JP6242806B2 - N−アルキル(メタ)アクリルアミドの製造方法 - Google Patents
N−アルキル(メタ)アクリルアミドの製造方法 Download PDFInfo
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- JP6242806B2 JP6242806B2 JP2014547803A JP2014547803A JP6242806B2 JP 6242806 B2 JP6242806 B2 JP 6242806B2 JP 2014547803 A JP2014547803 A JP 2014547803A JP 2014547803 A JP2014547803 A JP 2014547803A JP 6242806 B2 JP6242806 B2 JP 6242806B2
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- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 32
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000006386 neutralization reaction Methods 0.000 claims description 7
- 150000003973 alkyl amines Chemical class 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 150000003926 acrylamides Chemical class 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 14
- YQIGLEFUZMIVHU-UHFFFAOYSA-N 2-methyl-n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C(C)=C YQIGLEFUZMIVHU-UHFFFAOYSA-N 0.000 description 12
- 238000003860 storage Methods 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000005119 centrifugation Methods 0.000 description 4
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 3
- -1 carbenium ions Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical group CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- DZGUJOWBVDZNNF-UHFFFAOYSA-N azanium;2-methylprop-2-enoate Chemical compound [NH4+].CC(=C)C([O-])=O DZGUJOWBVDZNNF-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-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
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- 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
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
R2R3NH (2)
[式中、R2及びR3は、上述の意味を有する]のアルキルアミンの水溶液と反応させ、かつ生じたアミドを分離することにより行う。(メタ)アクリル酸無水物の表示は、メタクリル酸無水物も、アクリル酸無水物も意味する。意外にも、この方法は、WO2010/021956とは反対に、どんな時でも、ケーキングの形又は反応壁への堆積の形で制御されない沈殿物を生じさせないことが見出された。
N−イソプロピルメタクリルアミド(NIPMAA)の製造を、図1に従って行う。メタクリル酸無水物800kgを撹拌反応器(1)中に装入し、4−メチル−2,6−ジ−tert−ブチルフェノール135g及び4−ヒドロキシ−2,2,6,6−テトラメチル−ピペリジン−1−オキシル115gを添加した後に−5℃に冷却する。この反応器(1)を窒素でパージする。圧力保持を1.3barに設定する。70%のイソプロピルアミン溶液437kgを、ポンプ(2)を介して、冷却することができる貯蔵容器(4)中に圧送する。計量供給ポンプ(3)を介して、イソプロピルアミンを反応器(1)に、反応の間の反応温度が−5〜40℃の間にあるように計量供給する。この反応の間に、反応器内容物をポンプ(5)で熱交換器(6)を通して循環させる。この反応熱を、反応器(1)及び熱交換器(6)の塩水冷却器(7)を通して排出する。イソプロピルアミン量の添加が行われた後に、20〜40℃、好ましくは35〜40℃で15分の後反応を行う。この反応の後に生じる、メタクリル酸中のNIPMAAのスラリーは、粘度低下のためにVE−水(脱塩水)1100kgで希釈した。この希釈されたバッチを、ポンプ(5)で撹拌容器(8)中に移し、25%のアンモニア溶液355kgで撹拌しながら中和した。この中和の際に、大部分のNIPMAAが沈殿し、生成されたアンモニウムメタクリラートは溶液中に残留する。NIPMAA分離のために、この懸濁液を、結晶スラリー(Kristallmaische)の緩衝のために使用される緩衝貯蔵容器(9)を介して排出する。この緩衝貯蔵容器(9)は冷却されている(最大−5℃まで)。この緩衝された懸濁液を、ミル(10)を経由して遠心分離器(11)に導入する。VE水容器(14)を経由して、冷たいVE水(約5℃)を準備し、この冷たいVE水は、必要な純度を得る目的で、結晶の洗浄のために遠心分離器(11)中で使用する。NIPMAAの他に主にアンモニウムメタクリラートを有する水性の母液は、ポンプ(12)を用いて(8)又は(9)に圧送して戻される。この遠心分離の完了時に、この母液は完全に容器(13)に捕集される。NIPMAA貯蔵容器(15)中でのNIPMAAの収率は、メタクリル酸無水物を基準として84%である。
1 撹拌反応器
2 ポンプ
3 計量供給ポンプ
4 貯蔵容器
5 ポンプ
6 熱交換器
7 塩水冷却器
8 撹拌容器
9 緩衝貯蔵容器
10 ミル
11 遠心分離器
12 ポンプ
13 容器
14 VE水容器
15 NIPMAA貯蔵容器
Claims (7)
- 一般式(1)
装入された(メタ)アクリル酸無水物を、式(2)
R2R3NH (2)
[式中、R2及びR3は上記の意味を有する]のアルキルアミンの水溶液と反応させ、生じたアミドを分離し、前記反応を−5℃〜40℃で、0.5〜6barの圧力で行い、反応容器の冷却温度は、反応溶液中でのN−アルキル(メタ)アクリルアミドの結晶化温度を上回り、かつ装入物及びアルキルアミンの水溶液を反応の前に10〜−5℃に予め冷却することを特徴とする、N−アルキル(メタ)アクリルアミドの製造方法。 - N−アルキル(メタ)アクリルアミド及び(メタ)アクリル酸の生成された溶液を水で希釈し、引き続きアルカリ性溶液で中和し、沈殿したN−アルキル(メタ)アクリルアミドを分離することを特徴とする、請求項1に記載のN−アルキル(メタ)アクリルアミドの製造方法。
- 反応並びに中和及び沈殿を、それぞれ別個の容器中で行うことを特徴とする、請求項2に記載のN−アルキル(メタ)アクリルアミドの製造方法。
- 前記反応中で反応されるべきアルキルアミンを、50〜90%の水溶液の形で、前記(メタ)アクリル酸無水物に添加することを特徴とする、請求項1に記載のN−アルキル(メタ)アクリルアミドの製造方法。
- 前記反応を、不活性ガス下で作用する水溶性重合禁止剤の存在下で行うことを特徴とする、請求項1に記載のN−アルキル(メタ)アクリルアミドの製造方法。
- 中和後に、生じる結晶懸濁液をミルで粉砕した後、遠心分離器で分離することを特徴とする、請求項2に記載のN−アルキル(メタ)アクリルアミドの製造方法。
- 前記反応器に、外部型の熱交換器及び循環ポンプが装備されていることを特徴とする、請求項1に記載のN−アルキル(メタ)アクリルアミドの製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102011089363.6 | 2011-12-21 | ||
DE102011089363A DE102011089363A1 (de) | 2011-12-21 | 2011-12-21 | Verfahren zur Herstellung von N-Alkyl(meth)acrylamiden |
PCT/EP2012/073115 WO2013092076A1 (de) | 2011-12-21 | 2012-11-20 | Verfahren zur herstellung von n-alkyl(meth)acrylamiden |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2015502375A JP2015502375A (ja) | 2015-01-22 |
JP6242806B2 true JP6242806B2 (ja) | 2017-12-06 |
Family
ID=47222087
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014547803A Active JP6242806B2 (ja) | 2011-12-21 | 2012-11-20 | N−アルキル(メタ)アクリルアミドの製造方法 |
Country Status (11)
Country | Link |
---|---|
US (1) | US10138202B2 (ja) |
EP (1) | EP2794553B1 (ja) |
JP (1) | JP6242806B2 (ja) |
KR (1) | KR102058880B1 (ja) |
CN (2) | CN103906729A (ja) |
BR (1) | BR112014010061B1 (ja) |
DE (1) | DE102011089363A1 (ja) |
RU (1) | RU2622932C2 (ja) |
SG (2) | SG11201403413RA (ja) |
TW (2) | TW201815746A (ja) |
WO (1) | WO2013092076A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP7095635B2 (ja) | 2019-03-13 | 2022-07-05 | トヨタ自動車株式会社 | 不具合対応システム、その対応方法及びプログラム |
JP7095634B2 (ja) | 2019-03-13 | 2022-07-05 | トヨタ自動車株式会社 | 自動更新システム、その更新方法及びプログラム |
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US11136287B2 (en) | 2017-03-01 | 2021-10-05 | Api Corporation | Method for producing n-benzyl-2-bromo-3-methoxypropionamide and intermediates thereof |
CN107445856B (zh) * | 2017-09-19 | 2020-05-19 | 辽宁三洋新材料科技有限公司 | 一种n-异丙基丙烯酰胺的合成工艺 |
AU2019272745A1 (en) | 2018-05-23 | 2021-01-21 | Evonik Operations Gmbh | Method for preparing keto-functionalized aromatic (meth)acrylates |
SG11202100238TA (en) | 2018-07-17 | 2021-02-25 | Evonik Operations Gmbh | Method for preparing c-h acidic (meth)acrylates |
EP3599232A1 (de) | 2018-07-26 | 2020-01-29 | Evonik Operations GmbH | Verfahren zur herstellung von n-methyl(meth)acrylamid |
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JPS5331853B2 (ja) * | 1971-08-26 | 1978-09-05 | ||
DE3131096A1 (de) | 1981-08-06 | 1983-02-24 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung von n-substituierten methacryl- und acrylamiden |
DE3409159A1 (de) * | 1984-03-13 | 1985-09-26 | Deggendorfer Werft Und Eisenbau Gmbh, 8360 Deggendorf | Rohrbuendel-reaktionsapparat |
ES2062685T3 (es) * | 1990-06-13 | 1994-12-16 | Mitsui Toatsu Chemicals | Procedimiento de purificacion de metacrilamida. |
DE4027843A1 (de) | 1990-09-03 | 1992-03-05 | Roehm Gmbh | Kontinuierliches verfahren zur herstellung von n-substituierten acryl- und methacrylamiden |
JP4500160B2 (ja) | 2004-12-24 | 2010-07-14 | 大阪有機化学工業株式会社 | アミドフェノールの製造法 |
JP2007230966A (ja) | 2006-03-03 | 2007-09-13 | Kohjin Co Ltd | (メタ)アクリルアミドアルキルカルボン酸の製造方法 |
US8445723B2 (en) * | 2008-08-19 | 2013-05-21 | Nalco Company | Processes for producing N-alkyl (alkyl)acrylamides |
DE102008054612A1 (de) * | 2008-12-15 | 2010-06-17 | Evonik Röhm Gmbh | Verfahren zur Herstellung von N-Isopropyl(meth)acrylamid |
CN103772226A (zh) | 2009-05-01 | 2014-05-07 | 出光兴产株式会社 | α β不饱和羧酸-N,N二取代酰胺以及3-烷氧基羧酸-N,N二取代酰胺的制造方法 |
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JP7095634B2 (ja) | 2019-03-13 | 2022-07-05 | トヨタ自動車株式会社 | 自動更新システム、その更新方法及びプログラム |
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WO2013092076A1 (de) | 2013-06-27 |
RU2014129628A (ru) | 2016-02-10 |
TWI652252B (zh) | 2019-03-01 |
KR20140103266A (ko) | 2014-08-26 |
BR112014010061A8 (pt) | 2017-06-20 |
US20140288330A1 (en) | 2014-09-25 |
KR102058880B1 (ko) | 2019-12-26 |
EP2794553B1 (de) | 2018-09-05 |
RU2622932C2 (ru) | 2017-06-21 |
DE102011089363A1 (de) | 2013-06-27 |
BR112014010061A2 (pt) | 2017-06-13 |
TW201815746A (zh) | 2018-05-01 |
EP2794553A1 (de) | 2014-10-29 |
CN107793324A (zh) | 2018-03-13 |
SG10201807879VA (en) | 2018-10-30 |
JP2015502375A (ja) | 2015-01-22 |
US10138202B2 (en) | 2018-11-27 |
BR112014010061B1 (pt) | 2019-11-12 |
CN103906729A (zh) | 2014-07-02 |
SG11201403413RA (en) | 2014-10-30 |
TW201343611A (zh) | 2013-11-01 |
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