JP5684797B2 - N,n−ジアルキルアミノエチルアクリレート(メタクリレート)類の製造 - Google Patents
N,n−ジアルキルアミノエチルアクリレート(メタクリレート)類の製造 Download PDFInfo
- Publication number
- JP5684797B2 JP5684797B2 JP2012511882A JP2012511882A JP5684797B2 JP 5684797 B2 JP5684797 B2 JP 5684797B2 JP 2012511882 A JP2012511882 A JP 2012511882A JP 2012511882 A JP2012511882 A JP 2012511882A JP 5684797 B2 JP5684797 B2 JP 5684797B2
- Authority
- JP
- Japan
- Prior art keywords
- reboiler
- acrylate
- distillation
- distillation column
- alkyl
- 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.)
- Active
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- MUZDXNQOSGWMJJ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(=C)C(O)=O MUZDXNQOSGWMJJ-UHFFFAOYSA-N 0.000 title description 3
- 238000004821 distillation Methods 0.000 claims description 57
- 239000003795 chemical substances by application Substances 0.000 claims description 44
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 37
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 35
- 239000003054 catalyst Substances 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 27
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- -1 dialkylamino alcohol Chemical compound 0.000 claims description 15
- 239000003112 inhibitor Substances 0.000 claims description 11
- 238000005809 transesterification reaction Methods 0.000 claims description 11
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical group CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- JJLKTTCRRLHVGL-UHFFFAOYSA-L [acetyloxy(dibutyl)stannyl] acetate Chemical compound CC([O-])=O.CC([O-])=O.CCCC[Sn+2]CCCC JJLKTTCRRLHVGL-UHFFFAOYSA-L 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- NFTVTXIQFYRSHF-UHFFFAOYSA-N 1-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)C(C)OC(=O)C=C NFTVTXIQFYRSHF-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 239000006227 byproduct Substances 0.000 description 13
- 238000000746 purification Methods 0.000 description 7
- 238000000066 reactive distillation Methods 0.000 description 7
- 239000012535 impurity Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000002841 Lewis acid Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000000895 extractive distillation Methods 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 238000010923 batch production Methods 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- WCRDXYSYPCEIAK-UHFFFAOYSA-N dibutylstannane Chemical compound CCCC[SnH2]CCCC WCRDXYSYPCEIAK-UHFFFAOYSA-N 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000012974 tin catalyst Substances 0.000 description 2
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- KZVBBTZJMSWGTK-UHFFFAOYSA-N 1-[2-(2-butoxyethoxy)ethoxy]butane Chemical compound CCCCOCCOCCOCCCC KZVBBTZJMSWGTK-UHFFFAOYSA-N 0.000 description 1
- KTSVVTQTKRGWGU-UHFFFAOYSA-N 1-[2-[2-(2-butoxyethoxy)ethoxy]ethoxy]butane Chemical compound CCCCOCCOCCOCCOCCCC KTSVVTQTKRGWGU-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- RERATEUBWLKDFE-UHFFFAOYSA-N 1-methoxy-2-[2-(2-methoxypropoxy)propoxy]propane Chemical compound COCC(C)OCC(C)OCC(C)OC RERATEUBWLKDFE-UHFFFAOYSA-N 0.000 description 1
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 1
- 125000004825 2,2-dimethylpropylene group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[*:1])C([H])([H])[*:2] 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011020 pilot scale process Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 210000000707 wrist Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
および式3のジアルキルアミノアルコール、
c)同時に、共沸剤とアルコールの共沸混合物を蒸留カラムから除去し、N,N−ジアルキルアミノアルキルアクリレートおよび残留反応物をリボイラーから除去する工程を含む。
<反応蒸留によるN,N−ジメチルアミノエチルアクリレートの調製>
この実施例のために、ステンレス鋼パイロットスケール反応蒸留ユニットを使用した。これは、15.2cm離された35シーブトレイを有する内径15.4cmの蒸留カラムから構成された。関連する構成要素としては、頂部凝縮物の一部を凝縮し、戻すための凝縮器およびアキュムレータ、およびユニットに熱を供給するための標準構成のケトル型リボイラーが挙げられる。51部のDMAE反応物、47.5部のヘキサン共沸剤、および1.5部のDBTA触媒を含む溶液を、蒸留カラムの底からの第5プレートに約10.5ポンド/時間の速度で連続して添加した。同時に、メチルアクリレート(MA)反応物を約7.75ポンド/時間の速度でリボイラーに添加し、これは1.5:1のMA/DMAEモル供給比に相当した。メタノール副産物を蒸留カラムから除去し、熱交換器でヘキサン/メタノール共沸物として凝縮させた。蒸留物をカラム頂上から約7.4ポンド/時間の速度および約14.2psia(絶対圧)のカラム上部圧力で回収した。DMAEA生成物を系から、すべての未反応MAおよびDMAEと共に、系の底から除去した。底部は、リボイラーから約11.0ポンド/時間の速度で引き出した。リボイラーの内容物の温度は約92℃であった。
<反応蒸留によるN,N−ジメチルアミノエチルアクリレートの調製>
DMAEAは、プロセス条件を下記表で記載されるように変化させたことを除き、実施例1において上述したように生成させた。プロセス変数は、MA/DMAEモル供給比(MA/DMAE)、DMAE反応物の総重量に基づく重量%触媒(wt.%触媒)、下記で記載されるGC分析に基づくDMAEからDMAEAへの%反応変換(%変換)、底部温度(TB(℃))、時間で表されるリボイラー内での滞留時間(滞留時間(h))を含んだ。一般に、制限的なDMAE反応物の所望のDMAEA生成物への高い化学変換は、所望のプロセス条件(低いMA/DMAE供給比、低い触媒量、および低いリボイラー温度(100℃未満))下で達成され得るであろう。実験プロセス条件を表す底部サンプルの揮発性成分をガスクロマトグラフィー(GC)により測定し、結果を表内の「揮発性成分」見出し下で列挙する。実施例1および2から得られる底部組成物は、底部における高いDMAEA濃度(60wt.%超)、高いDMAE変換(85モル%超)、および低い不純物レベル(1wt.%未満)の達成を示す。実施例5および7から得られる結果から、高いDMAE変換(90%超)および低レベルの副生成物(1%未満)が、1.6(実施例6)または1.7(実施例7)のかなり低いMA/DMAE供給比で達成できることが確認される。実施例3は、MA/DMAE供給比は望ましく、さらにもっと減少させることができる(実施例3では1.2まで)が、リボイラー温度は、この場合100℃超まで増加し、このため、より高い不純物レベルとなることを示す。実施例4および6は、リボイラー滞留時間が約2時間まで減少された場合、DMAEからDMAEAへの化学変換が損なわれることを示す。
Claims (11)
- 式1のN,N−ジアルキルアミノアルキルアクリレートを調製する方法であって、
a)蒸留カラムおよびリボイラーを備える蒸留反応器を提供する工程と、
b)蒸留カラム又はリボイラーに、共沸剤、ジ−N−ブチルスズジアセテート触媒、重合防止剤、ならびに式2のアルキルアクリレート
および式3のジアルキルアミノアルコールを、
c)同時に、前記共沸剤と前記アルコールの共沸混合物を前記蒸留カラムから除去し、前記N,N−ジアルキルアミノアルキルアクリレートを前記リボイラーから除去する工程と、を含む、方法。 - R1はHまたはメチルであり、R2はエチレンであり、R3、R4およびR5はメチルである、請求項1記載の方法。
- 前記共沸剤はメチルペンタン、ヘキサン、ヘプタン、C4〜C8直鎖炭化水素類、C4〜C8環状炭化水素類、C4〜C8分枝炭化水素類、およびそれらの任意の組み合わせからなるリストより選択される、請求項2記載の方法。
- 前記共沸剤、触媒、防止剤、ジアルキルアミノアルコールおよびアルキルアクリレートはすべて、リボイラーに添加される、請求項3記載の方法。
- 前記共沸剤、触媒、防止剤およびジアルキルアミノアルコールは前記蒸留カラムに添加され、前記アルキルアクリレートは前記リボイラーに添加される請求項3記載の方法。
- 前記蒸留カラムは前記カラムの底からカラムの頂上まで連続して配列された1から60の蒸留トレイを備える、請求項1記載の方法。
- 前記共沸剤、前記触媒、および前記防止剤から選択される1つのアイテムは前記蒸留カラムに真ん中の蒸留トレイよりも低い位置で供給される、請求項6記載の方法。
- R1はHであり、メチルアクリレートのN,N−ジメチルアミノエタノールに対するモル供給比は1.7以下であり、N,N−ジメチルアミノエタノールのN,N−ジメチルアミノエチルアクリレートへの前記化学変換は、88%を超える、請求項3記載の方法。
- 前記リボイラーから除去される前記N,N−ジアルキルアミノアルキルアクリレートには、共沸剤が混入していない、請求項1記載の方法。
- 前記蒸留カラム内の圧力は14〜14.4psiaの範囲内にある、請求項9記載の方法。
- 前記リボイラーはケトル型リボイラーである、請求項1記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/468,585 | 2009-05-19 | ||
US12/468,585 US7829738B1 (en) | 2009-05-19 | 2009-05-19 | Production of N,N-dialklylaminoethyl (meth)acrylates |
PCT/US2010/033980 WO2010135092A2 (en) | 2009-05-19 | 2010-05-07 | The production of n,n-dialkylaminoethyl (meth)acrylates |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2012527462A JP2012527462A (ja) | 2012-11-08 |
JP5684797B2 true JP5684797B2 (ja) | 2015-03-18 |
Family
ID=43034808
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012511882A Active JP5684797B2 (ja) | 2009-05-19 | 2010-05-07 | N,n−ジアルキルアミノエチルアクリレート(メタクリレート)類の製造 |
Country Status (9)
Country | Link |
---|---|
US (1) | US7829738B1 (ja) |
EP (1) | EP2432758B1 (ja) |
JP (1) | JP5684797B2 (ja) |
KR (1) | KR101770001B1 (ja) |
CN (1) | CN102482199B (ja) |
BR (1) | BRPI1011168B1 (ja) |
CA (1) | CA2761707C (ja) |
MX (1) | MX2011011922A (ja) |
WO (1) | WO2010135092A2 (ja) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9828324B2 (en) | 2010-10-20 | 2017-11-28 | Sirrus, Inc. | Methylene beta-diketone monomers, methods for making methylene beta-diketone monomers, polymerizable compositions and products formed therefrom |
US9249265B1 (en) | 2014-09-08 | 2016-02-02 | Sirrus, Inc. | Emulsion polymers including one or more 1,1-disubstituted alkene compounds, emulsion methods, and polymer compositions |
JP2014532625A (ja) | 2011-10-19 | 2014-12-08 | シラス・インコーポレイテッド | メチレンβ−ジケトンモノマー、メチレンβ−ジケトンモノマーを製造するための方法、これらから作られる重合可能な組成物および製品 |
CN105164797B (zh) | 2012-11-30 | 2019-04-19 | 瑟拉斯公司 | 用于电子应用的复合组合物 |
US9410288B2 (en) | 2013-08-08 | 2016-08-09 | Ecolab Usa Inc. | Use of nanocrystaline cellulose and polymer grafted nanocrystaline cellulose for increasing retention in papermaking process |
US9034145B2 (en) | 2013-08-08 | 2015-05-19 | Ecolab Usa Inc. | Use of nanocrystaline cellulose and polymer grafted nanocrystaline cellulose for increasing retention, wet strength, and dry strength in papermaking process |
US9303360B2 (en) | 2013-08-08 | 2016-04-05 | Ecolab Usa Inc. | Use of nanocrystaline cellulose and polymer grafted nanocrystaline cellulose for increasing retention in papermaking process |
DE202013008305U1 (de) | 2013-09-20 | 2013-11-25 | Basf Se | Härtbare Beschichtung, hergestellt mit einem aus Alkylaminoalkyl(meth)acrylaten aufgebauten Copolymer |
US9834730B2 (en) | 2014-01-23 | 2017-12-05 | Ecolab Usa Inc. | Use of emulsion polymers to flocculate solids in organic liquids |
US9416091B1 (en) | 2015-02-04 | 2016-08-16 | Sirrus, Inc. | Catalytic transesterification of ester compounds with groups reactive under transesterification conditions |
US9315597B2 (en) | 2014-09-08 | 2016-04-19 | Sirrus, Inc. | Compositions containing 1,1-disubstituted alkene compounds for preparing polymers having enhanced glass transition temperatures |
US10501400B2 (en) | 2015-02-04 | 2019-12-10 | Sirrus, Inc. | Heterogeneous catalytic transesterification of ester compounds with groups reactive under transesterification conditions |
CA3001717A1 (en) | 2015-10-15 | 2017-04-20 | Ecolab Usa Inc. | Nanocrystalline cellulose and polymer-grafted nanocrystalline cellulose as rheology modifying agents for magnesium oxide and lime slurries |
KR101644629B1 (ko) * | 2016-01-06 | 2016-08-02 | 이종천 | Dmaea 제조방법 및 이를 위한 제조장치 |
US10428177B2 (en) | 2016-06-03 | 2019-10-01 | Sirrus, Inc. | Water absorbing or water soluble polymers, intermediate compounds, and methods thereof |
US9617377B1 (en) | 2016-06-03 | 2017-04-11 | Sirrus, Inc. | Polyester macromers containing 1,1-dicarbonyl-substituted 1 alkenes |
US10196481B2 (en) | 2016-06-03 | 2019-02-05 | Sirrus, Inc. | Polymer and other compounds functionalized with terminal 1,1-disubstituted alkene monomer(s) and methods thereof |
US9567475B1 (en) | 2016-06-03 | 2017-02-14 | Sirrus, Inc. | Coatings containing polyester macromers containing 1,1-dicarbonyl-substituted 1 alkenes |
US10822442B2 (en) | 2017-07-17 | 2020-11-03 | Ecolab Usa Inc. | Rheology-modifying agents for slurries |
EP3778554B1 (en) * | 2018-04-12 | 2024-02-07 | SNF Group | Method for producing 2-dimethylaminoethyl (meth)acrylate |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS54163517A (en) * | 1978-06-09 | 1979-12-26 | Mitsubishi Chem Ind Ltd | Production of dialkylaminoalkyl acrylate or dialkylaminoalkyl methacrylate |
JPH0653711B2 (ja) * | 1986-02-24 | 1994-07-20 | 三井東圧化学株式会社 | アクリル酸またはメタクリル酸のアルキルアミノアルキルエステルの精製方法 |
FR2617840B1 (fr) * | 1987-07-08 | 1989-09-01 | Charbonnages Ste Chimique | Procede de fabrication de (meth)acrylate de dialkylaminoalkyle |
DE69807406T2 (de) * | 1997-10-01 | 2003-04-24 | Nippon Catalytic Chem Ind | Verfahren zur Herstellung von Alkylamino-(meth)Acrylat und eine Vorrichtung dafür |
JP3466904B2 (ja) * | 1998-02-04 | 2003-11-17 | 株式会社日本触媒 | アルキルアミノ(メタ)アクリレートの製造法 |
JPH11246495A (ja) * | 1998-03-05 | 1999-09-14 | Nippon Shokubai Co Ltd | アルキルアミノ(メタ)アクリレートを製造する方法 |
FR2777561B1 (fr) * | 1998-04-21 | 2000-06-02 | Atochem Elf Sa | Procede de fabrication en continu de (meth)acrylates de dialkylaminoalkyle |
JP4477178B2 (ja) * | 1999-12-21 | 2010-06-09 | ダイヤニトリックス株式会社 | (メタ)アクリル酸アルキルアミノアルキルエステルの製造方法 |
JP2001187763A (ja) * | 1999-12-28 | 2001-07-10 | Mitsubishi Rayon Co Ltd | (メタ)アクリル酸エステルの製造方法 |
FR2839070A1 (fr) * | 2002-04-30 | 2003-10-31 | Atofina | Procede de fabrication en continu de l'acrylate de dimethylaminoethyle |
JP4520310B2 (ja) * | 2003-05-28 | 2010-08-04 | ダイヤニトリックス株式会社 | (メタ)アクリル酸n−アルキルアミノアルキルエステルの製造方法 |
GB0523340D0 (en) | 2005-11-16 | 2005-12-28 | Ciba Sc Holding Ag | Manufacture of esters |
FR2913612B1 (fr) * | 2007-03-16 | 2009-05-08 | Arkema France | Procede de preparation d'un catalyseur et son utilisation dans un procede en continu de transesterification d'esters (meth)acryliques |
CN201424446Y (zh) | 2009-04-29 | 2010-03-17 | 北京恒聚化工集团有限责任公司 | 阳离子单体二甲胺基乙基丙烯酸脂氯甲烷季铵盐生产*** |
-
2009
- 2009-05-19 US US12/468,585 patent/US7829738B1/en active Active
-
2010
- 2010-05-07 CN CN201080022554.1A patent/CN102482199B/zh active Active
- 2010-05-07 JP JP2012511882A patent/JP5684797B2/ja active Active
- 2010-05-07 EP EP10778105.6A patent/EP2432758B1/en active Active
- 2010-05-07 KR KR1020117030330A patent/KR101770001B1/ko active IP Right Grant
- 2010-05-07 MX MX2011011922A patent/MX2011011922A/es active IP Right Grant
- 2010-05-07 BR BRPI1011168-9A patent/BRPI1011168B1/pt active IP Right Grant
- 2010-05-07 CA CA2761707A patent/CA2761707C/en active Active
- 2010-05-07 WO PCT/US2010/033980 patent/WO2010135092A2/en active Application Filing
Also Published As
Publication number | Publication date |
---|---|
EP2432758A4 (en) | 2012-11-21 |
KR101770001B1 (ko) | 2017-08-21 |
WO2010135092A2 (en) | 2010-11-25 |
US20100298594A1 (en) | 2010-11-25 |
MX2011011922A (es) | 2011-12-08 |
CA2761707C (en) | 2015-09-15 |
BRPI1011168A2 (pt) | 2016-03-15 |
CN102482199A (zh) | 2012-05-30 |
CN102482199B (zh) | 2016-12-21 |
US7829738B1 (en) | 2010-11-09 |
EP2432758A2 (en) | 2012-03-28 |
WO2010135092A3 (en) | 2011-02-24 |
BRPI1011168B1 (pt) | 2018-03-20 |
JP2012527462A (ja) | 2012-11-08 |
CA2761707A1 (en) | 2010-11-25 |
KR20120018362A (ko) | 2012-03-02 |
EP2432758B1 (en) | 2015-03-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5684797B2 (ja) | N,n−ジアルキルアミノエチルアクリレート(メタクリレート)類の製造 | |
JP5558717B2 (ja) | エステルの製造 | |
JP2010516809A (ja) | テレフタル酸ジエステルの製造 | |
JP5582032B2 (ja) | (メタ)アクリル酸エステルの製造方法 | |
KR19990083363A (ko) | 디알킬아미노알킬(메트)아크릴레이트의연속제조방법 | |
US8067633B2 (en) | Method for the synthesis of (meth)acrylic esters catalysed by a polyol titanate | |
US9776946B2 (en) | Process for producing 2-propylheptyl acrylate by transesterification | |
JP5369438B2 (ja) | ジアルキルアミノアルキル(メタ)アクリレートの連続製造方法 | |
JP6008600B2 (ja) | 4−ヒドロキシブチルアクリレートの製造方法 | |
JPH1143466A (ja) | ヒドロキシアルキルモノアクリレートの製造方法 | |
JP4042227B2 (ja) | 4−ヒドロキシブチルアクリレートの製造方法 | |
WO2019027953A1 (en) | PROCESS FOR PRODUCING FORMIC ACID USING HIGH BOILING POINT FORMATAS ESTERS | |
US5567838A (en) | Transesterification reaction of alkoxylated bisphenol-a and methyl methacrylate | |
JP2733034B2 (ja) | カルボン酸エステルの製造方法 | |
JPH061780A (ja) | メタクリル酸グリシジルの製造方法 | |
JP2004307366A (ja) | エチレングリコールの精製方法 | |
JPH0873412A (ja) | 炭酸エステルの製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20130415 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20140220 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140318 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140612 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20150106 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20150115 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5684797 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |