CN101343209A - Method for separating and recycling chloromethane with chloromethane mixture gas - Google Patents
Method for separating and recycling chloromethane with chloromethane mixture gas Download PDFInfo
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- CN101343209A CN101343209A CNA2008101202151A CN200810120215A CN101343209A CN 101343209 A CN101343209 A CN 101343209A CN A2008101202151 A CNA2008101202151 A CN A2008101202151A CN 200810120215 A CN200810120215 A CN 200810120215A CN 101343209 A CN101343209 A CN 101343209A
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Abstract
Disclosed is a method for separating a mixed gas of methyl chloride to recover methyl chloride, and the method at least has two absorption tower systems filled with adsorbents, and obtains the methyl chloride gas separated and removed of impurities from discharge ports of the absorption towers through temperature swing adsorption processes of both adsorption and desorption to the mixed gas containing methyl chloride in the absorption towers respectively by means of interlock of time sequence; the adsorbent is at least one of allochroic silicagel, active carbon, aluminum silicate salt zeolite molecular sieve or alumina zeolite molecular sieve; and the method adopts the dry separation and recovery of temperature swing adsorption, one set of apparatus can remove water, methanol, methylal, methyl oxide and air simultaneously, and the methyl chloride product is obtained relying on high purity and/or high rate of recovery, the flow is simple and operation costs are low; and the method can realize the zero discharge of waste sulfuric acid and waste desiccant and green and environment-friendly production compared with the traditional treatment method.
Description
Technical field
The present invention relates to a kind of method by Separation and Recovery methyl chloride in the mixed gas that contains methyl chloride, more specifically say it is from glyphosphonic acid, dimethylphosphite, in the tail gas that is produced in the production of trimethyl phosphite etc. and the purification process, through removing methyl alcohol, methylal is behind the impurity such as water, the method of high-level efficiency is pollution-free recovery methyl chloride, and this method does not produce secondary pollution.
Background technology
Glyphosphonic acid is the fastest steriland herbicide of the maximum rate of growth of sales volume in the world, and it has residual fewly be extensive use of in the whole world in remarkable herbicidal performance and the soil, for the development of glyphosphonic acid has launched prospect.The production of glyphosphonic acid at present mainly contains two kinds of methods, and a kind of is the IDA method, and it is that what to wait all that company generally adopts with U.S. Meng Shan is the IDA method of starting raw material with the diethanolamine; Another kind method is that alkyl esterification method is adopted by domestic most of enterprise, this method is open at document DEOLSNO.P2942898.6, this method is heating for dissolving in containing the methanol solution of triethylamine with Paraformaldehyde 96 or formaldehyde, add glycine and dimethylphosphite more respectively and carry out condensation reaction, add then hydrochloric acid be hydrolyzed (being called hydrolyzing process) obtain the hydrochloride of glyphosate acid, the glyphosate acid crystal was separated out after underpressure distillation removed solvent methanol and excessive hydrochloric acid, filter after scouring, filter cake is glyphosate acid.If produce glyphosphonic acid with trimethyl phosphite, technology is similar.
Employing is in the production of alkyl phosphite technology (comprising with the phosphorus trichloride being raw material synthesizing phosphorous acid dimethyl ester operation) synthesizing glyphosate acid of starting raw material with dimethylphosphite or trimethyl phosphite, in dimethylphosphite synthesis procedure and the synthetic hydrolyzing process that reaches after glyphosphonic acid synthesizes of glyphosphonic acid, produce a large amount of tail gas that contains methyl chloride.
Above methyl chloride tail gas recycle can be used for carboxymethyl cellulose after purifying, methyl chlorosilane, the important industrial chemicals that chloroprene rubber etc. are produced.Simultaneously, if do not recycle effectively, not only increase production cost waste resource, and environment is polluted.
Patent of invention 99119970.7 (franchise the applicant) discloses a kind of industrial method that reclaims the methyl chloride that produces in the alkyl phosphite method glyphosphonic acid building-up process, adopt be hydrolysis tail gas through washing, alkali cleaning, dry tertiary treatment, the storage of recompression condensation liquefaction.Owing to be subjected to the influence of methylal and methyl alcohol solubleness and rate of mass transfer in water, need a large amount of water to wash (6 tons of water/ton methyl chloride), cause waste water too much, bring pressure to environmental protection, there is certain solubleness (0.38 grams per liter) in methyl chloride in water simultaneously, cause the methyl chloride partial loss, influence the rate of recovery.
The mixed tail gas that contains impurity such as methyl chloride, methyl alcohol and methylal, water and hydrogenchloride to producing in the glyphosphonic acid production process is disclosed in the patent of publication number CN1446782A, CN1629111A, CN1629112A (franchise the applicant), respectively by the pressurization condensation method, add in the fluid that contains hydrogenchloride with the organic solvent absorption impurity or with partial impurities such as methyl alcohol, methylal and to make its method that is converted into methyl chloride obtain highly purified methyl chloride.Since this process using organic solvent, cause secondary pollution problems.
Disclose in the patent of publication number CN101012146A by pressure swing adsorption (PSA) and separated the method that the methyl chloride mixed gas reclaims methyl chloride.The loop cycle of transformation absorption is generally all very short, generally be that the several seconds was to several minutes, in the so short time, methyl chloride and other gases are difficult to penetrate sorbent material in order, and most methyl chloride is adsorbed, and yield is lower, and the desorb of adsorbate is by the nitrogen purging under the normal temperature in the document, be difficult to desorption, sorbent material can not reuse, and does not possess the industrialization condition.
Summary of the invention
The objective of the invention is to overcome the deficiency that prior art exists, and provide a kind of methyl chloride of high yield of realizing to reclaim, a large amount of simultaneously minimizing waste water produce, and thoroughly solve the method by methyl chloride mixed gas Separation and Recovery methyl chloride of glyphosphonic acid suitability for industrialized production discharging waste gas waste water to the influence of environment.
The objective of the invention is to finish by following technical solution, what it adopted is the dry method separation and recovery method that alternating temperature absorption (TSA) method is handled, this method is at least by in two adsorption tower systems that are filled with sorbent material, to the mixed gas that contains methyl chloride with mode staggered on the sequential in each adsorption tower respectively all through adsorbing and the alternating temperature adsorption process of desorb, obtain separating the methyl chloride gas of removing impurity component by the adsorption tower relief outlet; Described sorbent material is at least a in discolour silica gel, gac, pure aluminium silicate salt zeolite molecular sieve or the alumina type zeolite molecular sieve.
The particle diameter of described discolour silica gel sorbent material is 2-5mm, the water adsorption amount during relative humidity 50%＞20%.
Described pure aluminium silicate salt zeolite molecular sieve class sorbent material is 3A or 4A or 5A or 13X or 10X zeolite molecular sieve or its combination, and its granularity is 3-5mm, and tap density is 0.6-0.8g/mL, and water adsorption amount is greater than 18%.
Described pure aluminium silicate salt zeolite molecular sieve class sorbent material is the mordenite with high silicon aluminum ratio molecular sieve analog sorbent material of sial atomic ratio at 10-20.
The described mixed gas that contains methyl chloride is the uncooled property gas under gauge pressure 0-0.7MPa and the temperature 1-30 ℃ condition.
Adsorption temp in the described alternating temperature adsorption process is a room temperature to 50 ℃, desorption temperature is 50-250 ℃, preferred 150-200 ℃, the control adsorption time, reach the purpose of separating the methyl chloride mixed gas, adsorption time determines that by conditions such as mixed gas flow and sorbent material loadings the sorbent material loadings is big, then adsorption time is long, and adsorption time is 15-30 minute usually.Desorption time is determined by the height of desorption temperature.The temperature height more helps the desorption rate of stripping gas.Adsorptive pressure can be gauge pressure 0-0.6MPa.
Behind the indirect condensing under gauge pressure 0.6-1.0MPa and-23 ℃ of-35 ℃ of conditions, obtain liquid methyl chloride product by the methyl chloride gas of temperature swing adsorption system Separation and Recovery.
A kind of in the tail gas mixture that contains methyl chloride and methyl alcohol, methylal, methyl ether and water that the described mixed gas that contains methyl chloride comprises at least is that produce in the dimethylphosphite production, that produce in the trimethyl phosphite production, produce in the glyphosphonic acid production process.
Described sorbent material is a kind of and pure aluminium silicate salt zeolite molecular sieve in discolour silica gel or the gac or a kind of combination in the alumina type zeolite molecular sieve, and its admission space is than being 2-6: 6-2.
The acid of table 1. glyphosate is produced discharging tail gas and is formed:
| Composition | Methyl chloride | Air | Methyl alcohol | Methylal | Water | Hydrogenchloride | Other |
| Content (%) V/V | 20-90 | 8-20 | 2-15 | 4-20 | 2-10 | 1-5 | 1-5 |
Methyl alcohol wherein and methylal are in saturated or hypersaturated state, the boiling point of methyl alcohol, methylal and methyl chloride is respectively 64.5 ℃, 42.3 ℃ and-23.73 ℃ under normal pressure, the emergent pressure of methyl alcohol and methylal is respectively 240 ℃ and 215 ℃, far above 143 ℃ of methyl chloride, therefore, the method that can adopt compression is methyl alcohol in the gas phase and the most of condensation of methylal, thereby can reduce the load of follow-up alternating temperature absorption significantly.During actually operating, can adopt gauge pressure 0.2-1MPa, be preferably 0.2-0.7MPa, be preferably 0.3-0.6MPa and temperature-10-40 ℃ (combination of certainly adopting multiple pressure and temperature is to reach same effect).
The alternating temperature adsorption process can be carried out in a conventional way.Increase the adsorption tower quantity of temperature swing adsorption system and the loadings of regulating each adsorption tower, control the conditions such as temperature and time of heating desorption, help improving the purity of separation efficiency and/or product gas.Test shows, mixed gas has passed through the temperature swing adsorption system selective adsorption behind the impurity such as methyl alcohol wherein, methylal and water, can obtain the methyl chloride gas of Separation and Recovery from the exit of adsorption tower, wherein water content can be less than 2ppm, and foreign matter contents such as methyl alcohol and methylal are generally all less than 20PPm.
By the methyl chloride gas of above-mentioned alternating temperature adsorption treatment Separation and Recovery, behind the indirect condensing under gauge pressure 0.6-1.0MPa and-23 ℃～-35 ℃ conditions, can obtain liquid methyl chloride product, its content can reach 99.9%.The stripping gas of the compositions such as the methane that contains small amounts of chlorine methane, methylal and water that desorb by temperature swing adsorption system, can be further under-10-30 ℃, carry out condensation process, behind cutting out partial methyl alcohol, methylal and the water, merge in methyl chloride mixing raw material gas to be separated, send into temperature swing adsorption system again and handle.
The mixed gas that contains methyl chloride can reach more than 98% the rate of recovery of methyl chloride in the mixed gas after above-mentioned alternating temperature fractionation by adsorption of the present invention, and methyl alcohol after the separation and methylal can be used for other chemical processes through further purification.Therefore, the present invention has good economic benefit and environmental benefit, does not have the waste discharge and the handling problem of present traditional methods such as vitriol oil method fully, has accomplished environmental protection production.
The present invention can also be to comprising the Separation and Recovery processing that reaches multiple chloride methane blended gases such as purification that reaches generation in purification, the trimethyl phosphite production of generation in the dimethylphosphite production except that can separating the methyl chloride mixed gas that produces in the glyphosphonic acid production process.
Embodiment
What the present invention adopted is the dry method separation and recovery method that alternating temperature absorption (TSA) method is handled, this method is at least by in two adsorption tower systems that are filled with sorbent material, to the mixed gas that contains methyl chloride with mode staggered on the sequential in each adsorption tower respectively all through adsorbing and the alternating temperature adsorption process of desorb, obtain separating the methyl chloride gas of removing impurity component by the adsorption tower relief outlet; Described sorbent material is at least a in discolour silica gel, gac, pure aluminium silicate salt zeolite molecular sieve or the alumina type zeolite molecular sieve.
The particle diameter of described discolour silica gel sorbent material is 2-5mm, the water adsorption amount during relative humidity 50%＞20%.
Described pure aluminium silicate salt zeolite molecular sieve class sorbent material is 3A or 4A or 5A or 13X or 10X zeolite molecular sieve or its combination, and its granularity is 3-5mm, and tap density is 0.6-0.8g/mL, and water adsorption amount is greater than 18%.
Described pure aluminium silicate salt zeolite molecular sieve class sorbent material is the mordenite with high silicon aluminum ratio molecular sieve analog sorbent material of sial atomic ratio at 10-20.
The described mixed gas that contains methyl chloride is the uncooled property gas under gauge pressure 0-0.7MPa and the temperature 1-30 ℃ condition.
Adsorption temp in the described alternating temperature adsorption process is a room temperature to 50 ℃, desorption temperature is 50-250 ℃, preferred 150-200 ℃, the control adsorption time, reach the purpose of separating the methyl chloride mixed gas, adsorption time determines that by conditions such as mixed gas flow and sorbent material loadings the sorbent material loadings is big, and then adsorption time is long.Desorption time is determined by the height of desorption temperature.The temperature height more helps the desorption rate of stripping gas.Adsorptive pressure can be gauge pressure 0-0.6MPa.
Behind the indirect condensing under gauge pressure 0.6-1.0MPa and-23 ℃ of-35 ℃ of conditions, obtain liquid methyl chloride product by the methyl chloride gas of temperature swing adsorption system Separation and Recovery.
A kind of in the tail gas mixture that contains methyl chloride and methyl alcohol, methylal, methyl ether and water that the described mixed gas that contains methyl chloride comprises at least is that produce in the dimethylphosphite production, that produce in the trimethyl phosphite production, produce in the glyphosphonic acid production process.
Described sorbent material is a kind of and pure aluminium silicate salt zeolite molecular sieve in discolour silica gel or the gac or a kind of combination in the alumina type zeolite molecular sieve, and its admission space is than being 2-6: 6-2.
Form the mixed gas by recovery in glyphosphonic acid and dimethylphosphite or the trimethyl phosphite production as shown in table 1, after alkali cleaning removes hydrogenchloride, adopt following scheme to test respectively, with the content (weight) of methyl chloride and other compositions in the gas chromatograph analytical gas, in each process of the test from adsorption tower pipeline thief hole sampling analysis methyl chloride content.The part technological process that following examples just adopt does not represent to have only following separation combination, can carry out various combinations according to unstripped gas condition and required separation requirement.Embodiments of the invention are not limited to following several, and all combinations in above-mentioned scope change and all belong within the practical range of this patent with the replacement that routine techniques carries out.
The present invention will be described in detail below in conjunction with specific embodiment:
Embodiment 1
Methyl chloride gas mixture behind 15%-30% sodium hydroxide lye absorbing hydrogen chloride, enter compressor inlet through surge tank, be pressurized to gauge pressure 0.5MPa, be cooled to 5 ℃, after condensation separation goes out impurity such as part methyl alcohol, methylal and water, entering under normal pressure by two towers series connection adsorption unit is that the temperature swing adsorption system of one group, two groups tower parallel connection carries out the alternating temperature fractionation by adsorption and handles, and is obtained the methyl chloride gas of non-absorption phase by the outlet of adsorption tower.One group of tower in the adsorption system at room temperature moves, and another group tower with nitrogen purging regeneration, recycles under 150 ℃.The conversion of adsorption tower device is moved automatically by computer control.Two groups of adsorption towers are followed successively by discolour silica gel and 4A molecular sieve by the sorbent material of same way as filling respectively, and the admission space ratio is 1: 1.Adsorption time is determined by conditions such as quantity of sorbent, is generally 15-30 minute.
Embodiment 2
Mode by embodiment 1 is carried out lock out operation, and sorbent material is selected gac and 4A molecular sieve for use, and the admission space ratio is 1: 2.
Embodiment 3
Mode by embodiment 1 is carried out lock out operation, and sorbent material is selected discolour silica gel and 5A molecular sieve for use, and the admission space ratio is 1: 2.
Embodiment 4
Mode by embodiment 1 is carried out lock out operation, and sorbent material is selected gac and 5A molecular sieve for use, and the admission space ratio is 1: 1.
The various embodiments described above are as shown in table 2 to the Separation and Recovery result of methyl chloride gas mixture.
Embodiment 5
Mode by embodiment 1 is carried out lock out operation, and the adsorption tower in a group is single, and sorbent material is selected discolour silica gel for use.
Each embodiment of table 2. is to the Separation and Recovery result of methyl chloride
Claims (9)
1, a kind of method by methyl chloride mixed gas Separation and Recovery methyl chloride, it is characterized in that: this method is at least by in two adsorption tower systems that are filled with sorbent material, to the mixed gas that contains methyl chloride with mode staggered on the sequential in each adsorption tower respectively all through adsorbing and the alternating temperature adsorption process of desorb, obtain separating the methyl chloride gas of removing impurity component by the adsorption tower relief outlet; Described sorbent material is at least a in discolour silica gel, gac, pure aluminium silicate salt zeolite molecular sieve or the alumina type zeolite molecular sieve.
2, the method by methyl chloride mixed gas Separation and Recovery methyl chloride according to claim 1 is characterized in that the particle diameter of described discolour silica gel sorbent material is 2-5mm, the water adsorption amount during relative humidity 50%＞20%.
3, the method by methyl chloride mixed gas Separation and Recovery methyl chloride according to claim 1, it is characterized in that described pure aluminium silicate salt zeolite molecular sieve class sorbent material is 3A or 4A or 5A or 13X or 10X zeolite molecular sieve or its combination, its granularity is 3-5mm, tap density is 0.6-0.8g/mL, and water adsorption amount is greater than 18%.
4,, it is characterized in that described pure aluminium silicate salt zeolite molecular sieve class sorbent material is the mordenite with high silicon aluminum ratio molecular sieve analog sorbent material of sial atomic ratio at 10-20 according to claim 1 or 3 described methods by methyl chloride mixed gas Separation and Recovery methyl chloride.
5, the method by methyl chloride mixed gas Separation and Recovery methyl chloride according to claim 1 is characterized in that the described mixed gas that contains methyl chloride is the uncooled property gas under gauge pressure 0-0.7MPa and the temperature 1-30 ℃ condition.
6, the method by methyl chloride mixed gas Separation and Recovery methyl chloride according to claim 1, it is characterized in that adsorption temp in the described alternating temperature adsorption process is a room temperature to 50 ℃, desorption temperature is 50-250 ℃, and preferred 150-200 ℃, desorption pressures is gauge pressure 0-0.6Mpa.
7, the method by methyl chloride mixed gas Separation and Recovery methyl chloride according to claim 1 is characterized in that obtaining liquid methyl chloride product by the methyl chloride gas of temperature swing adsorption system Separation and Recovery behind the indirect condensing under gauge pressure 0.6-1.0MPa and-23 ℃ of-35 ℃ of conditions.
8,, it is characterized in that the described mixed gas that contains methyl chloride comprises a kind of in the tail gas mixture that contains methyl chloride and methyl alcohol, methylal, methyl ether and water that produces in that produce in the dimethylphosphite production, that produce in the trimethyl phosphite production, the glyphosphonic acid production process at least according to claim 1 or 5 by the method for methyl chloride mixed gas Separation and Recovery methyl chloride.
9, the method by methyl chloride mixed gas Separation and Recovery methyl chloride according to claim 1, it is characterized in that described sorbent material is a kind of and pure aluminium silicate salt zeolite molecular sieve in discolour silica gel or the gac or a kind of combination in the alumina type zeolite molecular sieve, its admission space is than being 2-6: 6-2.
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| CNA2008101202151A CN101343209A (en) | 2008-08-11 | 2008-08-11 | Method for separating and recycling chloromethane with chloromethane mixture gas |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102093160A (en) * | 2010-12-29 | 2011-06-15 | 天津市康科德科技有限公司 | Method for preparing chromatographically-pure trichloromethane |
| CN102093159A (en) * | 2010-12-29 | 2011-06-15 | 天津市康科德科技有限公司 | Method for preparing chromatographic pure dichloromethane |
| CN102977137A (en) * | 2012-11-29 | 2013-03-20 | 湖北泰盛化工有限公司 | Condensate recovery method for glyphosate synthesis solution |
| CN103567170A (en) * | 2012-07-31 | 2014-02-12 | 曹汉平 | Method for removing scaling substances of methane chloride of chlorinating device |
| CN105837400A (en) * | 2016-03-19 | 2016-08-10 | 安徽东至广信农化有限公司 | Method for recovering methyl chloride from glyphosate production |
| CN107384470A (en) * | 2017-07-31 | 2017-11-24 | 森松（江苏）重工有限公司 | A kind of organic solvent molecule sieve dehydration dealcoholysis regenerating unit |
| CN108047063A (en) * | 2017-12-28 | 2018-05-18 | 浙江新安化工集团股份有限公司 | A kind of preparation method of methyl triethyl ammonium chloride |
| CN108084037A (en) * | 2017-12-28 | 2018-05-29 | 浙江新安化工集团股份有限公司 | A kind of preparation method of methyl triethyl ammonium chloride |
| CN109012015A (en) * | 2018-07-09 | 2018-12-18 | 天吉人吉环保节能（苏州）有限公司 | A kind of chlorinated organics low energy consumption recovery process of chloride containing organic matter gaseous mixture |
| CN110041164A (en) * | 2019-05-08 | 2019-07-23 | 江西金龙化工有限公司 | A method of recycling chloromethanes |
| CN112479797A (en) * | 2020-11-30 | 2021-03-12 | 安徽泽升科技有限公司 | Preparation method of ultra-dry organic solvent |
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2008
- 2008-08-11 CN CNA2008101202151A patent/CN101343209A/en active Pending
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102093160A (en) * | 2010-12-29 | 2011-06-15 | 天津市康科德科技有限公司 | Method for preparing chromatographically-pure trichloromethane |
| CN102093159A (en) * | 2010-12-29 | 2011-06-15 | 天津市康科德科技有限公司 | Method for preparing chromatographic pure dichloromethane |
| CN102093160B (en) * | 2010-12-29 | 2013-05-29 | 天津市康科德科技有限公司 | Method for preparing chromatographically-pure trichloromethane |
| CN103567170A (en) * | 2012-07-31 | 2014-02-12 | 曹汉平 | Method for removing scaling substances of methane chloride of chlorinating device |
| CN102977137A (en) * | 2012-11-29 | 2013-03-20 | 湖北泰盛化工有限公司 | Condensate recovery method for glyphosate synthesis solution |
| CN105837400A (en) * | 2016-03-19 | 2016-08-10 | 安徽东至广信农化有限公司 | Method for recovering methyl chloride from glyphosate production |
| CN107384470A (en) * | 2017-07-31 | 2017-11-24 | 森松（江苏）重工有限公司 | A kind of organic solvent molecule sieve dehydration dealcoholysis regenerating unit |
| CN108084037A (en) * | 2017-12-28 | 2018-05-29 | 浙江新安化工集团股份有限公司 | A kind of preparation method of methyl triethyl ammonium chloride |
| CN108047063A (en) * | 2017-12-28 | 2018-05-18 | 浙江新安化工集团股份有限公司 | A kind of preparation method of methyl triethyl ammonium chloride |
| CN108084037B (en) * | 2017-12-28 | 2019-06-11 | 浙江新安化工集团股份有限公司 | A kind of preparation method of methyl triethyl ammonium chloride |
| CN108047063B (en) * | 2017-12-28 | 2019-06-11 | 浙江新安化工集团股份有限公司 | A kind of preparation method of methyl triethyl ammonium chloride |
| CN109012015A (en) * | 2018-07-09 | 2018-12-18 | 天吉人吉环保节能（苏州）有限公司 | A kind of chlorinated organics low energy consumption recovery process of chloride containing organic matter gaseous mixture |
| CN110041164A (en) * | 2019-05-08 | 2019-07-23 | 江西金龙化工有限公司 | A method of recycling chloromethanes |
| CN110041164B (en) * | 2019-05-08 | 2021-11-09 | 浙江金帆达生化股份有限公司 | Method for recovering methyl chloride |
| CN112479797A (en) * | 2020-11-30 | 2021-03-12 | 安徽泽升科技有限公司 | Preparation method of ultra-dry organic solvent |
| CN112479797B (en) * | 2020-11-30 | 2023-03-07 | 安徽泽升科技有限公司 | Preparation method of ultra-dry organic solvent |
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Open date: 20090114 |