GB592106A - Improvements in and relating to the production of esters of dibasic aliphatic acids - Google Patents
Improvements in and relating to the production of esters of dibasic aliphatic acidsInfo
- Publication number
- GB592106A GB592106A GB1254545A GB1254545A GB592106A GB 592106 A GB592106 A GB 592106A GB 1254545 A GB1254545 A GB 1254545A GB 1254545 A GB1254545 A GB 1254545A GB 592106 A GB592106 A GB 592106A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alcohol
- adipamide
- adipate
- octadecyl
- cetyl
- 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
- 150000002148 esters Chemical class 0.000 title abstract 4
- 125000001931 aliphatic group Chemical group 0.000 title abstract 2
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 abstract 6
- 235000019441 ethanol Nutrition 0.000 abstract 6
- 150000001298 alcohols Chemical class 0.000 abstract 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 3
- VDBXLXRWMYNMHL-UHFFFAOYSA-N decanediamide Chemical compound NC(=O)CCCCCCCCC(N)=O VDBXLXRWMYNMHL-UHFFFAOYSA-N 0.000 abstract 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N Cetyl alcohol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 abstract 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N Dodecanol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 abstract 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N Pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 abstract 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N Sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 abstract 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N Stearyl alcohol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atoms Chemical group C* 0.000 abstract 2
- 229960000541 cetyl alcohol Drugs 0.000 abstract 2
- 150000001470 diamides Chemical class 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 229920000728 polyester Polymers 0.000 abstract 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 2
- XFQHIELVPOKJIM-UHFFFAOYSA-N 1,4-dioxacyclotetradecane-5,14-dione Chemical compound O=C1CCCCCCCCC(=O)OCCO1 XFQHIELVPOKJIM-UHFFFAOYSA-N 0.000 abstract 1
- PAALZGOZEUHCET-UHFFFAOYSA-N 1,4-dioxecane-5,10-dione Chemical compound O=C1CCCCC(=O)OCCO1 PAALZGOZEUHCET-UHFFFAOYSA-N 0.000 abstract 1
- GIGYJAKGGCCFLM-UHFFFAOYSA-M 10-dodecoxy-10-oxodecanoate Chemical compound CCCCCCCCCCCCOC(=O)CCCCCCCCC([O-])=O GIGYJAKGGCCFLM-UHFFFAOYSA-M 0.000 abstract 1
- JBQKDXQJSYBVEN-UHFFFAOYSA-M 6-dodecoxy-6-oxohexanoate Chemical compound CCCCCCCCCCCCOC(=O)CCCCC([O-])=O JBQKDXQJSYBVEN-UHFFFAOYSA-M 0.000 abstract 1
- BPOSRHRZGSYVSR-UHFFFAOYSA-M 6-hexadecoxy-6-oxohexanoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CCCCC([O-])=O BPOSRHRZGSYVSR-UHFFFAOYSA-M 0.000 abstract 1
- ABXNBKQSDWIZQP-UHFFFAOYSA-M 6-octadecoxy-6-oxohexanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCC([O-])=O ABXNBKQSDWIZQP-UHFFFAOYSA-M 0.000 abstract 1
- OCGYMBADNKTFGU-UHFFFAOYSA-N C(CCCCC(=O)OCCCCCCCCCCCCCCCCCC)(=O)OCCCCCCCCCCCCCCCC Chemical compound C(CCCCC(=O)OCCCCCCCCCCCCCCCCCC)(=O)OCCCCCCCCCCCCCCCC OCGYMBADNKTFGU-UHFFFAOYSA-N 0.000 abstract 1
- WWSHFDBYWOBAJC-UHFFFAOYSA-M C(CCCCCCCCC(=O)[O-])(=O)OCCCCCCCCCCCCCCCC Chemical compound C(CCCCCCCCC(=O)[O-])(=O)OCCCCCCCCCCCCCCCC WWSHFDBYWOBAJC-UHFFFAOYSA-M 0.000 abstract 1
- AWPXEIYCCPDZOV-UHFFFAOYSA-M C(CCCCCCCCC(=O)[O-])(=O)OCCCCCCCCCCCCCCCCCC Chemical compound C(CCCCCCCCC(=O)[O-])(=O)OCCCCCCCCCCCCCCCCCC AWPXEIYCCPDZOV-UHFFFAOYSA-M 0.000 abstract 1
- FANBESOFXBDQSH-UHFFFAOYSA-N Ethyladipic acid Chemical compound CCC(C(O)=O)CCCC(O)=O FANBESOFXBDQSH-UHFFFAOYSA-N 0.000 abstract 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M Sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 abstract 1
- 230000002745 absorbent Effects 0.000 abstract 1
- 239000002250 absorbent Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 230000000875 corresponding Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 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
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
Abstract
Esters of dibasic aliphatic acids which contain at least 6 carbon atoms in a chain are produced by condensing an aliphatic alcohol at a temperature of at least 190 DEG C. with a diamide having the general formula H2N-OC-(CH2)n-CO-NH2, n being not less than 4, and simultaneously removing the liberated ammonia. Suitable diamides for use are adipamide and sebacamide which may be prepared as described in U.S.A. Specification 2,109,941 by heating 1 mol. of urea with 1 mol. of adipic or sebacic acid at about 160-180 DEG C. for 4-6 hours, other dibasic acids such as pimelic acid may also be used. When 1 mol of the diamide is condensed with 1 mol. of each of two different alcohols having the general formula R-OH and R1-OH, mixed esters of the type ROOC-(CH2)n-COOR1, R and R1 being alkyl groups and n not less than 4, can be obtained. The process is particularly useful for preparing long chain esters having the same or different alkyl groups containing at least 12 carbon atoms and reaction between the higher alcohols used and the diamides is readily effected by heating them together in an open flask until evolution of ammonia closes. When using the lower alcohols, the reaction must be effected in a closed vessel under pressure to obtain the desired reaction temperature and the liberated ammonia must be removed, e.g. by using an absorbent such as sodium bisulphate. When dihydric or polyhydric alcohols are used, the products are polyesters, e.g. with equimolecular quantities of ethylene glycol and adipamide, the product is a polymeric ethylene adipate having a structural unit of the formula (-OC-(CH2)4-CO-O-(CH2)2-O-). In examples: (1) cetyl adipate is obtained from adipamide and cetyl alcohol, heated together at 200-250 DEG C.; (2) and (3) lauryl adipate and n-octadecyl adipate are similarly obtained, using lauryl alcohol and n-octadecyl alcohol respectively; (4), (5) and (6) n-octadecyl sebacate, lauryl sebacate and cetyl sebacate are obtained from sebacamide and n-octadecyl alcohol, lauryl alcohol and cetyl alcohol respectively; (7) ethyl adipate is obtained by heating ethyl alcohol and adipamide under pressure at 200-250 DEG C.; (8) cetyl octadecyl adipate is obtained from adipamide and the corresponding alcohols; (9) sebacamide and ethylene glycol are reacted to produce a polymeric ethylene sebacate; (10) a resinous high molecular weight polyester is obtained from adipamide and glycerol. The Provisional Specification is not limited to the use of an aliphatic alcohol.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB592106A true GB592106A (en) | 1947-09-08 |
Family
ID=1719431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1254545A Expired GB592106A (en) | 1945-05-18 | Improvements in and relating to the production of esters of dibasic aliphatic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB592106A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2809208A (en) * | 1954-12-13 | 1957-10-08 | Allied Chem & Dye Corp | Production of dialkyl esters of isophthalic and terephthalic acids from nitriles |
| US2914553A (en) * | 1955-09-22 | 1959-11-24 | Distillers Co Yeast Ltd | Alcoholysis of aromatic carboxylic acid amides with polyhydric alcohols |
| US2921088A (en) * | 1955-11-25 | 1960-01-12 | Distillers Co Yeast Ltd | Alcoholysis of aromatic nitriles with polyhydric alcohols |
| WO2012024808A1 (en) * | 2010-08-25 | 2012-03-01 | Panolin Ag | Ester oils |
-
1945
- 1945-05-18 GB GB1254545A patent/GB592106A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2809208A (en) * | 1954-12-13 | 1957-10-08 | Allied Chem & Dye Corp | Production of dialkyl esters of isophthalic and terephthalic acids from nitriles |
| US2914553A (en) * | 1955-09-22 | 1959-11-24 | Distillers Co Yeast Ltd | Alcoholysis of aromatic carboxylic acid amides with polyhydric alcohols |
| US2921088A (en) * | 1955-11-25 | 1960-01-12 | Distillers Co Yeast Ltd | Alcoholysis of aromatic nitriles with polyhydric alcohols |
| WO2012024808A1 (en) * | 2010-08-25 | 2012-03-01 | Panolin Ag | Ester oils |
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