JP4959683B2 - アクリルアミドの製造方法 - Google Patents
アクリルアミドの製造方法 Download PDFInfo
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- JP4959683B2 JP4959683B2 JP2008509793A JP2008509793A JP4959683B2 JP 4959683 B2 JP4959683 B2 JP 4959683B2 JP 2008509793 A JP2008509793 A JP 2008509793A JP 2008509793 A JP2008509793 A JP 2008509793A JP 4959683 B2 JP4959683 B2 JP 4959683B2
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- Prior art keywords
- acrylamide
- polymer
- acid
- polymerization
- weight
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- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 2
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
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- RKSYJNCKPUDQET-UHFFFAOYSA-N n,n-dipropylprop-2-enamide Chemical compound CCCN(CCC)C(=O)C=C RKSYJNCKPUDQET-UHFFFAOYSA-N 0.000 description 1
- YRDNVESFWXDNSI-UHFFFAOYSA-N n-(2,4,4-trimethylpentan-2-yl)prop-2-enamide Chemical compound CC(C)(C)CC(C)(C)NC(=O)C=C YRDNVESFWXDNSI-UHFFFAOYSA-N 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- BLIQQXSBYNKXAC-UHFFFAOYSA-N n-[4-(oxiran-2-ylmethoxy)butyl]prop-2-enamide Chemical compound C=CC(=O)NCCCCOCC1CO1 BLIQQXSBYNKXAC-UHFFFAOYSA-N 0.000 description 1
- MMMCIGSNLXGQIZ-UHFFFAOYSA-N n-[6-(oxiran-2-ylmethoxy)hexyl]prop-2-enamide Chemical compound C=CC(=O)NCCCCCCOCC1CO1 MMMCIGSNLXGQIZ-UHFFFAOYSA-N 0.000 description 1
- XQPVIMDDIXCFFS-UHFFFAOYSA-N n-dodecylprop-2-enamide Chemical compound CCCCCCCCCCCCNC(=O)C=C XQPVIMDDIXCFFS-UHFFFAOYSA-N 0.000 description 1
- ZIWDVJPPVMGJGR-UHFFFAOYSA-N n-ethyl-2-methylprop-2-enamide Chemical compound CCNC(=O)C(C)=C ZIWDVJPPVMGJGR-UHFFFAOYSA-N 0.000 description 1
- SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical compound CCNC(=O)C=C SWPMNMYLORDLJE-UHFFFAOYSA-N 0.000 description 1
- AWGZKFQMWZYCHF-UHFFFAOYSA-N n-octylprop-2-enamide Chemical compound CCCCCCCCNC(=O)C=C AWGZKFQMWZYCHF-UHFFFAOYSA-N 0.000 description 1
- WDFKEEALECCKTJ-UHFFFAOYSA-N n-propylprop-2-enamide Chemical compound CCCNC(=O)C=C WDFKEEALECCKTJ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000004391 petroleum recovery Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006327 polystyrene foam Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- QJWFJOSRSZOLKK-UHFFFAOYSA-N prop-2-enamide Chemical compound NC(=O)C=C.NC(=O)C=C QJWFJOSRSZOLKK-UHFFFAOYSA-N 0.000 description 1
- BNMCQIRVFUGISV-UHFFFAOYSA-N propan-2-one;prop-2-enamide Chemical compound CC(C)=O.NC(=O)C=C BNMCQIRVFUGISV-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- REAPNPHEZNJFRY-UHFFFAOYSA-M sodium;4-cyanopentanoate Chemical compound [Na+].N#CC(C)CCC([O-])=O REAPNPHEZNJFRY-UHFFFAOYSA-M 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F20/56—Acrylamide; Methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
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- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
ニトリルヒドラターゼを含有する菌体、またはその菌体処理物を用い、アクリルニトリルを水和して得られるアクリルアミドに、ジメドン、バルビツール酸、ヒダントイン、およびこれらの塩からなる群より選ばれる少なくとも1つの化合物および/または少なくとも1つの上記化合物の塩をアクリルアミドに添加する点に特徴がある。また本発明のアクリルアミド系重合体は、上記アクリルアミドを単独重合、または上記アクリルアミドと共重合可能な少なくとも1種の不飽和単量体と共重合することにより得られる。
本発明で用いるアクリルアミドは、ニトリルヒドラターゼを含有する微生物菌体、またはその菌体処理物を触媒とし、アクリロニトリルを水和して得られる。このようにして得られるアクリルアミドは、例えば、銅触媒によりアクリロニトリルを接触水和して得られるアクリルアミドと比べ、一般的に、不純物が少なくアクリルアミドの重合に悪影響を与えない。しかし、品質の向上、およびこのアクリルアミドを重合して得られる重合体の品質については問題となる場合があった。
本発明では上記アクリルアミドにジメドン、バルビツール酸、ヒダントイン、およびこれらの塩からなる群より選ばれる少なくとも1つの化合物および/または少なくとも1つの上記化合物の塩をアクリルアミドに添加する。
本発明のアクリルアミドを用いて、アクリルアミドを単独重合、またはアクリルアミドをその他の単量体と共重合することができる。
アクリル酸、メタクリル酸、イタコン酸、マレイン酸、フマル酸などの不飽和カルボン酸およびそれらの塩;
ビニルスルホン酸、スチレンスルホン酸、アクリルアミドメチルプロパンスルホン酸およびそれらの塩;
N,N−ジメチルアミノエチルメタクリレート、N,N−ジエチルアミノエチルメタクリレート、N,N−ジメチルアミノエチルアクリレートアクリル酸などの(メタ)アクリル酸のアルキルアミノアルキルエステル、またはそれらの第4級アンモニウム誘導体;
N−N−ジメチルアミノプロピルメタクリルアミド、N,N−ジメチルアミノプロピルアクリルアミドなどのN−N−ジアルキルアミノアルキル(メタ)アクリルアミド、またはそれらの4級アンモニウム誘導体;
アセトンアクリルアミド、N,N−ジメチルアクリルアミド、N,N−ジメチルメタクリルアミド、N−エチルメタクリルアミド、N−エチルアクリルアミド、N,N−ジエチルアクリルアミド、N−プロピルアクリルアミドなどの親水性アクリルアミド;
N−アクリロイルピロリジン、N−アクリロイルピペリジン、N−アクリロイルモルホリン;
ヒドロキシエチルメタクリレート、ヒドロキシエチルアクリレート、ヒドロキシプロピルメタクリレート、ヒドロキシプロピルアクリレート;
メトキシポリエチレングリコール(メタ)アクリレート、N−ビニル−2−ピロリドン;N,N−ジ−n−プロピルアクリルアミド、N−n−ブチルアクリルアミド、N−n−ヘキシルアクリルアミド、N−n−ヘキシルメタクリルアミド、N−n−オクチルアクリルアミド、N−n−オクチルメタクリルアミド、N−tert−オクチルアクリルアミド、N−ドデシルアクリルアミド、N−n−ドデシルメタクリルアミドなどのN−アルキル(メタ)アクリルアミド誘導体;
N,N−ジグリシジルアクリルアミド、N,N−ジグリシジルメタクリルアミド、N−(4−グリシドキシブチル)アクリルアミド、N−(4−グリシドキシブチル)メタクリルアミド、N−(5−グリシドキシペンチル)アクリルアミド、N−(6−グリシドキシヘキシル)アクリルアミドなどのN−(ω−グリシドキシアルキル)(メタ)アクリルアミド誘導体;
メチル(メタ)アクリレート、エチル(メタ)アクリレート、ブチル(メタ)アクリレート、ラウリル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、グリシジル(メタ)アクリレートなどの(メタ)アクリレート誘導体;
アクリロニトリル、メタクリロニトリル、酢酸ビニル、塩化ビニル、塩化ビニリデン、エチレン、プロピレン、ブテン等のオレフィン類、スチレン、αメチルスチレン、ブタジエン、イソプレン、メタクリルアミドなどが挙げられる。
過硫酸カリウム、過硫酸アンモニウム、過酸化水素、過酸化ベンゾイル等の過酸化物;アゾビスイソブチロニトリル、2・2’−アゾビス(4−アミジノプロパン)2塩酸塩、4・4’−アゾビス(4−シアノバレリアン酸ナトリウム)などのアゾ系遊離基開始剤;上記過酸化物と重亜硫酸ナトリウム、トリエタノールアミン、硫酸第一鉄アンモニウム等の還元剤を併用するいわゆるレドックス系触媒、ジメチルアミノプロピオニトリルが挙げられる。
(アクリルアミドの製造)
[ニトロリルヒドラターゼを含む菌体の培養]
特開2001−340091号の実施例1に記載の方法に従い、No.3クローン菌体を取得し、同じく、同実施例1の方法で培養してニトロリルヒドラターゼを含む湿菌体を得た。
第1反応器として攪拌器を備えた1Lガラス製フラスコ、第二反応器として内径5mmのテフロン(登録商標)製チューブ40mを準備した。第一反応器には、予め400gの水を仕込んだ。
[実施例2]
実施例1で得られたアクリルアミド水溶液にバルビツール酸を100重量ppm加えたのち、水を加え濃度20重量%のアクリルアミド水溶液とした。この20重量%アクリルアミド水溶液500gを1lポリエチレン容器に入れ、18℃に保ちながら、窒素を通じて液中の溶存酸素を除き、直ちに、発泡スチロール製の保温用ブロックの中に入れた。
実施例1で得られたアクリルアミド水溶液に、バルビツール酸の代わりにジメドンを100重量ppm添加した以外は、実施例2と同様な操作を行い、ポリマーサンプルを得た。
実施例1で得られたアクリルアミド水溶液に、バルビツール酸の代わりにヒダントインを500重量ppm添加した以外は、実施25と同様な操作を行い、ポリマーサンプルを得た。
実施例1で得られたアクリルアミド水溶液に、バルビツール酸を添加しなかった以外は、実施例2と同様な操作を行い、ポリマーサンプルを得た。
(マロン酸(塩)添加)
実施例1で得られたアクリルアミド水溶液に、バルビツール酸の代わりに、マロン酸を100重量ppm添加した以外は、実施例2と同様な操作を実施したが、重合反応が進行せずポリマーサンプルは得られなかった。
(銅触媒によるアクリルアミドの製造)
水和反応の触媒:80メッシュ以下のラネー銅合金を常法により苛性ソーダを用いて展開し、洗浄して、ラネー銅触媒を製造した。製造中およびその後の取り扱いに際して、空気等の酸素含有ガスとの接触を避けた。
そこで、含有している銅イオンおよびアクリル酸の除去を以下の方法で行った。
こうして得られた、約50重量%アクリルアミド水溶液に対し、苛性ソーダおよび硫酸を用いてpH7.0に調製した。
参考例1で得られたアクリルアミド水溶液に、ジメドンを100重量ppmとなるように添加して実施例2と同様な操作を実施しポリマーサンプルを得た。
上記実施例2、3、4、比較例1、3で得られたポリマーサンプルの水溶性の評価、標準粘度の測定、および色調の評価を以下の方法で行った。
水溶性:水溶性は、1 lビーカーに水600mlを入れ、定められた形状の攪拌羽根で25℃で攪拌しながらポリマーサンプル0.66g(純分0.6g)を添加し、400rpmで2時間攪拌を行い、得られた溶液を150メッシュの金網で濾過し、不溶解分の多少と濾過性から、水溶性を判断した。即ち、完溶のものを◎、完溶に近いものを○、不溶解分があるが、それを濾別する事ができるものを△、濾液の通過が遅く、不溶解分の濾過が事実上出来ないものを×とした。
標準粘度:上記の水溶性試験により得られる濾液は、濃度0.1重量%のポリマー水溶液であるが、これに1M濃度相当の塩化ナトリウムを加え、BL型粘度計でBLアダプターを用いて25℃、ローター回転数60rpmで粘度を測定した(標準粘度)。このような方法で得られる標準粘度は分子量に相関のある値として慣用される。
色調:ポリマーの色調についてはポリマ−粉体を目視で評価した。
評価結果を表−1に示した。
Claims (2)
- ニトリルヒドラターゼを含有する菌体、またはその菌体処理物を用い、アクリルニトリルを水和して得られるアクリルアミドに、ヒダントイン、およびその塩からなる群より選ばれる少なくとも1つの化合物および/または少なくとも1つの上記化合物の塩を添加して、品質の向上したアクリルアミドを製造する方法。
- 請求項1に記載のアクリルアミドを単独重合、または上記アクリルアミドをアクリルアミドと共重合可能な少なくとも1種の不飽和単量体と共重合して、アクリルアミド系重合体を製造する方法。
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DE60133691T2 (de) * | 2000-01-17 | 2009-05-28 | Mitsui Chemicals, Inc. | Verfahren zur reinigung von amiden |
JP4672161B2 (ja) | 2000-03-29 | 2011-04-20 | 三井化学株式会社 | アミド化合物の製造方法 |
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2007
- 2007-03-28 KR KR1020087024564A patent/KR101226380B1/ko active IP Right Grant
- 2007-03-28 EP EP07739984.8A patent/EP2006390B1/en active Active
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- 2007-03-28 WO PCT/JP2007/056546 patent/WO2007116781A1/ja active Application Filing
- 2007-03-28 CN CNA2007800121860A patent/CN101415832A/zh active Pending
- 2007-03-28 KR KR1020117014999A patent/KR20110093919A/ko not_active Application Discontinuation
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Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
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US4001081A (en) * | 1974-12-18 | 1977-01-04 | Agence Nationale De Valorisation De La Recherche (Anvar) | Process for the preparation of amides by biological hydrolysis |
WO1983001784A1 (en) * | 1981-11-18 | 1983-05-26 | Hideaki Yamada | Process for biologically producing amide |
JPH10316714A (ja) * | 1997-05-15 | 1998-12-02 | Mitsubishi Rayon Co Ltd | アクリルアミド系重合体の製造方法 |
WO2001073101A1 (fr) * | 2000-03-29 | 2001-10-04 | Mitsui Chemicals, Inc. | Procede de production de composes amidiques |
JP2002145963A (ja) * | 2000-11-09 | 2002-05-22 | Daiyanitorikkusu Kk | N−ビニルカルボン酸アミド系共重合体の製造方法および得られたn−ビニルカルボン酸アミド系共重合体の用途 |
WO2004113405A1 (ja) * | 2003-06-23 | 2004-12-29 | Dia-Nitrix Co., Ltd. | 高品質なカチオン性アクリルアミドポリマーの製造方法 |
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EP2006390A4 (en) | 2012-03-28 |
JP2012090643A (ja) | 2012-05-17 |
WO2007116781A1 (ja) | 2007-10-18 |
KR101226380B1 (ko) | 2013-01-24 |
CN101415832A (zh) | 2009-04-22 |
KR20080105149A (ko) | 2008-12-03 |
KR20110093919A (ko) | 2011-08-18 |
EP2006390B1 (en) | 2017-07-19 |
EP2006390A1 (en) | 2008-12-24 |
JPWO2007116781A1 (ja) | 2009-08-20 |
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