JPH04330031A - Method for stabilizing aqueous solution of formaldehyde - Google Patents
Method for stabilizing aqueous solution of formaldehydeInfo
- Publication number
- JPH04330031A JPH04330031A JP2108491A JP2108491A JPH04330031A JP H04330031 A JPH04330031 A JP H04330031A JP 2108491 A JP2108491 A JP 2108491A JP 2108491 A JP2108491 A JP 2108491A JP H04330031 A JPH04330031 A JP H04330031A
- Authority
- JP
- Japan
- Prior art keywords
- formaldehyde
- aqueous solution
- compounds
- paraformaldehyde
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims abstract description 117
- 238000000034 method Methods 0.000 title claims abstract description 8
- 239000007864 aqueous solution Substances 0.000 title abstract description 28
- 230000000087 stabilizing effect Effects 0.000 title abstract description 3
- 125000000524 functional group Chemical group 0.000 claims abstract description 12
- 150000002923 oximes Chemical class 0.000 claims abstract description 5
- -1 ketone compounds Chemical class 0.000 claims description 20
- 239000008098 formaldehyde solution Substances 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 230000006641 stabilisation Effects 0.000 claims description 3
- 238000011105 stabilization Methods 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229930040373 Paraformaldehyde Natural products 0.000 abstract description 16
- 229920002866 paraformaldehyde Polymers 0.000 abstract description 16
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 150000002576 ketones Chemical class 0.000 abstract 2
- 238000000151 deposition Methods 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 235000019256 formaldehyde Nutrition 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000001556 precipitation Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 7
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GFAZHVHNLUBROE-UHFFFAOYSA-N 1-hydroxybutan-2-one Chemical compound CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- BCDGQXUMWHRQCB-UHFFFAOYSA-N aminoacetone Chemical compound CC(=O)CN BCDGQXUMWHRQCB-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- RSBQFKJVGZVGFM-UHFFFAOYSA-N 1,3-diaminopropan-2-one Chemical compound NCC(=O)CN RSBQFKJVGZVGFM-UHFFFAOYSA-N 0.000 description 1
- VFPKIWATTACVJR-UHFFFAOYSA-N 1-(dimethylamino)propan-2-one Chemical compound CN(C)CC(C)=O VFPKIWATTACVJR-UHFFFAOYSA-N 0.000 description 1
- TYXULUBCBKMSSK-UHFFFAOYSA-N 1-hydroxypentan-3-one Chemical compound CCC(=O)CCO TYXULUBCBKMSSK-UHFFFAOYSA-N 0.000 description 1
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 1
- HDKKRASBPHFULQ-UHFFFAOYSA-N 3-Hydroxy-2-pentanone Chemical compound CCC(O)C(C)=O HDKKRASBPHFULQ-UHFFFAOYSA-N 0.000 description 1
- BNDRWEVUODOUDW-UHFFFAOYSA-N 3-Hydroxy-3-methylbutan-2-one Chemical compound CC(=O)C(C)(C)O BNDRWEVUODOUDW-UHFFFAOYSA-N 0.000 description 1
- OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 description 1
- SKCYVGUCBRYGTE-UHFFFAOYSA-N 4-hydroxyhexan-3-one Chemical compound CCC(O)C(=O)CC SKCYVGUCBRYGTE-UHFFFAOYSA-N 0.000 description 1
- BVEYJWQCMOVMAR-UHFFFAOYSA-N 5-Hydroxy-4-octanone Chemical compound CCCC(O)C(=O)CCC BVEYJWQCMOVMAR-UHFFFAOYSA-N 0.000 description 1
- JSHPTIGHEWEXRW-UHFFFAOYSA-N 5-hydroxypentan-2-one Chemical compound CC(=O)CCCO JSHPTIGHEWEXRW-UHFFFAOYSA-N 0.000 description 1
- 238000005705 Cannizzaro reaction Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、ホルムアルデヒド水溶
液の安定化に関する。更に詳しくは、高濃度ホルムアル
デヒド水溶液におけるパラホルムアルデヒドの沈殿生成
を効果的に防止する方法に関する。FIELD OF THE INVENTION This invention relates to the stabilization of aqueous formaldehyde solutions. More specifically, the present invention relates to a method for effectively preventing precipitation of paraformaldehyde in a highly concentrated formaldehyde aqueous solution.
【０００２】0002
【従来の技術】ホルムアルデヒドは一般的に３７ｗｔ％
のホルムアルデヒド水溶液として市販されている。また
、近年になって、高濃度ホルムアルデヒド水溶液として
４０〜５０ｗｔ％のホルムアルデヒド水溶液が工業的に
使用されるようになった。ホルムアルデヒドの利用の観
点からみると、ホルムアルデヒドの濃度は高いほど好ま
しいが、高濃度のホルムアルデヒド水溶液はパラホルム
アルデヒドの沈殿析出のために著しく安定性に乏しく、
その取扱いは非常に困難である。[Prior art] Formaldehyde is generally 37 wt%
It is commercially available as an aqueous formaldehyde solution. Moreover, in recent years, 40 to 50 wt % formaldehyde aqueous solutions have come to be used industrially as highly concentrated formaldehyde aqueous solutions. From the perspective of formaldehyde utilization, the higher the concentration of formaldehyde, the better; however, highly concentrated formaldehyde aqueous solutions are extremely unstable due to precipitation of paraformaldehyde.
Its handling is extremely difficult.
【０００３】一般に、ホルムアルデヒドは水溶液中では
大部分が水和し、下記化１に示すようなメチレングリコ
ール又は低級ポリオキシメチレングリコールの平衡混合
物として存在している。Generally, formaldehyde is mostly hydrated in an aqueous solution, and exists as an equilibrium mixture of methylene glycol or lower polyoxymethylene glycol as shown in Formula 1 below.
【０００４】0004
【化１】[Chemical formula 1]
【０００５】この平衡はホルムアルデヒド濃度が高くな
るにしたがって高重合度側に移動し、高重合度成分は水
に不溶のパラホルムアルデヒドとして沈殿してくる。著
しい場合には全体が固化することもある。また、ホルム
アルデヒド水溶液の温度が低くなってもポリオキシメチ
レングリコールの溶解度の低下が起き、パラホルムアル
デヒドが沈殿する。パラホルムアルデヒドの沈殿が析出
したホルムアルデヒド水溶液は濃度が変化している為に
その取扱いが困難なばかりでなく、装置・配管等の閉塞
の原因ともなり、工業用の原料としては利用しがたい。[0005] As the formaldehyde concentration increases, this equilibrium shifts toward a higher degree of polymerization, and components with a higher degree of polymerization precipitate as paraformaldehyde which is insoluble in water. In severe cases, the entire product may solidify. Further, even if the temperature of the formaldehyde aqueous solution becomes low, the solubility of polyoxymethylene glycol decreases, and paraformaldehyde precipitates. An aqueous formaldehyde solution in which paraformaldehyde has precipitated is not only difficult to handle because of its varying concentration, but also causes clogging of equipment, piping, etc., making it difficult to use as an industrial raw material.
【０００６】ホルムアルデヒド水溶液におけるパラホル
ムアルデヒドの沈殿を防止するために、ホルムアルデヒ
ド水溶液の温度を高くする、メタノール含有率を高くす
る、種々の添加剤を加える、等の方法が取られている。
しかしながら、温度を高くするとカニッツァロ反応によ
り蟻酸が生成し、腐食の問題が生じてくる。また、メタ
ノールの含有率が高いと使用に際してメタノールの分離
等の問題がある。ホルムアルデヒド水溶液におけるパラ
ホルムアルデヒドの沈殿析出防止剤としては種々の化合
物が開示されており、ポリビニルアルコール及びそのホ
ルマール化物は特公昭４４−１８２８２号公報、特開昭
６３−３０３９４４号公報等から公知である。また、ト
リアジン系化合物は特公昭４０−９０号公報、特公昭５
７−６１００９号公報等により公知であり、多価アルコ
ール系化合物は特公昭３７−４１０９号公報、特公昭３
８−６７５６号公報等により、アミド系化合物は特公昭
４１−１２２１３号公報、特公昭４２−２６７６３号公
報により公知である。[0006] In order to prevent precipitation of paraformaldehyde in an aqueous formaldehyde solution, methods such as increasing the temperature of the aqueous formaldehyde solution, increasing the methanol content, and adding various additives have been taken. However, when the temperature is raised, formic acid is produced by the Cannizzaro reaction, causing corrosion problems. Furthermore, if the methanol content is high, there are problems such as separation of methanol during use. Various compounds have been disclosed as agents for preventing the precipitation of paraformaldehyde in an aqueous formaldehyde solution, and polyvinyl alcohol and formalized products thereof are known from Japanese Patent Publication No. 44-18282, Japanese Patent Application Laid-open No. 63-303944, and the like. In addition, triazine compounds are disclosed in Japanese Patent Publication No. 40-90 and Japanese Patent Publication No. 5
It is known from Japanese Patent Publication No. 7-61009, etc., and polyhydric alcohol compounds are disclosed in Japanese Patent Publication No. 37-4109, Japanese Patent Publication No. 3
Amide compounds are known from Japanese Patent Publication No. 12213/1982 and Japanese Patent Publication No. 26763/1989.
【０００７】[0007]
【発明が解決しようとする課題】しかしながら、上記の
添加剤は、上記各公報の実施例に記載されているが如く
ホルムアルデヒドの濃度が約５５ｗｔ％以下の場合は十
分な効果を発揮するが、５５ｗｔ％以上の高濃度のホル
ムアルデヒド水溶液の安定化については記載されていな
い。[Problems to be Solved by the Invention] However, the above-mentioned additives exhibit sufficient effects when the concentration of formaldehyde is about 55 wt% or less, as described in the examples of the above-mentioned publications; There is no description of stabilization of a formaldehyde aqueous solution with a high concentration of % or more.
【０００８】本発明の目的は、５５ｗｔ％以上の高濃度
のホルムアルデヒド水溶液においてもパラホルムアルデ
ヒドの沈殿析出を防止する安定化剤を提供することにあ
る。An object of the present invention is to provide a stabilizer that prevents precipitation of paraformaldehyde even in a formaldehyde aqueous solution with a high concentration of 55 wt % or more.
【０００９】[0009]
【課題を解決するための手段】本発明者らは、上記の問
題を解決するために鋭意検討を行った結果、ホルムアル
デヒド水溶液に溶解し、且つ、官能基を有するケトン類
化合物を１種類以上添加することにより、５５ｗｔ％を
越えるホルムアルデヒド水溶液においてもパラホルムア
ルデヒドの沈殿析出を効果的に防止することを見出し、
本発明を完成した。[Means for Solving the Problems] As a result of extensive studies in order to solve the above problems, the present inventors have discovered that one or more ketone compounds that are dissolved in an aqueous formaldehyde solution and have a functional group are added. It was discovered that by doing so, precipitation of paraformaldehyde can be effectively prevented even in formaldehyde aqueous solutions exceeding 55 wt%,
The invention has been completed.
【００１０】即ち、本発明は、ホルムアルデヒド水溶液
に溶解し、かつ、官能基を有するケトン類化合物、また
はホルムアルデヒド水溶液に溶解するケトン類化合物の
オキシムから選ばれた１種以上を添加するホルムアルデ
ヒド水溶液を安定化させる方法である。本発明によるホ
ルムアルデヒド水溶液の安定化剤として用いられる官能
基を有するケトン類化合物としては、ホルムアルデヒド
水溶液に溶解しうる化合物である。詳しくは、官能基と
して水酸基、アミノ基、カルボキシル基を有するケトン
類化合物、又は、ケトン類化合物のオキシムの中から選
ばれた少なくとも１種類の化合物である。That is, the present invention stabilizes a formaldehyde aqueous solution by adding one or more selected from ketone compounds having a functional group or oximes of ketone compounds soluble in the formaldehyde aqueous solution. This is a method to make it easier to understand. The ketone compound having a functional group used as a stabilizer for an aqueous formaldehyde solution according to the present invention is a compound that can be dissolved in an aqueous formaldehyde solution. Specifically, it is at least one type of compound selected from ketone compounds having a hydroxyl group, amino group, or carboxyl group as a functional group, or oximes of ketone compounds.
【００１１】更に詳しくは、官能基を有するケトン類化
合物の例として例えば、アセトール、プロピオニルカル
ビノール、アセチルメチルカルビノール、アセチルエチ
ルカルビノール、プロピオニルメチルカルビノール、ア
セチルジメチルカルビノール、プロピオノイン、ブチロ
イン、２−アセトエチルアルコール、ジアセトンアルコ
ール、γ−アセトプロパノール、δ−アセトブタノール
等のケトール類化合物、オキシメチレンアセトン、オキ
シメチレンメチルエチルケトン等のオレフィンケトール
類化合物、アミノアセトン、アミノメチルケトン、ジメ
チルアミノアセトン、ジエチルアミノアセトン、アミノ
アセトフェノン等のアミノケトン類化合物、アセトンカ
ルボン酸、アセトンジカルボン酸等のカルボキシル基を
有するケトン類化合物、アセトンオキシム等のケトン類
化合物のオキシムなどが挙げられる。これらの単独又は
二種以上を組み合わせて使用される。More specifically, examples of ketone compounds having functional groups include acetol, propionylcarbinol, acetylmethylcarbinol, acetylethylcarbinol, propionylmethylcarbinol, acetyldimethylcarbinol, propionoin, butyroin, 2 - Ketols such as acetoethyl alcohol, diacetone alcohol, γ-acetopropanol, δ-acetobutanol, olefin ketols such as oxymethylene acetone, oxymethylene methyl ethyl ketone, aminoacetone, aminomethyl ketone, dimethylaminoacetone, diethylamino Examples include aminoketone compounds such as acetone and aminoacetophenone, ketone compounds having a carboxyl group such as acetone carboxylic acid and acetone dicarboxylic acid, and oximes of ketone compounds such as acetone oxime. These may be used alone or in combination.
【００１２】これらケトン類化合物がホルムアルデヒド
水溶液の安定化にどのようなメカニズムで作用している
かは明確ではないが、これらケトン類化合物はホルムア
ルデヒド水溶液中においてホルムアルデヒドとの反応に
よりメチロール化物等を生成し、これがホルムアルデヒ
ド水溶液の安定化に寄与していると推定される。ホルム
アルデヒド水溶液におけるパラホルムアルデヒドの沈殿
生成を抑制するための官能基を有するケトン類化合物の
添加量は、ホルムアルデヒド水溶液のホルムアルデヒド
濃度、温度、含有するメタノール濃度等により決定され
るが、０．００１ｗｔ％以上添加することが好ましく、
より好ましくは０．０１ｗｔ％以上、更に好ましくは０
．１ｗｔ％以上添加することが望ましい。Although it is not clear what mechanism these ketone compounds act to stabilize the formaldehyde aqueous solution, these ketone compounds produce methylolated compounds etc. by reaction with formaldehyde in the formaldehyde aqueous solution. It is estimated that this contributes to stabilizing the formaldehyde aqueous solution. The amount of the ketone compound having a functional group for suppressing precipitation of paraformaldehyde in the formaldehyde aqueous solution is determined by the formaldehyde concentration of the formaldehyde aqueous solution, the temperature, the methanol concentration contained, etc., but the addition amount is 0.001 wt% or more. It is preferable to
More preferably 0.01 wt% or more, still more preferably 0
．． It is desirable to add 1 wt% or more.
【００１３】本発明でいうホルムアルデヒド水溶液は、
ホルムアルデヒドを含む水溶液を意味しており、例えば
、メチラール、メタノール又はジメチルエーテル等の酸
化反応により得たホルムアルデヒドを水に吸収させて製
造した溶液、パラホルムアルデヒドを水に溶解させて製
造した溶液、これらの溶液の蒸留、ストリッピング等の
操作により得られる溶液等が挙げられる。また、これら
のホルムアルデヒド水溶液は、ホルムアルデヒドの由来
や操作等により、メチラール、メタノール、ジメチルエ
ーテル、蟻酸、蟻酸メチル、トリオキサン等の化合物を
含んでいても差し支えない。[0013] The formaldehyde aqueous solution referred to in the present invention is
This refers to an aqueous solution containing formaldehyde, such as a solution produced by absorbing formaldehyde obtained through an oxidation reaction of methylal, methanol, or dimethyl ether in water, a solution produced by dissolving paraformaldehyde in water, and these solutions. Examples include solutions obtained by operations such as distillation and stripping. Further, these formaldehyde aqueous solutions may contain compounds such as methylal, methanol, dimethyl ether, formic acid, methyl formate, trioxane, etc., depending on the origin of formaldehyde, operation, etc.
【００１４】[0014]
【実施例】以下、実施例を挙げて本発明を詳細に説明す
る。
〔実施例１及び比較例１〕６５ｗｔ％のホルムアルデヒ
ド水溶液（メタノール５．５ｗｔ％含有）に表１に示す
官能基を有するケトン類化合物を添加し、９０℃で１Ｈ
ｒ維持した後、徐々に温度を下げて６７℃に維持し、３
Ｈｒ後にパラホルムアルデヒドの沈殿析出（白濁）の状
況を目視観察した。その結果を表１に示す。
〔実施例２及び比較例２〕５０ｗｔ％のホルムアルデヒ
ド水溶液（メタノール４．０ｗｔ％含有）に表２に示す
官能基を有するケトン類化合物を添加し、溶液の温度を
３０℃に維持し、１日後にパラホルムアルデヒドの沈殿
析出（白濁）の状況を観察した。その結果を表２に示す
。
〔実施例３及び比較例３〕３７ｗｔ％のホルムアルデヒ
ド水溶液（メタノール３．０ｗｔ％含有）に表３に示す
官能基を有するケトン類化合物を添加し、溶液の温度を
０℃に維持し、１日後のパラホルムアルデヒドの沈殿析
出（白濁）の状況を観察した。その結果を表３に示す。[Examples] The present invention will be explained in detail below with reference to Examples. [Example 1 and Comparative Example 1] A ketone compound having a functional group shown in Table 1 was added to a 65 wt% formaldehyde aqueous solution (containing 5.5 wt% methanol), and the mixture was heated at 90°C for 1 H.
After maintaining r, the temperature was gradually lowered and maintained at 67℃, and
After hours, the state of precipitation (white turbidity) of paraformaldehyde was visually observed. The results are shown in Table 1. [Example 2 and Comparative Example 2] A ketone compound having a functional group shown in Table 2 was added to a 50 wt% formaldehyde aqueous solution (containing 4.0 wt% methanol), and the temperature of the solution was maintained at 30°C for 1 day. Afterwards, the state of precipitation (white turbidity) of paraformaldehyde was observed. The results are shown in Table 2. [Example 3 and Comparative Example 3] A ketone compound having a functional group shown in Table 3 was added to a 37 wt% formaldehyde aqueous solution (containing 3.0 wt% methanol), the temperature of the solution was maintained at 0°C, and after 1 day. The state of precipitation (white turbidity) of paraformaldehyde was observed. The results are shown in Table 3.
【００１５】[0015]
【表１】[Table 1]
【００１６】[0016]
【表２】[Table 2]
【００１７】[0017]
【表３】[Table 3]
【００１８】[0018]
【発明の効果】本発明は、５５％以上のホルムアルデヒ
ド水溶液においてもパラホルムアルデヒドの沈殿析出を
効果的に防止することができ、低い温度においても安定
に取り扱うことができる。Effects of the Invention The present invention can effectively prevent precipitation of paraformaldehyde even in an aqueous formaldehyde solution of 55% or more, and can be stably handled even at low temperatures.
Claims (2)
つ、官能基を有するケトン類化合物、またはホルムアル
デヒド水溶液に溶解するケトン類化合物のオキシムから
選ばれた１種類以上を添加することを特徴とするホルム
アルデヒド水溶液の安定化方法。1. An aqueous formaldehyde solution, which is soluble in an aqueous formaldehyde solution and contains one or more selected from ketone compounds having a functional group, or oximes of ketone compounds soluble in an aqueous formaldehyde solution. Stabilization method.
キシル基であることを特徴とする請求項１記載の方法。2. The method according to claim 1, wherein the functional group is a hydroxyl group, an amino group, or a carboxyl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2108491A JPH04330031A (en) | 1991-02-14 | 1991-02-14 | Method for stabilizing aqueous solution of formaldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2108491A JPH04330031A (en) | 1991-02-14 | 1991-02-14 | Method for stabilizing aqueous solution of formaldehyde |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04330031A true JPH04330031A (en) | 1992-11-18 |
Family
ID=12045016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2108491A Withdrawn JPH04330031A (en) | 1991-02-14 | 1991-02-14 | Method for stabilizing aqueous solution of formaldehyde |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04330031A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5912389A (en) * | 1996-04-17 | 1999-06-15 | Katayama Chemical, Inc. | Stabilizer and stabilizing method for aqueous aliphatic aldehyde solution |
-
1991
- 1991-02-14 JP JP2108491A patent/JPH04330031A/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5912389A (en) * | 1996-04-17 | 1999-06-15 | Katayama Chemical, Inc. | Stabilizer and stabilizing method for aqueous aliphatic aldehyde solution |
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