CN109797398B - Application of diaryl iodonium salt compound as metal corrosion inhibitor - Google Patents
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- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
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- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
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Abstract
The invention discloses an application of diaryl iodonium salt compounds as a metal corrosion inhibitor, wherein the structure of the diaryl iodonium salt compounds is as follows:
wherein R is1Selected from hydrogen, C1-5 alkyl, C1-5 alkoxy, nitro, halogen, fluorine substituted C1-5 alkyl, and fluorine substituted C1-5 alkoxy. The diaryl iodonium salt compound prepared by the invention can be used as a novel metal corrosion inhibitor, and has the advantages of safety, environmental protection, high efficiency and the like when being applied to the field of metal corrosion inhibition.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to an application of diaryl iodonium salt compounds as metal corrosion inhibitors.
Background
As early as 1845, people applied corrosion inhibitors to the acid leaching process of iron plate rust removal to achieve the purpose of delaying corrosion of acid liquor to the iron plate, most of the current corrosion inhibitors are plant-type corrosion inhibitors, for example, the first corrosion inhibitor patent is a mixture of syrup and vegetable oil. Until the beginning of the 20 th century, researchers found that coal tar can be used as an acidic medium corrosion inhibitor, and organic substances such as anthraquinone, pyridine, quinoline, thiourea and the like were separated from the coal tar, so that the organic corrosion inhibitor has entered the era of rapid development. Inorganic salts such as chromates, nitrates, etc. have also been found to be useful as corrosion inhibitors for steel in water. However, the corrosion inhibitors have some problems more or less, for example, the main source of the organic corrosion inhibitor is coal tar, coal resources are exhausted day by day and pollute the environment, and the concept of green chemistry is not met; the use of inorganic salts such as chromate has safety risks and certain harm to the environment. Therefore, after the 21 st century, researchers mainly focused on the green corrosion inhibitors, wherein polyaspartic acid and polyepoxysuccinic acid, which are natural products, have become the green corrosion inhibitors with phosphorus-free and biodegradable properties that are internationally acknowledged at present. Meanwhile, in the aspect of inorganic corrosion inhibitors, inorganic compounds such as tungstate, molybdate and the like which have no pollution to the ecological environment are environment-friendly corrosion inhibitors which are widely applied at present.
The diaryl iodonium salt has simple synthesis and does not produce by-products harmful to the environment. The main structure of the corrosion inhibitor is that one end of the corrosion inhibitor is provided with positive charges, and the other end of the corrosion inhibitor is provided with a hydrophobic chain, so that the corrosion inhibitor can be applied to the field of metal corrosion inhibition. One end with positive charge and electrons on the metal surface are adsorbed on the metal surface by virtue of electrostatic action, and the hydrophobic end forms a hydrophobic film on the metal surface to isolate moisture, so that the corrosion of the metal is delayed. The diaryl iodonium salt not only delays corrosion when contacting with metal, but also protects the metal surface for a long time after forming a protective film. The diaryl iodonium salt has obvious advantage for the corrosion inhibition effect of the steel sheet in the water solution compared with the commonly used green corrosion inhibitors of sodium tungstate, polyaspartic acid and sodium phytate.
In conclusion, the application of the diaryl iodonium salt in the field of metal corrosion inhibition has the advantages of safety, environmental protection, high efficiency and the like, and the application research of the diaryl iodonium salt as the corrosion inhibitor has no forecase.
Disclosure of Invention
The first purpose of the invention is to provide the application of diaryl iodonium salt compounds as metal corrosion inhibitors.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
the invention provides an application of diaryl iodonium salt compound as a metal corrosion inhibitor.
The diaryl iodide salt compound has the following structure:
wherein R is1Selected from hydrogen, C1-5 alkyl, C1-5 alkoxy, nitro, halogen, fluorine substituted C1-5 alkyl, and fluorine substituted C1-5 alkoxy.
Preferably, R1Selected from hydrogen, methyl, ethyl, methoxy, ethoxy, nitro, fluorine, chlorine, bromine, iodine, trifluoromethyl and trifluoromethoxy.
More preferably, the diaryl iodonium salt compound is selected from one of the following structures:
the preparation method of the diaryl iodonium salt compound comprises the following steps:
dissolving a substituted benzene compound 2 in concentrated sulfuric acid, heating to 50-60 ℃, adding sodium periodate in batches, adding the sodium periodate in 1-2 hours, continuing to react for 1-10 hours at the temperature of 50-60 ℃, cooling to room temperature after complete reaction, then pouring the reaction liquid into an ice water mixture, carrying out reduced pressure filtration to remove filter residues, extracting the filtrate for four times by using ethyl acetate, removing an organic phase, adding a potassium bromide aqueous solution into the water phase, violently stirring for 0.1-5 hours, precipitating solids, carrying out reduced pressure filtration, washing with water until the filtrate is neutral, and drying the obtained solids to obtain the diaryl iodide compound I; the molar ratio of the substituted benzene compound 2 to the sodium periodate to the potassium bromide is (4-8) to (3-6).
The substituted benzene compound 2 is benzene, toluene, trifluoromethyl benzene, fluorobenzene, chlorobenzene, bromobenzene or nitrobenzene.
The preparation method of the diaryl iodonium salt compound comprises the following steps:
dissolving iodobenzene diacetic acid in a solvent, dripping trifluoromethanesulfonic acid into the solvent at 0 ℃, stirring at room temperature, enabling the color of a reaction solution to turn yellow, then cooling the reaction temperature to 0 ℃, dripping benzene into the solvent to continue the reaction at room temperature, drying the solvent after the reaction is finished, adding anhydrous ether, separating out white solid, performing vacuum filtration, washing a filter cake with the anhydrous ether, and performing vacuum drying on the solid to obtain a compound II-1, wherein the molar ratio of the iodobenzene diacetic acid to the trifluoromethanesulfonic acid to the benzene is 1 (1.5-2.5) to (1-2).
The solvent is dichloromethane, ethyl acetate and chloroform.
The preparation method of the diaryl iodonium salt compound comprises the following steps:
dissolving m-chloroperoxybenzoic acid and elemental iodine in a solvent, reducing the temperature to 0 ℃, dropwise adding a substituted benzene compound 2 and trifluoromethanesulfonic acid to obtain a yellow system, reacting at normal temperature, spin-drying the solvent after complete reaction, adding anhydrous ether, stirring at room temperature to separate out an off-white solid, freezing at 0 ℃, carrying out vacuum filtration, washing a filter cake with the anhydrous ether, and carrying out vacuum drying on the filter cake to obtain a compound II (the preparation method of the compound except the compound II-1, namely R1Except for H), the molar ratio of m-chloroperoxybenzoic acid, elementary iodine, substituted benzene compound 2 and trifluoromethanesulfonic acid is (3-5): 1, (9-11): 3-5.
The mol ratio of the m-chloroperoxybenzoic acid to the elementary iodine to the substituted benzene compound 2 to the trifluoromethanesulfonic acid is 4:1:10: 4.
The substituted benzene compound 2 is toluene, trifluoromethyl benzene, fluorobenzene, chlorobenzene or bromobenzene.
The solvent is dichloromethane, ethyl acetate and chloroform.
Due to the adoption of the technical scheme, the invention has the following advantages and beneficial effects:
the diaryl iodide compound prepared by the invention is simple to synthesize, does not generate byproducts harmful to the environment, and has the characteristics of safety and environmental protection, and compared with common green corrosion inhibitors of sodium tungstate, sodium phytate and polyaspartic acid, the diaryl iodide compound has obvious advantage on the corrosion inhibition effect of a steel sheet in an aqueous solution, so that the diaryl iodide compound has the advantages of safety, environmental protection, high efficiency and the like in the field of metal corrosion inhibition.
The diaryl iodonium salt compound prepared by the invention can be used as a novel metal corrosion inhibitor, the structure of the diaryl iodonium salt compound comprises two aryl groups, an iodide positive ion and an anion, and the application of the diaryl iodonium salt compound in the field of metal corrosion inhibition has the advantages of safety, environmental protection, high efficiency and the like due to the fact that one end of the main structure of the diaryl iodonium salt compound is provided with a positive charge and the other end of the main structure of the diaryl iodonium salt compound is provided with a hydrophobic chain.
The diaryl iodide compound prepared by the invention has the characteristics of mildness, no toxicity, no harm and stable property, and can be used as an arylation reagent and a polymerization initiator.
Detailed Description
In order to more clearly illustrate the invention, the invention is further described below in connection with preferred embodiments. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
The experimental methods of the following examples, which are not specified under specific conditions, are generally determined according to national standards. If there is no corresponding national standard, it is carried out according to the usual international standards, to the conventional conditions or to the conditions recommended by the manufacturer. Unless otherwise indicated, all parts are parts by weight, all percentages are percentages by weight, and the molecular weight of the polymer is the number average molecular weight.
Unless defined or stated otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In addition, any methods and materials similar or equivalent to those described herein can be used in the methods of the present invention.
The medicines used in the invention are all sold in the market, and are all AR pure without special description, and comprise: concentrated sulfuric acid (500 mL); benzene (500 mL); toluene (500 mL); anhydrous ether (500 mL); ethyl acetate (5L); dichloromethane (5L); chloroform (500 mL); the above pharmaceutical agents are purchased from Shanghai Tantake Technique, Inc. Sodium periodate (100 g); iodophenylenediacetic acid (25 g); m-chloroperoxybenzoic acid (85%) (100 g); elemental iodine (100 g); the above pharmaceutical agents are available from Shanghai Michelin Biochemical technology, Inc. Trifluoromethanesulfonic acid (500mL) was purchased from Michelle chemical technology, Inc., Shanghai. Potassium bromide was purchased from Shanghai Aladdin Biotechnology Ltd.
Example 1
The preparation method of the diaryl iodonium salt compound I-1 comprises the following steps:
benzene (52.00mmol) was dissolved in 20mL of concentrated sulfuric acid, the temperature was raised to 55 deg.C, sodium periodate (1.84g, 8.60mmol) was added in portions over 1.5 hours, and the reaction was continued at 55 deg.C for 1.5 hours. After the reaction is completed, cooling to room temperature, then pouring the reaction liquid into an ice-water mixture, carrying out vacuum filtration to remove filter residues, extracting the filtrate for four times by using ethyl acetate, removing an organic phase, adding a potassium bromide (4.00g, 34.00mmol) aqueous solution into the water phase, carrying out vigorous stirring for 1 hour, separating out a solid, carrying out vacuum filtration, washing with water until the filtrate is neutral, placing the solid obtained by carrying out vacuum filtration on the filter cake on a watch glass, and airing to obtain a white solid I-1 (the yield is 63%).1H NMR(400MHz,DMSO)δ8.19(d,J＝8.0Hz,4H),7.61(t,J＝7.3Hz,2H),7.48(t,J＝7.6Hz,4H).
Example 2
The preparation method of the diaryl iodonium salt compound II-1 comprises the following steps:
mixing iodobenzene diacetic acid PhI (OAc)2(0.66g, 2.05mmol) was dissolved in dichloromethane (10mL), trifluoromethanesulfonic acid TfOH (0.36mL, 4.07mmol) was added dropwise to the dichloromethane solution at 0 deg.C, and the reaction mixture was stirred at room temperature for 1 hour. During which the reaction solution turned yellow in color. After 1 hour, the reaction temperature is reduced to 0 ℃, benzene (2.20mmol) is dripped into the system, the reaction is continued for half an hour at the room temperature, after the reaction is finished, dichloromethane is dried in a spinning mode, anhydrous ether is added, white solid is separated out, the pressure reduction and suction filtration are carried out, a filter cake is washed by the anhydrous ether, and the filter cake is dried in vacuum to obtain a white powdery solid compound II-1 (the yield is 85%).1H NMR(400MHz,DMSO)δ8.25(d,J＝8.1Hz,4H),7.67(t,J＝7.4Hz,2H),7.53(t,J＝7.6Hz,4H).
Example 3
The preparation method of the diaryl iodonium salt compound II-2 comprises the following steps:
m-chloro-peroxy benzeneFormic acid mCPBA (85%, 40.00mmol, 4.00equiv.) and elemental iodine (10.00mmol, 1.00equiv.) were dissolved in dichloromethane 100mL, the system became red-black, then the temperature was lowered to 0 ℃ and toluene (100.00mmol, 10.00equiv.) and TfOH (3.50mL, 40.00mmol, 4.00equiv.) were added dropwise to the system successively, and the system became yellow. The system was then reacted at a temperature of 25 ℃ for 20 minutes. After the reaction is completed, the solvent is dried by spinning, anhydrous ether is added, stirring is carried out for 30 minutes at room temperature, an off-white solid is separated out, in order to obtain more solid products, the system is placed into a freezer (0 ℃) for 30 minutes, then decompression suction filtration is carried out, the filter cake is washed by the anhydrous ether, and the filter cake is dried in vacuum to obtain a white solid II-2 (yield is 63%).1H NMR(400MHz,DMSO)δ8.37(d,J＝8.7Hz,4H),7.44(m,4H),2.37(s,6H).
Example 4
The preparation method of the diaryl iodonium salt compound II-3 comprises the following steps:
mCPBA (85%, 40.00mmol, 4.00equiv.) and elemental iodine (10.00mmol, 1.00equiv.) were dissolved in 100mL of dichloromethane, the system turned red-black, and then the temperature was lowered to 0 ℃. Trifluoromethyl benzene (100.00mmol, 10.00equiv.) and TfOH (3.50mL, 40.00mmol, 4.00equiv.) were added dropwise to the system successively, and the system became yellow. The system was then reacted at 25 ℃ for 20 minutes. After the reaction is completed, the solvent is dried by spinning, anhydrous ether is added, stirring is carried out for 30 minutes at room temperature, an off-white solid is separated out, in order to obtain more solid products, the system is placed into a freezer for 30 minutes, then the system is taken out, vacuum filtration is carried out, a filter cake is washed by the anhydrous ether, and the filter cake is dried in vacuum to obtain a white solid compound II-3 (the yield is 63%).1H NMR(400MHz,DMSO)δ8.27(d,J＝8.7Hz,4H),7.68(m,4H)
Example 5
The preparation method of the diaryl iodonium salt compound II-4 comprises the following steps:
mCPBA (85%, 40.00mmol, 4.00equiv.) and elemental iodine (10.00mmol, 1.00equiv.) were dissolved in 100mL of dichloromethane, the system turned red-black, and then the temperature was lowered to 0 ℃. Fluorobenzene (100.00mmol, 10.00equiv.) and TfOH (3.50mL, 40.00mmol, 4.00equiv.) were added dropwise to the system successively, and the system turned yellow. The system was then reacted at 25 ℃ for 20 minutes. After the reaction is completed, the solvent is dried by spinning, anhydrous ether is added, stirring is carried out for 30 minutes at room temperature, off-white solid is separated out, in order to obtain more solid products, the system is placed into a freezer for 30 minutes, then the system is taken out, vacuum filtration is carried out, the filter cake is washed by the anhydrous ether, and the filter cake is dried in vacuum to obtain white solid II-4 (the yield is 71%).1H NMR(400MHz,DMSO)δ8.36-8.27(m,4H),7.41(t,J＝8.6Hz,4H).
Example 6
The preparation method of the diaryl iodonium salt compound II-5 comprises the following steps:
mCPBA (85%, 40.00mmol, 4.00equiv.) and elemental iodine (10.00mmol, 1.00equiv.) were dissolved in 100mL of dichloromethane, the system turned red-black, and then the temperature was lowered to 0 ℃. Chlorobenzene (100.00mmol, 10.00equiv.) and TfOH (3.50mL, 40.00mmol, 4.00equiv.) were added dropwise to the system successively, and the system became yellow. The system was then reacted at 25 ℃ for 20 minutes. After the reaction is completed, the solvent is dried by spinning, anhydrous ether is added, stirring is carried out for 30 minutes at room temperature, off-white solid is separated out, in order to obtain more solid products, the system is placed into a freezer for 30 minutes, then the system is taken out, vacuum filtration is carried out, the filter cake is washed by the anhydrous ether, and the filter cake is dried in vacuum to obtain white solid II-5 (the yield is 57%).1H NMR(400MHz,DMSO)δ8.26(d,J＝8.7Hz,4H),7.67-7.59(m,4H).
Example 7
And evaluating the corrosion inhibition effect of the diaryl iodide compound by adopting a static coupon weight loss method. The experimental procedure was as follows:
1) polishing a 45# steel sheet by using sand paper, removing rust and an oxide film on the surface of the steel sheet, cleaning the surface of the steel sheet by using ethanol after polishing, wiping by using absorbent cotton, cleaning the steel sheet by using petroleum ether, and drying in a 40 ℃ oven.
2) After the steel sheet is dried, weighing and recording the initial mass m0The steel sheet is hung in a beaker filled with standard configuration water (simulating water-based cleaning agent cleaning equipment) and a certain amount of corrosion inhibitor (0 mg/L-1000 mg/L), and a plurality of blank control groups and parallel experimental groups are set up. The beaker is placed in a constant temperature oven at 40 ℃ for 24 h.
3) Taking out the steel sheet after 24h, removing rust products by using a rust remover, then washing with water, degreasing with acetone, drying in an oven at 40 ℃ for 2h, weighing and recording the mass as m1. Is composed of (m)1-m0) And obtaining the mass difference delta m before and after the mass difference, and averaging the blank control group and the parallel experiment group.
4) The corrosion rate is calculated by the formula:
in the formula:
v-corrosion Rate, g/(m)2·h)；
Δ m-weight loss of coupon, g;
t-corrosion time, h;
a-hanging piece surface area, m;
the corrosion inhibition rate calculation formula is as follows:
in the formula:
V0corrosion rate without addition of corrosion inhibitor, g/(m)2·h)；
V1Corrosion rate with addition of corrosion inhibitor, g/(m)2·h)；
Because the corrosion time is controlled to be consistent with the surface area of the hanging piece in the experiment, the calculation formula of the corrosion inhibition rate can be simplified as follows:
in the formula:
Δm0g, hanging piece weight loss when no corrosion inhibitor is added;
Δm1g, weight loss of the coupon when the corrosion inhibitor is added.
The corrosion inhibition rates of different corrosion inhibitors under the same experimental conditions are shown in table 1:
TABLE 1 Corrosion inhibition efficiency of different corrosion inhibitors under the same experimental conditions
Note: sodium tungstate, sodium phytate and polyaspartic acid are commonly used green corrosion inhibitors.
As can be seen from Table 1, the corrosion inhibition effect of the diaryl iodide compound I-1 and the diaryl iodide compound II-5 is obviously better than that of other diaryl iodides and is also better than that of common green corrosion inhibitors sodium tungstate, polyaspartic acid and sodium phytate. The common corrosion inhibitor in the market is generally a compound of a plurality of corrosion inhibitors, and the diaryl iodide salt compound is simple and green in synthesis and remarkable in corrosion inhibition effect, can be used for a single corrosion inhibitor system and research and development of a green high-efficiency corrosion inhibitor compound, and has good market prospect.
Example 8
The diaryl iodide salt compound I-1 (structural formula shown in example 1) with good corrosion inhibition effect is selected for concentration gradient experiment, the diaryl iodide salt compound I-1 is prepared into aqueous solutions with the concentrations of 0mg/L, 20mg/L, 60mg/L, 100mg/L, 150mg/L, 200mg/L, 250mg/L, 300mg/L, 400mg/L and 1000mg/L respectively, the corrosion inhibition rate is determined by adopting a static hanging piece weight loss method, and the determination result is shown in Table 2.
TABLE 2 Corrosion inhibition efficiency of diaryl iodonium salt compounds I-1 with different concentrations
| Concentration of corrosion inhibitor (mg/L) | Δm(mg) | E |
| 0 | 6.30 | |
| 20 | 3.30 | 47.62％ |
| 60 | 2.10 | 66.67％ |
| 100 | 0.55 | 91.27％ |
| 150 | 0.15 | 97.62％ |
| 200 | 0.10 | 98.41％ |
| 250 | 0.25 | 96.03％ |
| 300 | 0.90 | 85.71％ |
| 400 | 1.25 | 80.16％ |
| 1000 | 1.80 | 71.43％ |
As can be seen from Table 2, the corrosion inhibition effect is firstly improved and then reduced along with the increase of the concentration of the diaryl iodide salt compound I-1, and the corrosion inhibition rate reaches 98.41% at the concentration of 200mg/L, so that the corrosion inhibition effect is optimal, and the compound has certain advantages compared with a common green corrosion inhibitor. Therefore, the diaryl iodonium salt compound I-1 is an excellent carbon steel corrosion inhibitor, can be used for a single corrosion inhibitor system, can also be used for the research and development of green high-efficiency corrosion inhibitor compounds, and has good market prospect.
Although the present invention has been described with reference to a preferred embodiment, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (6)
1. The application of diaryl iodonium salt compound as metal corrosion inhibitor;
wherein, the diaryl iodonium salt compound is a compound shown as a formula I-1 or a formula II:
in the formula II, R1Is hydrogen, fluorine or chlorine.
2. The use according to claim 1, wherein the diaryliodonium salt compound is a compound represented by formula II-4 or formula II-5:
3. the use according to claim 1, wherein the diaryl iodonium salt compound is prepared by a preparation method comprising the steps of:
dissolving benzene in concentrated sulfuric acid, heating to 50-60 ℃, adding sodium periodate in batches, adding the sodium periodate in 1-2 hours, continuously reacting for 1-10 hours at 50-60 ℃, cooling to room temperature, then pouring the reaction liquid into an ice water mixture, carrying out vacuum filtration, discarding filter residues, extracting the filtrate for four times by using ethyl acetate, discarding an organic phase, adding a potassium bromide aqueous solution into the water phase, violently stirring for 0.1-5 hours, separating out solids, carrying out vacuum filtration, washing the filter cake until the filtrate is neutral, and drying the obtained solids to obtain the compound shown in the formula I-1;
or the like, or, alternatively,
dissolving iodobenzene diacetic acid in a solvent, dripping trifluoromethanesulfonic acid into the solvent at 0 ℃, stirring at room temperature to turn yellow, cooling to 0 ℃, dripping benzene, continuously reacting at room temperature for at least half an hour, spin-drying the solvent, adding anhydrous ether, separating out white solid, vacuum-filtering, washing filter cake with anhydrous ether, and vacuum-drying the solid to obtain R1A compound of formula II which is hydrogen;
or the like, or, alternatively,
dissolving m-chloroperoxybenzoic acid and elemental iodine in a solvent, changing the system into red black, dropwise adding substituted benzene and trifluoromethanesulfonic acid at 0 ℃ to change the system into yellow, reacting at room temperature for at least 20 minutes, adding anhydrous ether, stirring at room temperature to separate out an off-white solid, freezing at 0 ℃, carrying out vacuum filtration, washing a filter cake with the anhydrous ether, and carrying out vacuum drying on the filter cake to obtain the product R1A compound of formula II that is fluorine or chlorine;
wherein the solvent is dichloromethane, ethyl acetate or chloroform, and the substituted benzene is fluorobenzene or chlorobenzene.
4. The use according to claim 3, wherein the molar ratio of benzene, sodium periodate and potassium bromide is (4-8) to 1 (3-6).
5. The method of claim 3, wherein the molar ratio of the iodobenzene diacetic acid to the trifluoromethanesulfonic acid to the benzene is 1 (1.5-2.5) to (1-2).
6. The use of claim 3, wherein the molar ratio of m-chloroperoxybenzoic acid, elemental iodine, substituted benzene and trifluoromethanesulfonic acid is (3-5): 1 (9-11): (3-5).
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