CN1468845A - Chemical synthesis of p-methoxyphenyl isocyanate - Google Patents
Chemical synthesis of p-methoxyphenyl isocyanate Download PDFInfo
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- CN1468845A CN1468845A CNA03124291XA CN03124291A CN1468845A CN 1468845 A CN1468845 A CN 1468845A CN A03124291X A CNA03124291X A CN A03124291XA CN 03124291 A CN03124291 A CN 03124291A CN 1468845 A CN1468845 A CN 1468845A
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- Prior art keywords
- nethoxyaniline
- trichloromethyl
- chemical synthesis
- toluene
- synthesis process
- 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.)
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- FMDGXCSMDZMDHZ-UHFFFAOYSA-N 1-isocyanato-4-methoxybenzene Chemical compound COC1=CC=C(N=C=O)C=C1 FMDGXCSMDZMDHZ-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 81
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 33
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 5
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims abstract description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229960001701 chloroform Drugs 0.000 claims abstract description 3
- 229940117389 dichlorobenzene Drugs 0.000 claims abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 33
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 28
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 15
- SNDGLCYYBKJSOT-UHFFFAOYSA-N 1,1,3,3-tetrabutylurea Chemical compound CCCCN(CCCC)C(=O)N(CCCC)CCCC SNDGLCYYBKJSOT-UHFFFAOYSA-N 0.000 claims description 14
- 150000002170 ethers Chemical class 0.000 claims description 13
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical group CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims description 11
- 238000010521 absorption reaction Methods 0.000 claims description 11
- 239000006227 byproduct Substances 0.000 claims description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 11
- 230000000630 rising effect Effects 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 5
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- NYCCIHSMVNRABA-UHFFFAOYSA-N 1,3-diethylimidazolidin-2-one Chemical compound CCN1CCN(CC)C1=O NYCCIHSMVNRABA-UHFFFAOYSA-N 0.000 claims description 2
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 claims description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims description 2
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002699 waste material Substances 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 3
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract 3
- -1 methoxyphenyl amine Chemical class 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 abstract 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 abstract 1
- 150000002118 epoxides Chemical class 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The chemical synthesis of p-methoxyphenyl isocyanate is one process inside organic solvent with methoxyphenyl amine and di(trichloromethyl) carbonate as material and in the presence of catalyst. The process has the material molar ratio of methoxyphenyl amine to di(trichloromethyl) carbonate to catalyst being 1 to 0.34-0.8 to 0.01-0.1; organic solvent amount is 3-12 times mass of methoxyphenyl amine; the reaction temperature is 20-180 deg.c and reaction period is 4-10 hr. The organic solvent may be benzene, toluene, xylene, chlorobenzene, dichloro benzene, dichloro methane, trichloro methane, carbon tetrachloride, ethylidene dichloride, tetrafuran or hexaalkane epoxide. The said process uses no virulent phosgene and diphosgene, and is safe, reliable, high in yield, low in cost, and less corrosive and waste exhaust.
Description
Technical field
The present invention relates to synthetic medicine, agricultural chemicals and dye field, mainly is a kind of chemical synthesis process of p-Methoxyphenyl isocyanate.
Background technology
P-Methoxyphenyl isocyanate is important medicine, agricultural chemicals and macromolecular material intermediate.The chemical synthesis process of prior art p-Methoxyphenyl isocyanate is to be that raw material reaction makes with phosgene and P-nethoxyaniline.The shortcoming of this technology is to use in the world the hypertoxic raw material phosgene that restriction is used, and potential safety hazard is big, and reaction time is long, and equipment corrosion is serious, and what bother most is that quantity of three wastes is big, and difficult treatment, expense height.
Summary of the invention
Technical problem to be solved by this invention provides that a kind of technology is reasonable, production safety is reliable, reaction yield is high, production cost is low, does not have the p-Methoxyphenyl isocyanate chemical synthesis process of the three wastes substantially.
The technical solution adopted for the present invention to solve the technical problems.The chemical synthesis process of this p-Methoxyphenyl isocyanate, is that raw material is synthesized in the organic solvent in the presence of catalyzer with P-nethoxyaniline with two (trichloromethyl) carbonic ethers, and its molar ratio is a P-nethoxyaniline: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.34～0.8: 0.01-0.1; Its consumption of organic solvent is 3-12 a times of P-nethoxyaniline quality; Its temperature of reaction is 20-180 ℃; Its reaction times is 4～10h.
Its reaction equation is:
The technical solution adopted for the present invention to solve the technical problems can also be further perfect.Described organic solvent can be benzene or toluene or dimethylbenzene or chlorobenzene or dichlorobenzene or methylene dichloride or trichloromethane or tetracol phenixin or ethylene dichloride or tetrahydrofuran (THF) or epoxy six alkane.
Described catalyzer can be 1,3-dimethyl-2-imidazolidone or 1,3-diethyl-2-imidazolidone or other 1,3-dialkyl group-2-imidazolidone or triethylamine or pyridine or 3-picoline or N-methylpyrrole or N-methyl Pyrrolidine or tetrabutyl urea.
It is P-nethoxyaniline that molar ratio can be preferably its molar ratio: two (trichloromethyl) carbonic ether: toluene: 1, and 3-dimethyl-2-imidazolidone=1: 0.35: 0.02 (mol ratio), the charging capacity of toluene are 8 times of P-nethoxyaniline quality.At first with P-nethoxyaniline, 1,3-dimethyl-2-imidazolidone and toluene are added in the reactor, after stirring, at room temperature drip the toluene solution of two (trichloromethyl) carbonic ethers in the 30min, open the absorption system of byproduct hydrogen chloride system technical hydrochloric acid simultaneously, then temperature rising reflux reaction 4h, reaction is finished, toluene is reclaimed in elder generation's air distillation, and 106-108 ℃ cut is collected in vacuum distilling then under 2KPa.
Or molar ratio is a P-nethoxyaniline: two (trichloromethyl) carbonic ether: tetrabutyl urea=1: 0.35: 0.01 (mol ratio), solvent chlorobenzene.At first with P-nethoxyaniline, tetrabutyl urea and chlorobenzene are added in the reactor, after stirring, at room temperature drip the chlorobenzene solution of two (trichloromethyl) carbonic ethers in the 45min, open the absorption system of byproduct hydrogen chloride system technical hydrochloric acid simultaneously, temperature rising reflux reacts 4h then, and solvent is reclaimed in first air distillation, 106-108 ℃ cut is collected in vacuum distilling then under 2KPa.
Or its molar ratio is a P-nethoxyaniline: two (trichloromethyl) carbonic ether: tetrabutyl urea=1: 0.35: 0.02 (mol ratio), the charging capacity of benzene are 10 times of P-nethoxyaniline quality.At first with P-nethoxyaniline, tetrabutyl urea and benzene are added in the reactor, after stirring, at room temperature drip the benzole soln of two (trichloromethyl) carbonic ethers in the 45min, open the absorption system of byproduct hydrogen chloride system technical hydrochloric acid simultaneously, temperature rising reflux reacts 5h then, and solvent is reclaimed in first air distillation, 106-108 ℃ cut is collected in vacuum distilling then under 2KPa.
The effect that the present invention is useful is: the present invention compared with prior art, the operational path advanced person, processing condition are reasonable, and used raw material has been avoided hypertoxic phosgene and trichloromethylchloroformate, and production safety is reliable, the reaction yield height, generally more than 93%, production cost is lower, and equipment corrosion is little, few and the easy processing of the three wastes has bigger implementary value and economic results in society.
Embodiment
Below in conjunction with embodiment the present invention is further described.
Embodiment 1
P-nethoxyaniline: two (trichloromethyl) carbonic ether: toluene: 1,3-dimethyl-2-imidazolidone=1: 0.35: 0.02 (mol ratio), the charging capacity of toluene are 8 times of P-nethoxyaniline quality.
P-nethoxyaniline, 1,3-dimethyl-2-imidazolidone and toluene are added in the reactor, after stirring, at room temperature drip the toluene solution of two (trichloromethyl) carbonic ethers in the 30min, open the absorption system of byproduct hydrogen chloride system technical hydrochloric acid simultaneously, temperature rising reflux reaction 4h reacts and finishes then, and toluene is reclaimed in first air distillation, vacuum distilling then, under 2KPa, collect 106-108 ℃ cut, yield 95.6%, content (GC) 99.4%.
Embodiment 2
P-nethoxyaniline: two (trichloromethyl) carbonic ether: 1,3-dimethyl-2-imidazolidone=1: 0.35: 0.01 (mol ratio), the charging capacity that reclaims toluene is 8 times of P-nethoxyaniline quality.
P-nethoxyaniline, 1,3-dimethyl-2-imidazolidone and recovery toluene are added in the reactor, after stirring, at room temperature drip the toluene solution of two (trichloromethyl) carbonic ethers in the 30min, open the absorption system of byproduct hydrogen chloride system technical hydrochloric acid simultaneously, temperature rising reflux reaction 4h reacts and finishes then, and toluene is reclaimed in first air distillation, vacuum distilling then, under 2KPa, collect 106-108 ℃ cut, yield 96.3%, content (GC) 99.3%.
Embodiment 3
P-nethoxyaniline: two (trichloromethyl) carbonic ether: 1,3-dimethyl-2-imidazolidone=1: 0.50: 0.02 (mol ratio), the charging capacity of toluene are 8 times of P-nethoxyaniline quality.
By embodiment 1 reaction that feeds intake, the last cut of under 2 KPa, collecting 106-108 ℃, yield 97.0%, content (GC) 99.0%.
Embodiment 4
P-nethoxyaniline: two (trichloromethyl) carbonic ether: 1,3-dimethyl-2-imidazolidone=1: 0.80: 0.02 (mol ratio), the charging capacity of toluene are 8 times of P-nethoxyaniline quality.
By embodiment 1 reaction that feeds intake, the last cut of under 2 KPa, collecting 106-108 ℃, yield 96.1%, content (GC) 98.8%.
Embodiment 5
P-nethoxyaniline: two (trichloromethyl) carbonic ether: tetrabutyl urea=1: 0.35: 0.02 (mol ratio), the charging capacity of benzene are 10 times of P-nethoxyaniline quality.
P-nethoxyaniline, tetrabutyl urea and benzene are added in the reactor, after stirring, at room temperature drip the benzole soln of two (trichloromethyl) carbonic ethers in the 45min, open the absorption system of byproduct hydrogen chloride system technical hydrochloric acid simultaneously, temperature rising reflux reacts 5h then, solvent is reclaimed in elder generation's air distillation, and 106-108 ℃ cut is collected in vacuum distilling then under 2KPa, yield 93.6%, content (GC) 99.8%.
Embodiment 6
P-nethoxyaniline: two (trichloromethyl) carbonic ether: tetrabutyl urea=1: 0.35: 0.01 (mol ratio), solvent chlorobenzene.
P-nethoxyaniline, tetrabutyl urea and chlorobenzene are added in the reactor, after stirring, at room temperature drip the chlorobenzene solution of two (trichloromethyl) carbonic ethers in the 45min, open the absorption system of byproduct hydrogen chloride system technical hydrochloric acid simultaneously, temperature rising reflux reaction 4h reacts and finishes then, and other is with embodiment 5.Yield 93.8%, content (GC) 99.7%.
Embodiment 7
P-nethoxyaniline: two (trichloromethyl) carbonic ether: pyridine=1: 0.35: 0.2 (mol ratio), solvent toluene.
P-nethoxyaniline, pyridine and toluene are added in the reactor, after stirring, at room temperature drip the toluene solution of two (trichloromethyl) carbonic ethers in the 45min, open the absorption system of byproduct hydrogen chloride system technical hydrochloric acid simultaneously, then temperature rising reflux reaction 4h, reaction is finished, and other is with embodiment 5.Yield 93.1%, content (GC) 99.5%.
Claims (9)
1, a kind of chemical synthesis process of p-Methoxyphenyl isocyanate, it is characterized in that: is that raw material is synthesized in the organic solvent in the presence of catalyzer with P-nethoxyaniline with two (trichloromethyl) carbonic ethers, and its molar ratio is a P-nethoxyaniline: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.34～0.8: 0.01-0.1; Its consumption of organic solvent is 3-12 a times of P-nethoxyaniline quality; Its temperature of reaction is 20-180 ℃; Its reaction times is 4～10h.
2, the chemical synthesis process of p-Methoxyphenyl isocyanate according to claim 1 is characterized in that: described organic solvent can be benzene or toluene or dimethylbenzene or chlorobenzene or dichlorobenzene or methylene dichloride or trichloromethane or tetracol phenixin or ethylene dichloride or tetrahydrofuran (THF) or epoxy six alkane.
3, the chemical synthesis process of p-Methoxyphenyl isocyanate according to claim 1, it is characterized in that: described catalyzer can be 1,3-dimethyl-2-imidazolidone or 1,3-diethyl-2-imidazolidone or other 1,3-dialkyl group-2-imidazolidone or triethylamine or pyridine or 3-picoline or N-methylpyrrole or N-methyl Pyrrolidine or tetrabutyl urea.
4, according to the chemical synthesis process of claim 1 or 2 or 3 described p-Methoxyphenyl isocyanates, it is characterized in that: its molar ratio is a P-nethoxyaniline: two (trichloromethyl) carbonic ether: toluene: 1,3-dimethyl-2-imidazolidone=1: 0.35: 0.02 (mol ratio), the charging capacity of toluene are 8 times of P-nethoxyaniline quality.
5, according to the chemical synthesis process of claim 1 or 2 or 3 described p-Methoxyphenyl isocyanates, it is characterized in that: its molar ratio P-nethoxyaniline: two (trichloromethyl) carbonic ether: tetrabutyl urea=1: 0.35: 0.02 (mol ratio), the charging capacity of benzene are 10 times of P-nethoxyaniline quality.
6, according to the chemical synthesis process of claim 1 or 2 or 3 described p-Methoxyphenyl isocyanates, it is characterized in that: its molar ratio is a P-nethoxyaniline: two (trichloromethyl) carbonic ether: tetrabutyl urea=1: 0.35: 0.01 (mol ratio), solvent chlorobenzene.
7, the chemical synthesis process of p-Methoxyphenyl isocyanate according to claim 4, it is characterized in that: at first with P-nethoxyaniline, 1,3-dimethyl-2-imidazolidone and toluene are added in the reactor, after stirring, at room temperature drip the toluene solution of two (trichloromethyl) carbonic ethers in the 30min, open the absorption system of byproduct hydrogen chloride system technical hydrochloric acid simultaneously, temperature rising reflux reacts 4h then, reaction is finished, toluene is reclaimed in elder generation's air distillation, 106-108 ℃ cut is collected in vacuum distilling then under 2KPa.
8, the chemical synthesis process of p-Methoxyphenyl isocyanate according to claim 5, it is characterized in that: at first with P-nethoxyaniline, tetrabutyl urea and benzene are added in the reactor, after stirring, at room temperature drip the benzole soln of two (trichloromethyl) carbonic ethers in the 45min, open the absorption system of byproduct hydrogen chloride system technical hydrochloric acid simultaneously, temperature rising reflux reacts 5h then, solvent is reclaimed in elder generation's air distillation, and 106-108 ℃ cut is collected in vacuum distilling then under 2KPa.
9, the chemical synthesis process of p-Methoxyphenyl isocyanate according to claim 6, it is characterized in that: at first with P-nethoxyaniline, tetrabutyl urea and chlorobenzene are added in the reactor, after stirring, at room temperature drip the chlorobenzene solution of two (trichloromethyl) carbonic ethers in the 45min, open the absorption system of byproduct hydrogen chloride system technical hydrochloric acid simultaneously, temperature rising reflux reacts 4h then, solvent is reclaimed in elder generation's air distillation, and 106-108 ℃ cut is collected in vacuum distilling then under 2KPa.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03124291 CN1228316C (en) | 2003-05-08 | 2003-05-08 | Chemical synthesis of p-methoxyphenyl isocyanate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03124291 CN1228316C (en) | 2003-05-08 | 2003-05-08 | Chemical synthesis of p-methoxyphenyl isocyanate |
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| Publication Number | Publication Date |
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| CN1468845A true CN1468845A (en) | 2004-01-21 |
| CN1228316C CN1228316C (en) | 2005-11-23 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 03124291 Expired - Lifetime CN1228316C (en) | 2003-05-08 | 2003-05-08 | Chemical synthesis of p-methoxyphenyl isocyanate |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101318913B (en) * | 2008-07-21 | 2011-04-27 | 国家农药创制工程技术研究中心 | Method for preparing parachlorobenzyl isocyanic ester |
| CN1939899B (en) * | 2005-09-26 | 2011-12-21 | 杭州崇舜化学有限公司 | Synthesis of 1,5-naphthalene isocyanate |
| CN102617401A (en) * | 2012-03-08 | 2012-08-01 | 象山志华新材料有限公司 | Synthesis method for co-producing p-chloroaniline and p-chlorophenol isocyanate |
-
2003
- 2003-05-08 CN CN 03124291 patent/CN1228316C/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1939899B (en) * | 2005-09-26 | 2011-12-21 | 杭州崇舜化学有限公司 | Synthesis of 1,5-naphthalene isocyanate |
| CN101318913B (en) * | 2008-07-21 | 2011-04-27 | 国家农药创制工程技术研究中心 | Method for preparing parachlorobenzyl isocyanic ester |
| CN102617401A (en) * | 2012-03-08 | 2012-08-01 | 象山志华新材料有限公司 | Synthesis method for co-producing p-chloroaniline and p-chlorophenol isocyanate |
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| Publication number | Publication date |
|---|---|
| CN1228316C (en) | 2005-11-23 |
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Owner name: ZHEJIANG PROVINCE TONGFENG MEDICAL CHEMICAL INDUST Free format text: FORMER OWNER: CAI GEDONG Effective date: 20090731 |
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Effective date of registration: 20090731 Address after: Linhai Town, Linhai City, Zhejiang Patentee after: Zhejiang Tongfeng Pharmaceutical Chemical Co., Ltd. Address before: Hangzhou City, Zhejiang Province Road No. 316 21 free Huamen staff apartment block A room 1907 Patentee before: Cai Gedong |
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