JP2003521478A - 平衡律速反応を行う方法 - Google Patents
平衡律速反応を行う方法Info
- Publication number
- JP2003521478A JP2003521478A JP2001504872A JP2001504872A JP2003521478A JP 2003521478 A JP2003521478 A JP 2003521478A JP 2001504872 A JP2001504872 A JP 2001504872A JP 2001504872 A JP2001504872 A JP 2001504872A JP 2003521478 A JP2003521478 A JP 2003521478A
- Authority
- JP
- Japan
- Prior art keywords
- separation column
- fraction
- acid
- alcohol
- acid separation
- 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.)
- Pending
Links
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 209
- 238000000926 separation method Methods 0.000 claims abstract description 190
- 239000002253 acid Substances 0.000 claims abstract description 188
- 238000000034 method Methods 0.000 claims abstract description 88
- 238000005886 esterification reaction Methods 0.000 claims abstract description 31
- 230000032050 esterification Effects 0.000 claims abstract description 28
- 239000000047 product Substances 0.000 claims description 136
- 238000004821 distillation Methods 0.000 claims description 127
- 150000002148 esters Chemical class 0.000 claims description 123
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 107
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 75
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 74
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 66
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 63
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 58
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 48
- 239000003112 inhibitor Substances 0.000 claims description 42
- 239000003054 catalyst Substances 0.000 claims description 37
- 239000006227 byproduct Substances 0.000 claims description 30
- 239000007788 liquid Substances 0.000 claims description 30
- 238000009835 boiling Methods 0.000 claims description 28
- 230000008569 process Effects 0.000 claims description 28
- 238000006116 polymerization reaction Methods 0.000 claims description 25
- 238000011084 recovery Methods 0.000 claims description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 14
- 238000010926 purge Methods 0.000 claims description 12
- 238000006845 Michael addition reaction Methods 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 11
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000004064 recycling Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 238000005336 cracking Methods 0.000 claims description 7
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 239000010410 layer Substances 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 230000003134 recirculating effect Effects 0.000 claims 1
- 238000006136 alcoholysis reaction Methods 0.000 abstract description 8
- 239000000376 reactant Substances 0.000 description 26
- 239000012074 organic phase Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 14
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 14
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 14
- 239000008346 aqueous phase Substances 0.000 description 9
- -1 alkyl acetate Chemical compound 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 7
- 229950000688 phenothiazine Drugs 0.000 description 7
- 238000007086 side reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000009825 accumulation Methods 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000005187 foaming Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000005250 alkyl acrylate group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000013000 chemical inhibitor Substances 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000005446 dissolved organic matter Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052698 phosphorus Chemical group 0.000 description 3
- 239000011574 phosphorus Chemical group 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Chemical group 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- BNHGVULTSGNVIX-UHFFFAOYSA-N 1-(2-ethoxyethoxy)ethanol Chemical compound CCOCCOC(C)O BNHGVULTSGNVIX-UHFFFAOYSA-N 0.000 description 1
- SXYRTDICSOVQNZ-UHFFFAOYSA-N 1-(2-methoxyethoxy)ethanol Chemical compound COCCOC(C)O SXYRTDICSOVQNZ-UHFFFAOYSA-N 0.000 description 1
- HMNZROFMBSUMAB-UHFFFAOYSA-N 1-ethoxybutan-1-ol Chemical compound CCCC(O)OCC HMNZROFMBSUMAB-UHFFFAOYSA-N 0.000 description 1
- JLBXCKSMESLGTJ-UHFFFAOYSA-N 1-ethoxypropan-1-ol Chemical compound CCOC(O)CC JLBXCKSMESLGTJ-UHFFFAOYSA-N 0.000 description 1
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- LXSVWFRZICUOLU-UHFFFAOYSA-N 2-butoxypropanoic acid Chemical compound CCCCOC(C)C(O)=O LXSVWFRZICUOLU-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- CRHLZRRTZDFDAJ-UHFFFAOYSA-N butoxymethanol Chemical compound CCCCOCO CRHLZRRTZDFDAJ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical group 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012465 retentate Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US98782999A | 1999-06-17 | 1999-06-17 | |
| US08/987,829 | 1999-06-17 | ||
| US09/361,395 | 1999-07-26 | ||
| US09/361,395 US6482976B1 (en) | 1999-06-17 | 1999-07-26 | Processes for conducting equilibrium-limited reactions |
| PCT/US2000/016040 WO2000078702A1 (en) | 1999-06-17 | 2000-06-12 | Processes for conducting equilibrium-limited reactions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003521478A true JP2003521478A (ja) | 2003-07-15 |
| JP2003521478A5 JP2003521478A5 (enExample) | 2007-08-02 |
Family
ID=56290031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001504872A Pending JP2003521478A (ja) | 1999-06-17 | 2000-06-12 | 平衡律速反応を行う方法 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP2003521478A (enExample) |
| KR (1) | KR100642037B1 (enExample) |
| CN (1) | CN100347146C (enExample) |
| AU (1) | AU5605400A (enExample) |
| WO (1) | WO2000078702A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007297352A (ja) * | 2006-05-02 | 2007-11-15 | Toho Earthtech Inc | ヨウ化アルキルの製造方法および２−アルキル置換シクロヘキサノンの製造方法 |
| JP2008530170A (ja) * | 2005-02-16 | 2008-08-07 | ビーエーエスエフ ソシエタス・ヨーロピア | シクロヘキシル（メタ）アクリレートの連続的な製造法 |
| KR20160036627A (ko) * | 2013-07-29 | 2016-04-04 | 아르끄마 프랑스 | 미정제 에스테르-등급 아크릴산의 에스테르화에 의한 경질 아크릴레이트의 연속 제조 방법 |
| JP2020531460A (ja) * | 2017-08-17 | 2020-11-05 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | アクリル酸−ｎ−ブチルエステルまたはアクリル酸イソブチルエステルの連続的製造方法 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10238142A1 (de) * | 2002-08-15 | 2004-03-11 | Basf Ag | Verfahren zur Aufarbeitung von (Meth)acrylsäure und (Meth)acrylsäureestern |
| MX256948B (es) | 2003-02-28 | 2008-05-07 | Union Carbide Chem Plastic | Proceso para realizar las reacciones de equilibrio limitado. |
| MY158588A (en) * | 2008-12-16 | 2016-10-31 | Basf Se | Method for producing carboxylic acid esters |
| TWI654177B (zh) | 2013-10-31 | 2019-03-21 | 德商巴斯夫歐洲公司 | 製備羧酸酯的方法及其作爲塑化劑的用途 |
| KR101877874B1 (ko) * | 2016-07-05 | 2018-07-12 | (주)동신화학 | 고순도 및 고수율의 메틸 ３메톡시 프로피오네이트의 제조방법 및 이를 위한 제조장치 |
| CN106278882A (zh) * | 2016-07-29 | 2017-01-04 | 江门谦信化工发展有限公司 | 一种无须碱中和的丙烯酸丁酯生产系统及其生产方法 |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5877845A (ja) * | 1981-11-02 | 1983-05-11 | Nippon Shokubai Kagaku Kogyo Co Ltd | アクリル酸エステルまたはメタクリル酸エステルの製造方法 |
| JPH05194318A (ja) * | 1991-07-02 | 1993-08-03 | Union Carbide Chem & Plast Technol Corp | エステル化方法 |
| JPH09110789A (ja) * | 1995-09-28 | 1997-04-28 | Basf Ag | （メタ）アクリル酸のアルキルエステルを連続的に製造するための方法及び装置 |
| JPH09208520A (ja) * | 1995-12-15 | 1997-08-12 | Rohm & Haas Co | ブチルアクリレートの製造方法 |
| JPH09208519A (ja) * | 1996-02-06 | 1997-08-12 | Basf Ag | （メタ）アクリル酸アルキルエステルの連続的製法 |
| JPH09295958A (ja) * | 1996-04-30 | 1997-11-18 | Toagosei Co Ltd | （メタ）アクリル酸エステルの製造方法及びその製造装置 |
| US5734074A (en) * | 1995-03-24 | 1998-03-31 | Basf Aktiengesellschaft | Continuous preparation of alkyl esters of (meth) acrylic acid |
| WO1998052904A1 (en) * | 1997-05-20 | 1998-11-26 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for refining butylacrylate |
| WO1999023060A1 (en) * | 1997-10-31 | 1999-05-14 | Celanese International Corporation | Sulfur removal process from an acrylate waste stream |
| EP0916643B1 (en) * | 1997-11-17 | 2001-12-19 | Rohm And Haas Company | A process for preparing alkyl (meth)acrylates |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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2000
- 2000-06-12 CN CNB008090246A patent/CN100347146C/zh not_active Expired - Fee Related
- 2000-06-12 JP JP2001504872A patent/JP2003521478A/ja active Pending
- 2000-06-12 KR KR1020017016202A patent/KR100642037B1/ko not_active Expired - Fee Related
- 2000-06-12 AU AU56054/00A patent/AU5605400A/en not_active Abandoned
- 2000-06-12 WO PCT/US2000/016040 patent/WO2000078702A1/en not_active Ceased
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008530170A (ja) * | 2005-02-16 | 2008-08-07 | ビーエーエスエフ ソシエタス・ヨーロピア | シクロヘキシル（メタ）アクリレートの連続的な製造法 |
| JP2007297352A (ja) * | 2006-05-02 | 2007-11-15 | Toho Earthtech Inc | ヨウ化アルキルの製造方法および２−アルキル置換シクロヘキサノンの製造方法 |
| KR20160036627A (ko) * | 2013-07-29 | 2016-04-04 | 아르끄마 프랑스 | 미정제 에스테르-등급 아크릴산의 에스테르화에 의한 경질 아크릴레이트의 연속 제조 방법 |
| JP2016525565A (ja) * | 2013-07-29 | 2016-08-25 | アルケマ フランス | 精製されていないエステルグレードのアクリル酸のエステル化によって軽質アクリレートを連続的に製造するための方法 |
| KR102207641B1 (ko) | 2013-07-29 | 2021-01-25 | 아르끄마 프랑스 | 미정제 에스테르-등급 아크릴산의 에스테르화에 의한 경질 아크릴레이트의 연속 제조 방법 |
| JP2020531460A (ja) * | 2017-08-17 | 2020-11-05 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | アクリル酸−ｎ−ブチルエステルまたはアクリル酸イソブチルエステルの連続的製造方法 |
| JP7222977B2 (ja) | 2017-08-17 | 2023-02-15 | ビーエーエスエフ ソシエタス・ヨーロピア | アクリル酸－ｎ－ブチルエステルまたはアクリル酸イソブチルエステルの連続的製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU5605400A (en) | 2001-01-09 |
| CN100347146C (zh) | 2007-11-07 |
| KR20020016835A (ko) | 2002-03-06 |
| CN1355780A (zh) | 2002-06-26 |
| KR100642037B1 (ko) | 2006-11-03 |
| WO2000078702A1 (en) | 2000-12-28 |
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