DE1255104B - Verfahren zur Herstellung von beta-Hydroxyalkylmonoestern der Acryl- und Methacrylsaeure - Google Patents
Verfahren zur Herstellung von beta-Hydroxyalkylmonoestern der Acryl- und MethacrylsaeureInfo
- Publication number
- DE1255104B DE1255104B DER38935A DER0038935A DE1255104B DE 1255104 B DE1255104 B DE 1255104B DE R38935 A DER38935 A DE R38935A DE R0038935 A DER0038935 A DE R0038935A DE 1255104 B DE1255104 B DE 1255104B
- Authority
- DE
- Germany
- Prior art keywords
- hours
- iron
- acid
- ester
- acrylate
- 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 12
- 125000005395 methacrylic acid group Chemical class 0.000 title 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 16
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 8
- 229910052742 iron Inorganic materials 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
- ZWZHJDRBENYHMK-UHFFFAOYSA-L iron(2+);2-methylprop-2-enoate Chemical compound [Fe+2].CC(=C)C([O-])=O.CC(=C)C([O-])=O ZWZHJDRBENYHMK-UHFFFAOYSA-L 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910000831 Steel Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- RBURNKQMEAEGBB-UHFFFAOYSA-K iron(3+);2-methylprop-2-enoate Chemical compound [Fe+3].CC(=C)C([O-])=O.CC(=C)C([O-])=O.CC(=C)C([O-])=O RBURNKQMEAEGBB-UHFFFAOYSA-K 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229920000647 polyepoxide Polymers 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 239000010959 steel Substances 0.000 claims description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 12
- WNWBIDPJHFYYLM-UHFFFAOYSA-K iron(3+);prop-2-enoate Chemical compound [Fe+3].[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C WNWBIDPJHFYYLM-UHFFFAOYSA-K 0.000 claims 5
- -1 3-hydroxy-butoxypropyl acrylate Chemical compound 0.000 claims 3
- 238000004821 distillation Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 claims 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 claims 1
- JRJNSEMUYTUGLA-UHFFFAOYSA-N 3-phenoxypropyl prop-2-enoate Chemical compound C=CC(=O)OCCCOC1=CC=CC=C1 JRJNSEMUYTUGLA-UHFFFAOYSA-N 0.000 claims 1
- QLQSJLSVPZCPPZ-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hept-3-ene Chemical compound C1C=CCC2OC12 QLQSJLSVPZCPPZ-UHFFFAOYSA-N 0.000 claims 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims 1
- YDQCKWDAEAJVAJ-UHFFFAOYSA-N [C].OC(=O)C=C Chemical compound [C].OC(=O)C=C YDQCKWDAEAJVAJ-UHFFFAOYSA-N 0.000 claims 1
- NJFMNPFATSYWHB-UHFFFAOYSA-N ac1l9hgr Chemical compound [Fe].[Fe] NJFMNPFATSYWHB-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- SVOAENZIOKPANY-CVBJKYQLSA-L copper;(z)-octadec-9-enoate Chemical compound [Cu+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O SVOAENZIOKPANY-CVBJKYQLSA-L 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 239000011521 glass Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims 1
- 229910052753 mercury Inorganic materials 0.000 claims 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
- 239000012299 nitrogen atmosphere Substances 0.000 claims 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- 238000005292 vacuum distillation Methods 0.000 claims 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 239000004146 Propane-1,2-diol Substances 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- GNOZLGOOOBMHRC-UHFFFAOYSA-L iron(2+);prop-2-enoate Chemical compound [Fe+2].[O-]C(=O)C=C.[O-]C(=O)C=C GNOZLGOOOBMHRC-UHFFFAOYSA-L 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1054614D GB1054614A (fr) | 1964-10-06 | ||
| DER38935A DE1255104B (de) | 1964-10-06 | 1964-10-06 | Verfahren zur Herstellung von beta-Hydroxyalkylmonoestern der Acryl- und Methacrylsaeure |
| CH1053765A CH459180A (de) | 1964-10-06 | 1965-07-28 | Verfahren zur Herstellung von B-Hydroxyalkylestern der Acryl- und Methacrylsäure |
| FR28944A FR1445143A (fr) | 1964-10-06 | 1965-08-20 | Procédé pour la préparation d'esters beta-hydroxyalkyliques des acides acrylique et méthacrylique |
| BE669781D BE669781A (fr) | 1964-10-06 | 1965-09-17 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER38935A DE1255104B (de) | 1964-10-06 | 1964-10-06 | Verfahren zur Herstellung von beta-Hydroxyalkylmonoestern der Acryl- und Methacrylsaeure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1255104B true DE1255104B (de) | 1967-11-30 |
Family
ID=7405643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER38935A Pending DE1255104B (de) | 1964-10-06 | 1964-10-06 | Verfahren zur Herstellung von beta-Hydroxyalkylmonoestern der Acryl- und Methacrylsaeure |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE669781A (fr) |
| CH (1) | CH459180A (fr) |
| DE (1) | DE1255104B (fr) |
| GB (1) | GB1054614A (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1911447A1 (de) * | 1968-03-09 | 1970-01-02 | Bp Chem Int Ltd | Herstellung von Carbonsaeureestern |
| US5017720A (en) * | 1989-03-16 | 1991-05-21 | Chisso Corporation | Methods of producing and reserving alkylene glycol monosorbates |
| WO2004014837A1 (fr) * | 2002-08-02 | 2004-02-19 | Basf Aktiengesellschaft | Procede pour produire des esters d'acide hydroxyalkylcarboxylique |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1381588A1 (fr) * | 2001-04-06 | 2004-01-21 | Basf Aktiengesellschaft | Procede pour la production d'esters d'acide hydroxyalkylcarboxylique |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE147938C (fr) * | 1901-06-08 | |||
| US2822348A (en) * | 1951-11-14 | 1958-02-04 | Du Pont | Ester interchange catalysts |
-
0
- GB GB1054614D patent/GB1054614A/en active Active
-
1964
- 1964-10-06 DE DER38935A patent/DE1255104B/de active Pending
-
1965
- 1965-07-28 CH CH1053765A patent/CH459180A/de unknown
- 1965-09-17 BE BE669781D patent/BE669781A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE147938C (fr) * | 1901-06-08 | |||
| US2822348A (en) * | 1951-11-14 | 1958-02-04 | Du Pont | Ester interchange catalysts |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1911447A1 (de) * | 1968-03-09 | 1970-01-02 | Bp Chem Int Ltd | Herstellung von Carbonsaeureestern |
| US5017720A (en) * | 1989-03-16 | 1991-05-21 | Chisso Corporation | Methods of producing and reserving alkylene glycol monosorbates |
| WO2004014837A1 (fr) * | 2002-08-02 | 2004-02-19 | Basf Aktiengesellschaft | Procede pour produire des esters d'acide hydroxyalkylcarboxylique |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1054614A (fr) | |
| BE669781A (fr) | 1966-01-17 |
| CH459180A (de) | 1968-07-15 |
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