GB591710A - Improvement in ethers of esters of lactic acid - Google Patents
Improvement in ethers of esters of lactic acidInfo
- Publication number
- GB591710A GB591710A GB1181845A GB1181845A GB591710A GB 591710 A GB591710 A GB 591710A GB 1181845 A GB1181845 A GB 1181845A GB 1181845 A GB1181845 A GB 1181845A GB 591710 A GB591710 A GB 591710A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- alkyl
- acetal
- ethers
- lactic acid
- 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
- 150000002170 ethers Chemical class 0.000 title abstract 2
- 239000004310 lactic acid Substances 0.000 title abstract 2
- 235000014655 lactic acid Nutrition 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 title 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 title 1
- 150000001241 acetals Chemical class 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- -1 2-ethyl-hexyl Chemical group 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 2
- 150000003903 lactic acid esters Chemical class 0.000 abstract 2
- 239000011707 mineral Substances 0.000 abstract 2
- AIJULSRZWUXGPQ-UHFFFAOYSA-N pyruvic aldehyde Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 abstract 2
- RNCAOJWMVLSWPT-UHFFFAOYSA-N 2-ethylhexyl 2-(2-ethylhexoxy)propanoate Chemical compound CCCCC(CC)COC(C)C(=O)OCC(CC)CCCC RNCAOJWMVLSWPT-UHFFFAOYSA-N 0.000 abstract 1
- QSAKAEANBZKQIW-UHFFFAOYSA-N COCCOC(C(=O)OCCOC)C Chemical compound COCCOC(C(=O)OCCOC)C QSAKAEANBZKQIW-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000001476 alcoholic Effects 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- IKRARXXOLDCMCX-UHFFFAOYSA-N butyl 2-butoxypropanoate Chemical compound CCCCOC(C)C(=O)OCCCC IKRARXXOLDCMCX-UHFFFAOYSA-N 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 229920003086 cellulose ether Polymers 0.000 abstract 1
- 230000000875 corresponding Effects 0.000 abstract 1
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 abstract 1
- 238000005194 fractionation Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N methoxyethyl Chemical group CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- JLCZWXOYGCHPFJ-UHFFFAOYSA-N propan-2-yl 2-propan-2-yloxypropanoate Chemical compound CC(C)OC(C)C(=O)OC(C)C JLCZWXOYGCHPFJ-UHFFFAOYSA-N 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 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
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
- C07C69/68—Lactic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Ethers of lactic acid esters are produced by heating a di-acetal of pyruvic aldehyde at above 100 DEG C. in the presence of an acid catalyst such as hydrochloric, sulphuric, phosphoric and sulphonic acids, and an alcohol. Instead of the di-acetal, there may be used its components, viz. pyruvic aldehyde and more than two molar proportions of alcohol. The acetal may have the formula CH3.CO.CH(OR)2, where R is alkyl, alkoxy-alkyl, aroxy-alkyl or aralkyl, and the alcohol may correspond to the alkyl or substituted alkyl group thereof. Specified acetals are the di-ethyl, isopropyl, butyl, 2-ethyl-hexyl, lauryl, methoxy-ethyl and b -chlorethyl acetals, the corresponding ether of lactic acid ester being ethyl 2-ethoxypropionate, isopropyl - 2 - isopropoxypropionate, butyl 2-butoxypropionate, 2 - ethylhexyl 2 - (2 - ethyl - hexoxy) - propionate, lauryl 2 - lauroxypro - pionate, methoxyethyl 2 - methoxyethoxy - propionate and b -chlorethyl a -b -chlorethoxy-propionate. The products may be separated by selective acid hydrolysis of the unconverted acetal followed by fractionation or recovered as lactic acid ethers by saponification with alcoholic alkali metal hydroxide followed by addition of mineral hydroxide followed by addition of mineral acid. They are useful as solvents and plasticisers for vinyl resins and cellulose esters and ethers. In examples, sulphuric acid is the catalyst used, temperatures being 130-150 DEG C.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB591710A true GB591710A (en) | 1947-08-26 |
Family
ID=1712479
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1181845A Expired GB591710A (en) | 1945-05-11 | Improvement in ethers of esters of lactic acid |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB591710A (en) |
-
1945
- 1945-05-11 GB GB1181845A patent/GB591710A/en not_active Expired
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