CN104250218B - A kind of tert-butyl acrylamide sulfonate production method - Google Patents
A kind of tert-butyl acrylamide sulfonate production method Download PDFInfo
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- CN104250218B CN104250218B CN201310268069.8A CN201310268069A CN104250218B CN 104250218 B CN104250218 B CN 104250218B CN 201310268069 A CN201310268069 A CN 201310268069A CN 104250218 B CN104250218 B CN 104250218B
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- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 title claims abstract description 31
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- 239000000047 product Substances 0.000 claims abstract description 27
- 239000002699 waste material Substances 0.000 claims abstract description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 26
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000007788 liquid Substances 0.000 claims abstract description 20
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 239000000706 filtrate Substances 0.000 claims abstract description 17
- 239000012065 filter cake Substances 0.000 claims abstract description 14
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000002156 mixing Methods 0.000 claims abstract description 12
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 10
- 239000007787 solid Substances 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims abstract description 10
- 239000012043 crude product Substances 0.000 claims abstract description 6
- 238000000926 separation method Methods 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 45
- 239000000243 solution Substances 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- PRNMXSACOXQQRF-UHFFFAOYSA-N 3-amino-3-oxoprop-1-ene-2-sulfonic acid Chemical compound NC(=O)C(=C)S(O)(=O)=O PRNMXSACOXQQRF-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000009826 distribution Methods 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 238000009834 vaporization Methods 0.000 claims description 2
- 230000008016 vaporization Effects 0.000 claims description 2
- 238000006277 sulfonation reaction Methods 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 8
- 239000007791 liquid phase Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000011084 recovery Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- -1 printing and dyeing Substances 0.000 description 5
- 230000006837 decompression Effects 0.000 description 4
- 239000000178 monomer Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- DZSVIVLGBJKQAP-UHFFFAOYSA-N 1-(2-methyl-5-propan-2-ylcyclohex-2-en-1-yl)propan-1-one Chemical compound CCC(=O)C1CC(C(C)C)CC=C1C DZSVIVLGBJKQAP-UHFFFAOYSA-N 0.000 description 1
- BXALRZFQYDYTGH-UHFFFAOYSA-N 1-oxoprop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)C(=O)C=C BXALRZFQYDYTGH-UHFFFAOYSA-N 0.000 description 1
- GASMGDMKGYYAHY-UHFFFAOYSA-N 2-methylidenehexanamide Chemical compound CCCCC(=C)C(N)=O GASMGDMKGYYAHY-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000005373 pervaporation Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to the production method of a kind of tert-butyl acrylamide sulfonate, including: 1) form the acrylonitrile solution containing sulfonating agent；2) solution is passed through continuously in described Horizontal stirring reactor and contacts with isobutene, form pulpous state product；3) described pulpous state product is filtrated to get the filter cake containing tert-butyl acrylamide sulfonate and filtrate；4) filter cake obtaining step 3) is dried, and obtains tert-butyl acrylamide sulfonate crude product；5) the tert-butyl acrylamide sulfonate crude product using aqueous acetic acid to obtain step 4) carries out recrystallization purifying, obtains tert-butyl acrylamide sulfonate and residual waste solution that mass content is more than 99.3%；6) obtain waste residue after the filtrate in step 3) and/or the residual waste solution in step 4 being evaporated, waste residue is contacted with processing solvent mixing, then carries out separation of solid and liquid, obtain tert-butyl acrylamide sulfonate and N-tert-butyl acrylamide.
Description
Technical field
The present invention relates to the production method of a kind of organic compound, be specifically related to a kind of tert-butyl acrylamide sulfonate
Production method.
Background technology
Tert-butyl acrylamide sulfonate (molecular formula C7H13NO4S, hereinafter referred to as ATBS) it is a kind of multi-functional
Soluble anionic monomers, owing to molecular structure has carbon-carbon double bond and the sulfonic group insensitive to salt, the most easily
In polymerization, and its homopolymerization and copolymer have much special character, have broad application prospects, can be extensive
Be applied to oilfield chemistry, water treatment agent, chemical fibre, plastics, printing and dyeing, coating, surfactant, antistatic additive,
The fields such as pottery, photograph, washing assisant, ion exchange resin, gas separation membrane, electronics industry.
The technique of current most typical production ATBS, is to be that raw material exists with acrylonitrile, oleum and isobutene
Reaction preparation ATBS is carried out under the conditions of relatively mild.United States Patent (USP) US3544597 first reported this preparation
The method of amidosulfonic acid compounds, and obtained the monomer that purity is higher, but reaction condition is the harshest.
Dong chemical company of Japan (DE2904444A1, DE2904465A1) improves said method, and proposes
Obtain the technical scheme of higher purity ATBS.Method described in this patent is that the acrylonitrile of excess is doubled as reaction
Solvent, adds oleum in inert gas atmosphere under low temperature, is under agitation passed through isobutene so that it is anti-
Should, product ATBS separates out from mixed liquor, obtains muddy product, is subsequently adding acetic acid and heats up, steamed
Amount acrylonitrile, adds a certain amount of water, is warming up to more than 90 DEG C and makes it dissolve, place in cold water, make product
Crystallization, and clean with acetic acid, then by 60 DEG C of heated-air dryings, i.e. obtain high-purity monomer.Existing technique is passed through
Improve, after obtaining muddy product, filter, and then be vacuum dried, then thick product is used
Aqueous acetic acid carries out recrystallization and purifies, and obtains high purity product.
In existing ATBS production technology, the filtrate that thick product filters, after reclaiming, can produce accessory substance
Accessory substance for N-tert-butyl acrylamide.Additionally containing substantial amounts of in the waste liquid after recrystallization process filters
ATBS and tert-butyl group acryloyl sulfonic acid are main byproduct of reaction.In the prior art, two kinds of sides of main employing
Method processes, and one is to be neutralized first by alkaline matter, is then fed into biochemistry pool and carries out biochemistry, to reach
To emission request；Second method is to use the method burned to process.Both approaches does not the most produce warp
Ji benefit, and production cost can be increased.
Summary of the invention
The invention aims to provide a kind of tert-butyl acrylamide sulfonate production method, it comprises the tert-butyl group
Acrylamide sulfonic acid produces the recovery method of waste liquid.
The present inventor finds under study for action, and prior art is producing 2-acrylamide-2-methylpro panesulfonic acid
Method in a large amount of waste liquids containing accessory substance N-tert-butyl acrylamide of producing (hereinafter simply referred to as " reaction is useless
Liquid ").In the prior art waste reaction solution processing method is not the most produced economic benefit, and life can be increased
Produce cost.
The invention provides the method for comprehensive utilization of a kind of waste reaction solution, the method include solvent washing, stirring,
The steps such as filtration and solvent recovery.
The invention provides the production method of a kind of tert-butyl acrylamide sulfonate, the method comprises the following steps:
1) acrylonitrile is mixed with sulfonating agent, form the acrylonitrile solution containing sulfonating agent；
2) provide Horizontal stirring reactor, and step 1) is obtained mixed solution be passed through described horizontal stir continuously
Mix in reactor and contact with isobutene, form pulpous state product；
3) described pulpous state product continuous print from Horizontal stirring reactor flows out and through being filtrated to get containing the tert-butyl group third
The filter cake of acrylamide sulfonic acid and filtrate；
4) filter cake obtaining step 3) is dried, and obtains the tert-butyl group third that mass content is more than 96.0%
Acrylamide sulfonic acid crude product；
5) the tert-butyl acrylamide sulfonate crude product using aqueous acetic acid to obtain step 4) recrystallizes
Purify, obtain tert-butyl acrylamide sulfonate and residual waste solution that mass content is more than 99.3%；
Wherein, by the waste residue obtained after the residue mother liquid evaporation in the filtrate in step 3) and/or step 4 and place
Reason solvent mixing contact, then carries out separation of solid and liquid, and is dried by the solid of isolated thus obtains uncle
Butylacrylamide sulfonic acid, carries out distillating recovering solvent by the liquid of isolated thus obtains tert-butyl group acryloyl
Amine.
In the recovery method of invention, reaction is reclaimed waste residue source and is mainly derived from two parts, Part I waste residue
Come from the product filtrate in production upstream device, described filtrate comprises N-tert-butyl acrylamide and the tert-butyl group third
The content of acrylamide sulfonic acid is 3-15 weight %；Part II waste residue is from tert-butyl acrylamide sulfonate product weight
Residual waste solution after filtering in crystallization process, the N-tert-butyl acrylamide in described residual waste solution and tert-butyl group acryloyl
The content of amine sulfonic acid is 5-30 mass %.
Described product filtrate is that tert-butyl acrylamide sulfonate product reaction obtained is from the mixing of product
Remaining liquid substance after filtering in thing.
In a preferred embodiment of the recovery method of invention, described two parts waste liquid can in processing procedure
To process after mixing with solvent after mixing, or described two parts waste liquid is mixed into described solvent respectively again
Row reclaims.
In a preferred embodiment of the present invention, step 2) described in horizontal reactor include:
Kettle；
Chuck, described chuck is wrapped in the outside of kettle, for controlling the temperature within kettle；
Agitator, described agitator is arranged at inside kettle, for being mixed by reactant；And
Annex, described annex is arranged at kettle inside side walls.
In above-mentioned horizontal reactor, the most described kettle draw ratio is 1.5～10, and preferred draw ratio is 3～7.
In above-mentioned horizontal reactor, the axial distribution of the sidewall of the most described kettle has vent line, and being used for will
After vaporization, isobutene is passed through described kettle.
In above-mentioned horizontal reactor, the most described agitator includes:
Driving means, for providing power for agitator；
It is arranged at the shaft of axial direction in still, the axial direction of described shaft is at least fixed with one group radially
Paddle, each paddle at least two panels blade.
In above-mentioned horizontal reactor, the most described annex includes thermocouple and/or Pressure gauge.
In a preferred embodiment of the present invention, the temperature that acrylonitrile described in step 1) mixes with sulfonating agent
Degree is-15 DEG C to 10 DEG C, preferably-10-0 DEG C.
In a preferred embodiment of the present invention, by step 2) in material join in horizontal reacting still,
It is 1:1～1.3:1 that isobutene is passed through in molar rate and step 1) the ratio of the molar rate adding sulfonating agent.
In a preferred embodiment of the present invention, the temperature in described horizontal reactor is at 10～45 DEG C.
In the present invention, described process solvent selects Main Basis to be to have good dissolving to N-tert-butyl acrylamide
Performance, and insoluble ATBS.It preferably is selected from one or more in following compound: chloroform, acetone, ethyl
Tertbutyl ether and acetic acid etc..
Described mixing can be to select the modes such as stirring, so that solvent and waste liquid are fully contacted, usual mixing time exists
5min-600min。
Invention recovery method a preferred embodiment in, the method for described separation of solid and liquid be any can
The method realizing solid-liquor separation, such as filtration method, including natural filtration method, vacuum filtration process etc..
According to the present invention, the filter cake obtained after filtration, can be dried to obtain by vacuum drying method
Product, described vacuum drying condition can be normal condition, as baking temperature can be 50-130 DEG C, is dried
Pressure can be less than 30KPa, and the desciccate obtained is mainly composed of ATBS, and content is higher than 95%.
According to the present invention, the filtrate obtained after filtration, carry out distilling or after distillation operation, can be recycled,
Then the product after distillation or rectifying is further dried, it is thus achieved that the second product, is mainly composed of tertiary fourth
Base acrylamide.Selective rectification or distillation procedure, the composition of Main Basis solvent and the requirement to process.
The tert-butyl acrylamide sulfonate that the present invention provides produces the recovery method of waste liquid, is by waste liquid two kinds of masters
Want composition to separate, thus obtain two kinds of useful products, significantly improve economic benefit.
Detailed description of the invention
Below by embodiment, the method for the present invention is described further, but the scope of the present invention is not limited to
Following example.
By liquid chromatogram (LC), compare with standard specimen, so that it is determined that mainly comprise and purity, liquid chromatogram
Analysis condition is: Zorbax SAX chromatographic column, and flowing is 0.1mol/L KH mutually2PO4Solution, flow velocity is
1.0mL/min, UV-detector.
Embodiment 1
The production method of the ATBS that the present embodiment provides for the present invention is described.
(1) add the acrylonitrile 496g of aqueous 0.25 mass % in a mixer, and temperature be reduced to-5 DEG C,
It is subsequently adding 73.6g SO3Content is the oleum of 3%, after stirring, enters steady state operation.Concrete side
Method is: the acrylonitrile by aqueous 0.25% is joined above-mentioned by measuring pump with the flow velocity of 248.0g/h by flowmeter
In blender, being simultaneously introduced oleum, wherein dissociate SO3Mass content is 3%, by measuring pump with 36.8g/h
Flow velocity is added by quantifier, obtains mixed liquor.
(2) in the middle part of the blended device of mixed liquor, overfall continuously flows in horizontal reactor, and horizontal reactor has three
Individual isobutene air inlet pipeline, after being vaporized by isobutene, is added continuously to horizontal reactor with overall flow rate 11.5g/h
In, controlling reactor temperature is 37～38 DEG C.Reaction gained white slurries are by the overflow of horizontal reactor right part
Mouth enters in the flask of 1000ml bottom opening, and continuous 3 lab scales collect product slurry 590g, by centrifugation,
Obtaining white crystalline powder shape product 151.0g and filtrate after drying, in terms of oleum, liquid chromatography detects
After, product purity is 98.5%(mass), product synthesis yield is 96.6%(mass).
3) product thick to ATBS uses the aqueous acetic acid of 10% to recrystallize, and obtains high-purity ATBS, pure
Degree is 99.5%(mass) and residual waste solution.
4) in step 2) in the building-up process that obtains obtain after in filtrate and step 3), recrystallization process filters
The waste liquid mixing obtained, can obtain the waste residue containing ATBS and N-tert-butyl acrylamide through pervaporation.Will repeatedly
The ATBS mass content of the 150g ATBS mixed sludge of process collection is 85.5%, N-tert-butyl acrylamide
Mass content is 12.0%, and containing other impurity a certain amount of.Described waste residue is joined in acetone, often
It is stirred 120min under temperature, after having stirred, uses filter centrifugal to filter.Filter cake is carried out vacuum
Dry baking temperature is 100 DEG C, and drying pressure is 10KPa(gauge pressure), obtain dried filter cake 131.5g altogether,
Main component is ATBS, is 96.7%(mass by liquid-phase chromatographic analysis purity)；Filtrate decompression is distilled,
Solvent carries out condensing reuse, and the solid main component obtained after distillation is N-tert-butyl acrylamide, altogether 18.3g,
It is 97.9%(mass by liquid-phase chromatographic analysis purity).
Embodiment 2
Step 1)-3) same as in Example 1, in step 4), use chloroform is as processing solvent, by filter cake
Carrying out being vacuum dried baking temperature is 100 DEG C, and drying pressure is 10KPa(gauge pressure), obtain dried filter
Cake 130.2g altogether, main component is ATBS, is 98.3%(mass by liquid-phase chromatographic analysis purity)；Will
Filtrate decompression is distilled, and solvent carries out condensing reuse, and the solid main component obtained after distillation is tert-butyl group acryloyl
Amine, 19.4g, is 95.0%(mass by liquid-phase chromatographic analysis purity altogether).
Embodiment 3
Step 1)-3) same as in Example 1, the mixing time in step 4) is fixed as 300min, will
It is 100 DEG C that filter cake carries out being vacuum dried baking temperature, and drying pressure is 10KPa(gauge pressure), obtain dried
Filter cake altogether 130.4g, main component is ATBS, is 97.2%(mass by liquid-phase chromatographic analysis purity)；
Filtrate decompression being distilled, solvent carries out condensing reuse, and the solid main component obtained after distillation is tert-butyl group propylene
Acid amides, 19.4g, is 96.2%(mass by liquid-phase chromatographic analysis purity altogether).
Embodiment 4
Step 1)-3) same as in Example 1, mixing time is fixed as 15min by step 4), will filter
It is 100 DEG C that cake carries out being vacuum dried baking temperature, and drying pressure is 10KPa(gauge pressure), obtain dried
Filter cake 134.8g altogether, main component is ATBS, is 95.2%(mass by liquid-phase chromatographic analysis purity)；
Filtrate decompression being distilled, solvent carries out condensing reuse, and the solid main component obtained after distillation is tert-butyl group propylene
Acid amides, 14.9g, is 97.0%(mass by liquid-phase chromatographic analysis purity altogether).
Claims (7)
1. a production method for tert-butyl acrylamide sulfonate, the method comprises the following steps:
1) acrylonitrile is mixed with sulfonating agent, form the acrylonitrile solution containing sulfonating agent, the temperature wherein mixed
Degree is for-15 DEG C to 10 DEG C；
2) Horizontal stirring reactor is provided, and by step 1) obtain mixed solution and be passed through described horizontal stir continuously
Mixing in reactor and contact with isobutene, form pulpous state product, wherein, isobutene is passed through molar rate and step 1)
The ratio of the molar rate of middle addition sulfonating agent is 1:1～1.3:1, and the temperature in described horizontal reactor exists
10～45 DEG C, described horizontal reactor includes: kettle；Chuck, described chuck is wrapped in the outside of kettle, uses
In controlling the temperature within kettle；Agitator, described agitator is arranged at inside kettle, for being mixed by reactant
Close；And annex, described annex is arranged at kettle inside side walls；
3) described pulpous state product continuous print from Horizontal stirring reactor flows out and through being filtrated to get containing the tert-butyl group third
The filter cake of acrylamide sulfonic acid and filtrate；
4) to step 3) filter cake that obtains is dried, and obtains the tert-butyl group third that mass content is more than 96.0%
Acrylamide sulfonic acid crude product；
5) aqueous acetic acid is used to step 4) the tert-butyl acrylamide sulfonate crude product that obtains recrystallizes
Purify, obtain tert-butyl acrylamide sulfonate and residual waste solution that mass content is more than 99.3%；
Wherein, by step 3) in filtrate evaporation after the waste residue that obtains with process solvent and mix and contact, then enter
Row separation of solid and liquid, and the solid of isolated is dried thus obtains tert-butyl acrylamide sulfonate, will point
Carry out distillating recovering solvent from the liquid obtained thus obtain N-tert-butyl acrylamide, described process solvent selected from
One or more in lower compound: chloroform, acetone, ethyl tert-butyl ether (ETBE) and acetic acid.
Method the most according to claim 1, it is characterised in that described kettle draw ratio is 1.5～10.
Method the most according to claim 1, it is characterised in that described kettle draw ratio is 3～7.
Method the most according to claim 1, it is characterised in that the axial distribution of the sidewall of described kettle
There is vent line, for isobutene after vaporization is passed through described kettle.
Method the most according to claim 1, it is characterised in that described agitator includes:
Driving means, for providing power for agitator；
It is arranged at the shaft of axial direction in still, the axial direction of described shaft is at least fixed with one group radially
Paddle, each paddle at least two panels blade.
Method the most according to claim 1, it is characterised in that described annex includes thermocouple and/or pressure
Power table.
Method the most according to claim 1, it is characterised in that step 1) described in acrylonitrile and sulfonation
The temperature of agent mixing is-10-0 DEG C.
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| CN108003067A (en) * | 2016-10-31 | 2018-05-08 | 中国石油化工股份有限公司 | A kind of production method of tert-butyl acrylamide sulfonate |
| CN108017562A (en) * | 2016-10-31 | 2018-05-11 | 中国石油化工股份有限公司 | A kind of production method of tert-butyl acrylamide sulfonate |
| CN112679390A (en) * | 2019-10-18 | 2021-04-20 | 中国石油化工股份有限公司 | Production device and production method of tert-butyl acrylamide sulfonic acid |
| CN112047855A (en) * | 2020-09-19 | 2020-12-08 | 寿光市荣晟新材料有限公司 | N-tert-butyl acrylamide extraction method |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US4219498A (en) * | 1978-06-12 | 1980-08-26 | Nitto Chemical Industry Co., Ltd. | Process for preparing highly pure-2-acrylamido-2-methylpropanesulfonic acid |
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