CN106423219B - It is the method for catalyst production trimellitate using atlapulgite as the solid acid of carrier - Google Patents
It is the method for catalyst production trimellitate using atlapulgite as the solid acid of carrier Download PDFInfo
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- CN106423219B CN106423219B CN201610842534.8A CN201610842534A CN106423219B CN 106423219 B CN106423219 B CN 106423219B CN 201610842534 A CN201610842534 A CN 201610842534A CN 106423219 B CN106423219 B CN 106423219B
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- atlapulgite
- trimellitate
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- 125000005591 trimellitate group Chemical group 0.000 title claims abstract description 61
- 239000011973 solid acid Substances 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims abstract description 16
- 239000003054 catalyst Substances 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title description 6
- 239000002841 Lewis acid Substances 0.000 claims abstract description 15
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 230000000694 effects Effects 0.000 claims abstract description 9
- 238000005470 impregnation Methods 0.000 claims abstract description 6
- 239000012043 crude product Substances 0.000 claims description 19
- 239000000725 suspension Substances 0.000 claims description 12
- 229910000360 iron(III) sulfate Inorganic materials 0.000 claims description 11
- 239000011259 mixed solution Substances 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- 230000003068 static effect Effects 0.000 claims description 8
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 239000006228 supernatant Substances 0.000 claims description 6
- 238000010521 absorption reaction Methods 0.000 claims description 5
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 5
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 claims description 4
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004439 Isononyl alcohol Substances 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 230000002411 adverse Effects 0.000 abstract description 2
- 230000008092 positive effect Effects 0.000 abstract description 2
- 230000008569 process Effects 0.000 abstract description 2
- 238000003672 processing method Methods 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 2
- 239000010725 compressor oil Substances 0.000 description 2
- -1 pentaerythritol ester Chemical class 0.000 description 2
- 238000012805 post-processing Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
- B01J27/053—Sulfates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/16—Clays or other mineral silicates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to chemosynthesis technical fields, it is related to trimellitate, more particularly to it is a kind of using atlapulgite as the solid acid of carrier be catalyst produce trimellitate method, it is activity component impregnation atlapulgite the invention firstly uses Lewis acid, the solid acid that atlapulgite is carrier is prepared, then it is that catalyst is added in the reaction of trimellitate using atlapulgite as the solid acid of carrier, then carries out separation, the purification of product, finally obtain trimellitate.Compared with prior art, the advantages and positive effects of the present invention are, the present invention is by providing the solid acid that a kind of atlapulgite is carrier, it is set to substitute the concentrated sulfuric acid as the catalyst in trimellitate synthesis process, the adverse consequences that the concentrated sulfuric acid is generated as catalyst is avoided, meanwhile, the processing method by improveing traditional trimellitate, the yield of the trimellitate made is high, high-quality, and large-scale promotion is suitble to use.
Description
Technical field
The invention belongs to chemosynthesis technical fields, are related to trimellitate, more particularly to one kind is to carry with atlapulgite
The solid acid of body is the method that catalyst produces trimellitate.
Background technique
Trimellitate has excellent high temperature performance, and high temperature evaporation is small, coking amount is low, can have with various additives
There is good compatibility, is synthesizing high temperature chain oils, synthesis high viscosity air compressor oil and the ideal base of Hmp grease
Plinth oil.Trimellitate is for that compared with pentaerythritol ester, can reduce the use of tackifier when preparing high viscosity high-temperature chain oil
Amount, to improve the high-temperature behavior of chain oils；When for preparing synthesis high viscosity air compressor oil, thickening can not be used
Agent improves viscosity, therefore has good market prospects.
Using the concentrated sulfuric acid as catalyst in the synthetic method of traditional trimellitate, with trimellitic anhydride and unitary C10-13
Fatty alcohol is that raw material carries out esterification, and then obtains trimellitate, although such reaction can obtain trimellitate,
It will lead to the side reactions such as sulfonation, carbonization polymerization during the reaction, finally make that product yield is low, color is deep, post-processing is multiple
It is miscellaneous, corrosion equipment, pollution environment.
Summary of the invention
Technical problem present in synthetic method of the present invention for above-mentioned trimellitate, provides one kind and is able to solve
The catalyst of above-mentioned technical problem, while under the action of this catalyst, obtain product yield height, high-quality, post-processing letter
Just using atlapulgite as the solid acid of carrier be catalyst produce trimellitate method.
In order to achieve the above object, the technical solution adopted by the present invention is that the present invention provides one kind with atlapulgite as load
The solid acid of body is the method that catalyst produces trimellitate, including following effective procedure:
A, montmorillonite is added in the aqueous sulfuric acid that concentration is 5%~10% according to the ratio of 1:10~20, is impregnated
12h separates, discards supernatant liquor, obtains atlapulgite；
B, Lewis acid is added into obtained atlapulgite, using Lewis acid as activity component impregnation atlapulgite, obtains
PH value is 3~6 mixed solutions；
C, mixed solution is heated to 50 DEG C, after being sufficiently stirred, obtains the atlapulgite suspension of load Lewis acid；
D, by after the atlapulgite suspension static layering of obtained load Lewis acid, the suspension on upper layer is filtered out, is obtained
To the atlapulgite mixed liquor of load Lewis acid；
E, the atlapulgite mixed liquor for obtaining load Lewis acid is dry at 90~120 DEG C, granularity can be obtained and exist
The atlapulgite of 100~600 mesh is the solid acid of carrier, for use, wherein the Lewis acid is Fe2(SO4)3；
F, by trimellitic anhydride and unitary saturated alcohols according to 1% that the ratio and dosage of 1:3~5 are total inventory~
2% atlapulgite is that the solid acid of carrier is added in reaction kettle, 150~180 DEG C of reactor temperature of control, pressure≤
1KPa reacts 5~10h, obtains the trimellitate crude product containing the solid acid that atlapulgite is carrier；
G, the trimellitate crude product containing the solid acid that atlapulgite is carrier was carried out using the strainer of≤500 mesh
Filter isolates the solid acid that atlapulgite is carrier, obtains trimellitate crude product；
H, trimellitate crude product is rejoined in reaction kettle, control reactor temperature to 130 DEG C~180 DEG C,
Pressure≤1KPa is controlled, after being evaporated under reduced pressure 0.5h~1h, obtains trimellitate；
I, absorption, filtering of the trimellitate for obtaining h step by active carbon, obtains trimellitate finished product,
In, unitary saturated alcohols are at least one of the isooctanol containing C8~C10, isononyl alcohol, isodecanol substance in the f step.
Compared with prior art, the advantages and positive effects of the present invention are,
1, the present invention makes it substitute concentrated sulfuric acid as trimellitic acid by providing the solid acid that a kind of atlapulgite is carrier
Catalyst during Lipase absobed avoids the adverse consequences that the concentrated sulfuric acid is generated as catalyst, meanwhile, it is traditional by improveing
The processing method of trimellitate, the yield of the trimellitate made is high, high-quality, and large-scale promotion is suitble to use.
Specific embodiment
To better understand the objects, features and advantages of the present invention, below with reference to embodiment to this hair
It is bright to be described further.It should be noted that in the absence of conflict, the feature in embodiments herein and embodiment can
To be combined with each other.
In the following description, numerous specific details are set forth in order to facilitate a full understanding of the present invention, still, the present invention may be used also
To be implemented using other modes described herein are different from, therefore, the present invention is not limited to the specific of specification is described below
The limitation of embodiment.
Embodiment 1, the present embodiment provides a kind of preparation methods for the solid acid that atlapulgite is carrier
The aqueous sulfuric acid that montmorillonite and concentration are 5% is mixed according to the ratio of 1:10 first, after static 12h,
It separates, discard supernatant liquor, obtain atlapulgite, Fe then is added into obtained atlapulgite2(SO4)3, with Fe2(SO4)3
For activity component impregnation atlapulgite, obtaining pH value is 3.8 mixed solutions, and mixed solution is then heated to 50 DEG C, is sufficiently stirred
After mixing, load Fe is obtained2(SO4)3Atlapulgite suspension；Then the load Fe that will be obtained again2(SO4)3Atlapulgite it is outstanding
After supernatant liquid static layering, it is filled into the suspension on upper layer, obtains load Fe2(SO4)3Atlapulgite mixed liquor；It will finally obtain
Load Fe2(SO4)3Atlapulgite mixed liquor it is dry at 90 DEG C, granularity can be obtained in the atlapulgite of 100 mesh to carry
The solid acid of body.
Embodiment 2, the present embodiment provides a kind of preparation methods for the solid acid that atlapulgite is carrier
The aqueous sulfuric acid that montmorillonite and concentration are 10% is mixed according to the ratio of 1:20 first, after static 12h,
It separates, discard supernatant liquor, obtain atlapulgite, Fe then is added into obtained atlapulgite2(SO4)3, with Fe2(SO4)3
For activity component impregnation atlapulgite, obtaining pH value is 6 mixed solutions, and mixed solution is then heated to 50 DEG C, is sufficiently stirred
Afterwards, load Fe is obtained2(SO4)3Atlapulgite suspension；Then the load Fe that will be obtained again2(SO4)3Atlapulgite suspend
After liquid static layering, it is filled into the suspension on upper layer, obtains load Fe2(SO4)3Atlapulgite mixed liquor；It will finally be born
Carry Fe2(SO4)3Atlapulgite mixed liquor it is dry at 120 DEG C, it is carrier that granularity, which can be obtained, in the atlapulgite of 500 mesh
Solid acid.
Embodiment 3, the present embodiment provides a kind of preparation methods for the solid acid that atlapulgite is carrier
The aqueous sulfuric acid that montmorillonite and concentration are 8% is mixed according to the ratio of 1:15 first, after static 12h,
It separates, discard supernatant liquor, obtain atlapulgite, Fe then is added into obtained atlapulgite2(SO4)3, with Fe2(SO4)3
For activity component impregnation atlapulgite, obtaining pH value is 4 mixed solutions, and mixed solution is then heated to 50 DEG C, is sufficiently stirred
Afterwards, load Fe is obtained2(SO4)3Atlapulgite suspension；Then the load Fe that will be obtained again2(SO4)3Atlapulgite suspend
After liquid static layering, it is filled into the suspension on upper layer, obtains load Fe2(SO4)3Atlapulgite mixed liquor；It will finally be born
Carry Fe2(SO4)3Atlapulgite mixed liquor it is dry at 110 DEG C, it is carrier that granularity, which can be obtained, in the atlapulgite of 300 mesh
Solid acid.
Embodiment 4, the present embodiment provides using implement 1 using it is obtained above by the solid acid of carrier of atlapulgite be catalysis
The method of agent production trimellitate
It is first the 1% of total inventory by trimellitic anhydride and the ratio and dosage according to 1:3 containing C8 isooctanol
Atlapulgite is that the solid acid of carrier is added in reaction kettle, controls 150 DEG C of reactor temperature, and pressure≤1KPa reacts 5h,
Obtain the trimellitate crude product containing the solid acid that atlapulgite is carrier；Then, using the strainer of≤500 mesh to containing live
Property carclazyte be that the trimellitate crude product of solid acid of carrier is filtered, isolate the solid acid that atlapulgite is carrier, obtain
To trimellitate crude product；Then trimellitate crude product is rejoined in reaction kettle, control reactor temperature to 130
DEG C, pressure≤1KPa is controlled, after being evaporated under reduced pressure 1h, obtains trimellitate；Then, by obtained trimellitate by activity
Absorption, the filtering of charcoal, obtain trimellitate finished product.
Embodiment 5, the present embodiment provides using implement 2 using it is obtained above by the solid acid of carrier of atlapulgite be catalysis
The method of agent production trimellitate
It is first the 2% of total inventory by trimellitic anhydride and the ratio and dosage according to 1:5 containing C10 isononyl alcohol
Atlapulgite is that the solid acid of carrier is added in reaction kettle, controls 180 DEG C of reactor temperature, and pressure≤1KPa reacts 7h,
Obtain the trimellitate crude product containing the solid acid that atlapulgite is carrier；Then, using the strainer of≤500 mesh to containing live
Property carclazyte be that the trimellitate crude product of solid acid of carrier is filtered, isolate the solid acid that atlapulgite is carrier, obtain
To trimellitate crude product；Then trimellitate crude product is rejoined in reaction kettle, control reactor temperature to 180
DEG C, pressure≤1KPa is controlled, after being evaporated under reduced pressure 1h, obtains trimellitate；Then, by obtained trimellitate by activity
Absorption, the filtering of charcoal, obtain trimellitate finished product.
Embodiment 6, the present embodiment provides using implement 3 using it is obtained above by the solid acid of carrier of atlapulgite be catalysis
The method of agent production trimellitate
First by the mixture of trimellitic anhydride and the isooctanol containing C8~C10, isononyl alcohol and isodecanol according to
The ratio and dosage of 1:5 is that 2% atlapulgite of total inventory is that the solid acid of carrier is added in reaction kettle, control reaction
180 DEG C of temperature in the kettle, pressure≤1KPa reacts 7h, and it is thick to obtain the trimellitate containing the solid acid that atlapulgite is carrier
Product；Then, the trimellitate crude product containing the solid acid that atlapulgite is carrier was carried out using the strainer of≤500 mesh
Filter isolates the solid acid that atlapulgite is carrier, obtains trimellitate crude product；Then trimellitate crude product is added again
Enter into reaction kettle, controls reactor temperature to 180 DEG C, control pressure≤1KPa, after being evaporated under reduced pressure 1h, obtain trimellitic acid
Ester；Then, the absorption by obtained trimellitate by active carbon, filtering, obtain trimellitate finished product.
At this it should be noted that the amount for the carbon atom that unitary saturated fatty alcohol contains is that production obtains one of high-quality
Essential condition can generate under the cooperation of pressure and temperature under the catalytic action for the solid acid that atlapulgite is carrier
Better effect, meanwhile, the proportion of trimellitic anhydride and unitary saturated fatty alcohol is also another prerequisite, these because
Under the cooperation all linked with one another of element, keep final trimellitate finished product yield high, high-quality.
Product quality detection
By above table it will be seen that trimellitate produced reaches standard, and this through the invention
Method provided by inventing is easy to process, easy to operate, and yield is high, high-quality, and large-scale promotion is suitble to use.
The above described is only a preferred embodiment of the present invention, being not that the invention has other forms of limitations, appoint
What those skilled in the art changed or be modified as possibly also with the technology contents of the disclosure above equivalent variations etc.
It imitates embodiment and is applied to other fields, but without departing from the technical solutions of the present invention, according to the technical essence of the invention
Any simple modification, equivalent variations and remodeling to the above embodiments, still fall within the protection scope of technical solution of the present invention.
Claims (1)
1. it is a kind of using atlapulgite as the solid acid of carrier be catalyst produce trimellitate method, which is characterized in that packet
Include following effective procedure:
A, montmorillonite is added in the aqueous sulfuric acid that concentration is 5%~10% according to the ratio of 1:10~20, impregnates 12h, point
From, discard supernatant liquor, obtain atlapulgite；
B, Lewis acid is added into obtained atlapulgite, using Lewis acid as activity component impregnation atlapulgite, obtains pH value
For 3~6 mixed solutions；
C, mixed solution is heated to 50 DEG C, after being sufficiently stirred, obtains the atlapulgite suspension of load Lewis acid；
D, by after the atlapulgite suspension static layering of obtained load Lewis acid, the suspension on upper layer is filtered out, is born
Carry the atlapulgite mixed liquor of Lewis acid；
E, the atlapulgite mixed liquor for obtaining load Lewis acid is dry at 90~120 DEG C, granularity can be obtained 100
The atlapulgite of~600 mesh is the solid acid of carrier, for use, wherein the Lewis acid is Fe2(SO4)3；
F, by trimellitic anhydride and unitary saturated alcohols according to 1%~2% that the ratio and dosage of 1:3~5 are total inventory
Atlapulgite is that the solid acid of carrier is added in reaction kettle, 150~180 DEG C of reactor temperature of control, pressure≤1KPa, instead
5~10h is answered, the trimellitate crude product containing the solid acid that atlapulgite is carrier is obtained；
G, the trimellitate crude product containing the solid acid that atlapulgite is carrier is filtered using the strainer of≤500 mesh,
The solid acid that atlapulgite is carrier is isolated, trimellitate crude product is obtained；
H, trimellitate crude product is rejoined in reaction kettle, controls reactor temperature to 130 DEG C~180 DEG C, controls
Pressure≤1KPa obtains trimellitate after being evaporated under reduced pressure 0.5h~1h；
I, absorption, filtering of the trimellitate for obtaining h step by active carbon, obtains trimellitate finished product, wherein institute
Stating unitary saturated alcohols in f step is at least one of the isooctanol containing C8~C10, isononyl alcohol, isodecanol substance.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102924280A (en) * | 2012-10-25 | 2013-02-13 | 浙江皇马科技股份有限公司 | Preparation method of trimellitate |
| CN102924279A (en) * | 2012-10-16 | 2013-02-13 | 江苏正丹化学工业股份有限公司 | Catalytic synthesis method of tri-octyl tri-meta-benzoate |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102924279A (en) * | 2012-10-16 | 2013-02-13 | 江苏正丹化学工业股份有限公司 | Catalytic synthesis method of tri-octyl tri-meta-benzoate |
| CN102924280A (en) * | 2012-10-25 | 2013-02-13 | 浙江皇马科技股份有限公司 | Preparation method of trimellitate |
Non-Patent Citations (1)
| Title |
|---|
| "蒙脱土负载型催化剂的制备及性能研究";李海花;《中国优秀博硕士论文全文数据库（硕士） 工程科技I辑》;20041215(第4期);第9页第2.3.2.1节、表3-1-1 |
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