JPH02270846A - Stabilization of n-vinylacetamide - Google Patents
Stabilization of n-vinylacetamideInfo
- Publication number
- JPH02270846A JPH02270846A JP9418989A JP9418989A JPH02270846A JP H02270846 A JPH02270846 A JP H02270846A JP 9418989 A JP9418989 A JP 9418989A JP 9418989 A JP9418989 A JP 9418989A JP H02270846 A JPH02270846 A JP H02270846A
- Authority
- JP
- Japan
- Prior art keywords
- nva
- stabilizer
- vinylacetamide
- salt
- organic
- 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.)
- Granted
Links
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 230000006641 stabilisation Effects 0.000 title 1
- 238000011105 stabilization Methods 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 10
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 239000007864 aqueous solution Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 8
- -1 amine compound Chemical class 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000002484 inorganic compounds Chemical class 0.000 claims 1
- 229910010272 inorganic material Inorganic materials 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 abstract description 16
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 abstract description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract description 5
- 230000006866 deterioration Effects 0.000 abstract description 5
- 239000001632 sodium acetate Substances 0.000 abstract description 5
- 235000017281 sodium acetate Nutrition 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 abstract description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 abstract description 4
- 239000000243 solution Substances 0.000 abstract description 3
- 229920003169 water-soluble polymer Polymers 0.000 abstract description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 abstract description 2
- 239000005695 Ammonium acetate Substances 0.000 abstract description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 abstract description 2
- 235000019257 ammonium acetate Nutrition 0.000 abstract description 2
- 229940043376 ammonium acetate Drugs 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 239000006185 dispersion Substances 0.000 abstract description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 abstract description 2
- 235000011009 potassium phosphates Nutrition 0.000 abstract description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract description 2
- 235000017550 sodium carbonate Nutrition 0.000 abstract description 2
- 229960003080 taurine Drugs 0.000 abstract description 2
- 239000003513 alkali Substances 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 229910017053 inorganic salt Inorganic materials 0.000 abstract 1
- 239000006076 specific stabilizer Substances 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- 238000004821 distillation Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- 238000005979 thermal decomposition reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- VETPHHXZEJAYOB-UHFFFAOYSA-N 1-n,4-n-dinaphthalen-2-ylbenzene-1,4-diamine Chemical compound C1=CC=CC2=CC(NC=3C=CC(NC=4C=C5C=CC=CC5=CC=4)=CC=3)=CC=C21 VETPHHXZEJAYOB-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000005819 Potassium phosphonate Substances 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- YXXXKCDYKKSZHL-UHFFFAOYSA-M dipotassium;dioxido(oxo)phosphanium Chemical compound [K+].[K+].[O-][P+]([O-])=O YXXXKCDYKKSZHL-UHFFFAOYSA-M 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000001055 magnesium Nutrition 0.000 description 1
- 229940091250 magnesium supplement Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SJSZBOAQWPKFMU-UHFFFAOYSA-N n-(1-acetamidoethyl)acetamide Chemical group CC(=O)NC(C)NC(C)=O SJSZBOAQWPKFMU-UHFFFAOYSA-N 0.000 description 1
- MQLURDBHIIRSQU-UHFFFAOYSA-N n-(1-butoxyethyl)acetamide Chemical group CCCCOC(C)NC(C)=O MQLURDBHIIRSQU-UHFFFAOYSA-N 0.000 description 1
- RYGPJMDKDKHOTB-UHFFFAOYSA-N n-(1-methoxyethyl)acetamide Chemical group COC(C)NC(C)=O RYGPJMDKDKHOTB-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 239000004324 sodium propionate Substances 0.000 description 1
- 235000010334 sodium propionate Nutrition 0.000 description 1
- 229960003212 sodium propionate Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- NCPXQVVMIXIKTN-UHFFFAOYSA-N trisodium;phosphite Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])[O-] NCPXQVVMIXIKTN-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（１）産業上の利用分野
本発明はＮ−ビニルアセトアミド（以下ｒＮＶＡＪと略
す）の安定化方法に関する。更に詳しくはＮＶＡの貯蔵
時、蒸留精製時、または反応時等に安定化剤を添加して
ＮＶＡの変質を防止する方法に関する。ＮＶＡは、ポリ
ビニルアミンをはじめとする水溶性ポリマーの原料、あ
るいはタウリン、システアミン等の有機薬品の中間原料
として有用であることが知られている。DETAILED DESCRIPTION OF THE INVENTION (1) Industrial Application Field The present invention relates to a method for stabilizing N-vinylacetamide (hereinafter abbreviated as rNVAJ). More specifically, the present invention relates to a method for preventing deterioration of NVA by adding a stabilizer during storage, distillation purification, reaction, etc. of NVA. NVA is known to be useful as a raw material for water-soluble polymers such as polyvinylamine, or as an intermediate raw material for organic chemicals such as taurine and cysteamine.
（２）従来の技術
ＮＶＡは、水溶性ポリマーを与える重合性モノマーとし
て、また、有機薬品の中間原料として有用なものであり
（たとえば米国特許第４０１８８２６号公報、特開昭６
１−１．９１６７１号、同６１．−２８２３５４号）、
また、その製造法も種々の提案かある（たとえばジャー
ナル・オブ・アメリカン・ケミカル・ソサエティー第９
６巻、 ５９９６頁、 １９７６年、特開昭５５−１５
３７５４号）。しかし、Ｎ Ｖ Ａ ＋；ｔ、貯蔵時、
蒸留精製時、あるいは反応時にその一部が変質し、損失
を招きやすいことが知られている。(2) Conventional technology NVA is useful as a polymerizable monomer that provides water-soluble polymers and as an intermediate raw material for organic drugs (for example, U.S. Pat. No. 4,018,826, JP-A No. 6
No. 1-1.91671, 61. -282354),
There are also various proposals for manufacturing methods (for example, Journal of American Chemical Society, No. 9).
Volume 6, page 5996, 1976, Japanese Patent Publication No. 55-15
No. 3754). However, N V A +;t, during storage;
It is known that a part of it deteriorates during distillation and purification or during reaction, which tends to lead to losses.
（３）発明が解決しようとする課題
本発明は、上記実状に鑑み、貯蔵時、蒸留精製時、ある
いは反応時等のＮＶＡの変質による損失を防止するため
の簡便な方法の提供を目的とする。(3) Problems to be Solved by the Invention In view of the above-mentioned circumstances, the present invention aims to provide a simple method for preventing loss of NVA due to deterioration during storage, distillation purification, reaction, etc. .
（４）課題を解決するための手段 本発明の目的は、本発明の方法に従ってＮＶＡ。(4) Means to solve the problem The object of the invention is to perform NVA according to the method of the invention.
あるいはその溶液またはその分散液に安定化剤を添加す
ることにより達成される。Alternatively, this can be achieved by adding a stabilizer to the solution or dispersion.
すなわち本発明により、ＮＶＡに安定化剤を添加するこ
とでＮＶＡの安定化方法が提供される。That is, the present invention provides a method for stabilizing NVA by adding a stabilizer to NVA.
ＮＶＡは貯蔵時、蒸留精製時、あるいは反応時等に熱、
混在する不純物、溶媒、分散媒等の作用により一部変質
する傾向かある。本発明者等は、ＮＶＡの変質防止方法
につき鋭意検討を重ねた結果、本発明において特定する
安定化剤を添加した場合にＮＶＡの安定化か図れること
を見いだし本発明を完成するに至った。NVA is exposed to heat during storage, distillation purification, reaction, etc.
There is a tendency for some parts to change in quality due to the effects of mixed impurities, solvents, dispersion media, etc. The present inventors have conducted extensive studies on methods for preventing deterioration of NVA, and as a result, have found that NVA can be stabilized by adding the stabilizer specified in the present invention, and have completed the present invention.
本発明において対象となるＮＶＡはいかなる製法による
かは問わないが、たとえばアセトアルデヒドとアセトア
ミドの反応で得られるエチリデンビスアセトアミドの熱
分解（特開昭６１−１０Ｅｉ５４６号）、Ｎ−（α−ア
ルコキンエチル）アセトアミドの熱分解（特開昭５０−
７６０１５号）等によって合成される。NVA, which is the object of the present invention, can be produced by any method, but for example, thermal decomposition of ethylidene bisacetamide obtained by the reaction of acetaldehyde and acetamide (Japanese Unexamined Patent Publication No. 61-10Ei546), N-(α-alcokyne ethyl ) Thermal decomposition of acetamide
76015) etc.
本発明においてＮＶＡの安定化剤として用いられる化合
物としては、ジフェニルアミン、トリエチルアミン、α
−ナフチルアミン、β−ナフチルアミン、フェニルナフ
チルアミン、Ｎ、Ｎ′−ジ−β−ナフチル−ｐ−フェニ
レンジアミン、フェノチアジン等の有機アミン化合物；
炭酸ナトリウム、炭酸カルシウム、炭酸水素ナトリウム
、リン酸カリウム、リン酸ナトリウム、リン酸水素二カ
リウム、亜リン酸ナトリウム、亜リン酸カリウム、炭、
酸アンモニウム、リン酸アンモニウム等の、アルカリ金
属またはアルカリ土類金属の弱酸塩もしくは弱酸水素塩
あるいは弱酸のアンモニウム塩類であって、鎖環の水溶
液がアルカリ性を示す無機塩類、酢酸ナトリウム、酢酸
カリウム、酢酸マグネシウム、酢酸アンモニウム、プロ
ピオン酸ナトリウム、安息香酸すトリウム、安息香酸カ
リウム、ナトリウムフェノラート等の有機弱酸のアルカ
リ金属塩、アルカリ土類金属塩またはアンモニウム塩等
が挙げられる。Compounds used as stabilizers for NVA in the present invention include diphenylamine, triethylamine, α
- organic amine compounds such as naphthylamine, β-naphthylamine, phenylnaphthylamine, N,N'-di-β-naphthyl-p-phenylenediamine, phenothiazine;
Sodium carbonate, calcium carbonate, sodium hydrogen carbonate, potassium phosphate, sodium phosphate, dipotassium hydrogen phosphate, sodium phosphite, potassium phosphite, charcoal,
Weak acid salts or weak acid hydrogen salts of alkali metals or alkaline earth metals, or ammonium salts of weak acids, such as ammonium acid and ammonium phosphate, inorganic salts in which the aqueous solution of the chain ring is alkaline, sodium acetate, potassium acetate, acetic acid Examples include alkali metal salts, alkaline earth metal salts, or ammonium salts of organic weak acids such as magnesium, ammonium acetate, sodium propionate, striium benzoate, potassium benzoate, and sodium phenolate.
これらの安定化剤の使用量は、通常ＮＶＡに対して１１
０−５００００ｐｐ、好ましくは１００〜１００００１
）ｐＩｌｌの範囲であり、使用量が少なすぎるとＮＶＡ
の変質を十分に抑制できず、また多すぎてもその効果は
変わらないので経済的でない。上記の使用量の範囲で２
種以上の安定化剤を併用することも可能である。The amount of these stabilizers used is usually 11 to NVA.
0-50000pp, preferably 100-100001
) pIll range, and if used too little, NVA
It is not economical because the deterioration of the substance cannot be sufficiently suppressed, and even if the amount is too large, the effect remains the same. 2 within the above usage range
It is also possible to use more than one type of stabilizer.
本発明の安定化剤は、ＮＶＡの貯蔵時、蒸留精製時、あ
るいは反応時等に適宜添加することによりその目的か達
成される。The purpose of the stabilizer of the present invention can be achieved by appropriately adding it during storage, distillation purification, reaction, etc. of NVA.
（５）実施例
以下、実施例により本発明を更に詳しく説明するが、本
発明はこれらの実施例のみに限定されないことは言うま
でもない。(5) Examples Hereinafter, the present invention will be explained in more detail with reference to Examples, but it goes without saying that the present invention is not limited only to these Examples.
実施例 Ｉ
Ｎ−（α−メトキシエチル）アセトアミドの熱分解によ
り得られたＮＶＡ （純度８５５％） ２００ｇ及び
酢酸ナトリウム０．５ｇを内容積５００ｍ１のナス型フ
ラスコに入れ、浴ａ１１０℃、圧力５．５ｍｍ１１ｇで
減圧蒸留した。蒸留に要した時間は約１．５時間であっ
た。留出温度８７５℃〜９０．５℃の留分１５９．４ｇ
が得られ、ガスクロマトグラフィーによる分析では純度
９９．５％のＮＶＡてあった。蒸留収率は９２．８％で
あった。Example I 200 g of NVA (purity 855%) obtained by thermal decomposition of N-(α-methoxyethyl)acetamide and 0.5 g of sodium acetate were placed in an eggplant-shaped flask with an internal volume of 500 ml, and the mixture was heated to a bath a of 110° C. and a pressure of 5. Distilled under reduced pressure using 11 g of 5 mm. The time required for distillation was approximately 1.5 hours. 159.4g of distillate with a distillation temperature of 875°C to 90.5°C
was obtained, and analysis by gas chromatography showed that the purity of NVA was 99.5%. The distillation yield was 92.8%.
比較例 １
実施例１と同し条件でＮＶＡ （純度８５．５％）２０
０ｇを、安定化剤を加えずに蒸留した。３時間加熱を続
けたか、留分は１１０．５ｇに過ぎなかった。ガスクロ
マトグラフィーによる分析では純度８８．５％のＮＶＡ
であり、蒸留収率は５７．２％であった。蒸留残渣は７
５．５ｇであり、粘度の高いタール状物質に変質してい
た。Comparative Example 1 NVA (purity 85.5%) 20 under the same conditions as Example 1
0 g was distilled without adding any stabilizer. Although heating was continued for 3 hours, the fraction was only 110.5 g. NVA with a purity of 88.5% according to gas chromatography analysis
The distillation yield was 57.2%. Distillation residue is 7
The amount was 5.5 g, and it had deteriorated into a tar-like substance with high viscosity.
実施例 ２
Ｎ−（α−ブトキシエチル）アセトアミドの熱分解によ
り得られたＮＶＡ （純度５２．５％） １５６０ｇ及
びジフェニルアミン０．５ｇを内容積５００ｍ１ノナス
型フラスコに入れ、浴温１１０℃、圧力４．５ｙｎ＋ａ
ｌ１ｇで減圧蒸留した。蒸留に要した時間は約２．５時
間であった。留出温度８５．５℃〜８９．５℃の留分７
７７．８ｇが得られ、ガスクロマトグラフィーによる分
析では純度９９，５％のＮＶＡであった。蒸留収率は９
４．５％であった。Example 2 1560 g of NVA (purity 52.5%) obtained by thermal decomposition of N-(α-butoxyethyl)acetamide and 0.5 g of diphenylamine were placed in a 500 ml nonas-type flask, and the bath temperature was 110°C and the pressure was 4. .5yn+a
Distilled under reduced pressure using 11 g. The time required for distillation was approximately 2.5 hours. Fraction 7 with a distillation temperature of 85.5°C to 89.5°C
77.8 g was obtained, and analysis by gas chromatography showed that the purity was 99.5% NVA. The distillation yield is 9
It was 4.5%.
実施例３〜１に比較例２〜４
実施例２で用いた純度５２．５％のＮＶＡに種々の安定
化剤を加えて熱安定性を試験した。Examples 3 to 1 and Comparative Examples 2 to 4 Various stabilizers were added to the 52.5% pure NVA used in Example 2 to test its thermal stability.
Ｎ Ｖ Ａ ＩＱ、Ｏｇに対して安定化剤を０．２重量
％加え、１１０℃で２時間加熱後、ガスクロマトグラフ
ィーにより残存するＮＶＡを分析した。その結果及び比
較例２として安定化剤を加えない場合のＮＶＡの残存率
、また、比較例３．４として一般のラジカル重合禁止剤
を添加したときの結果を表１に示した。A stabilizer was added in an amount of 0.2% by weight based on NVA IQ, Og, and after heating at 110° C. for 2 hours, remaining NVA was analyzed by gas chromatography. Table 1 shows the results, the residual rate of NVA when no stabilizer was added as Comparative Example 2, and the results when a general radical polymerization inhibitor was added as Comparative Example 3.4.
（以下余白）
表 １
実施例 ８
実施例１で使用したものと同じＮＶＡ （純度８５．５
％） Ｉｏｏ、０ｇ及び酢酸ナトリウム０．２５ｇを
試薬瓶に入れ密封し、１５０日間室温にて貯蔵した。(Margin below) Table 1 Example 8 Same NVA as used in Example 1 (purity 85.5
%) Ioo, 0 g and sodium acetate, 0.25 g, were placed in a reagent bottle, sealed, and stored at room temperature for 150 days.
ガスクロマトグラフィーにより分析したところＮＶＡの
２，３％が変質していた。Analysis by gas chromatography revealed that 2.3% of the NVA was altered.
比較例 ５
酢酸ナトリウムを添加しない以外は実施例８と同様にＮ
ＶＡを室温で１５０１Ｊ間貯蔵した。ガスクロマトグラ
フィーにより分析したところＮＶＡの１８．５％が変質
していた。Comparative Example 5 Same as Example 8 except that sodium acetate was not added.
VA was stored for 1501 J at room temperature. Analysis by gas chromatography revealed that 18.5% of the NVA was altered.
（６）発明の効果
本発明によれば、従来貯蔵時、蒸留精製時、または反応
時に変質し、損失を招く傾向のあったＮＶＡに安定化剤
を添加することにより簡便かつ経済的に安定化を図るこ
とが可能である。(6) Effects of the Invention According to the present invention, by adding a stabilizer to NVA, which has conventionally tended to change in quality and cause losses during storage, distillation purification, or reaction, it can be stabilized simply and economically. It is possible to achieve this.
したがって、ＮＶＡの取り扱いに際して安定化剤を適宜
添加することによりＮＶＡの一部が変質するのを防１１
−でき、そのためＮＶＡの損失が避けられる。Therefore, by appropriately adding a stabilizer when handling NVA, it is possible to prevent part of the NVA from deteriorating.
- possible, thus avoiding loss of NVA.
Claims (1)
しくは弱酸のアンモニウム塩であって、該塩の水溶液が
アルカリ性を示す無機塩類、 （３）炭素数１〜６の有機弱酸のアルカリ金属、アルカ
リ土類金属塩またはアンモニウム塩、 から成る群から選択された少くとも１種の安定化剤を添
加することを特徴とするＮ−ビニルアセトアミドの安定
化方法。[Scope of Claims] N-vinylacetamide, (1) an organic amine compound, (2) a weak acid salt of an alkali metal or alkaline earth metal, or an ammonium salt of a weak acid, which is an inorganic compound whose aqueous solution is alkaline. (3) an alkali metal, alkaline earth metal salt or ammonium salt of an organic weak acid having 1 to 6 carbon atoms; - Method for stabilizing vinyl acetamide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9418989A JP2619527B2 (en) | 1989-04-13 | 1989-04-13 | Method for stabilizing N-vinylacetamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9418989A JP2619527B2 (en) | 1989-04-13 | 1989-04-13 | Method for stabilizing N-vinylacetamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02270846A true JPH02270846A (en) | 1990-11-05 |
| JP2619527B2 JP2619527B2 (en) | 1997-06-11 |
Family
ID=14103359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9418989A Expired - Fee Related JP2619527B2 (en) | 1989-04-13 | 1989-04-13 | Method for stabilizing N-vinylacetamide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2619527B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5352828A (en) * | 1991-05-22 | 1994-10-04 | Nitto Chemical Industry Co., Ltd. | Process for stabilizing aqueous acrylamide solution |
| US5840976A (en) * | 1994-05-30 | 1998-11-24 | Mitsubishi Chemical Corporation | Method of stabilizing N-vinylamides |
| JP2002167369A (en) * | 2000-09-19 | 2002-06-11 | Showa Denko Kk | Method for preparing high polymeric n-vinylcarboxylic acid amide |
-
1989
- 1989-04-13 JP JP9418989A patent/JP2619527B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5352828A (en) * | 1991-05-22 | 1994-10-04 | Nitto Chemical Industry Co., Ltd. | Process for stabilizing aqueous acrylamide solution |
| US5840976A (en) * | 1994-05-30 | 1998-11-24 | Mitsubishi Chemical Corporation | Method of stabilizing N-vinylamides |
| JP2002167369A (en) * | 2000-09-19 | 2002-06-11 | Showa Denko Kk | Method for preparing high polymeric n-vinylcarboxylic acid amide |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2619527B2 (en) | 1997-06-11 |
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