ACTIVE HYDROGEN-CONTAINING ORGANIC COMPOUND SCAVENGER, COMPOSITION, AND APPLICATIONS THEREOF

Abstract

The present application provides a material for efficiently removing active hydrogen-containing compounds such as alcohol compounds. The present application uses an active hydrogen-containing organic compound scavenger having a bromine content of from 38 to 78 wt % represented by the formula (1) (wherein R.sup.1 and R.sup.2 each independently represent a hydrogen atom or a C.sub.1-4 alkyl group, each R.sup.3 independently represents a hydrogen atom, a C.sub.1-4 alkyl group or a bromine atom, m represents at least one selected from the group consisting of 0, 1, 2 and 3, and n represents a real number of 0 or more) (wherein the isocyanate compound may be a single species or a mixture of two or more species, and in the case of a mixture, n represents an average n of the mixture).

Claims

1. An active hydrogen-containing organic compound scavenger comprising an isocyanate compound having a bromine content of from 38 to 78 wt % represented by the following formula (1): ##STR00014## (wherein R.sup.1 and R.sup.2 each independently represent a hydrogen atom or a C.sub.1-4 alkyl group, each R.sup.3 independently represents a hydrogen atom, a C.sub.1-4 alkyl group or a bromine atom, m represents at least one selected from the group consisting of 0, 1, 2 and 3, and n represents a real number of 0 or more) (wherein the isocyanate compound may be a single species or a mixture of two or more species, and in the case of a mixture, n represents an average n of the mixture).

2. The active hydrogen-containing organic compound scavenger according to claim 1, wherein the isocyanate compound represented by the formula (1) (which may be a single species or a mixture of two or more species, wherein in the case of a mixture, n represents an average n of the mixture) is an isocyanate compound represented by the following formula (1a): ##STR00015## (wherein R.sup.1 and R.sup.2 each independently represent a hydrogen atom or a C.sub.1-4 alkyl group, each R.sup.3 independently represents a hydrogen atom, a C.sub.1-4 alkyl group or a bromine atom, m represents at least one selected from the group consisting of 0, 1, 2 and 3, and n represents a real number of 0 or more) (wherein the isocyanate compound may be a single species or a mixture of two or more species, and in the case of a mixture, n represents an average n of the mixture).

3. The active hydrogen-containing organic compound scavenger according to claim 1, wherein the isocyanate compound represented by the formula (1) (which may be a single species or a mixture of two or more species, wherein in the case of a mixture, n represents an average n of the mixture) is an isocyanate compound represented by the following formula (1b): ##STR00016## (wherein R.sup.1 and R.sup.2 each independently represent a hydrogen atom or a C.sub.1-4 alkyl group, each R.sup.3 independently represents a hydrogen atom, a C.sub.1-4 alkyl group or a bromine atom, and n represents a real number of 0 or more) (wherein the isocyanate compound may be a single species or a mixture of two or more species, and in the case of a mixture, n represents an average n of the mixture).

4. The active hydrogen-containing organic compound scavenger according to claim 1, wherein the bromine content is from 50 to 78 wt %.

5. The active hydrogen-containing organic compound scavenger according to claim 1, wherein R.sup.1 and R.sup.2 each represent a hydrogen atom or a methyl group.

6. The active hydrogen-containing organic compound scavenger according to claim 1, wherein R.sup.1 and R.sup.2 each independently represent a hydrogen atom.

7. The active hydrogen-containing organic compound scavenger according to claim 1, wherein each R.sup.3 in the formula (1) independently represents a hydrogen atom or a bromine atom.

8. The active hydrogen-containing organic compound scavenger according to claim 1, wherein n is a real number of from 0 to 3.

9. A method for removing at least one compound selected from the group consisting of alcohol compounds, thiol compounds, amine compounds, phenol compounds and carboxylic acid compounds, which comprises bringing the at least one compound into contact with the active hydrogen-containing organic compound scavenger as defined in claim 1.

10. A composition comprising an isocyanate compound having a bromine content of from 38 to 78 wt % represented by the following formula (1): ##STR00017## (wherein R.sup.1 and R.sup.2 each independently represent a hydrogen atom or a C.sub.1-4 alkyl group, each R.sup.3 independently represents a hydrogen atom, a C.sub.1-4 alkyl group or a bromine atom, m represents at least one selected from the group consisting of 0, 1, 2 and 3, and n represents a real number of 0 or more) (wherein the isocyanate compound may be a single species or a mixture of two or more species, and in the case of a mixture, n represents an average n of the mixture) and a support.

11. The composition according to claim 10, wherein the isocyanate compound represented by the formula (1) (which may be a single species or a mixture of two or more species, wherein in the case of a mixture, n represents an average n of the mixture) is an isocyanate compound represented by the following formula (1a): ##STR00018## (wherein R.sup.1 and R.sup.2 each independently represent a hydrogen atom or a C.sub.1-4 alkyl group, each R.sup.3 independently represents a hydrogen atom, a C.sub.1-4 alkyl group or a bromine atom, m represents at least one selected from the group consisting of 0, 1, 2 and 3, and n represents a real number of 0 or more) (wherein the isocyanate compound may be a single species or a mixture of two or more species, and in the case of a mixture, n represents an average n of the mixture).

12. The composition according to claim 10, wherein the isocyanate compound represented by the formula (1) (which may be a single species or a mixture of two or more species, wherein in the case of a mixture, n represents an average n of the mixture) is an isocyanate compound represented by the following formula (1b): ##STR00019## (wherein R.sup.1 and R.sup.2 each independently represent a hydrogen atom or a C.sub.1-4 alkyl group, each R.sup.3 independently represents a hydrogen atom, a C.sub.1-4 alkyl group or a bromine atom, and n represents a real number of 0 or more) (wherein the isocyanate compound may be a single species or a mixture of two or more species, and in the case of a mixture, n represents an average n of the mixture).

13. The composition according to claim 10, wherein each R.sup.3 independently represents a hydrogen atom or a bromine atom.

14. The composition according to claim 10, wherein the isocyanate compound is supported on the support.

15. The composition according to claim 10, wherein the amount of the isocyanate compound supported on the support is from 0.1 part by weight to 60 parts by weight per 100 parts by weight of the support.

16. The composition according to claim 10, wherein the support comprises one or more members of selected from the group consisting of activated carbon, activated clay, diatomaceous earth, a porous resin, non-woven cloth, mesoporous silica, silica gel, aluminosilicate, hydrotalcite, zeolite, activated alumina, titania, magnesia and zirconia.

17. An active hydrogen-containing organic compound scavenger comprising the composition as defined in claim 10.

18. A method for removing at least one compound selected from the group consisting of alcohol compounds, thiol compounds, amine compounds, phenol compounds and carboxylic acid compounds, which comprises bringing the at least one compound into contact with the composition as defined in claim 10.

Description

BRIEF DESCRIPTION OF DRAWINGS

[0095] FIG. 1 A schematic view of the system used to assess the removal of an active hydrogen-containing organic compound in Examples.

EXAMPLES

[0096] Now, the present invention will be described in further detail with reference to Examples. However, it should be understood that the present invention is by no means restricted thereto.

[Gcms Analysis]

[0097] Instrument: Electronic nose system HERACLES II manufactured by Alpha M.O.S. Japan [0098] Measurement conditions: column=Agilent J&W GC column DB-5 [0099] vaporization chamber temperature=220 C. [0100] detector temperature=260 C. [0101] column temperature=250 C. [0102] heating rate=1.5 C./sec

[Ft-Ir Analysis]

[0103] Instrument: Frontier MIR/NIR manufactured by PerkinElmer Inc. [0104] Measurement conditions: ATR method, MIR mode

[Determination of Bromine Content]

[0105] Combustion: the oxygen flask combustion method (in compliance with ISO7725-2020) [0106] Instrument: IC-2001 manufactured by Tosoh Corporation

Synthetic Example 1

[0107] ##STR00012##

[0108] A 2 L separable flask was loaded with 100 g of a 4,4-methylenedianiline composition obtained by condensation of aniline and formalin (comprising 65% of a binuclear product, 23% of a trinuclear product, 8% of a tetranuclear product and 4% of a pentanuclear or higher nuclear product), 5.00 g of ferric chloride and 700 mL of 1,2-dichloroethane. 338 g of bromine diluted with 300 mL of 1,2-dichloroethane was added dropwise to the 2 L separable flask over 1 hour with stirring, with an accompanying rise in the inner temperature to 50 C. The resulting solution was cooled to room temperature over 1 hour under stirring and then washed with aqueous hydrazine to remove the unreacted bromine until the pH came into the basic range. The 1,2-dichloroethane layer was separated from the aqueous layer and was added dropwise to methanol to precipitate a pale red solid. The solid was recovered by filtration and washed with methanol and dried to yield 153 g of a pale red solid (the bromination product of the 4,4-methylenedianiline composition). The bromine content of the solid determined by the oxygen flask combustion-IC method was 59.6 wt %.

Synthetic Example 2

[0109] ##STR00013##

[0110] A 2 L separable flask equipped with a stirrer was loaded with 12.5 g of the pale red solid obtained in Synthetic Example 1 (the bromination product of the 4,4-methylenedianiline composition) and 987.5 g of chlorobenzene under nitrogen and heated to 130 C., and 13.4 g of hydrogen chloride gas was blown into the resulting solution over 90 minutes to convert the brominating product to a salt. Then, 44 g of phosgene gas was blown into the solution over 2 hours, and after 2 hours of aging at 125 C., nitrogen gas was bubbled into the solution to remove the phosgene gas from the system until the absence of phosgene was confirmed. After cooling to room temperature, the reaction solution was filtered to remove the insoluble. The filtrate was concentrated on an evaporator, and the resulting concentrate was air-dried at 45 C. to yield 12.4 g (yield 79%) of a mixture (hereinafter referred to as the product of Synthetic Example 2) of 4,4-methylenebis(2,6-dibromoisocyanatobenzene) (binuclear compound) and its oligomers (comprising trinuclear, tetranuclear, pentanuclear and even higher nuclear compounds) as a brown powder. The NCO content (mass percentage of isocyanate groups to the total mass) was 14.5 mass %, and the bromine content was 54.3 wt %. The product of Synthetic Example 2 can be used as an active hydrogen-containing organic compound scavenger of the present invention, as described later.

Synthetic Example 3

[0111] A 2 L separable flask equipped with a stirrer was loaded with 30.0 g of 4,4-methylenebis(2-bromoanilie) (comprising 100% of a binuclear compound) and 1470.0 g of chlorobenzene under nitrogen and heated to 130 C. 12.3 g of hydrogen chloride gas was blown into the resulting solution over 120 minutes to convert 4,4-methylenebis(2-bromoanilie) to a salt. Then, 109.6 g of phosgene gas was blown into the solution over 6 hours, and nitrogen gas was bubbled into the solution to remove the phosgene gas from the system until the absence of phosgene was confirmed. After cooling to room temperature, the reaction solution was filtered to remove the insoluble. The filtrate was concentrated on an evaporator, and the resulting concentrate was air-dried at 45 C. to yield 33.0 g (yield 96%) of 4,4-methylenebis(2-bromoisocyantobenzene) (hereinafter referred to as the product of Synthetic Example 3) as a white powder. The NCO content (mass percentage of isocyanate groups to the total mass) was 21.0 mass %, and the bromine content was 39.1 wt %. The product of Synthetic Example 3 can be used as an active hydrogen-containing organic compound scavenger of the present invention, as described later.

Synthetic Example 4

[0112] A 300 mL three-necked flask was loaded with 5.00 g of a 4,4-methylenedianiline composition (comprising 65% of a binuclear compound, 23% of a trinuclear compound, 8% of a tetranuclear compound and 4% of a pentanuclear or higher nuclear compound), 0.25 g of ferric chloride and 100 mL of methanol, and 19.5 g of bromine diluted with 25 mL of methanol was added dropwise to the 200 mL separable flask over 1 hour under stirring. The reaction solution was post-treated in the same manner as in Synthetic Example 1 to yield 12.0 g of a red-brown solid (the bromination product of the 4,4-methylenedianline composition) (hereinafter referred to as the product of Synthetic Example 4). The bromine content of the solid determined by the oxygen flask combustion-IC method was 58.5 wt %.

Synthetic Example 5

[0113] A 300 mL three-necked flask was loaded with 10.0 g of 4,4-methylenedianiline (comprising 100% of a binuclear compound), 0.50 g of ferric chloride and 200 mL of methanol, and 19.5 g of bromine diluted with 25 mL of methanol was added to the 200 mL separable flask over 1 hour under stirring. The reaction solution was post-treated in the same manner as in Synthetic Example 1 to yield 25.5 g of a beige solid (the bromination product of the 4,4-methylenedianline composition) (hereinafter referred to as the product of Synthetic Example 5). The bromine content of the solid determined by the oxygen flask combustion-IC method was 59.4 wt %.

Synthetic Example 6

[0114] A 2 L separable flask equipped with a stirrer was loaded with 39.8 g of the product of Synthetic Example 5 (comprising 100% of a binuclear compound) and 1150.0 g of orthochlorobenzene under nitrogen and heated to 140 C., and 11.3 g of hydrogen chloride gas was blown into the resulting solution over 120 minutes to convert the product of Synthetic Example 5 to a salt. Then, 61.3 g of phosgene gas was blown into the solution over 4 hours, and nitrogen gas was bubbled into the solution to remove the phosgene gas from the system until the absence of phosgene was confirmed. After cooling to room temperature, the reaction solution was concentrated on an evaporator, and the resulting concentrate was air-dried at 45 C. to yield 42.7 g of 4,4-methylenebis(2,6-dibromoisocyanatobenzen) (hereinafter referred to as the product of Synthetic Example 6) as a brown powder. The NCO content (mass percentage of isocyanate groups to the total mass) was 14.3 mass %, and the bromine content was 56.0 wt %. The product of Synthetic Example 6 can be used as the active hydrogen-containing organic compound scavenger of the present invention, as described later.

Synthetic Example 7

[0115] A 2 L separable flask equipped with a stirrer was loaded with 50.0 g of 4,4-methylenebis(3-bromoaniline) (comprising 45% of a binuclear compound, 18% of a trinuclear compound, 17% of a tetranuclear compound and 20% of pentanuclear or higher nuclear compounds) and 1400.0 g of chlorobenzene under nitrogen and heated to 130 C. 20.0 g of hydrogen chloride gas was blown into the resulting solution over 120 minutes to convert 4,4-methylenebis(3-bromoaniline) to a salt. Then, 110.0 g of phosgene gas was blown into the solution over 6 hours, and nitrogen gas was bubbled into the solution to remove the phosgene gas from the system until the absence of phosgene was confirmed. After cooling to room temperature, the reaction solution was concentrated on an evaporator, and the resulting concentrate was washed with small amounts of toluene and tetrahydrofuran. The resulting powder was air-dried to yield 40.7 g of 4,4-methylenebis(3-bromoisocyanatobenzen) (hereinafter referred to as the product of Synthetic Example 7) as a brown powder. The bromine content was 38.3 wt %. The product of Synthetic Example 7 can be used as an active hydrogen-containing organic compound scavenger of the present invention, as described later.

[0116] The isocyanate compounds obtained above and the isocyanate compound (2,4,6-tribromoisocyanatobenzene) used in Example 5 are shown in the following table.

TABLE-US-00001 TABLE 1 Composition Y [wt %] Synthetic Ex. 2 65% of binuclear compound, 23% of a 54.3 trinuclear compound, 8% of a tetranuclear compound and 4% of pentanuclear and higher nuclear compounds Synthetic Ex. 3 100% of a binuclear compound 39.1 Synthetic Ex. 6 100% of a binuclear compound 56.0 Synthetic Ex. 7 45% of binuclear compound, 18% of a 38.3 trinuclear compound, 17% of a tetranuclear compound and 20% of pentanuclear and higher nuclear compounds Ex. 5 100% of a mononuclear compound 67.1

Example 1

[0117] 1.0 g of the product of Synthetic Example 2, 9.0 g of granular activated carbon Shirasagi KL (Osaka Gas Chemicals Co., Ltd.) and 40 mL of tetrahydrofuran were stirred in a 200 mL recovery flask using a stir bar at room temperature for 30 minutes, and after withdrawal of the stir bar, the solvent was removed by filtration. The recovered solid was dried under vacuum under heat at 100 C. for 8 hours to yield 10.0 g of the product of Synthetic Example 2 supported on activated carbon (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention).

Example 2

[0118] 1.0 g of the product of Synthetic Example 2, 9.0 g of granular activated carbon Shirasagi WH2C8/32 (Osaka Gas Chemicals Co., Ltd.) and 40 mL of tetrahydrofuran were stirred in a 200 mL recovery flask using a stir bar at room temperature for 30 minutes, and after withdrawal of the stir bar, the solvent was removed by filtration. The recovered solid was dried under vacuum under heat at 100 C. for 8 hours to yield 10.0 g of the product of Synthetic Example 2 supported on activated carbon (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention).

Example 3

[0119] 1.0 g of the product of Synthetic Example 2, 9.0 g of granular activated carbon Shirasagi X7100H-3DRY (Osaka Gas Chemicals Co., Ltd.) and 40 mL of tetrahydrofuran were stirred in a 200 mL recovery flask using a stir bar at room temperature for 30 minutes, and after withdrawal of the stir bar, the solvent was removed by filtration. The recovered solid was dried under vacuum under heat at 100 C. for 8 hours to yield 10.0 g of the product of Synthetic Example 2 supported on activated carbon (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention) as a black powder.

Example 4

[0120] A 20 mL glass vial was loaded with 20 mg of fine powder of the product of Synthetic Example 2 (an active hydrogen-containing organic compound scavenger of the present invention) and filled with a gas containing 10 ppm of 2-ethyl-1-hexanol (in nitrogen). The vial was left to stand at room temperature for 3 hours. Thereafter, the 2-ethyl-1-hexanol concentration in the gas in the vial was determined by GCMS (electronic nose system HERACLES II manufactured by Alpha M.O.S. Japan), and the results indicated that 81% of the 2-ethyl-1-hexanol was captured. After the standing, the atmosphere in the vial was replaced with nitrogen gas, and the vial was heated at 60 C. for 30 minutes. Thereafter, 2-ethyl-1-hexanol was determined by GCMS, and the results indicated that 0% of the captured 2-ethyl-1-hexanol was released.

Example 5

[0121] A 20 mL glass vial was loaded with 20 mg of 2,4,6-tribromoisocyanatobenzene (having a bromine content of 67.1 wt %, synthesized by isocyanation of 2,4,6-tribromoaniline (FUJIFILM Wako Pure Chemical Corporation)) (an active hydrogen-containing organic compound scavenger of the present invention in the form of fine powder) and filled with a gas containing 10 ppm of 2-ethyl-1-hexanol. The vial was left to stand at room temperature for 3 hours. Thereafter, the 2-ethyl-1-hexanol concentration in the gas in the vial was determined by GCMS (electronic nose system HERACLES II manufactured by Alpha M.O.S. Japan), and the results indicated that 90% of the 2-ethyl-1-hexanol was captured. After the standing, the atmosphere in the vial was replaced with nitrogen gas, and the vial was heated at 60 C. for 30 minutes. Thereafter, 2-ethyl-1-hexanol was determined by GCMS, and the results indicated that 0% of the captured 2-ethyl-1-hexanol was released.

Example 6

[0122] The procedure in Example 4 was followed except that a gas containing 10 ppm of 2-methyl-1-butanol (in nitrogen) was used instead of the gas containing 10 ppm of 2-ethyl-1-hexanol (in nitrogen) to assess removal and release of 2-methyl-1-butanol. The results indicated that 89% of the 2-methyl-1-butanol was captured and that 0% of the captured 2-methyl-1-butanol was released.

Example 7

[0123] The procedure in Example 4 was followed except that a gas containing 10 ppm of 2-methyl-1-proptanol (in nitrogen) was used instead of the gas containing 10 ppm of 2-ethyl-1-hexanol (in nitrogen) to assess removal and release of 2-methyl-1-proptanol. The results indicate that 48% of the 2-methyl-1-propanol was captured and that 0% of the captured 2-methyl-1-propanol was released.

Comparative Example 1

[0124] The procedure in Example 4 was followed except that an empty vial (not loaded with 20 mg of the product of Synthetic Example 2) was filled with a gas containing 10 ppm of 2-ethyl-1-hexanol (in nitrogen) to assess removal of 2-ethyl-1-hexanol. The results indicate that 0% of the 2-ethyl-1-hexanol was captured.

Comparative Example 2

[0125] The procedure in Example 4 was followed except that 20 mg of pi-cyclodextrin (Tokyo Chemical Industry Co., Ltd.) was used instead of 20 mg of the product of Synthetic Example 2 to assess removal and release of 2-ethyl-1-hexanol. The results indicated that 0% of the 2-ethyl-1-hexanol was captured.

Comparative Example 3

[0126] The procedure in Example 4 was followed except that 5 mg of activated carbon (powder of reagent grade manufactured by FUJIFILM Wako Pure Chemical Corporation) was used instead of 20 mg of the product of Synthetic Example 2 to assess removal and release of 2-ethyl-1-hexanol. The results indicated that 99% of the 2-ethyl-1-hexanol was captured, and 13% of the captured 2-ethyl-1-hexanol was released.

Comparative Example 4

[0127] The procedure in Example 4 was followed except that 5 mg of activated carbon (powder of reagent grade manufactured by FUJIFILM Wako Pure Chemical Corporation) was used instead of 20 mg of the product of Synthetic Example 2, and a gas containing 10 ppm of 2-methyl-1-butanol (in nitrogen) was used instead of the gas containing 10 ppm of 2-ethyl-1-hexanol (in nitrogen) to assess removal and release of 2-methyl-1-butanol. The results indicated that 92% of the 2-methyl-1-butanol was captured, and 6% of the captured 2-methyl-1-butanol was released.

Comparative Example 5

[0128] The procedure in Example 4 was followed except that 5 mg of activated carbon (powder of reagent grade manufactured by FUJIFILM Wako Pure Chemical Corporation) was used instead of 20 mg of the product of Synthetic Example 2, and a gas containing 10 ppm of 2-methyl-1-propanol (in nitrogen) was used instead of the gas containing 10 ppm of 2-ethyl-1-hexanol (in nitrogen) to assess removal and release of 2-methyl-1-propanol. The results indicated that 95% of the 2-methyl-1-propanol was captured, and 12% of the captured 2-methyl-1-propanol was released.

Comparative Example 6

[0129] The procedure in Example 4 was followed except that 5 mg of CARiACT Q-50 (manufactured by FUJI SILYSIA CHEMICAL LTD.) was used instead of 20 mg of the product of Synthetic Example 2 to assess removal and release of 2-ethyl-1-hexanol. The results indicated that 86% of the 2-ethyl-1-hexanol was captured, and 25% of the captured 2-ethyl-1-hexanol was released.

Comparative Example 7

[0130] The procedure in Example 4 was followed except that 5 mg of silica gel NIPGEL AY-001 (Tosoh Silica Corporation) was used instead of 20 mg of the product of Synthetic Example 2 to assess removal and release of 2-ethyl-1-hexanol. The results indicated that 92% of the 2-ethyl-1-hexanol was captured, and 21% of the captured 2-ethyl-1-hexanol was released.

TABLE-US-00002 TABLE 2 Removal and release of alcohol Removal (%) during 3 Release (%) during Item Scavenger hours at room temperature 30 min at 60 C. Example 4 Product of Synthetic Example 2 81 0 (2-Ethyl-1-hexanol) Example 5 2,4,6-Tribromoisocyanatobenzene 90 0 (2-Ethyl-1-hexanol) Example 6 Product of Synthetic Example 2 89 0 (2-Ethyl-1-butanol) Example 7 Product of Synthetic Example 2 48 0 (2-Ethyl-1-propanol) Comparative Example 1 Nil 0 (2-Ethyl-1-hexanol) Comparative Example 2 -Cyclodextrin 0 (2-Ethyl-1-hexanol) Comparative Example 3 Activated carbn 99 13 (2-Ethyl-1-hexanol) Comparative Example 4 Activated carbn 92 6 (2-Ethyl-1-butanol) Comparative Example 5 Activated carbn 95 12 (2-Ethyl-1-propanol) Comparative Example 6 Silica gel CARiACT Q-50 86 25 (2-Ethyl-1-hexanol) Comparative Example 7 Silica gel NIPGEL AY-001 92 21 (2-Ethyl-1-hexanol)

Example 8

[0131] 30 mg of the product of Synthetic Example 2 (an active hydrogen-containing organic compound scavenger of the present invention) was stirred with 10 mL of water using a stir bar in a capped 20 mL vial at room temperature for 3 months, then recovered as a brown powder by filtering off the water and analyzed by FT-IR. The FT-IR spectrum showed no change in peak intensity or peak pattern from that of the initial sample, which indicates that the sample did not hydrolyze during the long-term contact with water. The results are shown in Table 3.

Example 9

[0132] 100 mg of the product of Synthetic Example 2 (an active hydrogen-containing organic compound scavenger of the present invention) was stirred using a stir bar in an uncapped 20 mL vial at 60 C. in the atmosphere for 2 months, and the resulting brown powder was analyzed by FT-IR. The FT-IR spectrum showed no change in peak intensity or peak pattern from that of the initial sample, which indicates that the isocyanate groups did not hydrolyze with water during the long-term contact with the atmosphere containing a small amount of water under heat. The results are shown in Table 3.

Example 10

[0133] 30 mg of the product of Synthetic Example 2 (an active hydrogen-containing organic compound scavenger of the present invention) was stirred with 10 mL of 30% aqueous ethanol using a stir bar in a capped 20 mL vial at 45 C. for 3 days, then recovered as a brown powder by filtering off the solvent and analyzed by FT-IR. The FT-IR spectrum contained a carbonyl peak attributable to the reaction product of ethanol and the isocyanato group, instead of the isocyanate peak contained in the spectrum of the initial sample, and did not contain a peak attributable to a hydrolysis product, which indicates that the isocyanate groups in the product of Synthetic Example 2 reacted selectively with ethanol and did not react with water. The results are shown in Table 3.

Example 11

[0134] 30 mg of the product of Synthetic Example 2 (an active hydrogen-containing organic compound scavenger of the present invention) was stirred with 5 mL of toluene and 5 mL of 5% aqueous ethanol using a stir bar in a capped 20 mL vial at 45 C. for 3 days, then recovered as a brown powder by evaporating toluene to dryness and analyzed by FT-IR. The FT-IR spectrum contained a carbonyl peak attributable to the reaction product of ethanol and the isocyanato group, instead of the isocyanate peak contained in the spectrum of the initial sample, and did not contain a peak attributable to a hydrolysis product, which indicates that the isocyanate groups in the product of Synthetic Example 2 reacted selectively with ethanol and did not react with water. The results are shown in Table 3.

Example 12

[0135] 30 mg of the product of Synthetic Example 3 (an active hydrogen-containing organic compound scavenger of the present invention) was stirred with 30% aqueous ethanol using a stir bar in a capped 20 mL vial at 45 C. for 3 days, then recovered as a powder by filtering off the solvent and analyzed by FT-IR. The FT-IR spectrum contained a carbonyl peak, instead of the isocyanate peak, which indicates capture of ethanol through the reaction of the isocyanate groups and ethanol, and did not contain a peak attributable to a hydrolysis product, which indicates that the isocyanate groups in the product of Synthetic Example 3 reacted selectively with ethanol and did not react with water. The results are shown in Table 3.

Example 27

[0136] 30 mg of the product of Synthetic Example 6 (an active hydrogen-containing organic compound scavenger of the present invention) was stirred with 10 mL of water using a stir bar in a capped 20 mL vial at room temperature for 3 months, then recovered as a brown powder by filtering off the water and analyzed by FT-IR. The FT-IR spectrum showed no change in peak intensity or peak pattern from that of the initial sample, which indicates that the sample did not hydrolyze during the long-term contact with water. The results are shown in Table 3.

Example 28

[0137] 100 mg of the product of Synthetic Example 6 (an active hydrogen-containing organic compound scavenger of the present invention) was stirred using a stir bar in an uncapped 20 mL vial at 60 C. in the atmosphere for 2 months, and the resulting brown powder was analyzed by FT-IR. The FT-IR spectrum showed no change in peak intensity or peak pattern from that of the initial sample, which indicates that the isocyanate groups did not hydrolyze with water during the long-term contact with the atmosphere containing a small amount of water under heat. The results are shown in Table 3.

Example 29

[0138] 30 mg of the product of Synthetic Example 6 (an active hydrogen-containing organic compound scavenger of the present invention) was stirred with 10 mL of 30% aqueous ethanol using a stir bar in a capped 20 mL vial at 45 C. for 3 days, then recovered as a brown powder by filtering off the solvent and analyzed by FT-IR. The FT-IR spectrum contained a carbonyl peak attributable to the reaction product of ethanol and the isocyanato group, instead of the isocyanate peak contained in the spectrum of the initial sample, and did not contain a peak attributable to a hydrolysis product, which indicates that the isocyanate groups in the product of Synthetic Example 6 reacted selectively with ethanol and did not react with water. The results are shown in Table 3.

Example 30

[0139] 30 mg of the product of Synthetic Example 6 (an active hydrogen-containing organic compound scavenger of the present invention) was stirred with 5 mL of toluene and 5 mL of 5% aqueous ethanol using a stir bar in a capped 20 mL vial at 45 C. for 3 days, then recovered as a brown powder by evaporating toluene to dryness and analyzed by FT-IR. The FT-IR spectrum contained a carbonyl peak attributable to the reaction product of ethanol and the isocyanato group, instead of the isocyanate peak contained in the spectrum of the initial sample, and did not contain a peak attributable to a hydrolysis product, which indicates that the isocyanate groups in the product of Synthetic Example 6 reacted selectively with ethanol and did not react with water. The results are shown in Table 3.

Comparative Example 8

[0140] 30 mg of polymeric MDI (Millionate MR-200, manufactured by Tosoh Corporation) was stirred with 10 mL of water using a stir bar in a capped 20 mL vial at room temperature for 1 month, then recovered as a solid by filtering off the water and analyzed by FT-IR. The FT-IR spectrum was quite different in peak intensity and peak pattern from that of the initial sample, which indicates that MDI hydrolyzed during the contact with water. The results are shown in Table 3.

Comparative Example 9

[0141] 100 mg of polymeric MDI (Millionate MR-200, manufactured by Tosoh Corporation) was stirred using a stir bar in an uncapped 20 mL vial at 60 C. in the atmosphere for 14 days, and the resulting solid was analyzed by FT-IR. The FT-IR spectrum was quite different in peak intensity and peak pattern from that of the initial sample, which indicates that the polymeric MDI hydrolyzed during the contact with the atmosphere containing a small amount of water under heat. The results are shown in Table 3.

Comparative Example 10

[0142] 30 mg of polymeric MDI (Millionate MR-200, manufactured by Tosoh Corporation) was stirred with 30% aqueous ethanol using a stir bar in a capped 20 mL vial at 45 C. for 3 days, then recovered as a solid by filtering off the solvent and analyzed by FT-IR. The FT-IR spectrum contained a carbonyl peak attributable to the reaction product of ethanol and the polymeric MDI, instead of the isocyanate peak contained in the spectrum of the initial sample, and also contained a peak attributable to a hydrolysis product of the polymeric MDI, which indicates that the polymeric MDI showed no reaction selectivity between water and ethanol. The results are shown in Table 3.

Comparative Example 11

[0143] 30 mg of 2,4,6-tri-tertiary-butylisocyanatobenzen was stirred with 30% aqueous ethanol using a stir bar in a capped 20 mL vial at 45 C. for 3 days, then recovered as a solid by filtering off the solvent and analyzed by FT-IR. The FT-IR spectrum contained the isocyanate peak, like the spectrum of the initial sample, and had no difference from that of the initial sample in the shape of other peaks, which indicates that 2,4,6-tri-tertiary-butylisocyanatobenzene did not react with water or ethanol. The results are shown in Table 3.

[0144] From Table 3, it is clear that scavengers comprising an isocyanate compound represented by the formula (1) are resistant to ambient water and can capture alcohol compounds.

TABLE-US-00003 TABLE 3 Reactivity Results of IR analysis assessment Reaction with water Reaction with Item Scavenger condition (hydrolysis) alcohol Example 8 Product of Synthetic Example 2 In water No Example 9 Product of Synthetic Example 2 In atmosphere No Example 10 Product of Synthetic Example 2 In aqueous ethanol No Occurred Example 11 Product of Synthetic Example 2 In aqueous ethanol No Occurred Example 12 Product of Synthetic Example 3 In aqueous ethanol No Occurred Example 27 Product of Synthetic Example 6 In water No Example 28 Product of Synthetic Example 6 In atmosphere No Example 29 Product of Synthetic Example 6 In aqueous ethanol No Occurred Example 30 Product of Synthetic Example 6 In aqueous ethanol No Occurred Comparative Polymeric MDI In water Occurred Example 8 Comparative Polymeric MDI In atmosphere Occurred Example 9 Comparative Polymeric MDI In aqueous ethanol Occurred Occurred Example 10 Comparative 2,4,6-Tri-tertiary- In aqueous ethanol No No Example 11 butylisocyanatobenzene

Example 13 (Silica Gel-Supported Scavenger 1 Cariact Q-10)

[0145] 1.0 g of the product of Synthetic Example 2, 9.0 g of silica gel CARiACT Q-10 (FUJI SILYSIA CHEMICAL LTD.) and 200 mL of dichloromethane were stirred using a stir bar in a 500 mL recovery flask at room temperature for 30 minutes, and after withdrawal of the stir bar, the solvent was slowly removed on an evaporator under vacuum. The solid residue was dried by blowing nitrogen gas at 60.sup.00 for 3 hours and then at room temperature for 24 hours to yield the product of Synthetic Example 2 supported on silica gel (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention).

Example 14 (Silica Gel-Supported Scavenger 2 Cariact G-10)

[0146] 0.5 g of the product of Synthetic Example 2, 9.5 g of silica gel CARiACT G-10 (FUJI SILYSIA CHEMICAL LTD.) and 200 mL of dichloromethane were stirred using a stir bar in a 500 mL recovery flask at room temperature for 30 minutes, and after withdrawal of the stir bar, the solvent was slowly removed on an evaporator under vacuum. The solid residue was dried by blowing nitrogen gas at 60 C. for 3 hours and then at room temperature for 24 hours to yield the product of Synthetic Example 2 supported on silica gel (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention).

Example 15 (Silica Gel-Supported Scavenger 3 Nipgel Ay-001)

[0147] 0.5 g of the product of Synthetic Example 2, 9.5 g of silica gel NIPGEL AY-001 (Tosoh Silica Corporation) and 200 mL of dichloromethane were stirred using a stir bar in a 500 mL recovery flask at room temperature for 30 minutes, and after withdrawal of the stir bar, the solvent was slowly removed on an evaporator under vacuum. The solid residue was dried by blowing nitrogen gas at 60 C. for 3 hours and then at room temperature for 24 hours to yield the product of Synthetic Example 2 supported on silica gel (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention).

Example 16 (Silica Gel-Supported Scavenger 4 Nipgel Ay-220D)

[0148] 0.5 g of the product of Synthetic Example 2, 9.5 g of silica gel NIPGEL AY-220D (Tosoh Silica Corporation) and 200 mL of dichloromethane were stirred using a stir bar in a 500 mL recovery flask at room temperature for 30 minutes, and after withdrawal of the stir bar, the solvent was slowly removed on an evaporator under vacuum. The solid residue was dried by blowing nitrogen gas at 60 C. for 3 hours and then at room temperature for 24 hours to yield the product of Synthetic Example 2 supported on silica gel (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention).

Example 17 (Silica Gel-Supported Scavenger 4 Nipgel Cx-200)

[0149] 0.5 g of the product of Synthetic Example 2, 9.5 g of silica gel NIPGEL CX-200 (Tosoh Silica Corporation) and 200 mL of dichloromethane were stirred using a stir bar in a 500 mL recovery flask at room temperature for 30 minutes, and after withdrawal of the stir bar, the solvent was slowly removed on an evaporator under vacuum. The solid residue was dried by blowing nitrogen gas at 60 C. for 3 hours and then at room temperature for 24 hours to yield the product of Synthetic Example 2 supported on silica gel (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention).

Example 18 (Cellulose-Supported Scavenger Viscopearl a)

[0150] 0.5 g of the product of Synthetic Example 2, 9.5 g of cellulose Viscopearl A (Rengo Co., Ltd.) and 200 mL of dichloromethane were stirred using a stir bar in a 500 mL recovery flask at room temperature for 30 minutes, and after withdrawal of the stir bar, the solvent was slowly removed on an evaporator under vacuum. The solid residue was dried by blowing nitrogen gas at 60 C. for 3 hours and then at room temperature for 24 hours to yield the product of Synthetic Example 2 supported on cellulose (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention).

Example 19 (Silica Gel-Supported Scavenger 5 Cariact Q-50)

[0151] 0.5 g of the product of Synthetic Example 3, 9.5 g of silica gel CARiACT Q-50 (FUJI SILYSIA CHEMICAL LTD.) and 200 mL of dichloromethane were stirred using a stir bar in a 500 mL recovery flask at room temperature for 30 minutes, and after withdrawal of the stir bar, the solvent was slowly removed on an evaporator under vacuum. The solid residue was dried by blowing nitrogen gas at 60 C. for 3 hours and then at room temperature for 24 hours to yield the product of Synthetic Example 3 supported on silica gel (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention).

Example 20 (Silica Gel-Supported Scavenger 6 NIPGELAY-001)

[0152] 0.5 g of the product of Synthetic Example 3, 9.5 g of silica gel NIPGEL AY-001 (Tosoh Silica Corporation) and 200 mL of dichloromethane were stirred using a stir bar in a 500 mL recovery flask at room temperature for 30 minutes, and after withdrawal of the stir bar, the solvent was slowly removed on an evaporator under vacuum. The solid residue was dried by blowing nitrogen gas at 60 C. for 3 hours and then at room temperature for 24 hours to yield the product of Synthetic Example 3 supported on silica gel (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention).

Example 31 (Silica Gel-Supported Scavenger 7 Nipgel Cx-200)

[0153] 0.5 g of the product of Synthetic Example 6, 9.5 g of silica gel NIPGEL CX-200 (Tosoh Silica Corporation) and 200 mL of dichloromethane were stirred using a stir bar in a 500 mL recovery flask at room temperature for 30 minutes, and after withdrawal of the stir bar, the solvent was slowly removed on an evaporator under vacuum. The solid residue was dried by blowing nitrogen gas at 60 C. for 3 hours and then at room temperature for 24 hours to yield the product of Synthetic Example 6 supported on silica gel (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention).

Example 32 (Hydrotalcite-Supported Scavenger Kyowaad 500)

[0154] 0.5 g of the product of Synthetic Example 2, 9.5 g of KYOWAAD 500 (hydrotalcite manufactured by Kyowa Chemical Industry Co., Ltd.) and 200 mL of dichloromethane were stirred using a stir bar in a 500 mL recovery flask at room temperature for 30 minutes, and after withdrawal of the stir bar, the solvent was slowly removed on an evaporator under vacuum. The solid residue was dried by blowing nitrogen gas at 60 C. for 3 hours and then at room temperature for 24 hours to yield the product of Synthetic Example 2 supported on hydrotalcite (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention).

[Gas Removal Assessment]

[0155] Active hydrogen-containing organic compound scavengers of the present invention were assessed with the active hydrogen-containing organic compound gas removal assessment system illustrated in FIG. 1, which comprises a reservoir tank (made of SUS and having a 20 L capacity), a gas circulation pump, a column to be filled with a scavenger (made of glass and having a 0.1 L capacity), heaters and so on. The reservoir tank was filled with an active hydrogen-containing organic compound gas (such as ethanol, isopropanol or acetic acid) until an atmosphere (circulating gas) containing a prescribed concentration of the active hydrogen-containing organic compound gas (in nitrogen) was made in the system. The column was packed with 5 g of a scavenger of the present invention and then adjusted to 25 C. The circulating gas adjusted to 25 C. with a heater was flown through the column by the circulation pump at a rate of 10 L/min for 3 hours, and the concentration of the active hydrogen-containing organic compound in the reservoir tank after the 3-hour gas circulation was determined. Then, the column packed with the scavenger was adjusted to 60 C. with a heater, then the circulating gas adjusted to 60 C. was flown through the column by the circulation pump at a rate of 10 L/min for 30 minutes, and the concentration of the active hydrogen-containing organic compound in the reservoir tank after 30-minute gas circulation was determined.

Example 21 (Assessment of Ethanol Gas Removal)

[0156] An atmosphere containing 500 ppm ethanol gas (in nitrogen) was made in the active hydrogen-containing organic compound gas removal assessment system. Then, the column in the active hydrogen-containing organic compound gas removal assessment system was filled with the silica gel-supported scavenger of Example 13 (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention), and an assessment was carried out. The ethanol gas concentration in the system after the 3-hour gas circulation at 25 C. was 145 ppm, and the ethanol gas concentration in the system after the 30-minute gas circulation at 60 C. was 285 ppm. The 215 ppm concentration drop (=500 ppm-285 ppm) corresponds to the amount of ethanol captured by the silica gel-supported scavenger of Example 13 and was not released again. The results are shown in Table 4.

Example 22 (Assessment of Ethanol Gas Removal)

[0157] An atmosphere containing 500 ppm ethanol gas (in nitrogen) was made in the active hydrogen-containing organic compound gas removal assessment system. Then, the column in the active hydrogen-containing organic compound gas removal assessment system was filled with the silica gel-supported scavenger of Example 14 (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention), and an assessment was carried out. The ethanol gas concentration in the system after the 3-hour gas circulation at 25 C. was 15 ppm, and the ethanol gas concentration in the system after the 30-minute gas circulation at 60 C. was 160 ppm. The 340 ppm concentration drop (=500 ppm-160 ppm) corresponds to the amount of ethanol captured by the silica gel-supported scavenger of Example 14 and was not released again. The results are shown in Table 4.

Example 23 (Assessment of Ethanol Gas Removal)

[0158] An atmosphere containing 500 ppm ethanol gas (in nitrogen) was made in the active hydrogen-containing organic compound gas removal assessment system. Then, the column in the active hydrogen-containing organic compound gas removal assessment system was filled with the silica gel-supported scavenger of Example 15 (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention), and an assessment was carried out. The ethanol gas concentration in the system after the 3-hour gas circulation at 25 C. was less than 5 ppm, and the ethanol gas concentration in the system after the 30-minute gas circulation at 60 C. was 55 ppm. The 445 ppm concentration drop (=500 ppm-55 ppm) corresponds to the amount of ethanol captured by the silica gel-supported scavenger of Example 15 and was not released again. The results are shown in Table 4.

Example 24 (Assessment of Ethanol Gas Removal)

[0159] An atmosphere containing 500 ppm ethanol gas (in nitrogen) was made in the active hydrogen-containing organic compound gas removal assessment system. Then, the column in the active hydrogen-containing organic compound gas removal assessment system was filled with the silica gel-supported scavenger of Example 16 (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention), and an assessment was carried out. The ethanol gas concentration in the system after the 3-hour gas circulation at 25 C. was 10 ppm, and the ethanol gas concentration in the system after the 30-minute gas circulation at 60 C. was 70 ppm. The 430 ppm concentration drop (=500 ppm-70 ppm) corresponds to the amount of ethanol captured by the silica gel-supported scavenger of Example 16 irreversibly. The results are shown in Table 4.

Example 25 (Assessment of Ethanol Gas Removal)

[0160] An atmosphere containing 500 ppm ethanol gas (in nitrogen) was made in the active hydrogen-containing organic compound gas removal assessment system. Then, the column in the active hydrogen-containing organic compound gas removal assessment system was filled with the silica gel-supported scavenger of Example 17 (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention), and an assessment was carried out. The ethanol gas concentration in the system after the 3-hour gas circulation at 25 C. was less than 5 ppm, and the ethanol gas concentration in the system after the 30-minute gas circulation at 60 C. was 15 ppm. The 485 ppm concentration drop (=500 ppm-15 ppm) corresponds to the amount of ethanol captured by the silica gel-supported scavenger of Example 17 and was not released again. The results are shown in Table 4.

Example 26 (Assessment of Ethanol Gas Removal)

[0161] An atmosphere containing 500 ppm ethanol gas (in nitrogen) was made in the active hydrogen-containing organic compound gas removal assessment system. Then, the column in the active hydrogen-containing organic compound gas removal assessment system was filled with the silica gel-supported scavenger of Example 20 (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention), and an assessment was carried out. The ethanol gas concentration in the system after the 3-hour gas circulation at 25 C. was 10 ppm, and the ethanol gas concentration in the system after the 30-minute gas circulation at 60 C. was 50 ppm. The 450 ppm concentration drop (=500 ppm-50 ppm) corresponds to the amount of ethanol captured by the silica gel-supported scavenger of Example 20 and was not released again. The results are shown in Table 4.

Example 33 (Assessment of Ethanol Gas Removal)

[0162] An atmosphere containing 500 ppm ethanol gas (in nitrogen) was made in the active hydrogen-containing organic compound gas removal assessment system. Then, the column in the active hydrogen-containing organic compound gas removal assessment system was filled with the silica gel-supported scavenger of Example 31 (a composition of the present invention and an active hydrogen-containing organic compound scavenger of the present invention), and an assessment was carried out. The ethanol gas concentration in the system after the 3-hour gas circulation at 25 C. was 5 ppm, and the ethanol gas concentration in the system after the 30-minute gas circulation at 60 C. was 15 ppm. The 485 ppm concentration drop (=500 ppm-15 ppm) corresponds to the amount of ethanol captured by the silica gel-supported scavenger of Example 31 and was not released again. The results are shown in Table 4.

Example 34 (Assessment of Isopropanol Gas Removal)

[0163] The procedure in Example 33 was followed except that the gas species (the target active hydrogen-containing organic compound to be removed) was changed from ethanol to isopropanol. The isopropanol gas concentration in the system after the 3-hour gas circulation at 25 C. was 10 ppm, and the isopropanol gas concentration in the system after the 30-minute gas circulation at 60 C. was 30 ppm. The 470 ppm concentration drop (=500 ppm-30 ppm) corresponds to the amount of isopropanol captured by the silica gel-supported scavenger of Example 31 and was not released again. The results are shown in Table 4.

Example 35 (Assessment of Acetic Acid Gas Removal)

[0164] The procedure in Example 33 was followed except that the gas species (the target active hydrogen-containing organic compound to be removed) was changed from ethanol to acetic acid, and the initial acetic acid gas concentration was changed to 15.0 ppm. The acetic acid gas concentration in the system after the 3-hour gas circulation at 25 C. was 0.2 ppm, and the acetic acid gas concentration in the system after the 30-minute gas circulation at 60 C. was 0.4 ppm. The 14.7 ppm concentration drop (=15.0 ppm-0.4 ppm) corresponds to the amount of acetic acid captured by the silica gel-supported scavenger of Example 31 and was not released again. The results are shown in Table 4.

Example 36 (Assessment of Ethanol Gas Removal)

[0165] An atmosphere containing 500 ppm ethanol gas (in nitrogen) was made in the active hydrogen-containing organic compound gas removal assessment system. Then, the column in the active hydrogen-containing organic compound gas removal assessment system was filled with the hydrotalcite-supported scavenger of Example 32 (a composition of the present invention and an active hydrogen-containing organic 5 compound scavenger of the present invention), and an assessment was carried out. The ethanol gas concentration in the system after the 3-hour gas circulation at 25 C. was 55 ppm, and the ethanol gas concentration in the system after the 30-minute gas circulation at 60 C. was 80 ppm. The 420 ppm concentration drop (=500 ppm-80 ppm) corresponds to the amount of ethanol captured by the hydrotalcite-supported scavenger of Example 32 and was not released again. The results are shown in Table 4.

Comparative Example 12

[0166] An atmosphere containing 500 ppm ethanol gas (in nitrogen) was made in the active hydrogen-containing organic compound gas removal assessment system. Then, an assessment was carried out with nothing in the column in the active hydrogen-containing organic compound gas removal assessment system (i.e., with the column empty). The ethanol gas concentration in the system after the 3-hour gas circulation at 25 C. was 500 ppm, and the ethanol gas concentration in the system after the 30-minute gas circulation at 60 C. was 500 ppm. There was no drop in the ethanol concentration in the circulating gas. The results are shown in Table 4.

Comparative Example 13

[0167] An atmosphere containing 15.0 ppm acetic acid gas (in nitrogen) was made in the active hydrogen-containing organic compound gas removal assessment system. Then, an assessment was carried out with nothing in the column in the active hydrogen-containing organic compound gas removal assessment system (i.e., with the column empty). The acetic acid gas concentration in the system after the 3-hour gas circulation at 25 C. was 15.0 ppm, and the acetic acid gas concentration in the system after the 30-minute gas circulation at 60 C. was 15.0 ppm. There was no drop in the acetic acid concentration in the circulating gas. The results are shown in Table 4.

TABLE-US-00004 TABLE 4 Target gas concentration (ppm) After 3-hour After 30-minute Target circulation at circulation at Item Scavenger substance 25 C. 60 C. Example 21 Product of Synthetic Ethanol 145 285 Example 2/ silica gel Q-10 Example 22 Product of Synthetic Ethanol 15 160 Example 2/ silica gel G-10 Example 23 Product of Synthetic Ethanol less than 5 55 Example 2/ silica gel YA-001 Example 24 Product of Synthetic Ethanol 10 70 Example 2/ silica gel YA-220D Example 25 Product of Synthetic Ethanol less than 5 15 Example 2/ silica gel CX-200 Example 26 Product of Synthetic Ethanol 10 50 Example 3/ silica gel YA-001 Example 33 Product of Synthetic Ethanol 5 15 Example 6/ silica gel CX-200 Example 34 Product of Synthetic Isopropanol 10 30 Example 6/ silica gel CX-200 Example 35 Product of Synthetic Acetic acid 0.2 0.4 Example 6/ silica gel CX-200 Example 36 Product of Synthetic Ethanol 55 80 Example 6/ hydrotalcite Comparative Nil Ethanol 500 500 Example 12 Comparative Nil Acetic acid 15 15 Example 13

[0168] The present invention has been described in detail with reference to specific embodiments. However, it is apparent to those skilled in the art that various changes and modifications are possible without departing from the nature and the scope of the present invention.

[0169] The entire disclosures of Japanese Patent Application No. 2020-200086 filed on Dec. 2, 2020 and Japanese Patent Application No. 2021-125610 filed on Jul. 30, 2021 including specifications, claims, drawings and summaries are incorporated herein by reference in their entireties.

REFERENCE SYMBOLS

10. Reservoir tank (made of SUS and having a capacity of 20 L)

[0170] 11. Hygrothermograph [0171] 12. Gas flowmeter [0172] 13. Gas circulation pump [0173] 14. Heater [0174] 15. Thermometer [0175] 16. Manometer [0176] 17. Column to be filled with a scavenger [0177] 18. Heater [0178] 19. Valve [0179] 20. Direction of the flow of the circulating gas

INDUSTRIAL APPLICABILITY

[0180] The present invention makes it possible to efficiently remove active hydrogen-containing organic compounds which are difficult to remove by conventional techniques such as alcohol compounds. The active hydrogen-containing organic compound scavenger of the present invention has a long-lasting ability to remove active hydrogen-containing organic compounds irreversibly even in the presence of water and can be used in the environmental energy field, the medical and life science field and in other various scenes.