JP5216004B2 - 不飽和カルボン酸無水物の連続的製造方法 - Google Patents
不飽和カルボン酸無水物の連続的製造方法 Download PDFInfo
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- 150000001244 carboxylic acid anhydrides Chemical class 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims description 22
- 238000010924 continuous production Methods 0.000 title claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 15
- 239000006227 byproduct Substances 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 49
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 238000009835 boiling Methods 0.000 claims description 26
- 239000003054 catalyst Substances 0.000 claims description 15
- 239000007858 starting material Substances 0.000 claims description 15
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 13
- 150000008064 anhydrides Chemical group 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 8
- 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 7
- 239000000203 mixture Substances 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- -1 aliphatic carboxylic anhydride Chemical class 0.000 claims description 4
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002638 heterogeneous catalyst Substances 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000012429 reaction media Substances 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- 239000003921 oil Substances 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000012856 packing Methods 0.000 description 8
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 7
- 238000000926 separation method Methods 0.000 description 6
- 239000013067 intermediate product Substances 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 230000001788 irregular Effects 0.000 description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 229940023913 cation exchange resins Drugs 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- 229940005561 1,4-benzoquinone Drugs 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical compound OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 0.000 description 1
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical group CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- RWHRFHQRVDUPIK-UHFFFAOYSA-N 50867-57-7 Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O RWHRFHQRVDUPIK-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 241000534000 Berula erecta Species 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
- 229910000831 Steel Inorganic materials 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- TZODSDSWNKTCFL-UHFFFAOYSA-N acetyl 2-methylprop-2-enoate Chemical compound CC(=O)OC(=O)C(C)=C TZODSDSWNKTCFL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- ATMLPEJAVWINOF-UHFFFAOYSA-N acrylic acid acrylic acid Chemical compound OC(=O)C=C.OC(=O)C=C ATMLPEJAVWINOF-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/083—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/567—Preparation of carboxylic acid anhydrides by reactions not involving carboxylic acid anhydride groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
R−C(O)−O−C(O)−R (I)
[式中、Rは2〜12個のC原子を有する不飽和の有機基を表す]の不飽和カルボン酸無水物を、脂肪族カルボン酸無水物と、一般式II R−COOH(II)[式中、Rは上記の意味を表す]のカルボン酸との無水物交換により連続的に製造する方法において、
a) 前記塔の塔底に不活性な沸騰油(Siedeoel)を装入し、
b) 出発材料を化学量論的割合で反応領域に供給し、
c) 前記塔の塔頂で副生成物として生じるカルボン酸を取り出し、
d) 反応されない出発材料を反応領域に返送し、かつ
e) 一般式Iの生成物が、有利に中央部の塔領域と下部の塔領域との間の、側流搬出部(Seitenabzug)を介して得られることを特徴とする。
メタクリル酸と酢酸無水物の反応によるメタクリル酸無水物の製造のために、図1による試験装置を組み立てた。この精留塔(2)は、全体で約35の分離段(上部領域(2a)において15段、中央部領域(2b)において12段、下部領域(2c)において8段)を有していた。前記塔は、中間部分と塔底で5.5mの高さであり、100mmの内径を有し及びSulzer社のタイプCY(領域2a及び2b)及びMontz社のタイプBSH 400(領域2c)の規則充填物が充填されていた。重合防止剤としてフェノチアジンを使用した。塔頂の圧力は20mbarであった。定常条件で、164℃(塔底)から23℃(塔頂)の温度分布を調節した。塔頂での酢酸の搬出及び側流搬出部(領域2bと2cとの間)でのメタクリル酸無水物の搬出並びに塔底蒸発器の熱蒸気効率を、それぞれの領域の適切な温度の調節により制御した。
アクリル酸と無水酢酸との反応によるアクリル酸無水物の製造のために、実施例1で説明したのと同じ試験装置を使用した。
Claims (10)
- 一般式I
R−C(O)−O−C(O)−R (I)
[式中、Rは2〜12個のC原子を有する不飽和の有機基を表す]の不飽和カルボン酸無水物を、上部領域、中央部領域及び下部領域を有する精留塔中で脂肪族カルボン酸無水物と、一般式II R−COOH(II)[式中、Rは上記の意味を表す]のカルボン酸との無水物交換により連続的に製造する方法において、
a) 前記塔の塔底に、12〜20個の炭素原子を有する高級の鎖状の非分枝のパラフィン、芳香族化合物、アルキル置換フェノール又はナフタレン化合物、スルホラン又はこれらの混合物から選択された不活性な沸騰油を装入し、
b) 出発材料を化学量論的割合で反応領域に供給し、
c) 前記塔の塔頂で副生成物として生じるカルボン酸を取り出し、
d) 反応されない出発材料を反応領域に返送し、かつ
e) 一般式Iの生成物が、側流搬出部を介して得られることを特徴とする、不飽和カルボン酸無水物の連続的製造方法。 - e)において、一般式Iの生成物が、中央部の塔領域と下部の塔領域との間の、側流搬出部を介して得られることを特徴とする、請求項1記載の方法。
- 反応領域中で不均一系触媒を使用することを特徴とする、請求項1又は2記載の方法。
- 酸性固定床触媒を使用することを特徴とする、請求項3記載の方法。
- カチオン交換体を触媒として使用することを特徴とする、請求項3又は4記載の方法。
- 前記反応領域が前記塔の外部に存在することを特徴とする、請求項1から5までのいずれか1項記載の方法。
- 式Iの不飽和カルボン酸無水物が(メタ)アクリル酸無水物であり、無水酢酸と(メタ)アクリル酸の無水物交換により製造されることを特徴とする、請求項1から6までのいずれか1項記載の方法。
- 沸騰油として2,6−ジ−tert−ブチル−パラ−クレゾール、2,6−ジ−tert−ブチル−フェノール、スルホラン又はジフィル又はこれらの混合物を使用することを特徴とする、請求項1から7までのいずれか1項記載の方法。
- 沸騰油としてスルホランを使用することを特徴とする、請求項1から8までのいずれか1項記載の方法。
- 塔底から高沸点成分を排出し、蒸発する物質を前記塔内へ返送することを特徴とする、請求項1から9までのいずれか1項記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102006029320.7 | 2006-06-23 | ||
DE102006029320A DE102006029320B3 (de) | 2006-06-23 | 2006-06-23 | Verfahren zur kontinuierlichen Herstellung von ungesättigten Carbonsäureanhydriden |
PCT/EP2007/052398 WO2007147652A1 (de) | 2006-06-23 | 2007-03-14 | Verfahren zur kontinuierlichen herstellung von ungesättigten carbonsäureanhydriden |
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JP2009541407A JP2009541407A (ja) | 2009-11-26 |
JP5216004B2 true JP5216004B2 (ja) | 2013-06-19 |
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Country | Link |
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US (1) | US8084640B2 (ja) |
EP (1) | EP2032518B1 (ja) |
JP (1) | JP5216004B2 (ja) |
KR (1) | KR101372204B1 (ja) |
CN (1) | CN101466660B (ja) |
AT (1) | ATE469116T1 (ja) |
AU (1) | AU2007263230B2 (ja) |
BR (1) | BRPI0713339B1 (ja) |
CA (1) | CA2655820C (ja) |
DE (2) | DE102006029320B3 (ja) |
MX (1) | MX2008015863A (ja) |
RU (1) | RU2454397C2 (ja) |
TW (1) | TWI422572B (ja) |
WO (1) | WO2007147652A1 (ja) |
ZA (1) | ZA200810797B (ja) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
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DE102006060162A1 (de) * | 2006-12-18 | 2008-06-19 | Evonik Röhm Gmbh | Verbessertes Verfahren zur Herstellung von ungesättigten Carbonsäureanhybriden |
FR2927329B1 (fr) * | 2008-02-08 | 2010-04-16 | Arkema France | Procede ameliore de preparation d'anhydride (meth)acrylique. |
US8445723B2 (en) | 2008-08-19 | 2013-05-21 | Nalco Company | Processes for producing N-alkyl (alkyl)acrylamides |
AR088377A1 (es) * | 2011-10-20 | 2014-05-28 | Siena Biotech Spa | Proceso para la preparacion de 6-cloro-2,3,4,9-tetrahidro-1h-carbazol-1-carboxamida y compuestos intermedios de esta |
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RU2009101975A (ru) | 2010-07-27 |
EP2032518B1 (de) | 2010-05-26 |
BRPI0713339A2 (pt) | 2012-03-06 |
KR101372204B1 (ko) | 2014-03-14 |
CA2655820A1 (en) | 2007-12-27 |
WO2007147652A1 (de) | 2007-12-27 |
EP2032518A1 (de) | 2009-03-11 |
US20090264673A1 (en) | 2009-10-22 |
DE102006029320B3 (de) | 2007-10-11 |
CN101466660B (zh) | 2013-04-03 |
BRPI0713339B1 (pt) | 2016-07-12 |
AU2007263230B2 (en) | 2012-06-28 |
ZA200810797B (en) | 2009-12-30 |
CN101466660A (zh) | 2009-06-24 |
US8084640B2 (en) | 2011-12-27 |
CA2655820C (en) | 2014-06-10 |
TW200815336A (en) | 2008-04-01 |
TWI422572B (zh) | 2014-01-11 |
JP2009541407A (ja) | 2009-11-26 |
RU2454397C2 (ru) | 2012-06-27 |
ATE469116T1 (de) | 2010-06-15 |
KR20090036552A (ko) | 2009-04-14 |
DE502007003951D1 (de) | 2010-07-08 |
AU2007263230A1 (en) | 2007-12-27 |
MX2008015863A (es) | 2009-01-12 |
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