GB695503A - Improvements in or relating to the preparation of alkyl esters of aliphatic -a:-a-unsaturated carboxylic acids - Google Patents
Improvements in or relating to the preparation of alkyl esters of aliphatic -a:-a-unsaturated carboxylic acidsInfo
- Publication number
- GB695503A GB695503A GB12214/51A GB1221451A GB695503A GB 695503 A GB695503 A GB 695503A GB 12214/51 A GB12214/51 A GB 12214/51A GB 1221451 A GB1221451 A GB 1221451A GB 695503 A GB695503 A GB 695503A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- acid nitrile
- nitrile
- aliphatic
- addition
- 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
- 125000001931 aliphatic group Chemical group 0.000 title abstract 3
- 125000005907 alkyl ester group Chemical group 0.000 title abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 title abstract 2
- -1 Acrylic acid nitrile Chemical class 0.000 abstract 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 abstract 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 abstract 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000002028 premature Effects 0.000 abstract 1
- 235000019260 propionic acid Nutrition 0.000 abstract 1
- 229940079877 pyrogallol Drugs 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 abstract 1
- 235000018553 tannin Nutrition 0.000 abstract 1
- 229920001864 tannin Polymers 0.000 abstract 1
- 239000001648 tannin Substances 0.000 abstract 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Alkyl esters of aliphatic a : b -unsaturated carboxylic acids are prepared by a process in which aliphatic b -alkoxy carboxylic acid nitriles are reacted with sulphuric acid at elevated temperatures. Acrylic acid nitrile, methacrylic acid nitrile and their homologues such as ethacrylic acid nitrile may be converted into the esters if first converted by the addition of alcohols to b -alkoxypropionitrile, b -alkoxy, isobutyric acid nitrile and their homologues. The b -alkoxy carboxylic acid nitrile may be passed into hot sulphuric acid and the resulting unsaturated ester may be continuously distilled off, if desired under vacuum. Premature polymerization in the reaction mixture may be prevented by the addition of a polymerization inhibitor such as hydroquinone, pyrogallol, tannin or sulphur. In examples: Acrylic acid methyl ester (1) methacrylic acid methyl ester (2) and acrylic acid butyl ester (3) are obtained respectively from b -methoxy propionic acid nitrile, b -methoxyisobutyric acid nitrile and b -butoxypropionic acid nitrile respectively. b -Methoxypropionic acid nitrile is obtained by the addition of methanol to acrylic acid nitrile and b -methoxy isobutyric acid is similarly obtained. b -butoxy propionic acid nitrile is obtained by dropping acrylonitrile into butanol in which metallic sodium or sodium methacrylate is dissolved with cooling. The reaction product is neutralized and b -butoxy propionic acid is distilled.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP13112D DE868153C (en) | 1948-10-02 | 1948-10-02 | Process for the preparation of esters ª ‡, ª ‰ -unsaturated carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB695503A true GB695503A (en) | 1953-08-12 |
Family
ID=7364444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12214/51A Expired GB695503A (en) | 1948-10-02 | 1951-05-24 | Improvements in or relating to the preparation of alkyl esters of aliphatic -a:-a-unsaturated carboxylic acids |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE868153C (en) |
| GB (1) | GB695503A (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE729342C (en) * | 1938-05-20 | 1942-12-15 | Degussa | Process for the production of acrylic acid, methacrylic acid and their esters from ª ‰ -alkoxycarboxylic acids |
-
1948
- 1948-10-02 DE DEP13112D patent/DE868153C/en not_active Expired
-
1951
- 1951-05-24 GB GB12214/51A patent/GB695503A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE868153C (en) | 1953-02-23 |
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