GB489026A - Processes for the condensation of organic metal derivatives with acylated compounds - Google Patents
Processes for the condensation of organic metal derivatives with acylated compoundsInfo
- Publication number
- GB489026A GB489026A GB27946/36A GB2794636A GB489026A GB 489026 A GB489026 A GB 489026A GB 27946/36 A GB27946/36 A GB 27946/36A GB 2794636 A GB2794636 A GB 2794636A GB 489026 A GB489026 A GB 489026A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sodium
- acetylated
- castor oil
- fatty acid
- oil fatty
- 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
- 229910052751 metal Inorganic materials 0.000 title abstract 4
- 239000002184 metal Substances 0.000 title abstract 4
- 230000005494 condensation Effects 0.000 title abstract 3
- 238000009833 condensation Methods 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 239000000194 fatty acid Substances 0.000 abstract 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 11
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 9
- 229930195729 fatty acid Natural products 0.000 abstract 9
- 239000004359 castor oil Substances 0.000 abstract 8
- 235000019438 castor oil Nutrition 0.000 abstract 8
- 150000004665 fatty acids Chemical class 0.000 abstract 8
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 abstract 8
- -1 hydroxy fatty acids Chemical class 0.000 abstract 6
- 150000003388 sodium compounds Chemical class 0.000 abstract 6
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 abstract 6
- 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 5
- 239000011734 sodium Substances 0.000 abstract 5
- 229910052708 sodium Inorganic materials 0.000 abstract 5
- 235000011187 glycerol Nutrition 0.000 abstract 4
- 150000002736 metal compounds Chemical class 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- KGEKLUUHTZCSIP-HOSYDEDBSA-N [(1s,4s,6r)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Chemical compound C1C[C@]2(C)[C@H](OC(=O)C)C[C@H]1C2(C)C KGEKLUUHTZCSIP-HOSYDEDBSA-N 0.000 abstract 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- LSTDYDRCKUBPDI-UHFFFAOYSA-N palmityl acetate Chemical compound CCCCCCCCCCCCCCCCOC(C)=O LSTDYDRCKUBPDI-UHFFFAOYSA-N 0.000 abstract 2
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 abstract 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 abstract 2
- 229930006727 (-)-endo-fenchol Natural products 0.000 abstract 1
- WLXGQMVCYPUOLM-UHFFFAOYSA-N 1-hydroxyethanesulfonic acid Chemical compound CC(O)S(O)(=O)=O WLXGQMVCYPUOLM-UHFFFAOYSA-N 0.000 abstract 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 abstract 1
- NTXFWAVCYJWUCY-UHFFFAOYSA-N 3-oxobutanoic acid;sodium Chemical compound [Na].CC(=O)CC(O)=O NTXFWAVCYJWUCY-UHFFFAOYSA-N 0.000 abstract 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- IAIHUHQCLTYTSF-MRTMQBJTSA-N Fenchyl alcohol Chemical compound C1C[C@]2(C)[C@H](O)C(C)(C)[C@H]1C2 IAIHUHQCLTYTSF-MRTMQBJTSA-N 0.000 abstract 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract 1
- 229920002472 Starch Polymers 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
- GYGAZRPDUOHMAF-UHFFFAOYSA-N acetic acid elaidylester Natural products CCCCCCCCC=CCCCCCCCCOC(C)=O GYGAZRPDUOHMAF-UHFFFAOYSA-N 0.000 abstract 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229940115397 bornyl acetate Drugs 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 229940049297 cetyl acetate Drugs 0.000 abstract 1
- 229960000541 cetyl alcohol Drugs 0.000 abstract 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 abstract 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- IAIHUHQCLTYTSF-UHFFFAOYSA-N fenchyl alcohol Natural products C1CC2(C)C(O)C(C)(C)C1C2 IAIHUHQCLTYTSF-UHFFFAOYSA-N 0.000 abstract 1
- 239000008103 glucose Substances 0.000 abstract 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000003903 lactic acid esters Chemical class 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 abstract 1
- GYGAZRPDUOHMAF-KHPPLWFESA-N oleyl acetate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(C)=O GYGAZRPDUOHMAF-KHPPLWFESA-N 0.000 abstract 1
- 150000004707 phenolate Chemical class 0.000 abstract 1
- 229940049953 phenylacetate Drugs 0.000 abstract 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 abstract 1
- 229960003656 ricinoleic acid Drugs 0.000 abstract 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000344 soap Substances 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- LFQULJPVXNYWAG-UHFFFAOYSA-N sodium;phenylmethanolate Chemical compound [Na]OCC1=CC=CC=C1 LFQULJPVXNYWAG-UHFFFAOYSA-N 0.000 abstract 1
- 239000008107 starch Substances 0.000 abstract 1
- 235000019698 starch Nutrition 0.000 abstract 1
- 229960003080 taurine Drugs 0.000 abstract 1
- 229940116411 terpineol Drugs 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- 239000000080 wetting agent Substances 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/305—Saturated compounds containing more than one carboxyl group containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Esters of aliphatic carboxylic acids having four or less carbon atoms in the molecule are heated with alcoholates, phenolates or organic metal compounds in which a hydrogen atom attached to carbon is substituted by the metal whereby condensation occurs, the metal salt of the lower aliphatic carboxylic acid being split off. According to a modification, hydroxy fatty acids acylated at the hydroxy group with aliphatic, aromatic, alicyclic or heterocyclic carboxylic acids are condensed with alcoholates or organic metal compounds in which a hydrogen atom attached to carbon is substituted by the metal. The metal compounds may contain reactive groups such as carboxyl, carbonyl or sulphonic groups or other groups containing sulphur or nitrogen. In examples: (1) sodium butylate is heated with acetylated octanol-2, acetylated ricinoleic acid and terpenylacetate; (2) sodium amylate is heated with acetylated cetyl alcohol; (3) sodium is dissolved in butyl alcohol and reacted with terpineol and the resulting sodium compound heated with terpenylacetate; (4) the sodium compound of glycerine is heated with acetylated wool fat alcohol and with acetylated hydroquinone; (5) acetylated castor oil fatty acid is heated with the sodium compound of malonic ester, sodium phenolate and with the sodium compound of glycerol; (6) the ether-fatty acid obtained from acetylated castor oil fatty acid and sodium butylate is saponified, condensed with glycolchlorhydrin or glycerol chlorhydrin and sulphonated to give a wetting agent. The sodium soaps of the ether-fatty acids may themselves be sulphonated and the carboxylic group esterified. The ether-fatty acids may also be condensed with hydroxyethane sulphonic acid or taurine to give textile assistants. The condensation of sodium malonic ester with acetylated cellulose, starch and glucose is mentioned. Samples have been furnished under Sect. 2 (5) of products obtained by condensing the following components; (a) diethyloxalate and sodium butylate; (b) acetylated castor oil fatty acid and sodium malonic acid ester; (c) terpenyl acetate and sodium oleylate; (d) the sodium compound of fenchyl alcohol and oleylacetate; (e) cetyl acetate and sodium malonic acid ester; (f) bornyl acetate and sodium malonic acid ester; (g) butyl acetate and sodium acetyl acetic acid; (h) phenylacetate and sodium benzylate; (i) benzoylated castor oil fatty acid and sodium ethylate; (j) sodium butylate and the lactic acid ester of castor oil fatty acid; (k) sodium butylate and acetylated secondary octyl alcohol; (l) sodium compound of glycerol and acetylated castor oil fatty acid; (m) sodium butylate and acetylated castor oil fatty acid; (n) sodium phenolate and acetylated castor oil fatty acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB27946/36A GB489026A (en) | 1936-10-14 | 1936-10-14 | Processes for the condensation of organic metal derivatives with acylated compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB27946/36A GB489026A (en) | 1936-10-14 | 1936-10-14 | Processes for the condensation of organic metal derivatives with acylated compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB489026A true GB489026A (en) | 1938-07-14 |
Family
ID=10267815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27946/36A Expired GB489026A (en) | 1936-10-14 | 1936-10-14 | Processes for the condensation of organic metal derivatives with acylated compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB489026A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0541152A3 (en) * | 1991-11-04 | 1993-06-30 | Quest International B.V. | Ethers for aromatizing purposes |
-
1936
- 1936-10-14 GB GB27946/36A patent/GB489026A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0541152A3 (en) * | 1991-11-04 | 1993-06-30 | Quest International B.V. | Ethers for aromatizing purposes |
| US5313002A (en) * | 1991-11-04 | 1994-05-17 | Unilever Patent Holdings B.V. | Ethers for aromatizing purposes |
| US5432154A (en) * | 1991-11-04 | 1995-07-11 | Unilever Patent Holdings B.V. | Ethers for aromatizing purposes |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB836854A (en) | New imidazole derivatives and processes for their preparation | |
| US2109400A (en) | Esters of testosterone and process of making same | |
| US2182397A (en) | Manufacture of ether derivatives of polyhydric alcohols | |
| GB489026A (en) | Processes for the condensation of organic metal derivatives with acylated compounds | |
| Craig et al. | Quantitative analysis of short chain fatty acids using gas liquid chromatography | |
| IE34354B1 (en) | D-glucofuranose compounds and process for preparing them | |
| White | The Constitution of Mesquite Gum. IV. 4-Methoxy-D-glucuronic Acid1 | |
| Walton | Potential antimicrobial agents. I. Alkyl 4-oxo-2-alkenoates | |
| Kamal et al. | Studies in the biochemistry of micro-organisms—II: Constitution of curvulin, curvulinic acid and curvulol, metabolic products of curvularia siddiqui | |
| Marks et al. | The determination of the hydroxyl content of organic compounds: estimation of castor oil | |
| US2043476A (en) | Cabboxylates of aliphatic alcohols | |
| GB953775A (en) | Processes for the preparation of sorbic acid and alkyl esters of sorbic acid | |
| US4326070A (en) | Beta deuterated 2-ethylhexanol and derivatives | |
| Bell et al. | Selective reduction of esters with sodium trimethoxyborohydride | |
| US2253669A (en) | Estradiol higher fatty acid ester | |
| US2576897A (en) | Compositions of matter containing semiesters of dicarboxylic acids | |
| US2010727A (en) | Naphthenic alcohol esters of fatty acids | |
| McCutchon et al. | Derivatives of ricinelaidic acid. Their infrared spectra and conformation of the ricinelaidic moiety | |
| GB744582A (en) | Improvements in and relating to the production of unsaturated acids and esters | |
| Gensler et al. | Configuration of 9, 10-Dihydroxystearic Acid1 | |
| US2120544A (en) | Chloroether esters of dibasic acids | |
| GB436885A (en) | Improved process for the production of mixed esters of polyhydric alcohols and of carbohydrates | |
| GB841701A (en) | 4:4-diaminodiphenylsulphoxide derivatives | |
| GB499794A (en) | Manufacture of new esters of compounds of the oestrone series | |
| US2563846A (en) | Cyclopentanoperhydrophenanthrene compounds |