CN106554246A - Polymerization inhibitors for styrene rectification - Google Patents
Polymerization inhibitors for styrene rectification Download PDFInfo
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- CN106554246A CN106554246A CN201510639089.0A CN201510639089A CN106554246A CN 106554246 A CN106554246 A CN 106554246A CN 201510639089 A CN201510639089 A CN 201510639089A CN 106554246 A CN106554246 A CN 106554246A
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- styrene
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- polymerization inhibitors
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title claims abstract description 81
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 73
- 239000003112 inhibitor Substances 0.000 title claims abstract description 57
- 150000001555 benzenes Chemical class 0.000 claims abstract description 6
- 239000006227 byproduct Substances 0.000 claims abstract description 6
- 238000013329 compounding Methods 0.000 claims abstract description 5
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical group OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 4
- 239000012467 final product Substances 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 abstract description 14
- 230000005764 inhibitory process Effects 0.000 abstract description 14
- 239000000463 material Substances 0.000 abstract description 10
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000002243 precursor Substances 0.000 abstract description 5
- 229920000642 polymer Polymers 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 10
- 238000009835 boiling Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- -1 hydroxylamine compound Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 1
- HIBWGGKDGCBPTA-UHFFFAOYSA-N C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 HIBWGGKDGCBPTA-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- SYWDWCWQXBUCOP-UHFFFAOYSA-N benzene;ethene Chemical group C=C.C1=CC=CC=C1 SYWDWCWQXBUCOP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
Abstract
The present invention relates to a kind of polymerization inhibitors for styrene rectification, belongs to petrochemical industry polymerization inhibitor technical field.Polymerization inhibitors for styrene rectification of the present invention, is formed by tri- kinds of component compoundings of A, B and C, and component A is 4- hydroxyls-TEMPO, and B component is triethylene-glycol, and component C is the by-product benzene class during phenyl ethylene rectification；By percentage to the quality, each component content is as follows：A 4-50%, B 6-40%, C 10-90%.Low cost of the present invention, polymerization inhibition effect are good, addition is low, the fouling precursor existed in not only preventing the generation of styrene oligomer, and peace and quiet dispersed material, effectively prevents oligomer pre-polymerization, solution is made to keep homogeneous state for a long time, it is ensured that production of styrene system safety and steady runs.
Description
Technical field
The present invention relates to a kind of polymerization inhibitors for styrene rectification, belongs to petrochemical industry polymerization inhibitor technical field.
Background technology
Styrene (styrene) is a kind of basic material of petrochemical industry, can autohemagglutination generate polystyrene (PS) resin, be also easy to
Other double bond containing unsaturated compound copolymerization.
As cinnamic exocyclic double bond is very active, in distillation process, radical polymerization is produced by thermal initiation and forms high poly-
Thing, not only consumes styrene monomer, affects product quality, and seriously threatens the carrying out of continuous flow procedure.To reduce benzene
Ethylene autohemagglutination, except adopting negative-pressure operation to reduce in addition to rectification temperature, is usually added into electrophilic material as polymerization inhibitor.Polymerization inhibitor is
The material of activated monomer polymerization is prevented, generally by chain tra nsfer (dismutation reaction) or chain termination coupling reaction.
Since styrene monomer industrialized production, people constantly carry out the exploitation of polymerization inhibitors for styrene rectification, and some low toxicities are efficient
Compound polymerization inhibitor on Styrene Process use.So far, for the advantage with reference to retarder and true polymerization inhibitor, overcome
Shortcoming during exclusive use, Chinese scholars are true polymerization inhibitor and retarder compounding use.
United States Patent (USP) US 6409887B describes a kind of resistance by aromatic amine, organic acid and stable NO free radical compounding
Poly- agent, can be used as the high-efficiency polymerization inhibitor of olefin(e) compound.
CN201010211593 provides a kind of double solventss of extracting, rectifying and separating phenylethylene, including the N of 50-95wt%, N-
The monoalky lether of the glycol of the glycol or C2-C6 of the C2-C6 of dimethyl acetylamide and 5-50wt%.Main solvent N, N- dimethyl
The low boiling point of acetamide, with certain inhibition, is effectively reduced styrene polymerization, the higher hydrotropy of boiling point in still-process
Agent and main solvent complex effect, it is possible to increase the relatively cinnamic relative volatility of o-Dimethylbenzene, reducing energy consumption.
CN1392127A discloses a kind of styrene polymerization inhibitor and purposes, and the polymerization inhibitor selects NO free radical and phenolic compound
To compound component, constitute according to a certain ratio, preferable consumption is 400～800mg/kg, under the conditions of heating 2h, polymer contains
Amount 0.17%, the compound polymerization inhibitor of formation is significantly improved compared with the polymerization inhibition effect of the one-component of same concentration, and toxicity compares phenol generalization
Compound is low, higher using temperature, it is adaptable to cinnamic distillation process.
CN201010182390 provides a kind of cinnamic efficient and environment-friendly type polymerization inhibitor and its using method.The compound polymerization inhibitor by
NO free radical class compound, hydroxylamine compound, nitro-phenolic compound and phosphite ester compound are constituted, each group sub-prime
Amount is than being 6-12:5:5-21:3-12, the mass concentration of the compound polymerization inhibitor is 0.0001%-0.2% (relative to monomer mass).
The content of the invention
It is an object of the invention to provide a kind of polymerization inhibitors for styrene rectification, its low cost, polymerization inhibition effect are good, addition is low, not only
The fouling precursor existed in preventing the generation of styrene oligomer, and peace and quiet dispersed material, effectively prevents oligomer
Pre-polymerization, makes solution keep homogeneous state for a long time, it is ensured that production of styrene system safety and steady runs.
Polymerization inhibitors for styrene rectification of the present invention, is formed by tri- kinds of component compoundings of A, B and C, and component A is 4- hydroxyls
- TEMPO, B component are triethylene-glycol, and component C is the by-product during phenyl ethylene rectification
Thing benzene class；
By percentage to the quality, each component content is as follows：
A 4-50%,
B 6-40%,
C 10-90%.
Preferably, by percentage to the quality, each component content is as follows：
A 20-30%,
B 20-30%,
C 40-60%.
The by-product benzene class is one or more in ethylbenzene, benzene or toluene.
Addition of the polymerization inhibitors for styrene rectification in styrene rectification system for styrene quality 0.02%～0.2%, it is excellent
Elect 0.03%～0.1% as.
Component A and B component are added separately in component C, at normal temperatures stirring and dissolving, obtain final product polymerization inhibitors for styrene rectification.
The component A that the present invention is selected is 1- hydroxyls-TEMPO, is a kind of polymerization inhibitor, i.e.,
True polymerization inhibitor, inhibits efficiency high in induction period, can terminate the growth of living radical chain, and polymerization inhibition effect is more preferable.
The B component that the present invention is selected is triethylene-glycol, and the generation of oligomer can be prevented with component A collaboration, retarder is played
Effect, it is and lower than nitropheneol retarder toxicity, reduce the harm to environment and human body.B component is also assisted with component A
Same effect, with absorption and scattered effect, the fouling precursor existed in peace and quiet dispersed material (includes by material from upper
The fine polymer formed in trip carrying system, styrene dimer, trimer and mechanical admixture etc.), can be in fouling precursor table
Face forms adsorbed film, is stably dispersed in material, and prevention forms high polymer by oligomer and increases its deposition velocity so as to no
Easily high molecular weight polymers are formed in equipment surface, to reach inhibition purpose, so as to improve the inhibition efficiency of polymerization inhibitor, make resistance
The polymerization inhibition effect of poly- agent is more stable.
The component C that the present invention is selected is the by-product benzene class during phenyl ethylene rectification, and the addition of component C not only can be more preferable
Dissolved constituent A and B, and reduce production cost.It is without other novel solvent components are increased in distillation system, more excellent to show this
The dissolution conditions of polymerization inhibitor are without so harsh.
The invention has the advantages that：
(1) present invention is ingenious can effectively prevent the generation of styrene oligomer the characteristics of make use of two kinds of components of A, B each,
And can exist in peace and quiet dispersed material fouling precursor (include by material formed from the carrying system of upstream it is tiny poly-
Compound, styrene dimer, trimer and mechanical admixture) so as to be difficult high molecular weight polymers to be formed in equipment surface, effectively hinder
Only oligomer pre-polymerization, makes solution keep homogeneous state for a long time, it is ensured that production of styrene system safety and steady runs；
(2) retarder is played a part of in the addition of component B, it is to avoid using highly toxic substances such as phenols retarders, reduce to ring
Border and the harm of human body；
(3) addition of component C not only can more preferable dissolved constituent A and B, and reduce production cost.In distillation system
Without other novel solvent components are increased, the more excellent dissolution conditions for showing this polymerization inhibitor are without so harsh.
(4) low cost of the present invention, polymerization inhibition effect are good, and addition is low, are worth with higher industrial economy.
Specific embodiment
With reference to embodiment, the present invention is further illustrated, but which is not intended to limit the enforcement of the present invention.
It is raw materials used to be commercially available prod.
Component A and B component are added separately in component C, at normal temperatures stirring and dissolving, obtain final product polymerization inhibitors for styrene rectification.
Embodiment 1-8
A certain amount of styrene and polymerization inhibitors for styrene rectification are weighed, is added in three mouthfuls or four-hole boiling flask, use nitrogen displacement system
In air 5 minutes, to reduce the oxygen content in flask, thermometer, mechanically or magnetically reflux condenser, power stirring, at 120 DEG C
Under the conditions of heat 2h, sample analysis polystyrene content.
With the growing amount of gravimetric detemination polymer, using characteristic of the polymer insoluble in methanol, enough doing is added in the sample
Dry methanol, makes polymer precipitate completely, then filters, is dried, weighs, constant weight, can obtain generating the quality of polymer.
As shown in table 1, in table, the consumption of different ratio polymerization inhibitor is identical, under the conditions of 120 DEG C heat 2h, samples for experimental result
Analysis styrene polymer content.
1 different ratio polymerization inhibitor polymerization inhibition effect of table
Embodiment 9-15
Described polymerization inhibitors for styrene rectification is prepared according to 8 proportioning of embodiment, different shadows of the polymerization inhibitor consumption to polymerization inhibition effect are investigated
Ring, the results are shown in Table 2.
2 polymerization inhibitor consumption of table is affected on polymerization inhibition effect
| Embodiment | Polymerization inhibitor consumption/% | Polymer content/% |
| 9 | 0.01 | 2.94 |
| 10 | 0.04 | 1.85 |
| 11 | 0.06 | 1.03 |
| 12 | 0.08 | 0.91 |
| 13 | 0.12 | 0.84 |
| 14 | 0.18 | 0.65 |
| 15 | 0.20 | 0.43 |
From table 2, with the increase of polymerization inhibitor consumption, polymerization inhibition effect is significantly improved.In practical application, can use from polymerization inhibitor
Amount and economic benefit consider, the present invention preferably polymerization inhibitor consumption 0.03%～0.1%.
Under polymerization inhibitor consumption same case, by according to the polymerization inhibitor and existing polymerization inhibitor of 8 proportioning of embodiment to polymer content
Impact is evaluated, and using cinnamic quality as 100 parts of benchmarks, adds component A to be 4- in one of four-hole boiling flask
Hydroxyl-TEMPO, 0.015 part of consumption；B component is triethylene-glycol, 0.015 part of consumption；
C component ethylbenzene, 0.02 part of consumption；0.015 part of DNBP, 0.015 part of 628D, ethylbenzene 0.02 are added in another four-hole boiling flask
Part, add a condenser in the top of each four-hole boiling flask, with the air 5～10 minutes in nitrogen displacement system, to reduce flask
In oxygen content, then system sealing, by four-hole boiling flask be placed in thermostatic heater heat, the constant temperature 2 under the conditions of 120 DEG C
Hour, sample analysis polystyrene content the results are shown in Table 3.
3 different impacts of the polymerization inhibitor to polymer content of table
| Polymerization inhibitor | Polymer content/% | Oligomer/% |
| Existing polymerization inhibitor | 0.45 | 0.21 |
| Polymerization inhibitor of the present invention | 0.38 | 0.15 |
As can be seen here, with after polymerization inhibitor of the present invention, polymer and oligomer are all decreased obviously, and reach effectively prevention
Oligomer pre-polymerization, the purpose of inhibition efficiency high.
Claims (6)
1. a kind of polymerization inhibitors for styrene rectification, it is characterised in that：Formed by tri- kinds of component compoundings of A, B and C, component A is
4- hydroxyls-TEMPO, B component are triethylene-glycol, during component C is phenyl ethylene rectification
By-product benzene class；
By percentage to the quality, each component content is as follows：
A 4-50%,
B 6-40%,
C 10-90%.
2. polymerization inhibitors for styrene rectification according to claim 1, it is characterised in that：By percentage to the quality, each component contains
Amount is as follows：
A 20-30%,
B 20-30%,
C 40-60%.
3. polymerization inhibitors for styrene rectification according to claim 1, it is characterised in that：By-product benzene class is ethylbenzene, benzene or first
One or more in benzene.
4. polymerization inhibitors for styrene rectification according to claim 1, it is characterised in that：The polymerization inhibitors for styrene rectification is in benzene
Addition in ethylene distillation system for styrene quality 0.02%～0.2%.
5. polymerization inhibitors for styrene rectification according to claim 4, it is characterised in that：The polymerization inhibitors for styrene rectification is in benzene
Addition in ethylene distillation system for styrene quality 0.03%～0.1%.
6. polymerization inhibitors for styrene rectification according to claim 1, it is characterised in that：Component A and B component are added respectively
Enter in component C, at normal temperatures stirring and dissolving, obtain final product polymerization inhibitors for styrene rectification.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510639089.0A CN106554246A (en) | 2015-09-30 | 2015-09-30 | Polymerization inhibitors for styrene rectification |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510639089.0A CN106554246A (en) | 2015-09-30 | 2015-09-30 | Polymerization inhibitors for styrene rectification |
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| CN201510639089.0A Pending CN106554246A (en) | 2015-09-30 | 2015-09-30 | Polymerization inhibitors for styrene rectification |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107473923A (en) * | 2016-06-07 | 2017-12-15 | 中国石油化工股份有限公司 | Polymerization inhibitor and its preparation technology for phenyl ethylene rectification |
| CN115838322A (en) * | 2022-12-29 | 2023-03-24 | 杭州唯铂莱生物科技有限公司 | Polymerization inhibiting composition for olefin compound and polymerization inhibiting method |
| CN116715564A (en) * | 2023-04-24 | 2023-09-08 | 江苏太湖新材料控股有限公司 | Styrene green polymerization inhibitor and preparation method thereof |
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| JPH11171906A (en) * | 1997-12-10 | 1999-06-29 | Hakuto Co Ltd | Polymerization inhibitor composition |
| CN101857519A (en) * | 2010-06-08 | 2010-10-13 | 浙江大学 | Polymerization Inhibitors for Vinyl Aromatic Compounds |
| CN102295499A (en) * | 2010-06-25 | 2011-12-28 | 中国石油化工股份有限公司 | Polymerization inhibitor for inhibiting polymerization of vinyl compound |
| CN102295500A (en) * | 2010-06-25 | 2011-12-28 | 中国石油化工股份有限公司 | Method for inhibiting polymerization of vinyl compounds |
-
2015
- 2015-09-30 CN CN201510639089.0A patent/CN106554246A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11171906A (en) * | 1997-12-10 | 1999-06-29 | Hakuto Co Ltd | Polymerization inhibitor composition |
| CN101857519A (en) * | 2010-06-08 | 2010-10-13 | 浙江大学 | Polymerization Inhibitors for Vinyl Aromatic Compounds |
| CN102295499A (en) * | 2010-06-25 | 2011-12-28 | 中国石油化工股份有限公司 | Polymerization inhibitor for inhibiting polymerization of vinyl compound |
| CN102295500A (en) * | 2010-06-25 | 2011-12-28 | 中国石油化工股份有限公司 | Method for inhibiting polymerization of vinyl compounds |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107473923A (en) * | 2016-06-07 | 2017-12-15 | 中国石油化工股份有限公司 | Polymerization inhibitor and its preparation technology for phenyl ethylene rectification |
| CN115838322A (en) * | 2022-12-29 | 2023-03-24 | 杭州唯铂莱生物科技有限公司 | Polymerization inhibiting composition for olefin compound and polymerization inhibiting method |
| CN115838322B (en) * | 2022-12-29 | 2024-03-29 | 杭州唯铂莱生物科技有限公司 | Polymerization inhibiting composition for olefin compounds and polymerization inhibiting method |
| CN116715564A (en) * | 2023-04-24 | 2023-09-08 | 江苏太湖新材料控股有限公司 | Styrene green polymerization inhibitor and preparation method thereof |
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Application publication date: 20170405 |