CN100357266C - Process for producing methyl carbamate - Google Patents
Process for producing methyl carbamate Download PDFInfo
- Publication number
- CN100357266C CN100357266C CNB2005100424828A CN200510042482A CN100357266C CN 100357266 C CN100357266 C CN 100357266C CN B2005100424828 A CNB2005100424828 A CN B2005100424828A CN 200510042482 A CN200510042482 A CN 200510042482A CN 100357266 C CN100357266 C CN 100357266C
- Authority
- CN
- China
- Prior art keywords
- reaction
- urea
- methanol
- methyl alcohol
- urethylane
- 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
Links
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title abstract description 18
- 230000008569 process Effects 0.000 title abstract description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 74
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000004202 carbamide Substances 0.000 claims abstract description 18
- 239000000463 material Substances 0.000 claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 claims abstract description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 14
- YEYZNBKNDWPFSQ-UHFFFAOYSA-N methanol;urea Chemical compound OC.NC(N)=O YEYZNBKNDWPFSQ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 238000005516 engineering process Methods 0.000 claims abstract description 7
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 5
- 238000004090 dissolution Methods 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims 4
- 238000001816 cooling Methods 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 230000035484 reaction time Effects 0.000 abstract description 7
- 239000000376 reactant Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 9
- 244000287680 Garcinia dulcis Species 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000003905 agrochemical Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a technological process for producing methyl carbamate, which belongs to the technical field of a fine production technology of chemical industry. The present invention has the technical scheme that methanol and urea are dissolved according to the proportion of 1 to 20: 1 to cause the concentration of a urea methanol solution to be from 0.01 to 10 mol/L, the solution is added into a reaction kettle, and then, the solution reacts for 0.5 to 10 hours at the reaction temperature of 100 to 180 DEG C under the reaction pressure of 0.1 to 1.5MPa; in the process of reaction, after product ammonium which is carried over by the methanol which belongs to one of reactants is condensed by a condenser through a rectifying tower, a reaction system is separated to enter an ammonia generating system, and then, ammonia is generated. Meanwhile, after the methanol is separated for N<3> hours by the rectifying tower, the methanol returns to the reaction system to be circularly used; after the reaction is finished, the reaction solution is purified. The present invention has the advantages that the technological process realizes operation of using the urea and the methanol as raw materials to carry out homogeneous reaction to produce the methyl carbamate in an industrial way, causes the urea in a synthetic system to be converted into the methyl carbamate, greatly improves the yield of the methyl carbamate, simplifies operating processes and shortens reaction time. In the whole technological process, the material is balanced, and the energy exchange is balanced; raw materials and power consumption are reduced, and the production cost is greatly saved.
Description
One, technical field
The invention belongs to a kind of technical process of producing Urethylane, belong to fine chemistry industry production technique field.
Two, background technology
Urethylane (Methyl Carbamate is called for short MC), another name urethylan (Ureathylane), methyl Wu Laitan (Methylurethane) are a kind of important organic synthesis intermediates.Be mainly used in the synthetic of medicine, agricultural chemicals, its derivative obtains application more and more widely as weedicide, sterilant, rubber antioxygen, thermo-stabilizer etc. at agricultural, rubber industry.Carbamate chemicals for agriculture, since it with the agricultural chemicals of other kind compare people and other Mammals have low toxicity, poisoning specificity by force, easily by multiple factor degrade, residual low, to characteristics such as the side effect of environment are little, develop novel pesticide, weedicide and kill mosquito faster, fly agent so become countries in the world in recent years, and its Application Areas is expanded very fast.
The present existing MC synthetic production technique in home and abroad mainly adopts phosgene route, owing to produce raw materials used all poisonously with solvent, so complex process is very high to the equipment requirements condition, investment is huge, production cost is very high.The existing alcoholysis of urea technological process of production has also caused the complicated of technical process because of the separation that comprises various catalyzer, processing etc., because of catalyst system therefor equipment is had corrodibility simultaneously, and equipment material is had relatively high expectations, thereby has caused facility investment bigger.
Three, summary of the invention
The objective of the invention is defective, a kind of catalyst-free is provided, is the production technique of raw material homogeneous reaction production Urethylane with urea and methyl alcohol at the prior art existence.
Technical scheme of the present invention is to be raw material with urea and methyl alcohol, the production technique of producing Urethylane comprises that mainly material dissolution, reaction are synthesized, operation totally enclosed circulating reaction flow processs such as methyl alcohol, ammoniacal liquor formation are reclaimed in rectifying, production equipment mainly comprises reactor, rectifying tower, the ammoniacal liquor generating apparatus.
Technical process of the present invention is as follows:
With methyl alcohol, urea in 1～20: the dissolving of 1 ratio, join reactor, in temperature of reaction is 100～180 ℃, reaction pressure is to react 0.5～10 hour under the condition of 0.1～1.5Mpa, to after condenser condenses, isolate reaction system by the resultant ammonia that the methyl alcohol of one of reactant is taken out of through rectifying tower in the reaction process, and enter the ammoniacal liquor generation system and generate ammoniacal liquor.Rectifying tower separates NH simultaneously
3After methyl alcohol return the reaction system recycle.After reaction finishes reaction solution being carried out product purifies.In reaction is synthetic,, realize suppressing urea decomposition, impel molecular balance to move to generating the Urethylane direction by the burst size of control ammonia gas and the additional speed of urea methanol solution.
The invention has the advantages that: this technical process has realized with urea and methyl alcohol being the operation of raw material homogeneous reaction suitability for industrialized production Urethylane, increasing rectifying tower on reactor can make the ammonia that reacts generation break away from the synthetic system of reactor effectively, impel in the synthetic system urea to the conversion of Urethylane, improved the productive rate of Urethylane greatly, simplify schedule of operation, shortened the reaction times.The material balance of whole process flow, energy exchange balance are controlled the highly selective that has realized product by reaction conditions, have reached rational comprehensive utilization, have reduced raw material and energy expenditure, have saved production cost greatly.
Four, description of drawings: do not have.
Five, embodiment
Embodiment 1: urea and methyl alcohol pro rata magnitude relation are joined in the reactor, and 140 ℃ of reacting by heating temperature are opened reactor gas phase and rectifying tower connecting tube valve when pressure reaches 1.5Mpa, and rectifying tower begins
Work is with 0.2m
3It is the urea methanol solution of 1mol/L that/hour speed is replenished concentration, and the control reactor is to the gas phase rate of release of rectifying tower, with keep material in the reactor into and out of material balance, 4 hours reaction times.The Urethylane productive rate is 86%.While by-product 30% ammoniacal liquor.
Embodiment 2: urea and methyl alcohol pro rata magnitude relation are joined in the reactor, and 150 ℃ of reacting by heating temperature are opened reactor gas phase and rectifying tower connecting tube valve when pressure reaches 1.0Mpa, and rectifying tower is started working, with 0.5m
3/ hour speed is replenished the urea methanol solution of concentration 0.5mol/L, and the control reactor is to the gas phase rate of release of rectifying tower, with keep material in the reactor into and out of material balance, 3 hours reaction times.The Urethylane productive rate is 90%.While by-product 30% ammoniacal liquor.
Embodiment 3:
Urea and methyl alcohol pro rata magnitude relation are joined in the reactor, and 150 ℃ of reacting by heating temperature are opened reactor gas phase and rectifying tower connecting tube valve when pressure reaches 1.5Mpa, and rectifying tower is started working, with 0.2m
3/ hour speed is replenished the urea methanol solution of concentration 1.5mol/L, and the control reactor is to the gas phase rate of release of rectifying tower, with keep material in the reactor into and out of material balance, 4 hours reaction times.The Urethylane productive rate is 88%.While by-product 30% ammoniacal liquor.
Embodiment 4:
Urea and methyl alcohol pro rata magnitude relation are joined in the reactor, and 160 ℃ of reacting by heating temperature are opened reactor gas phase and rectifying tower connecting tube valve when pressure reaches 1.0Mpa, and rectifying is started working, with 1.0m
3/ hour speed is replenished the urea methanol solution of concentration 1.2mol/L, and the control reactor is to the gas phase rate of release of rectifying tower, with keep material in the reactor into and out of material balance, 3 hours reaction times.The Urethylane productive rate is 91%.While by-product 30% ammoniacal liquor.
Embodiment 5:
Urea and methyl alcohol pro rata magnitude relation are joined in the reactor, heating, 175 ℃ of temperature of reaction are opened reactor gas phase and rectifying tower connecting tube valve when pressure reaches 1.5Mpa, and rectifying tower is started working, with 0.05m
3It is the urea methanol solution of 1mol/L that/hour speed is replenished concentration, and the control reactor is to the gas phase rate of release of rectifying tower, with keep material in the reactor into and out of material balance, 2 hours reaction times.The Urethylane productive rate is 89%.While by-product 30% ammoniacal liquor.
Claims (4)
1, a kind of technology of producing Urethylane is characterized in that comprising
Material dissolution: with urea and methyl alcohol is raw material, and by urea: the ratio of the weight of methyl alcohol is to mix at 1～20: 1;
Reaction is synthetic: mixed urea methanol solution reacted 0.5～10 hour under the condition of 100～180 ℃ of temperature of reaction, reaction pressure 0.1～1.5Mpa;
Product is purified: after reaction finishes reaction solution is carried out product and purify;
In reaction is synthetic,, realize suppressing urea decomposition, impel molecular balance to move to generating the Urethylane direction by the burst size of control ammonia gas and the additional speed of urea methanol solution.
2, the technology of production Urethylane according to claim 1 is characterized in that also comprising Methanol Recovery: the ammonia that discharges in the reaction process-methanol mixed steam goes out ammonia gas and methyl alcohol by rectifying separation, and methyl alcohol reclaims after cooling off.
3, the technology of production Urethylane according to claim 2 is characterized in that isolating ammonia gas and isolate methyl alcohol once more, Methanol Recovery after cooling in the Methanol Recovery process.
4, the technology of production Urethylane according to claim 2 is characterized in that material dissolution realizes by the pre-mixing still; Reaction is synthetic to be to carry out in the totally enclosed reactor that has an agitator; It is to carry out in separating still that product is purified; Methanol Recovery realizes by rectifying tower, water cooler.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100424828A CN100357266C (en) | 2005-02-21 | 2005-02-21 | Process for producing methyl carbamate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100424828A CN100357266C (en) | 2005-02-21 | 2005-02-21 | Process for producing methyl carbamate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1683326A CN1683326A (en) | 2005-10-19 |
| CN100357266C true CN100357266C (en) | 2007-12-26 |
Family
ID=35262853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005100424828A Expired - Fee Related CN100357266C (en) | 2005-02-21 | 2005-02-21 | Process for producing methyl carbamate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100357266C (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101781202B (en) * | 2009-01-16 | 2014-04-23 | 亚申科技研发中心（上海）有限公司 | Reaction process and system for preparing organic carbonic ester by catalytic alcoholysis of urea |
| CN101570499A (en) * | 2009-03-07 | 2009-11-04 | 垦利三合新材料科技有限责任公司 | Preparation method of methyl carbamate |
| CN103254101B (en) * | 2013-04-03 | 2015-12-23 | 中北大学 | Prepare the method and apparatus of Urethylane |
| CN106631901B (en) * | 2016-12-14 | 2019-02-05 | 中榆化工科技有限公司 | A kind of method and device thereof preparing methyl carbamate using alcoholysis of urea |
| CN113651751B (en) * | 2021-09-28 | 2023-04-11 | 大连九信精细化工有限公司 | Preparation method of N-methoxycarbonyl-3-trifluoromethylpyridine-2-sulfonamide |
| CN114956119A (en) * | 2022-04-26 | 2022-08-30 | 山东禹城易澳科技有限公司 | Method for treating distillation residue of carbamate |
| CN114656375A (en) * | 2022-05-06 | 2022-06-24 | 山东禹城易澳科技有限公司 | Methyl carbamate refining process |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5534649A (en) * | 1994-10-21 | 1996-07-09 | Tama Chemicals Co., Ltd. | Process for preparing dialkyl carbonates |
| CN1475481A (en) * | 2003-07-11 | 2004-02-18 | 中国科学院山西煤炭化学研究所 | A kind of method of synthesizing methyl carbamate |
-
2005
- 2005-02-21 CN CNB2005100424828A patent/CN100357266C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5534649A (en) * | 1994-10-21 | 1996-07-09 | Tama Chemicals Co., Ltd. | Process for preparing dialkyl carbonates |
| CN1475481A (en) * | 2003-07-11 | 2004-02-18 | 中国科学院山西煤炭化学研究所 | A kind of method of synthesizing methyl carbamate |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1683326A (en) | 2005-10-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111362901B (en) | A kind of fluoroalcohol functionalized ionic liquid catalyzes the method for carbon dioxide to synthesize cyclic carbonate | |
| CN109748805A (en) | The method of liquid ammonia process for caustic soda purification production isopropanolamine | |
| CN106588758A (en) | Synthetic process for 2-hydrazinylpyridine derivative | |
| CN100357266C (en) | Process for producing methyl carbamate | |
| CN101279961B (en) | Method for preparing epoxy chloropropane by epoxidation of propylene chloride | |
| CN102786499B (en) | Method for preparing cyclohexene oxide | |
| CN106380375B (en) | A kind of method of the continuous synthesizing adipic acid of micro passage reaction | |
| CN114315749B (en) | Method for synthesizing aliskiren intermediate by continuous flow microreactor | |
| WO2016184038A1 (en) | Method for preparing cyclohexene oxide using micro-flow field reaction technology | |
| CN104262109B (en) | A kind of synthetic method of resorcinol | |
| CN101972642B (en) | Solid base catalyst and method for synthesizing 3-chloro-2-hydroxypropyl-trimethyl-ammonium chloride based on solid base catalyst | |
| CN115466164A (en) | Production process method of o-phenylphenol | |
| CN109675631B (en) | Catalyst for preparing glycol by hydrating epoxy compound and application thereof | |
| CN100415712C (en) | Process for producing methyl carbamate by low pressure solvation homogeneous phase reaction | |
| CN108530301B (en) | Synthetic method of 2,4, 6-trifluorobenzylamine | |
| CN106831595B (en) | A kind of benzyl imidazole ionic liquid and the method using its catalytically synthesizing cyclic carbonate ester | |
| CN101781202A (en) | Reaction process and system for preparing organic carbonic ester by catalytic alcoholysis of urea | |
| CN109675627B (en) | Solid catalyst for preparing glycol by hydrating epoxy compound and application thereof | |
| CN105439823A (en) | Method for synthesizing 3-methyl-3-butene-1-ol | |
| CN117299038A (en) | System and process for continuously preparing 2-methylimidazole | |
| US10252985B2 (en) | Solvent-free green ammoximation process based on film distribution | |
| CN116396179A (en) | A high-efficiency production method of high-purity oxamide under mild conditions | |
| CN117304036B (en) | Preparation method of octafluoro- [1,1 '-biphenyl ] -4,4' -diamine | |
| CN114621176B (en) | Imidazolium bromide catalyst in CO 2 Cycloaddition reaction method with styrene oxide | |
| CN110885286B (en) | Preparation method of α-isophorone |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20071226 Termination date: 20120221 |