CN116715841A - Preparation method of polyether polyol - Google Patents
Preparation method of polyether polyol Download PDFInfo
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- CN116715841A CN116715841A CN202310683446.8A CN202310683446A CN116715841A CN 116715841 A CN116715841 A CN 116715841A CN 202310683446 A CN202310683446 A CN 202310683446A CN 116715841 A CN116715841 A CN 116715841A
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- Prior art keywords
- polyether polyol
- amount
- preparation
- catalyst
- dipropylene glycol
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- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 36
- 229920000570 polyether Polymers 0.000 title claims abstract description 36
- 229920005862 polyol Polymers 0.000 title claims abstract description 32
- 150000003077 polyols Chemical class 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims abstract description 18
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052751 metal Inorganic materials 0.000 claims abstract description 15
- 239000002184 metal Substances 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 8
- 239000003463 adsorbent Substances 0.000 claims abstract description 7
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 7
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 239000003513 alkali Substances 0.000 claims abstract description 4
- 238000001816 cooling Methods 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 230000018044 dehydration Effects 0.000 claims description 11
- 238000006297 dehydration reaction Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000391 magnesium silicate Substances 0.000 claims description 5
- 229910052919 magnesium silicate Inorganic materials 0.000 claims description 5
- 235000019792 magnesium silicate Nutrition 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000440 bentonite Substances 0.000 claims description 2
- 229910000278 bentonite Inorganic materials 0.000 claims description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 2
- 239000002585 base Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract description 21
- 239000002994 raw material Substances 0.000 abstract description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 6
- -1 polyoxypropylene Polymers 0.000 abstract description 5
- 229920001451 polypropylene glycol Polymers 0.000 abstract description 5
- 150000001412 amines Chemical class 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 239000002932 luster Substances 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 230000032683 aging Effects 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 239000003999 initiator Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2648—Alkali metals or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2663—Metal cyanide catalysts, i.e. DMC's
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Toxicology (AREA)
- Polyethers (AREA)
Abstract
The application provides a preparation method of polyether polyol, which comprises the following steps: s1, putting dipropylene glycol and an alkaline catalyst into a reaction kettle, dehydrating, and continuously adding propylene oxide to perform polymerization reaction; s2, cooling the product obtained in the step S1 to 50-80 ℃, adding a certain amount of water, inorganic acid and adsorbent into the system, stirring, dehydrating and filtering to obtain the polyether polyol. The application selects dipropylene glycol as raw material and a compound of strong alkali and double metal cyanide complex catalyst as alkaline catalyst, the content of dipropylene glycol in the prepared polyoxypropylene ether is low, the content of propylene glycol is lower than 0.3%, the distribution is narrow, no further rectification treatment is needed, and the raw material has light color and luster, thus being very suitable for the preparation and subsequent application of low-color polyether amine.
Description
Technical Field
The application relates to the field of chemical industry, in particular to a preparation method of polyether polyol.
Background
Polyether polyols are prepared by reacting a hydroxyl-containing initiator with alkylene oxides such as ethylene oxide and propylene oxide in the presence of an alkali metal hydroxide catalyst. Polyether polyols of different functionalities can be prepared according to the number of reactive atoms contained in the initiator, the most commonly used polyether polyols being polyoxypropylene diols and polyoxypropylene triols.
Polyether polyols are important polymeric materials, especially for the preparation of polyurethanes. With the increasing expansion of application range, higher requirements are put on varieties and specifications, especially quality, of raw polyether, and polyether polyol with low color value, narrow distribution, no propylene glycol and low starter residue is a precondition for improving the quality of polyurethane products. This is because propylene glycol remains so that commercial polyether polyols tend to appear yellow, and in the cosmetic field of polyurethane, it is desirable that polyurethane be as colorless (white) as possible. In order to reduce the residual amount and the distribution degree, rectification treatment is generally required, and the preparation cost is obviously increased.
Disclosure of Invention
In view of the problems described in the background art, an object of the present application is to provide a method for preparing an anti-yellowing polyether polyol, wherein no further rectification treatment is required in the preparation process.
In order to solve the problems, the technical scheme adopted by the application is as follows:
a method for preparing polyether polyol, comprising the steps of:
s1, putting dipropylene glycol and an alkaline catalyst into a reaction kettle, dehydrating, and continuously adding propylene oxide to perform polymerization reaction;
s2, cooling the product obtained in the step S1 to 50-80 ℃, adding a certain amount of water, inorganic acid and adsorbent into the system, stirring, dehydrating and filtering to obtain the polyether polyol.
The polymerization conditions in S1 are: the reaction temperature is 100-150 ℃, and the relative pressure is less than or equal to 0.3MPa.
The dehydration condition in the S1 is that dehydration is carried out for 30-70 min under the temperature of 80-120 ℃ and the relative pressure of minus 0.08 to minus 0.1 MPa.
The alkaline catalyst in the step S1 is the combination of sodium hydroxide (or potassium hydroxide) and double metal cyanide complex catalyst.
In the alkaline catalyst, the dosage of sodium hydroxide (or potassium hydroxide) is 0.01 to 0.5 weight percent and the dosage of double metal cyanide complex catalyst DMC is 0.01 to 0.5 weight percent based on the weight ratio of the theoretical yield of polyether polyol. More preferably, the amount of sodium hydroxide (or potassium hydroxide) used in the basic catalyst is 0.05 to 0.2wt% and the amount of DMC double metal cyanide complex catalyst used is 0.05 to 0.2wt% based on the weight of the theoretical yield of polyether polyol.
The inorganic acid in S2 is selected from one of hydrochloric acid, phosphoric acid and sulfuric acid, preferably 85wt% phosphoric acid.
The amount of the inorganic acid used for adjusting the pH of the liquid to be treated to 3 to 6, preferably 4 to 5, depends on the pH of the liquid to be treated obtained by S1.
The adsorbent in the step S2 is selected from one of bentonite, montmorillonite, magnesium silicate and magnesium aluminum silicate, and preferably magnesium aluminum silicate. The amount of the adsorbent added is 0.01 to 1wt%, preferably 0.2 to 0.6wt%.
The dehydration condition in the S2 is that the dehydration is carried out for 0.5 to 2 hours until the water content of the system is less than or equal to 0.05 percent under the conditions that the temperature is 100 to 140 ℃ and the relative pressure is minus 0.08 to minus 0.1 MPa.
Compared with the prior art, the application has the beneficial effects that:
the dipropylene glycol is selected as a raw material, a compound of strong alkali and a double metal cyanide complex catalyst is selected as an alkaline catalyst, the dipropylene glycol content in the prepared polyoxypropylene ether is low, the propylene glycol content is lower than 0.3%, the distribution is narrow (the distribution coefficient is smaller than 1.08), no further rectification treatment is needed, the raw material color is very light (the raw material color is 1-10), and the polyoxypropylene ether is very suitable for the preparation and subsequent application of low-color polyether amine.
The present application will be described in further detail with reference to the following embodiments.
Detailed Description
Example 1:
the embodiment provides a preparation method of polyether polyol, in particular to a preparation method of PPG-230 with a molecular weight of 230, which comprises the following steps:
sequentially adding 500g of dipropylene glycol, sodium hydroxide and double metal cyanide complex catalyst into a 1L reaction kettle, dehydrating for 50min at 100 ℃ under the condition of the relative pressure of-0.09 MPa, continuously adding propylene oxide, then carrying out polymerization reaction at the reaction temperature of 110 ℃ under the condition that the relative pressure is less than or equal to 0.3MPa, and aging for 3h after 336g of propylene oxide is added;
the reaction temperature of the system is reduced to 50 ℃, 12.5g of deionized water, 4.6g of 85wt% phosphoric acid and 2.5g of magnesium silicate are added into the system and stirred for 30min, the temperature of the reaction kettle is controlled at 100 ℃, the relative pressure is-0.1 MPa, after dehydration is carried out for 2h until the water content of the system is less than or equal to 0.05wt%, the polyether polyol with the number average molecular weight of 230 (namely PPG-230 with the molecular weight of 230) is obtained by filtering, wherein the content of dipropylene glycol is 0.02%, the distribution coefficient is 1.04, and the Pt-Co color number of the polyether polyol product is 5.
The sodium hydroxide and the double metal cyanide complex catalyst were used in an amount of 0.2% by weight based on the theoretical yield of polyether polyol, and the double metal cyanide complex catalyst was used in an amount of 0.1%.
Comparative example 1:
the comparative example provides a preparation method of PPG-230 with a molecular weight of 230 in the prior art, which comprises the following steps:
sequentially adding 500g of propylene glycol, sodium hydroxide and double metal cyanide complex catalyst into a 1L reaction kettle, dehydrating for 50min at 100 ℃ under the condition of the relative pressure of-0.09 MPa, continuously adding propylene oxide, then carrying out polymerization reaction at the reaction temperature of 110 ℃ under the condition that the relative pressure is less than or equal to 0.3MPa, and aging for 3h after 336g of propylene oxide is added;
the reaction temperature of the system is reduced to 50 ℃, 12.5g of deionized water, 4.6g of 85wt% phosphoric acid and 2.5g of magnesium silicate are added into the system and stirred for 30min, the temperature of the reaction kettle is controlled at 100 ℃, the relative pressure is-0.1 MPa, after dehydration is carried out for 2h until the water content of the system is less than or equal to 0.05wt%, the polyether polyol (PPG-230 with the molecular weight of 230) with the number average molecular weight of 230 is obtained by filtering, wherein the content of dipropylene glycol is 6.2%, the content of propylene glycol is about 10ppm, the distribution coefficient is 1.15, and the Pt-Co color number of the polyether polyol product is 12.
The sodium hydroxide and the double metal cyanide complex catalyst were used in an amount of 0.2% by weight based on the theoretical yield of polyether polyol, and the double metal cyanide complex catalyst was used in an amount of 0.1%.
Compared with example 1, it is obvious that the comparative example 1 adopts propylene glycol as raw material, the prepared PPG-230 has higher dipropylene glycol content, larger distribution coefficient and larger Pt-Co color number of polyether polyol product. Therefore, the application adopts the dipropylene glycol, and the dipropylene glycol is low in content and narrow in distribution compared with the prior art under the condition that the rest reaction conditions are completely the same, no further rectification treatment is needed, and the raw material has light color and luster, thereby being suitable for the preparation and subsequent application of the low-color polyetheramine.
Comparative example 2:
sequentially adding 500g of dipropylene glycol and 0.3% of sodium hydroxide (calculated by weight ratio of theoretical yield of polyether polyol) into a 1L reaction kettle, dehydrating for 50min at 100 ℃ under the condition of relative pressure of-0.09 MPa, continuously adding propylene oxide, performing polymerization reaction at the reaction temperature of 110 ℃ under the condition that the relative pressure is less than or equal to 0.3MPa, and aging for 3h after 336g of propylene oxide is added;
the reaction temperature of the system is reduced to 50 ℃, 12.5g of deionized water, 4.6g of 85wt% phosphoric acid and 2.5g of magnesium silicate are added into the system and stirred for 30min, the temperature of the reaction kettle is controlled at 100 ℃, the relative pressure is-0.1 MPa, after dehydration is carried out for 2h until the water content of the system is less than or equal to 0.05wt%, the polyether polyol (PPG-230 with the molecular weight of 230) with the number average molecular weight of 230 is obtained by filtering, the content of dipropylene glycol in the product is 1.5%, the distribution coefficient is 1.12, and the Pt-Co color number of the polyether polyol product is 19.
Compared with example 1, it is evident that comparative example 2 also uses dipropylene glycol as a raw material, but uses a different catalyst, the content of dipropylene glycol of the prepared PPG-230 is higher, the distribution coefficient is larger, and the Pt-Co color number of the polyether polyol product is larger. Therefore, the application adopts sodium hydroxide and double metal cyanide complex catalyst as catalyst, and under the condition that the rest reaction conditions are completely the same, compared with the prior art, the sodium hydroxide is adopted as catalyst, the dipropylene glycol content in the product is low, the distribution is narrow, no further rectification treatment is needed, the raw material color is light, and the application is suitable for the preparation and subsequent application of low-color polyether amine.
The above embodiments are only preferred embodiments of the present application, and the scope of the present application is not limited thereto, but any insubstantial changes and substitutions made by those skilled in the art on the basis of the present application are intended to be within the scope of the present application as claimed.
Claims (10)
1. A process for preparing a polyether polyol comprising the steps of:
s1, putting dipropylene glycol and an alkaline catalyst into a reaction kettle, dehydrating, and continuously adding propylene oxide to perform polymerization reaction;
s2, cooling the product obtained in the step S1 to 50-80 ℃, adding a certain amount of water, inorganic acid and adsorbent into the system, stirring, dehydrating and filtering to obtain the polyether polyol.
2. The process according to claim 1, wherein the polymerization conditions in S1 are: the reaction temperature is 100-150 ℃, and the relative pressure is less than or equal to 0.3MPa.
3. The preparation method according to claim 1, wherein the conditions for dehydration in S1 are dehydration at 80 to 120℃and a relative pressure of-0.08 to-0.1 MPa for 30 to 70min.
4. The method of claim 1, wherein the basic catalyst in S1 is a combination of a strong base and a double metal cyanide complex catalyst, and the strong base is sodium hydroxide or potassium hydroxide.
5. The process according to claim 1, wherein the alkali catalyst is used in an amount of 0.01 to 0.5wt% and the double metal cyanide complex catalyst DMC is used in an amount of 0.01 to 0.5wt% based on the weight of the theoretical yield of polyether polyol.
6. The process according to claim 5, wherein the alkali is used in an amount of 0.05 to 0.2wt% and the DMC double metal cyanide complex catalyst is used in an amount of 0.05 to 0.2wt% based on the weight of the theoretical yield of polyether polyol.
7. The method according to claim 1, wherein the inorganic acid in S2 is one selected from the group consisting of hydrochloric acid, phosphoric acid and sulfuric acid.
8. The method according to claim 1, wherein the amount of the inorganic acid used for adjusting the pH of the liquid to be treated to 3 to 6 depends on the pH of the liquid to be treated obtained by S1.
9. The preparation method according to claim 1, wherein the adsorbent in S2 is one selected from bentonite, montmorillonite, magnesium silicate and magnesium aluminum silicate, and the addition amount of the adsorbent is 0.01-1 wt%.
10. The preparation method according to claim 1, wherein the dehydration condition in S2 is that dehydration is carried out for 0.5-2 h to the water content of the system less than or equal to 0.05% under the conditions that the temperature is 100-140 ℃ and the relative pressure is minus 0.08-minus 0.1 MPa.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202310683446.8A CN116715841A (en) | 2023-06-09 | 2023-06-09 | Preparation method of polyether polyol |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202310683446.8A CN116715841A (en) | 2023-06-09 | 2023-06-09 | Preparation method of polyether polyol |
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