GB561500A - Manufacture of acylated secondary alcohols - Google Patents
Manufacture of acylated secondary alcoholsInfo
- Publication number
- GB561500A GB561500A GB1089342A GB1089342A GB561500A GB 561500 A GB561500 A GB 561500A GB 1089342 A GB1089342 A GB 1089342A GB 1089342 A GB1089342 A GB 1089342A GB 561500 A GB561500 A GB 561500A
- Authority
- GB
- United Kingdom
- Prior art keywords
- lactonitrile
- reacted
- glycerol
- methyllactate
- dichlorhydrin
- 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
- 150000003333 secondary alcohols Chemical class 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 abstract 4
- -1 aliphatic monocarboxylic acids Chemical class 0.000 abstract 4
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 abstract 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 abstract 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 2
- 239000004348 Glyceryl diacetate Substances 0.000 abstract 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 abstract 2
- 235000019443 glyceryl diacetate Nutrition 0.000 abstract 2
- 229940057867 methyl lactate Drugs 0.000 abstract 2
- 229940117958 vinyl acetate Drugs 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 238000010908 decantation Methods 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 abstract 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 150000004760 silicates Chemical class 0.000 abstract 1
- 229910001220 stainless steel Inorganic materials 0.000 abstract 1
- 239000010935 stainless steel Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
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)
Abstract
Vinyl esters of aliphatic monocarboxylic acids having less than five carbon atoms are reacted with alcohols having the formula R1R2CHOH, in which R1 is halogenmethyl, cyano, cyanomethyl or aldomethyl and R2 is alkyl or the same as R1 in the presence of a reaction medium containing sufficient alkali-metal salt or tertiary amine to give a pH greater than 7.0. Examples of such secondary alcohols are: methyllactate, aldol, glycerol, diacetin, aldolcyanhydrin, lactonitrile and glycerol-a -d -dichlorhydrin and suitable catalysts are cyanides, silicates, carbonates and tetraborates of alkali metals, triethylamine and tributylamine. In examples: (1) vinyl acetate is reacted with aldol, lactonitrile, diacetin and glycerol-a : d -dichlorhydrin; (2) vinylformate is reacted with lactonitrile; (3) vinylpropionate is reacted with lactonitrile; (4) methyllactate containing some potassium cyanide is circulated through a reservoir, a stainless steel coil immersed in a cooling bath and back to the reservoir while vinylacetate is slowly introduced. The resulting ester of the secondary alcohol is usually recovered by distillation, the acetaldehyde simultaneously produced may be separated, however, by reacting with a compound which yields a product capable of removal by filtration or decantation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1089342A GB561500A (en) | 1942-08-05 | 1942-08-05 | Manufacture of acylated secondary alcohols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1089342A GB561500A (en) | 1942-08-05 | 1942-08-05 | Manufacture of acylated secondary alcohols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB561500A true GB561500A (en) | 1944-05-23 |
Family
ID=9976257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1089342A Expired GB561500A (en) | 1942-08-05 | 1942-08-05 | Manufacture of acylated secondary alcohols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB561500A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2509292A1 (en) * | 1981-07-10 | 1983-01-14 | Upjohn Co | BASED CATALYZED ACYLATION PROCESS USING ENERAL ESTERS |
-
1942
- 1942-08-05 GB GB1089342A patent/GB561500A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2509292A1 (en) * | 1981-07-10 | 1983-01-14 | Upjohn Co | BASED CATALYZED ACYLATION PROCESS USING ENERAL ESTERS |
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