatively low.
（2）It needs that using the self-control catalyst of higher price ideal recovery could be obtained, can not only cause to be produced into this way
Originally it significantly improves, and the self-control catalyst is not easy to obtain, is not suitable for industrialized production.
（3）Since phase transfer catalyst cannot reuse, solid waste can only be directly become, environmental pollution compared with
Greatly.
（4）Product purity is also undesirable, generally can only achieve 95%~97%.
Document 1：American documentation literature US4933469,12 days June nineteen ninety of publication date.
Document 2：" oxo-bis- (N-Methyl-o-phthalimide) synthesising process research ", Huang Lin etc.,《Xiangfan University
Report》, the 2nd phase of volume 27, the 33-35 pages, on March 31st, 2006.
Document 3：" improvement of oxo pair-(N-Methyl-o-phthalimide) synthesis technology ", Zhang Chunrong etc.,《Chemistry with
Bonding》, the 6th phase of volume 33, the 33-35 pages, on December 31st, 2011.
Document 4：Chinese patent literature CN102199118A, publication date September in 2011 28 days.
Invention content
It is an object of the invention to solve the above problems, provide that a kind of production cost is relatively low, environmental pollution is smaller, product
The oxo of purity and higher, the suitable industrialized production of yield-bis-（N-Methyl-o-phthalimide）Synthetic method.
Realizing the technical solution of the object of the invention is：A kind of oxo-bis-（N-Methyl-o-phthalimide）Synthesis side
Method, it is through nucleophilic displacement of fluorine by 4- nitros-N- methyl-phthalimide and 4- hydroxy-N-methvls-phthalimide
It is obtained by the reaction.
Specific synthetic route is as follows：
。
4- nitros-N- methyl-the phthalimide and the 4- hydroxy-N-methvls-phthalimide
Molar ratio is 1: 2~2: 1, preferably 1: 1.1~1.1: 1, more preferably 1: 1.
The nucleophilic substitution carries out in the presence of basic catalyst；The basic catalyst is hydroxide
One kind in sodium, potassium hydroxide, lithium hydroxide, cesium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, saleratus,
Preferably potassium carbonate.
The molar ratio of the basic catalyst and the 4- nitros-N- methyl-phthalimide is 1: 1~2: 1, excellent
It is selected as 1.5: 1.
The nucleophilic substitution is carried out in the mixed solvent；The mixed solvent is by benzene kind solvent and non-proton pole
Property solvent according to 1: 1~1: 5 volume ratio form, preferably 1: 1.5~1: 2.5.
The benzene kind solvent is benzene,toluene,xylene, one kind in mesitylene, preferably toluene.
The aprotic polar solvent is N,N-dimethylformamide（DMF）, DMAC N,N' dimethyl acetamide（DMAc）, N- first
Base pyrrolidones（NMP）, dimethyl sulfoxide (DMSO)（DMSO）, one kind in glycol dimethyl ether, preferably n,N-Dimethylformamide.
The mixed solvent is preferably by toluene and N,N-dimethylformamide（DMF）According to 1: 1.5~1: 2.5 volume ratio
Composition.
The weight ratio of the mixed solvent and the 4- nitros-N- methyl-phthalimide is 1: 1~5: 1.
The good effect that the present invention has：The method of the present invention without expensive self-control catalyst, without
Using the phase transfer catalyst polluted the environment, reacted only with conventional base catalysts in the mixed solvent,
The operation is simple, and process safety is high, and production cost is relatively low, and environmental pollution is smaller, and especially reaction yield is higher, production
Object purity is high, so as to be suitble to industrialized production.
Specific embodiment
（Embodiment 1）
The oxo of the present embodiment-bis-（N-Methyl-o-phthalimide）Synthetic method it is specific as follows：
4- nitros-N- methyl-phthalimide of 20.6g is sequentially added into reaction kettle（0.1mol）, 17.7g 4- hydroxyls
Base-N- methyl-phthalimide（0.1mol）, 20.7g potassium carbonate（0.15mol）, 20mL toluene and 40mL
DMF, stirring are warming up to reflux, react to complete.
After reaction, reaction system is down to room temperature（20±5℃）, then it is added with stirring in water, filters, filter cake
With 60mL ethyl alcohol recrystallizations, the oxo of 30.3g-bis- is obtained（N-Methyl-o-phthalimide）, yield 90.2%, purity is
99.6%（HPLC）.
（2~embodiment of embodiment 5）
The synthetic method of each embodiment is substantially the same manner as Example 1, and difference is shown in Table 1.
Table 1
| Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Embodiment 5 | |
| Potassium carbonate | 20.7g（0.15mol） | 20.7g（0.15mol） | 20.7g（0.15mol） | 13.8g（0.10mol） | 27.6g（0.2mol） |
| Toluene | 20mL | 20mL | 20mL | 20mL | 20mL |
| DMF | 40mL | 30mL | 50mL | 40mL | 40mL |
| Products weight | 30.3g | 29.5g | 28.6g | 29.4g | 30.5g |
| Yield | 90.2% | 87.8% | 85.1% | 87.5% | 90.8% |
| Purity | 99.6% | 99.6% | 99.5% | 99.6% | 99.7% |
（1~comparative example of comparative example 4）
With reference to the method for embodiment 1, respectively as a result mesh can not be obtained separately as solvent with toluene, dimethylbenzene, DMF, DMAc
Mark product oxo-bis-（N-Methyl-o-phthalimide）.
Claims (9)
1. a kind of oxo-bis-（N-Methyl-o-phthalimide）Synthetic method, it is characterised in that：It is by 4- nitros-N-
Methyl-phthalimide is obtained with 4- hydroxy-N-methvls-phthalimide nucleo philic substitution reaction.
2. oxo according to claim 1-bis-（N-Methyl-o-phthalimide）Synthetic method, it is characterised in that：
The molar ratio of the 4- nitros-N- methyl-phthalimide and the 4- hydroxy-N-methvls-phthalimide is 1
: 2~2: 1.
3. oxo according to claim 1-bis-（N-Methyl-o-phthalimide）Synthetic method, it is characterised in that：
The nucleophilic substitution carries out in the presence of basic catalyst；The basic catalyst is sodium hydroxide, hydroxide
One kind in potassium, lithium hydroxide, cesium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, saleratus.
4. oxo according to claim 3-bis-（N-Methyl-o-phthalimide）Synthetic method, it is characterised in that：
The basic catalyst is potassium carbonate.
5. oxo according to claim 3-bis-（N-Methyl-o-phthalimide）Synthetic method, it is characterised in that：
The molar ratio of the basic catalyst and the 4- nitros-N- methyl-phthalimide is 1: 1~2: 1.
6. oxo according to one of claim 1 to 5-bis-（N-Methyl-o-phthalimide）Synthetic method, it is special
Sign is：The nucleophilic substitution is carried out in the mixed solvent；The mixed solvent is by benzene kind solvent and non-proton pole
Property solvent according to 1: 1~1: 5 volume ratio form.
7. oxo according to claim 6-bis-（N-Methyl-o-phthalimide）Synthetic method, it is characterised in that：
The benzene kind solvent is benzene,toluene,xylene, one kind in mesitylene.
8. oxo according to claim 6-bis-（N-Methyl-o-phthalimide）Synthetic method, it is characterised in that：
The aprotic polar solvent is N,N-dimethylformamide, DMAC N,N' dimethyl acetamide, N-Methyl pyrrolidone, dimethyl are sub-
One kind in sulfone, glycol dimethyl ether.
9. oxo according to claim 6-bis-（N-Methyl-o-phthalimide）Synthetic method, it is characterised in that：
The mixed solvent is made of toluene and N,N-dimethylformamide according to 1: 1.5~1: 2.5 volume ratio.
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| CN201810078559.4A CN108129379B (en) | 2018-01-26 | 2018-01-26 | Synthesis method of oxo-bis (N-methylphthalimide) |
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| CN201810078559.4A CN108129379B (en) | 2018-01-26 | 2018-01-26 | Synthesis method of oxo-bis (N-methylphthalimide) |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1425644A (en) * | 2001-12-14 | 2003-06-25 | 上海市合成树脂研究所 | Process for preparing 2,2-di-[4-(3-nitro phenoxy) phenyl] propane |
| JP2012136470A (en) * | 2010-12-27 | 2012-07-19 | Manac Inc | 3,4'-oxybisphthalimide compound, and process for producing the same |
| WO2013179872A1 (en) * | 2012-05-31 | 2013-12-05 | 山本化成株式会社 | Ether compound and method for producing same |
-
2018
- 2018-01-26 CN CN201810078559.4A patent/CN108129379B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1425644A (en) * | 2001-12-14 | 2003-06-25 | 上海市合成树脂研究所 | Process for preparing 2,2-di-[4-(3-nitro phenoxy) phenyl] propane |
| JP2012136470A (en) * | 2010-12-27 | 2012-07-19 | Manac Inc | 3,4'-oxybisphthalimide compound, and process for producing the same |
| WO2013179872A1 (en) * | 2012-05-31 | 2013-12-05 | 山本化成株式会社 | Ether compound and method for producing same |
Non-Patent Citations (3)
| Title |
|---|
| LUO, SHUANGJIANG, ET AL.: ""Preparation and gas transport properties of triptycene-containing polybenzoxazole (PBO)-based polymers derived from thermal rearrangement (TR) and thermal cyclodehydration (TC) processes"", 《JOURNAL OF MATERIALS CHEMISTRY A 》 * |
| 张春荣等: ""氧代双-（N-甲基邻苯二甲酰亚胺）合成工艺的改进"", 《化学与黏合》 * |
| 闫琴等: ""3-3-4-4-二苯醚二酐的合成工艺研究"", 《精细与专用化学品》 * |
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