US1864884A - Process of producing acrylic acid esters - Google Patents
Process of producing acrylic acid esters Download PDFInfo
- Publication number
- US1864884A US1864884A US371966A US37196629A US1864884A US 1864884 A US1864884 A US 1864884A US 371966 A US371966 A US 371966A US 37196629 A US37196629 A US 37196629A US 1864884 A US1864884 A US 1864884A
- Authority
- US
- United States
- Prior art keywords
- acid esters
- acrylic acid
- producing acrylic
- esters
- beta
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title description 5
- 125000005396 acrylic acid ester group Chemical group 0.000 title description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000003151 propanoic acid esters Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- ZCLGVXACCAZJOX-UHFFFAOYSA-N ethyl 3-chloropropanoate Chemical compound CCOC(=O)CCCl ZCLGVXACCAZJOX-UHFFFAOYSA-N 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 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
Definitions
- My invention relates to esters and consists in a'new process of producing acrylic acid esters.
- alcohol as a solvent.
- the new process is carried out without any supply of heat.
- the occurring heat of reaction is removed by cooling.
- sensitive esters one preferably operates at temperatures below room temperature.
- Emample 13.65 kilograms of beta-chlorpropionic acid ethyl ester are treated with 20 kilo-- grams of 20% alcoholic soda lye at room temperature, cooling being resorted to.
- the re- 1 n sult is a yield of about 90% acrylic acid ethyl ester, which is purified.
- the process of producing acrylic acid esters which consists in treating a beta halcgen propionic acid ester ofan aliphatic monohydro alcohol with alkali metal hydroxide in t e presence of alcohol.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented June 28, 1932 I l I p I UNITED- STATES PATENT OFFICE WALTER BAUER, OF DARMSTADT, GERMANY, -.-A.SSIGNOR TO BOHI & HAAS unim- GESELLSOHAFT, OF DARMS'IADT, GERMANY, A CORPORATION OF GERMANY PROCESS OF PRODUCING ACRYLIC ACID ESTERS I No Drawing. Application filed June 18, 1929, Serial No. 871,966, and in Germany I 11y 80, 1938.
My invention relates to esters and consists in a'new process of producing acrylic acid esters.
Because of the sensitiveness of the ester group, it has, heretofore, been impossible to Y produce from beta-halogenated carboxylic acid esters by alkali metal hydroxides unsaturated esters.
Now, I have discovered that acrylic acid esters, in spite of the great sensitiveness of the ester group, can be produced from beta- I halogenated propionic acid esters by the action thereon of alkali metal hydroxides with good results, and further, I have found that together with the action of the alkalis,
it is advantageous to use alcohol as a solvent. The new process is carried out without any supply of heat. The occurring heat of reaction is removed by cooling. With sensitive esters one preferably operates at temperatures below room temperature.
Emample 13.65 kilograms of beta-chlorpropionic acid ethyl ester are treated with 20 kilo-- grams of 20% alcoholic soda lye at room temperature, cooling being resorted to. The re- 1 n sult is a yield of about 90% acrylic acid ethyl ester, which is purified. so I claim:
The process of producing acrylic acid esters, which consists in treating a beta halcgen propionic acid ester ofan aliphatic monohydro alcohol with alkali metal hydroxide in t e presence of alcohol.
In testimony whereof I aflix my signature.
WALTER BAUER.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1864884X | 1928-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1864884A true US1864884A (en) | 1932-06-28 |
Family
ID=7746635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US371966A Expired - Lifetime US1864884A (en) | 1928-07-30 | 1929-06-18 | Process of producing acrylic acid esters |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1864884A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2429373A (en) * | 1944-03-17 | 1947-10-21 | Universal Oil Prod Co | Manufacture of 2,2,3-trimethylbutane |
| US2434229A (en) * | 1945-07-26 | 1948-01-06 | Gen Aniline & Film Corp | Production of alpha-haloacrylic compounds |
| US2500005A (en) * | 1946-08-17 | 1950-03-07 | Sinclair Refining Co | Production of esters of unsaturated lower fatty acids |
| US2679530A (en) * | 1949-11-04 | 1954-05-25 | Ciba Ltd | Process for the manufacture of alpha:beta-unsaturated carboxylic acid esters from beta-halogen carboxylic acid esters |
| US2800231A (en) * | 1954-08-17 | 1957-07-23 | Gordon M Hicks | Drain strainer |
| US2818362A (en) * | 1954-05-18 | 1957-12-31 | American Cyanamid Co | N-vinyl-2-oxazolidone and polymerization products thereof and method of making |
| US3468947A (en) * | 1965-09-02 | 1969-09-23 | Nat Distillers Chem Corp | Preparation of alpha,beta-unsaturated acyl halides |
-
1929
- 1929-06-18 US US371966A patent/US1864884A/en not_active Expired - Lifetime
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2429373A (en) * | 1944-03-17 | 1947-10-21 | Universal Oil Prod Co | Manufacture of 2,2,3-trimethylbutane |
| US2434229A (en) * | 1945-07-26 | 1948-01-06 | Gen Aniline & Film Corp | Production of alpha-haloacrylic compounds |
| US2500005A (en) * | 1946-08-17 | 1950-03-07 | Sinclair Refining Co | Production of esters of unsaturated lower fatty acids |
| US2679530A (en) * | 1949-11-04 | 1954-05-25 | Ciba Ltd | Process for the manufacture of alpha:beta-unsaturated carboxylic acid esters from beta-halogen carboxylic acid esters |
| US2818362A (en) * | 1954-05-18 | 1957-12-31 | American Cyanamid Co | N-vinyl-2-oxazolidone and polymerization products thereof and method of making |
| US2800231A (en) * | 1954-08-17 | 1957-07-23 | Gordon M Hicks | Drain strainer |
| US3468947A (en) * | 1965-09-02 | 1969-09-23 | Nat Distillers Chem Corp | Preparation of alpha,beta-unsaturated acyl halides |
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