CA1051918A - Process for the production of higher alkylacrylates and methacrylates - Google Patents
Process for the production of higher alkylacrylates and methacrylatesInfo
- Publication number
- CA1051918A CA1051918A CA196,933A CA196933A CA1051918A CA 1051918 A CA1051918 A CA 1051918A CA 196933 A CA196933 A CA 196933A CA 1051918 A CA1051918 A CA 1051918A
- Authority
- CA
- Canada
- Prior art keywords
- water
- improvement
- ester
- mixture
- methyl
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 230000008569 process Effects 0.000 title claims abstract description 18
- 125000005250 alkyl acrylate group Chemical group 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 150000002734 metacrylic acid derivatives Chemical class 0.000 title abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 88
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- -1 alkyl acryl-ates Chemical class 0.000 claims abstract description 21
- 239000010936 titanium Substances 0.000 claims abstract description 16
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 239000003112 inhibitor Substances 0.000 claims abstract description 11
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 10
- 239000011541 reaction mixture Substances 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 239000007789 gas Substances 0.000 claims abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000006227 byproduct Substances 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 238000001256 steam distillation Methods 0.000 claims abstract description 6
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 6
- 239000012535 impurity Substances 0.000 claims abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 35
- 150000002148 esters Chemical class 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 230000000274 adsorptive effect Effects 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 4
- 238000011084 recovery Methods 0.000 claims description 4
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 239000011369 resultant mixture Substances 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 230000005587 bubbling Effects 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- 238000010025 steaming Methods 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract description 2
- 229940000425 combination drug Drugs 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 19
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229940063557 methacrylate Drugs 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 229960000907 methylthioninium chloride Drugs 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 241001163743 Perlodes Species 0.000 description 1
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- MDNFYIAABKQDML-UHFFFAOYSA-N heptyl 2-methylprop-2-enoate Chemical compound CCCCCCCOC(=O)C(C)=C MDNFYIAABKQDML-UHFFFAOYSA-N 0.000 description 1
- SCFQUKBBGYTJNC-UHFFFAOYSA-N heptyl prop-2-enoate Chemical compound CCCCCCCOC(=O)C=C SCFQUKBBGYTJNC-UHFFFAOYSA-N 0.000 description 1
- ZNAOFAIBVOMLPV-UHFFFAOYSA-N hexadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C(C)=C ZNAOFAIBVOMLPV-UHFFFAOYSA-N 0.000 description 1
- PZDUWXKXFAIFOR-UHFFFAOYSA-N hexadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C=C PZDUWXKXFAIFOR-UHFFFAOYSA-N 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- CFBXDFZIDLWOSO-UHFFFAOYSA-N icosyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)C(C)=C CFBXDFZIDLWOSO-UHFFFAOYSA-N 0.000 description 1
- NGYRYRBDIPYKTL-UHFFFAOYSA-N icosyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)C=C NGYRYRBDIPYKTL-UHFFFAOYSA-N 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- KQJBQMSCFSJABN-UHFFFAOYSA-N octadecan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCCCCCCCCCCCC[O-].CCCCCCCCCCCCCCCCCC[O-].CCCCCCCCCCCCCCCCCC[O-].CCCCCCCCCCCCCCCCCC[O-] KQJBQMSCFSJABN-UHFFFAOYSA-N 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- GYDSPAVLTMAXHT-UHFFFAOYSA-N pentyl 2-methylprop-2-enoate Chemical compound CCCCCOC(=O)C(C)=C GYDSPAVLTMAXHT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/62—Use of additives, e.g. for stabilisation
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2317226A DE2317226C3 (de) | 1973-04-06 | 1973-04-06 | Verfahren zur Herstellung von höhermolekularen Alkylacrylaten bzw. -methacrylaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1051918A true CA1051918A (en) | 1979-04-03 |
Family
ID=5877177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA196,933A Expired CA1051918A (en) | 1973-04-06 | 1974-04-05 | Process for the production of higher alkylacrylates and methacrylates |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3887609A (en, 2012) |
| JP (1) | JPS5724775B2 (en, 2012) |
| BE (1) | BE813349A (en, 2012) |
| CA (1) | CA1051918A (en, 2012) |
| DE (1) | DE2317226C3 (en, 2012) |
| FR (1) | FR2224437B1 (en, 2012) |
| GB (1) | GB1446147A (en, 2012) |
| IT (1) | IT1009702B (en, 2012) |
| NL (1) | NL179128C (en, 2012) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2524930C3 (de) * | 1975-06-05 | 1982-11-04 | Degussa Ag, 6000 Frankfurt | Verfahren zur Umesterung von Estern der Acryl- oder Methacrylsäure |
| JPS61131874U (en, 2012) * | 1985-02-06 | 1986-08-18 | ||
| JPH0747568B2 (ja) * | 1986-10-31 | 1995-05-24 | 三井東圧化学株式会社 | アクリル酸又はメタクリル酸のアルキルアミノアルキルエステルの製造方法 |
| JPH01258642A (ja) * | 1988-04-06 | 1989-10-16 | Mitsubishi Gas Chem Co Inc | （メタ）アクリル酸エステルの製造法 |
| DE3836093A1 (de) * | 1988-10-22 | 1990-04-26 | Degussa | Verfahren zur herstellung von hochsiedenden acrylaten bzw. methacrylaten |
| DE3843938A1 (de) * | 1988-12-24 | 1990-06-28 | Henkel Kgaa | Verfahren zur verbesserten herstellung von (meth)acrylsaeureestern mehrwertiger alkohole (ii) |
| US6037014A (en) | 1997-11-06 | 2000-03-14 | The Edgington Co. | Coating composition |
| FR2772375B1 (fr) * | 1997-12-15 | 2000-01-14 | Atochem Elf Sa | Procede de conditionnement d'acrylates d'alkyle a longue chaine |
| JP4591733B2 (ja) * | 2000-06-23 | 2010-12-01 | 日立化成工業株式会社 | メタクリル酸エステルの製造法 |
| JP4826026B2 (ja) * | 2001-05-18 | 2011-11-30 | 日立化成工業株式会社 | （メタ）アクリル酸エステルの製造法 |
| DE10127941A1 (de) | 2001-06-08 | 2002-05-29 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| DE10127939A1 (de) | 2001-06-08 | 2002-05-29 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| TW200617125A (en) * | 2004-09-27 | 2006-06-01 | Hitachi Chemical Co Ltd | Photocurable resin composition |
| JP2006182606A (ja) * | 2004-12-28 | 2006-07-13 | Miyoshi Oil & Fat Co Ltd | セメント混和剤及びセメント組成物 |
| JP5002905B2 (ja) * | 2005-04-05 | 2012-08-15 | 東亞合成株式会社 | （メタ）アクリル酸エステル中の揮発性物質の除去方法 |
| DE102005043719A1 (de) * | 2005-09-13 | 2007-03-15 | Röhm Gmbh | Vorrichtung und Verfahren für kontinuierlich durchgeführte Gleichgewichtsreaktionen |
| GB0523340D0 (en) * | 2005-11-16 | 2005-12-28 | Ciba Sc Holding Ag | Manufacture of esters |
| DE102006039420A1 (de) * | 2006-08-23 | 2008-02-28 | Evonik Rohmax Additves Gmbh | Verfahren zur Herstellung von Methacrylatestern |
| JP2010037313A (ja) * | 2008-08-08 | 2010-02-18 | Hitachi Chem Co Ltd | （メタ）アクリル酸エステルの製造方法及び樹脂組成物 |
| DE102009047228A1 (de) | 2009-11-27 | 2011-06-01 | Basf Se | Verfahren zur Herstellung von (Meth)acrylaten von C17-Alkoholgemischen |
| DE102010027458A1 (de) * | 2010-07-17 | 2012-01-19 | Oxea Gmbh | Verfahren zur Nachbehandlung von Polyolestern |
| EP3183310B1 (en) | 2014-08-08 | 2021-11-24 | NDSU Research Foundation | Bio-based acrylic monomers and polymers thereof |
| US20160090348A1 (en) | 2014-09-30 | 2016-03-31 | Basf Se | Preparation of c8-c24 alkyl (meth)acrylates |
| WO2016071052A1 (de) | 2014-11-05 | 2016-05-12 | Basf Se | Verfahren zur herstellung von c8-c22-alkyl(meth)acrylaten |
| CN107001296B (zh) | 2014-12-01 | 2020-07-28 | 巴斯夫欧洲公司 | 制备荷羟酮(甲基)丙烯酸酯的方法 |
| ES2745682T3 (es) * | 2015-02-26 | 2020-03-03 | Basf Se | Procedimiento para la preparación de di(met)acrilato de etoxilato de isosorbida |
| EP3262130B1 (de) * | 2015-02-26 | 2020-10-28 | Basf Se | Verfahren zur herstellung von isosorbiddi(meth)acrylat |
| CN108368020A (zh) | 2015-12-15 | 2018-08-03 | 巴斯夫欧洲公司 | 羟基二苯甲酮聚乙二醇醚(甲基)丙烯酸酯的制备方法 |
| DE102015226830A1 (de) | 2015-12-30 | 2017-07-06 | Basf Se | Verfahren zur Herstellung von hochsiedenden (Meth)acrylsäureestern |
| WO2018024563A1 (de) | 2016-08-05 | 2018-02-08 | Basf Se | Polyisobutengruppen tragende makromonomere und deren homo- oder copolymere |
| CN108558657A (zh) * | 2018-06-05 | 2018-09-21 | 李守莉 | 一种甲基丙烯酸特种酯的制备方法 |
| WO2025168399A1 (en) | 2024-02-09 | 2025-08-14 | Basf Se | Aqueous emulsion polymerization with long alkyl chain acrylates and methacrylates |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2822348A (en) * | 1951-11-14 | 1958-02-04 | Du Pont | Ester interchange catalysts |
| US3056818A (en) * | 1955-10-13 | 1962-10-02 | Goodrich Co B F | Titanium and zirconium esterification catalysts |
| US3056817A (en) * | 1955-10-13 | 1962-10-02 | Goodrich Co B F | Ester synthesis |
| US3639461A (en) * | 1967-08-17 | 1972-02-01 | Toa Gosei Chem Ind | Process for the preparation of alpha beta-unsaturated monocarboxylic acid esters |
-
1973
- 1973-04-06 DE DE2317226A patent/DE2317226C3/de not_active Expired
-
1974
- 1974-03-13 GB GB1123374A patent/GB1446147A/en not_active Expired
- 1974-03-29 FR FR7411440A patent/FR2224437B1/fr not_active Expired
- 1974-04-01 US US456584A patent/US3887609A/en not_active Expired - Lifetime
- 1974-04-04 NL NLAANVRAGE7404633,A patent/NL179128C/xx not_active IP Right Cessation
- 1974-04-05 JP JP3875374A patent/JPS5724775B2/ja not_active Expired
- 1974-04-05 CA CA196,933A patent/CA1051918A/en not_active Expired
- 1974-04-05 BE BE142887A patent/BE813349A/xx not_active IP Right Cessation
- 1974-04-08 IT IT20974/74A patent/IT1009702B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS49135916A (en, 2012) | 1974-12-27 |
| DE2317226A1 (de) | 1974-10-24 |
| BE813349A (fr) | 1974-10-07 |
| NL179128B (nl) | 1986-02-17 |
| IT1009702B (it) | 1976-12-20 |
| GB1446147A (en) | 1976-08-18 |
| NL179128C (nl) | 1986-07-16 |
| JPS5724775B2 (en, 2012) | 1982-05-26 |
| FR2224437B1 (en, 2012) | 1977-10-21 |
| DE2317226B2 (en, 2012) | 1975-06-05 |
| FR2224437A1 (en, 2012) | 1974-10-31 |
| NL7404633A (en, 2012) | 1974-10-08 |
| DE2317226C3 (de) | 1980-10-30 |
| US3887609A (en) | 1975-06-03 |
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