GB997959A - Esterification of ª,ª-unsaturated carboxylic acids with alkylene oxides - Google Patents
Esterification of ª,ª-unsaturated carboxylic acids with alkylene oxidesInfo
- Publication number
- GB997959A GB997959A GB48649/63A GB4864963A GB997959A GB 997959 A GB997959 A GB 997959A GB 48649/63 A GB48649/63 A GB 48649/63A GB 4864963 A GB4864963 A GB 4864963A GB 997959 A GB997959 A GB 997959A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formamide
- dimethyl
- alkyl
- hydrogen
- general formula
- 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
- 125000002947 alkylene group Chemical group 0.000 title abstract 2
- 230000032050 esterification Effects 0.000 title abstract 2
- 238000005886 esterification reaction Methods 0.000 title abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 title 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 10
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 abstract 2
- POTYORUTRLSAGZ-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) prop-2-enoate Chemical compound ClCC(O)COC(=O)C=C POTYORUTRLSAGZ-UHFFFAOYSA-N 0.000 abstract 1
- YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 abstract 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 abstract 1
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 abstract 1
- AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 abstract 1
- -1 2-hydroxypropyl crotonate Chemical compound 0.000 abstract 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- FHQXEHXFCKXTOW-UHFFFAOYSA-N N,N-dimethylacetamide 2-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=O)N(C)C.C(C(=C)C)(=O)OCC(C)O FHQXEHXFCKXTOW-UHFFFAOYSA-N 0.000 abstract 1
- KUANKECWFWSYLS-UHFFFAOYSA-N N,N-dimethylacetamide 2-hydroxypropyl prop-2-enoate Chemical compound CC(=O)N(C)C.C(C=C)(=O)OCC(C)O KUANKECWFWSYLS-UHFFFAOYSA-N 0.000 abstract 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 abstract 1
- 229940113088 dimethylacetamide Drugs 0.000 abstract 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003951 lactams Chemical class 0.000 abstract 1
- 125000005395 methacrylic acid group Chemical group 0.000 abstract 1
- NZMAJUHVSZBJHL-UHFFFAOYSA-N n,n-dibutylformamide Chemical compound CCCCN(C=O)CCCC NZMAJUHVSZBJHL-UHFFFAOYSA-N 0.000 abstract 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0245—Nitrogen containing compounds being derivatives of carboxylic or carbonic acids
- B01J31/0249—Ureas (R2N-C(=O)-NR2)
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0245—Nitrogen containing compounds being derivatives of carboxylic or carbonic acids
- B01J31/0247—Imides, amides or imidates (R-C=NR(OR))
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
- C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/48—Ring-opening reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/49—Esterification or transesterification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB69946A DE1248036B (de) | 1962-12-12 | 1962-12-12 | Verfahren zur Herstellung von alpha,beta-ungesaettigten Carbonsaeureestern durch Veresterung der Carbonsaeuren mit Alkylenoxyden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB997959A true GB997959A (en) | 1965-07-14 |
Family
ID=6976483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB48649/63A Expired GB997959A (en) | 1962-12-12 | 1963-12-10 | Esterification of ª,ª-unsaturated carboxylic acids with alkylene oxides |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3280176A (cg-RX-API-DMAC10.html) |
| BE (1) | BE641124A (cg-RX-API-DMAC10.html) |
| DE (1) | DE1248036B (cg-RX-API-DMAC10.html) |
| GB (1) | GB997959A (cg-RX-API-DMAC10.html) |
| NL (1) | NL141858B (cg-RX-API-DMAC10.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106795090A (zh) * | 2014-09-22 | 2017-05-31 | 三菱丽阳株式会社 | (甲基)丙烯酸3‑氯‑2‑羟基丙酯和(甲基)丙烯酸缩水甘油酯的制造方法 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0694437B2 (ja) * | 1989-03-16 | 1994-11-24 | チッソ株式会社 | アルキレングリコールモノソルベートの製造法及び保存法 |
| US6933401B2 (en) * | 2003-06-30 | 2005-08-23 | Frank Molock | Process for the production of vicinal diesters from epoxides |
| CN100516019C (zh) * | 2006-09-14 | 2009-07-22 | 南京林业大学 | （甲基）丙烯酸羟烷酯合成方法 |
| CN113443984A (zh) * | 2016-06-28 | 2021-09-28 | 清远市柯林达新材料有限公司 | 乙烯基含氟环氧羧酸酯中间体和水溶性氟改性丙烯酸酯及制备方法和丙烯酸酯涂料 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2484487A (en) * | 1948-09-08 | 1949-10-11 | Eastman Kodak Co | Process for preparing glycol monoesters of acrylic and alpha-methacrylic acids |
| US2819296A (en) * | 1956-06-07 | 1958-01-07 | American Cyanamid Co | Preparation of hydroxyalkyl acrylates |
| US2910490A (en) * | 1956-10-16 | 1959-10-27 | Jefferson Chem Co Inc | Process for preparing glycol monoesters of organic carboxylic acids |
| US2929835A (en) * | 1957-06-06 | 1960-03-22 | Firestone Tire & Rubber Co | Reacting an alkylene oxide with an acrylic-type acid using an alkaline organic or inorganic catalyst |
| US2901505A (en) * | 1957-11-20 | 1959-08-25 | Standard Oil Co | Process for preparing glycol esters of benzene dicarboxylic acids |
| NL236750A (cg-RX-API-DMAC10.html) * | 1958-03-06 | |||
| DE1147938B (de) | 1959-04-30 | 1963-05-02 | Roehm & Haas Gmbh | Herstellung von AEthan-1, 2-diol- und Propan-1, 2-diolmonoacrylat und -monomethacrylat |
| NL277092A (cg-RX-API-DMAC10.html) | 1961-04-11 |
-
1962
- 1962-12-12 DE DEB69946A patent/DE1248036B/de active Pending
-
1963
- 1963-12-09 US US329225A patent/US3280176A/en not_active Expired - Lifetime
- 1963-12-10 GB GB48649/63A patent/GB997959A/en not_active Expired
- 1963-12-11 NL NL63301668A patent/NL141858B/xx unknown
- 1963-12-11 BE BE641124A patent/BE641124A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106795090A (zh) * | 2014-09-22 | 2017-05-31 | 三菱丽阳株式会社 | (甲基)丙烯酸3‑氯‑2‑羟基丙酯和(甲基)丙烯酸缩水甘油酯的制造方法 |
| EP3199515A4 (en) * | 2014-09-22 | 2017-10-04 | Mitsubishi Chemical Corporation | Method for producing 3-chloro-2-hydroxypropyl (meth)acrylate and method for producing glycidyl (meth)acrylate |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1248036B (de) | 1967-08-24 |
| NL301668A (cg-RX-API-DMAC10.html) | |
| NL141858B (nl) | 1974-04-16 |
| US3280176A (en) | 1966-10-18 |
| BE641124A (cg-RX-API-DMAC10.html) | 1964-06-11 |
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