CN103012210B - Preparation method of isophorone diamidoformate - Google Patents
Preparation method of isophorone diamidoformate Download PDFInfo
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- CN103012210B CN103012210B CN201210539618.6A CN201210539618A CN103012210B CN 103012210 B CN103012210 B CN 103012210B CN 201210539618 A CN201210539618 A CN 201210539618A CN 103012210 B CN103012210 B CN 103012210B
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- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 title abstract 6
- 239000011949 solid catalyst Substances 0.000 claims abstract description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 26
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000012153 distilled water Substances 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 7
- GAXPEQDKLKWCFG-UHFFFAOYSA-N C(N)(O)=O.O=C1C=C(CC(C)(C)C1)C Chemical compound C(N)(O)=O.O=C1C=C(CC(C)(C)C1)C GAXPEQDKLKWCFG-UHFFFAOYSA-N 0.000 claims description 27
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 claims description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
- 239000000706 filtrate Substances 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 238000007598 dipping method Methods 0.000 claims description 10
- 238000011068 loading method Methods 0.000 claims description 10
- 239000011701 zinc Substances 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical group [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 8
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 claims description 8
- 229960001866 silicon dioxide Drugs 0.000 claims description 7
- 235000012239 silicon dioxide Nutrition 0.000 claims description 7
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 4
- 239000011787 zinc oxide Substances 0.000 claims description 4
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- XMFOQHDPRMAJNU-UHFFFAOYSA-N lead(ii,iv) oxide Chemical compound O1[Pb]O[Pb]11O[Pb]O1 XMFOQHDPRMAJNU-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 11
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract description 5
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- RLJMLMKIBZAXJO-UHFFFAOYSA-N lead nitrate Chemical compound [O-][N+](=O)O[Pb]O[N+]([O-])=O RLJMLMKIBZAXJO-UHFFFAOYSA-N 0.000 description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- HTUMBQDCCIXGCV-UHFFFAOYSA-N lead oxide Chemical compound [O-2].[Pb+2] HTUMBQDCCIXGCV-UHFFFAOYSA-N 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Inorganic materials [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000002608 ionic liquid Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- -1 reacts and makes Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 231100000004 severe toxicity Toxicity 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to a preparation method of isophorone diamidoformate. The method comprises the following steps: getting dimethyl carbonate and isophorone diamine as the raw materials; and catalyzing the raw materials to react by virtue of a loaded solid catalyst; and then separating by distilled water so as to obtain the product that is the isophorone diamidoformate. The method is free from hypertoxic phosgene, environmentally-friendly, and mild in reaction condition, can be carried out at medium and low temperature, and brings simple requirements to equipment; the catalyst can be conveniently separated and recycled; and the product is separated by adding the distilled water, and the rectification is saved, so that the operation is simple and convenient, and the purity of the product is higher.
Description
Technical field
The present invention relates to a kind of preparation method of isophorone carbamic acid ester, it adopts loaded solid catalyst, and aftertreatment adopts distilled water to separate out product.
Background technology
Isophorone carbamic acid ester (IPDC) is the important intermediate of producing isophorone diisocyanate (IPDI), and IPDI is one of important source material of producing urethane.IPDI has versatility vulcabond most, almost all mixes with all resins and all solvents, and its molecular weight is large, toxicity is little, weather resisteant is good, be difficult for yellowing, price is suitable, working life is longer, compares with other isocyanic ester, and resistance toheat is better.
The method of traditional production vulcabond is phosgenation, and amine light phosgenation is the Traditional Industrialization production method of synthetic IPDI, is also to realize at present the maximum production method of industrialization.But the processing of the removing of synthetic and art breading, phosgenation reaction, phosgene, product separation that the process of producing by the method comprises phosgene and refining, tail gas etc., in the method, intermediate is hypertoxic, and equipment corrosion is serious, and environmental pollution is serious.
The method of the green synthesizing isocyanate rising gradually in recent years, is that methylcarbonate ammonolysis process is produced isocyanic ester.Be mainly to take methylcarbonate and diamines to synthesize vulcabond as raw material, avoided the problems such as raw material in phosgenation route and intermediate severe toxicity, the three wastes and equipment corrosion be serious, avoided the dangerous and environmental pollution hidden danger in production process.
The synthetic method of the disclosed a kind of ammonia of Chinese patent 02158320.X and methylcarbonate, it adopts ionic liquid is solvent and catalyst system, feature is that reactive behavior is high, easy and simple to handle, product separation and catalyst recovery are easy, but ionic liquid is expensive, have increased production cost.
Summary of the invention
For the problems referred to above, the present invention is to provide a kind of method that non-phosgene is prepared isophorone carbamic acid ester, for producing isophorone diisocyanate, lays the foundation.
The present invention is mainly that to take methylcarbonate and isophorone diamine be raw material, under the catalysis of loaded solid catalyst, reacts and makes, and product purity is more than 96%, and yield is more than 85%.
Its concrete steps are:
(1) in the mixed system of methylcarbonate and loaded solid catalyst, drip isophorone diamine, 50-90 ℃ of reaction 3-16 hour, filters;
(2) in the filtrate after filtering, add distilled water, standing, filter the dry isophorone carbamic acid ester that to obtain.
In the yield that guarantees isophorone carbamic acid ester, avoid the waste of raw material, the mol ratio of isophorone diamine and methylcarbonate is 1:3-10.Because the too high meeting of temperature of reaction causes side reaction, increase, temperature of reaction is too low, and the yield of isophorone carbamic acid ester reduces, so temperature of reaction of the present invention is 50-90 ℃; Contriver finds in experiment, after the reaction times reaches 16h, then increases the reaction times, and product yield changes little, will be that 3-16h is advisable in the reaction times.When guaranteeing catalytic effect, avoid the waste of catalyzer, catalyst levels of the present invention is the 2-10% of isophorone diamine and methylcarbonate total mass.
After completion of the reaction, filter, remove catalyzer, then by adding distilled water in filtrate, standing, product isophorone carbamic acid ester is separated out, in order to guarantee fully separating out of product, the 3-10 that the consumption of distilled water is filtrate is doubly.Treat that product separates out completely, filter, washing leaching cake dry, obtain isophorone carbamic acid ester.
The loaded solid catalyst carrier adopting in the present invention is silicon-dioxide or aluminum oxide; The active ingredient of described loaded solid catalyst is zinc oxide or plumbous oxide or its mixture.When catalyst activity component is less, katalysis is not obvious; Cross conference and cause active constituent loading inhomogeneous, affect catalytic effect, therefore in described loaded solid catalyst, catalyst activity component loading is 5-30wt%.
Its concrete preparation method is:
(1) will in the nitrate of zinc or lead, add water, regulating pH value is 3-3.5;
(2) in the above-mentioned aqueous solution, add carrier, room temperature dipping 2-4.5 hour, 80-110 ℃ of dry 4-8 hour, 450-80 ℃ of roasting 3-5 hour, obtains loaded solid catalyst.
Zinc or plumbous nitrate can be removed nitrogen element with the form of gas in roasting process, and only remaining corresponding metal oxide, has avoided the residual of impurity element.In order to accelerate the dissolving in water of zinc or plumbous nitrate, adopt phosphoric acid or nitric acid to regulate pH value, pH value conference produce precipitation, too smallly can introduce a large amount of phosphoric acid/nitric acid, affect the activity of catalyzer, so pH value of the present invention is 3-3.5.
After the nitrate of zinc or lead dissolves completely, carrier is added wherein, room temperature dipping 2-4.5 hour, 80-110 ℃ is carried out roasting for dry 4-8 hour.Described carrier is silicon-dioxide or aluminum oxide.Too low or time of maturing temperature is too short stable form that to be difficult for zinc or plumbous nitrate transformation be active ingredient; The too high or oversize meeting of time of maturing temperature destroys the skeleton structure of support of the catalyst, so 450-580 of the present invention ℃ of roasting 3-5 hour.
The present invention compares with traditional technique, has following characteristics:
(1) hypertoxic phosgene, environmental protection have been avoided using;
(2) this technological reaction mild condition just can be carried out under middle low temperature, simple to equipment requirements;
(3) catalyzer adopting is loaded solid catalyst, is convenient to separation and recycling;
(4) separating out of product adding distil water, without rectifying, easy and simple to handle and purity is higher.
Embodiment
Embodiment 1
A preparation method for isophorone carbamic acid ester, its concrete steps are:
(1) in the mixed system of methylcarbonate and loaded solid catalyst, drip isophorone diamine, 50 ℃ are reacted 16 hours, filter; Wherein, methylcarbonate is 27g, isophorone diamine 17.0g, loaded solid catalyst 0.88g.
(2) to the distilled water that adds 3 times of volumes in the filtrate after filtering, standing, filter dry isophorone carbamic acid ester 24.7g, yield 86.3%, the purity 97.1% of obtaining.
The concrete preparation method of described loaded solid catalyst is:
(1) by 33.1g Pb (NO
3)
2soluble in water, phosphorus acid for adjusting pH value is 3;
(2) in the above-mentioned aqueous solution, add carrier silicon-dioxide 423.7g, room temperature dipping 2 hours, 110 ℃ dry 6 hours, 580 ℃ of roastings 3 hours, obtain loaded solid catalyst PbO/SiO
2, active ingredient loading is 5wt%.
Embodiment 2
A preparation method for isophorone carbamic acid ester, its concrete steps are:
(1) in the mixed system of methylcarbonate and loaded solid catalyst, drip isophorone diamine, 55 ℃ are reacted 12 hours, filter; Wherein, methylcarbonate is 90g, isophorone diamine 17.0g, loaded solid catalyst 10.7g.
(2) to the distilled water that adds 10 times of volumes in the filtrate after filtering, standing, filter dry isophorone carbamic acid ester 25.3g, yield 88.5%, the purity 98.2% of obtaining.
The concrete preparation method of described loaded solid catalyst is:
(1) by 33.1g Pb (NO
3)
2soluble in water, phosphorus acid for adjusting pH value is 3.1;
(2) in the above-mentioned aqueous solution, add alumina catalyst support 52g, room temperature dipping 2.5 hours, 100 ℃ dry 4 hours, 450 ℃ of roastings 5 hours, obtain loaded solid catalyst PbO/Al
2o
3, active ingredient loading is 30wt%.
Embodiment 3
A preparation method for isophorone carbamic acid ester, its concrete steps are:
(1) in the mixed system of methylcarbonate and loaded solid catalyst, drip isophorone diamine, 60 ℃ are reacted 9 hours, filter; Wherein, methylcarbonate is 54 g, isophorone diamine 17.0g, loaded solid catalyst 4.26g.
(2) to the distilled water that adds 6 times of volumes in the filtrate after filtering, standing, filter dry isophorone carbamic acid ester 25.0g, yield 87.3%, the purity 96.8% of obtaining.
The concrete preparation method of described loaded solid catalyst is:
(1) by 29.7g Zn(NO
3)
26H
2o is soluble in water, and phosphorus acid for adjusting pH value is 3.2;
(2) in the above-mentioned aqueous solution, add carrier silicon-dioxide 32.56g, room temperature dipping 3 hours, 110 ℃ dry 8 hours, 480 ℃ of roastings 4 hours, obtain loaded solid catalyst ZnO/SiO
2, active ingredient loading is 20wt%.
Embodiment 4
A preparation method for isophorone carbamic acid ester, its concrete steps are:
(1) in the mixed system of methylcarbonate and loaded solid catalyst, drip isophorone diamine, 65 ℃ are reacted 6 hours, filter; Wherein, methylcarbonate is 45g, isophorone diamine 17.0g, loaded solid catalyst 2.48g.
(2) to the distilled water that adds 5 times of volumes in the filtrate after filtering, standing, filter dry isophorone carbamic acid ester 25.5g, yield 89.2%, the purity 97.5% of obtaining.
The concrete preparation method of described loaded solid catalyst is:
(1) by 33.1g Pb (NO
3)
2soluble in water, nitre acid for adjusting pH value is 3.3;
(2) in the above-mentioned aqueous solution, add alumina catalyst support 200.7g, room temperature dipping 3.5 hours, 90 ℃ dry 8 hours, 515 ℃ of roastings 3.5 hours, obtain loaded solid catalyst PbO/Al
2o
3, active ingredient loading is 10wt%.
Embodiment 5
A preparation method for isophorone carbamic acid ester, its concrete steps are:
(1) in the mixed system of methylcarbonate and loaded solid catalyst, drip isophorone diamine, 90 ℃ are reacted 3 hours, filter; Wherein, methylcarbonate is 72g, isophorone diamine 17.0g, loaded solid catalyst 7.12g.
(2) to the distilled water that adds 7 times of volumes in the filtrate after filtering, standing, filter dry isophorone carbamic acid ester 25.7g, yield 89.8%, the purity 98.6% of obtaining.
The concrete preparation method of described loaded solid catalyst is:
(1) by 29.7g Zn(NO
3)
26H
2o is soluble in water, and nitre acid for adjusting pH value is 3.4;
(2) in the above-mentioned aqueous solution, add carrier silicon-dioxide 25g, room temperature dipping 4 hours, 80 ℃ dry 5 hours, 550 ℃ of roastings 4.5 hours, obtain loaded solid catalyst ZnO/SiO
2, active ingredient loading is 25wt%.
Embodiment 6
A preparation method for isophorone carbamic acid ester, its concrete steps are:
(1) in the mixed system of methylcarbonate and loaded solid catalyst, drip isophorone diamine, 80 ℃ are reacted 5 hours, filter; Wherein, methylcarbonate is 63g, isophorone diamine 17.0g, loaded solid catalyst 4.0g.
(2) to the distilled water that adds 8 times of volumes in the filtrate after filtering, standing, filter dry isophorone carbamic acid ester 25.8g, yield 90.2%, the purity 98.4% of obtaining.
The concrete preparation method of described loaded solid catalyst is:
(1) by 29.7g Zn(NO
3)
26H
2o and 33.1g Pb (NO
3)
2soluble in water, nitre acid for adjusting pH value is 3.5;
(2) in the above-mentioned aqueous solution, add alumina catalyst support 172g, room temperature dipping 4.5 hours, 95 ℃ dry 7 hours, 450 ℃ of roastings 5 hours, obtain loaded solid catalyst ZnO-PbO/Al
2o
3, active ingredient loading is 25wt%.
Embodiment 7
A preparation method for isophorone carbamic acid ester, its concrete steps are:
(1) in the mixed system of methylcarbonate and loaded solid catalyst, drip isophorone diamine, 80 ℃ are reacted 5 hours, filter; Wherein, methylcarbonate is 63g, isophorone diamine 17.0g, loaded solid catalyst 4.0g.
(2) to the distilled water that adds 8 times of volumes in the filtrate after filtering, standing, filter dry isophorone carbamic acid ester 25.8g, yield 90.2%, the purity 98.4% of obtaining.
The concrete preparation method of described loaded solid catalyst is:
(1) by 29.7g Zn(NO
3)
26H
2o and 33.1g Pb (NO
3)
2soluble in water, nitre acid for adjusting pH value is 3.5;
(2) in the above-mentioned aqueous solution, add alumina catalyst support 123.8g, room temperature dipping 4.5 hours, 95 ℃ dry 7 hours, 450 ℃ of roastings 5 hours, obtain loaded solid catalyst ZnO-Pb
3o
4/ Al
2o
3, active ingredient loading is 20wt%.
Claims (3)
1. a preparation method for isophorone carbamic acid ester, is characterized in that: take methylcarbonate and isophorone diamine as raw material, under the catalysis of loaded solid catalyst that supports active ingredient, react and make, its concrete steps are:
(1) in the mixed system of methylcarbonate and loaded solid catalyst, drip isophorone diamine, 50-90 ℃ of reaction 3-16 hour, filters;
(2) in the filtrate after filtering, add distilled water, standing, filter the dry isophorone carbamic acid ester that to obtain;
In step (1), the mol ratio of isophorone diamine and methylcarbonate is 1:3-10; The consumption of loaded solid catalyst is the 2-10% of isophorone diamine and methylcarbonate total mass; Loaded solid catalyst carrier is silicon-dioxide or aluminum oxide; The active ingredient of described loaded solid catalyst is zinc oxide or plumbous oxide or tri-lead tetroxide or its mixture;
In described loaded solid catalyst, catalyst activity component loading is 5-30wt%.
2. the preparation method of isophorone carbamic acid ester according to claim 1, is characterized in that: the 3-10 that in step (2), the consumption of distilled water is filtrate doubly.
3. the preparation method of isophorone carbamic acid ester according to claim 1, is characterized in that: the concrete preparation method of described loaded solid catalyst is:
(1) nitrate of zinc or lead is soluble in water, regulating pH value is 3-3.5;
(2) in the above-mentioned aqueous solution, add carrier, room temperature dipping 2-4.5 hour, 80-110 ℃ of dry 4-8 hour, 450-580 ℃ of roasting 3-5 hour, obtains loaded solid catalyst;
Described carrier is silicon-dioxide or aluminum oxide.
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