CN1235873C - Chemical synthesis method of isopropyl isocyanate - Google Patents
Chemical synthesis method of isopropyl isocyanate Download PDFInfo
- Publication number
- CN1235873C CN1235873C CN 02130078 CN02130078A CN1235873C CN 1235873 C CN1235873 C CN 1235873C CN 02130078 CN02130078 CN 02130078 CN 02130078 A CN02130078 A CN 02130078A CN 1235873 C CN1235873 C CN 1235873C
- Authority
- CN
- China
- Prior art keywords
- isopropyl isocyanate
- isopropylamine
- reaction
- chemical synthesis
- trichloromethyl
- 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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- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title abstract description 4
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 title abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 5
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 claims description 5
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims description 5
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 5
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims description 5
- 229940117389 dichlorobenzene Drugs 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002699 waste material Substances 0.000 abstract description 6
- 239000007788 liquid Substances 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract 2
- 239000002912 waste gas Substances 0.000 abstract 2
- 239000013067 intermediate product Substances 0.000 abstract 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 8
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 238000010907 mechanical stirring Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000000630 rising effect Effects 0.000 description 3
- LAYPMCGIWDGYKX-UHFFFAOYSA-N trichloromethyl hydrogen carbonate Chemical compound OC(=O)OC(Cl)(Cl)Cl LAYPMCGIWDGYKX-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- FEKWWZCCJDUWLY-UHFFFAOYSA-N 3-methyl-1h-pyrrole Chemical compound CC=1C=CNC=1 FEKWWZCCJDUWLY-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- -1 runs into gac Chemical compound 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Isopropyl isocyanate is an important intermediate product for organic synthesis. In the present invention, bis(trichloromethyl) carbonate directly reacts with isopropylamine in organic solvent to prepare isopropyl isocyanate. In the chemical synthesis method of the present invention, potential safety hazard, waste gas sources, waste liquid sources and waste residue sources are eliminated fundamentally. Thus, the method for preparing isopropyl isocyanate has the advantages of cheap and easy-obtainment raw material, safe and reliable preparation, high reaction yield, low preparation cost and basically no waste gas, waste liquid and waste residue.
Description
Technical field
The present invention relates to two (trichloromethyl) carbonic ethers of a kind of usefulness and substitute phosgene or trichloromethylchloroformate directly and the chemical synthesis process of Isopropylamine prepared in reaction n-Isopropyl isocyanate.N-Isopropyl isocyanate is mainly used in synthetic medicine and agricultural chemicals.
Background technology
Before the present invention made, the chemical synthesis process of prior art n-Isopropyl isocyanate was to be that raw material is synthesized into earlier by the Isopropylamine photoreactive gas.Because phosgene (COCL2) is hypertoxic gas, no matter is laboratory work or industrial production, slave unit and environmental angle are seen all can bring very burden.The equipment of phosgene is produced and stored to necessary many covers on producing; Leak if phosgene takes place, bring immeasurable loss then for human life's property and environment.Trichloromethylchloroformate is a liquid, though its security is good than phosgene, runs into gac, iron or organic amine etc. and resolve into phosgene, and storage and transportation etc. are also difficult, thereby still there is bigger potential safety hazard in use.
Summary of the invention
Task of the present invention is the shortcoming that overcomes prior art, provides one technology is reasonable, production safety is reliable, reaction yield is high, production cost is low, do not have substantially the n-Isopropyl isocyanate chemical synthesis process of the three wastes.
The chemical synthesis process of n-Isopropyl isocyanate, it is characterized in that with Isopropylamine and two (trichloromethyl) carbonic ethers be raw material in the presence of catalyst n-methylpyrrole, one of them is synthesized into as solvent to select tetrahydrofuran (THF), toluene, dichlorobenzene, methylene dichloride; Can dichlorobenzene be solvent also, one of them be synthesized into for catalyzer to select N-methyl Pyrrolidine, triethylamine, pyridine, 3-picoline; The molar ratio of above-mentioned reaction is an Isopropylamine: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.34-0.8: 0.001-0.5; Its consumption of organic solvent is 3-5 a times of different handle amine quality; Its temperature of reaction is 20-80 ℃; Its reaction times is 3-10h.Its reaction equation is:
The present invention compared with prior art, the operational path advanced person, processing condition are reasonable, used raw material is cheap and easy to get, hypertoxic raw material phosgene and trichloromethylchloroformate have been avoided, safety simple to operate, reaction yield height, production cost is low, does not have the three wastes substantially, has bigger implementary value and economic results in society.
Embodiment
Embodiment 1
Molar ratio is an Isopropylamine: two (trichloromethyl) carbonic ether: N-methylpyrrole=1: 0.35: 0.1.
In the 500ml four-hole boiling flask of mechanical stirring, constant pressure funnel, reflux condensing tube and thermometer is housed, add 1mol Isopropylamine and tetrahydrofuran (THF) 200ml solution, open and stir, under normal temperature, vigorous stirring, slowly drip two (trichloromethyl) carbonate solutions that are dissolved in the 100ml tetrahydrofuran (THF), finish, temperature rising reflux, and at 60-68 ℃ of following reaction 3h, reaction finishes the logical nitrogen in back and drives hydrogen chloride gas away, vacuum distilling steams product 42.5g after reclaiming tetrahydrofuran (THF), yield is 50.3%, and content is 99.6% (GC).
Embodiment 2
Molar ratio is an Isopropylamine: two (trichloromethyl) carbonic ether: N-methylpyrrole=1: 0.45: 0.1.
In the 500ml four-hole boiling flask of mechanical stirring, constant pressure funnel, reflux condensing tube and thermometer is housed, add 1mol Isopropylamine and tetrahydrofuran (THF) 180ml toluene, open and stir, under normal temperature, vigorous stirring, slowly drip two (trichloromethyl) carbonate solutions that are dissolved in 120ml toluene, finish, temperature rising reflux, and under 70-75 ℃ temperature stirring reaction 4h, reaction finishes the logical nitrogen in back and drives hydrogen chloride gas away, vacuum distilling steams product 45.1g, yield is 53%, and content is 99.5% (GC).
Embodiment 3
Molar ratio is an Isopropylamine: two (trichloromethyl) carbonic ether: N-methylpyrrole=1: 1.5: 0.1.
In the 500ml four-hole boiling flask of mechanical stirring, constant pressure funnel, reflux condensing tube and thermometer is housed, add 1mol Isopropylamine and dichlorobenzene 180ml solution, open and stir, under normal temperature, vigorous stirring, slowly drip two (trichloromethyl) carbonate solutions that are dissolved in 120ml toluene, finish, temperature rising reflux, and under 70-80 ℃ temperature stirring reaction 3h, reaction finishes the logical nitrogen in back and drives hydrogen chloride gas away, vacuum distilling steams product 46.8g, yield is 55%, and content is 99.8% (GC).
Embodiment 4
Catalyzer changes N-methyl Pyrrolidine into, and other gets product 48.1g with embodiment 3, and yield is 56.5%, and content is 99.9% (GC).
Embodiment 5
Catalyzer changes N-methyl Pyrrolidine into, and consumption increases by 1 times, and other is operated with embodiment 3, gets product 48.3g, and yield is 56.75%, and content is 99.9% (GC).
Embodiment 6
Catalyzer changes N-methyl Pyrrolidine into, and consumption reduces 5 times, and other is operated with embodiment 3, gets product 45.0g, and yield is 52.8%, and content is 99.1% (GC).
Embodiment 7
Catalyzer changes triethylamine into, and other gets product 34.0g with embodiment 3, and yield is 40.0%, and content is 98.8% (GC).
Embodiment 8
Catalyzer changes the pyrroles into, and other gets product 38.3g with embodiment 3, and yield is 45.0%, and content is 98.8% (GC).
Embodiment 9
Catalyzer changes the 3-methylpyrrole into, and other gets product 41.0g with embodiment 3, and yield is 48.2%, and content is 99.0% (GC).
Embodiment 10
Reaction times changes 5h into, and other gets product 43.3g with embodiment 1, and yield is 51.2%, and content is 99.6% (GC).
Embodiment 11
Reaction times changes 8h into, and other gets product 44.3g with embodiment 1, and yield is 52.4%, and content is 99.7% (GC).
Embodiment 12
Reaction solvent changes methylene dichloride into, and temperature of reaction changes 35-40 ℃ into, and the time changes 10h into, and other gets product 38.0g with embodiment 1, and yield is 46%, and content is 99.8% (GC).
The present invention and existing chemical synthesis process relatively, it is cheap and easy to get to have a raw material, safety simple to operate, reaction time is short, the reaction yield height, good product quality, advantages such as non-environmental-pollution are methods that is suitable for suitability for industrialized production.
Claims (1)
1. the chemical synthesis process of a n-Isopropyl isocyanate, it is characterized in that with Isopropylamine and two (trichloromethyl) carbonic ethers be raw material in the presence of catalyst n-methylpyrrole, one of them is synthesized into as solvent to select tetrahydrofuran (THF), toluene, dichlorobenzene, methylene dichloride; Perhaps be solvent with the dichlorobenzene, one of them is synthesized into for catalyzer to select N-methyl Pyrrolidine, triethylamine, pyridine, 3-picoline; The molar ratio of above-mentioned reaction is an Isopropylamine: two (trichloromethyl) carbonic ether: catalyzer is 1: 0.34～0.8: 0.001-0.5; Its consumption of organic solvent is 3-5 a times of Isopropylamine quality; Its temperature of reaction is 20-80 ℃, and its reaction times is 3～10h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 02130078 CN1235873C (en) | 2002-08-13 | 2002-08-13 | Chemical synthesis method of isopropyl isocyanate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 02130078 CN1235873C (en) | 2002-08-13 | 2002-08-13 | Chemical synthesis method of isopropyl isocyanate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1475479A CN1475479A (en) | 2004-02-18 |
| CN1235873C true CN1235873C (en) | 2006-01-11 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 02130078 Expired - Fee Related CN1235873C (en) | 2002-08-13 | 2002-08-13 | Chemical synthesis method of isopropyl isocyanate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1235873C (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5468289B2 (en) * | 2008-04-18 | 2014-04-09 | 石原産業株式会社 | Method for producing pyrimidine compounds |
| CN102584630A (en) * | 2011-12-24 | 2012-07-18 | 德州绿邦化工有限公司 | Method for synthesizing methacrylic acid isocyanate ethyl ester |
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2002
- 2002-08-13 CN CN 02130078 patent/CN1235873C/en not_active Expired - Fee Related
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| Publication number | Publication date |
|---|---|
| CN1475479A (en) | 2004-02-18 |
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