GB858257A - Cyclododecatriene- and trivinyl- cyclohexane-maleic anhydride adducts and derivatives thereof - Google Patents
Cyclododecatriene- and trivinyl- cyclohexane-maleic anhydride adducts and derivatives thereofInfo
- Publication number
- GB858257A GB858257A GB40013/58A GB4001358A GB858257A GB 858257 A GB858257 A GB 858257A GB 40013/58 A GB40013/58 A GB 40013/58A GB 4001358 A GB4001358 A GB 4001358A GB 858257 A GB858257 A GB 858257A
- Authority
- GB
- United Kingdom
- Prior art keywords
- anhydrides
- maleic anhydride
- anhydride
- carboxylic
- esters
- 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
- -1 Cyclododecatriene- and trivinyl- cyclohexane-maleic anhydride adducts Chemical class 0.000 title abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- 150000008064 anhydrides Chemical class 0.000 abstract 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000001735 carboxylic acids Chemical class 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- NWRZGFYWENINNX-UHFFFAOYSA-N 1,1,2-tris(ethenyl)cyclohexane Chemical compound C=CC1CCCCC1(C=C)C=C NWRZGFYWENINNX-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 abstract 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/08—Saturated compounds having a carboxyl group bound to a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/75—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention comprises carboxylic acid anhydrides detained by the thermal addition of from 1 to 4 molecules of maleic anhydride to 1 molecule of a cyclododecatri-(1, 5, 9)-ene or a trivinyl cyclohexane, carboxylic acids obtained by the saponification of such carboxylic anhydrides, esters obtained by the esterification of such carboxylic acids or anhydrides and saturated carboxylic acids, anhydrides and esters obtained by catalytic hydrogenation thereof. The initial products are anhydrides of dicarboxylic or higher polycarboxylic acids, e.g. tetra-, hexa- and octacarboxylic acids. Solvents for use in preparing the anhydride-olefine adducts include benzene, toluene and xylene. The composition of the products depends on the proportions of reactants and reaction times employed. The esters may be propared with mono- or polyhydric aliphatic alcohols which may be substituted. In examples: Cyclododeca-tri- (1, 5, 9)-ene and maleic acid are reacted in an autoclave to obtain an adduct in which the olefine and anhydride are combined in a proportion of 1 : 3 (1), in a similar process a similar product is obtained and hydrolysed, the free acid being esterified with ethanol in the presence of p-toluene sulphonic acid and benzene (2); an adduct in which olefine and maleic anhydride are combined in the proportion of 1 : 1 is similarly obtained and hydrogenated to the corresponding saturated di-carboxylic anhydride (3); 1 : 1 adduct of trivinyl cyclohexane and maleic anhydride is similarly obtained; (4) a 4 : 1-addition product is obtained under similar conditions and hydrolysed (5) and the 3 : 1 addition product of maleic anhydride and cyclododecatri (1, 5, 9)-ene is heated with hexan-1-ol, tetra-decan-(1)-ol and butan -(1)-ol to obtain the corresponding hexa-alkyl esters. Specifications 848,951 and 849,236 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE858257X | 1957-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB858257A true GB858257A (en) | 1961-01-11 |
Family
ID=6789794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB40013/58A Expired GB858257A (en) | 1957-12-23 | 1958-12-11 | Cyclododecatriene- and trivinyl- cyclohexane-maleic anhydride adducts and derivatives thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB858257A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0495175A2 (en) * | 1991-01-18 | 1992-07-22 | Hüls Aktiengesellschaft | Cyclohexane derivatives containing carboxyle groups |
-
1958
- 1958-12-11 GB GB40013/58A patent/GB858257A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0495175A2 (en) * | 1991-01-18 | 1992-07-22 | Hüls Aktiengesellschaft | Cyclohexane derivatives containing carboxyle groups |
| EP0495175A3 (en) * | 1991-01-18 | 1992-09-09 | Huels Aktiengesellschaft | Cyclohexane derivatives containing carboxyle groups |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH609321A5 (en) | Process for the preparation of carboxylic acid anhydrides | |
| GB1450994A (en) | Process for the preparation of a resin | |
| GB1032364A (en) | Improvements in or relating to the preparation of water-soluble alkyd resins | |
| GB858257A (en) | Cyclododecatriene- and trivinyl- cyclohexane-maleic anhydride adducts and derivatives thereof | |
| GB1161942A (en) | Process for the Preparation of Water-Soluble or Dilutable Synthetic Resins | |
| GB828202A (en) | Improvements in or relating to manufacture of rosin size | |
| GB859787A (en) | Esters in rosin sizes | |
| GB769260A (en) | Process for the preparation of isomeric racemic dihydrolysergic acids and their homologues | |
| GB957679A (en) | Process for the esterification of carboxylic acids | |
| GB646424A (en) | Process for producing aldehydes | |
| GB1331204A (en) | Alpha-methyl- butyric acid ester | |
| GB819684A (en) | Fireproof unsaturated polyester resins | |
| GB971570A (en) | A process for preparing alpha,beta-unsaturated carboxylic acids | |
| GB747970A (en) | Process of preparing diene adducts | |
| ES376421A1 (en) | Pregnane derivatives and process for preparation thereof | |
| GB570271A (en) | Improvements in or relating to the manufacture of carboxylic acid anhydrides | |
| GB321442A (en) | Improvements in and relating to the production of borneol and iso-borneol | |
| GB606607A (en) | Improvements in the manufacture of aliphatic acid anhydrides | |
| GB625203A (en) | Improvements in or relating to the manufacture of aliphatic diesters of aromatic dicarboxylic acids | |
| GB876902A (en) | New cyclopentanophenanthrene derivatives and process for the production thereof | |
| GB832292A (en) | 1ª‰-carboxy-5ª‰-hydroxy-8-ketohexahydronaphthalene lactone | |
| GB792896A (en) | Process for the preparation of unsaturated higher aliphatic alcohols | |
| GB875711A (en) | Process for increasing the resistance of leather to water | |
| GB809451A (en) | Oxidation of fatty acids | |
| GB952987A (en) | Thixotropy imparting agents, process for the manufacture thereof and products obtained therefrom |