GB578867A - Cyclopentadiene addition products - Google Patents
Cyclopentadiene addition productsInfo
- Publication number
- GB578867A GB578867A GB1710744A GB1710744A GB578867A GB 578867 A GB578867 A GB 578867A GB 1710744 A GB1710744 A GB 1710744A GB 1710744 A GB1710744 A GB 1710744A GB 578867 A GB578867 A GB 578867A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- trans
- dicyclopentadiene
- cis
- 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
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 title 2
- 239000002253 acid Substances 0.000 abstract 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 abstract 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 abstract 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000001530 fumaric acid Substances 0.000 abstract 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 abstract 2
- ZLYYJUJDFKGVKB-OWOJBTEDSA-N (e)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C\C(Cl)=O ZLYYJUJDFKGVKB-OWOJBTEDSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 abstract 1
- 229960004419 dimethyl fumarate Drugs 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000010438 heat treatment 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
3 : 6 - Endomethylene-D 4-tetrahydrophthalic acids are prepared by heating together maleic acid, fumaric acid or derivatives thereof and dicyclopentadiene at a temperature above that at which the latter decomposes. Specified derivatives are the anhydrides, esters, such as dimethyl or diethyl or acid esters such as ethyl or methyl esters or the acid halides. The reaction may take place in the presence of a solvent, e.g. o-dichlorobenzene. In the examples: (1) dicyclopentadiene is refluxed with (a) maleic anhydride; (b) dimethylfumarate; (c) dimethylmaleate to give (a) the anhydride of a and b cis-; (b) dimethylester of trans-; (c) dimethylester of a and b cis-3 : 6-endo-methylene-D 4-tetrahydrophthalic acid. (2) Dicyclopentadiene and o-dichlorobenzene are refluxed with (a) fumaric acid; (b) monomethylmaleate; (c) fumaryl chloride to give (a) trans-; (b) monomethylesters of isomeric cis- and trans-; (c) dichloride of trans-3 : 6-endomethylene-D 4-tetrahydrophthalic acids.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1710744A GB578867A (en) | 1944-09-07 | 1944-09-07 | Cyclopentadiene addition products |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1710744A GB578867A (en) | 1944-09-07 | 1944-09-07 | Cyclopentadiene addition products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB578867A true GB578867A (en) | 1946-07-15 |
Family
ID=10089374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1710744A Expired GB578867A (en) | 1944-09-07 | 1944-09-07 | Cyclopentadiene addition products |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB578867A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE960989C (en) * | 1954-04-18 | 1957-03-28 | Hoechst Ag | Process for the preparation of halogenated bicyclo- [2, 2, 1] -hepten- (2) - and bicyclo- [2, 2, 1] -heptadiene- (2, 5) -bis-oxyalkylene- (5, 6) - links |
| DE1006418B (en) * | 1952-12-23 | 1957-04-18 | Hoechst Ag | Process for the preparation of penta and hexachloro derivatives of 5-oxybicyclo- [2, 2, 1] -heptens- (2) |
| DE1037445B (en) * | 1955-04-01 | 1958-08-28 | Exxon Research Engineering Co | Process for the preparation of bicyclo- [2, 2, 1] -5-heptenecarboxylic acids and their derivatives |
| US3370027A (en) * | 1967-03-21 | 1968-02-20 | Velsicol Chemical Corp | Polymeric compositions prepared from a hydrocarbon fraction composed substantially of dimers and codimers of conjugated dienes |
| DE1269115B (en) * | 1953-06-17 | 1968-05-30 | Hoechst Ag | Process for the preparation of 2, 3, 4-trichlorobenzotrichloride |
| US3453293A (en) * | 1967-01-23 | 1969-07-01 | Ciba Geigy Corp | Process for the preparation of bicyclo-(2:2:1) hept-5-ene dicarboxylic acid anhydrides |
| EP0081888B1 (en) * | 1981-12-17 | 1986-08-27 | Dsm Resins B.V. | Resins and their use in coating compositions |
-
1944
- 1944-09-07 GB GB1710744A patent/GB578867A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1006418B (en) * | 1952-12-23 | 1957-04-18 | Hoechst Ag | Process for the preparation of penta and hexachloro derivatives of 5-oxybicyclo- [2, 2, 1] -heptens- (2) |
| DE1269115B (en) * | 1953-06-17 | 1968-05-30 | Hoechst Ag | Process for the preparation of 2, 3, 4-trichlorobenzotrichloride |
| DE960989C (en) * | 1954-04-18 | 1957-03-28 | Hoechst Ag | Process for the preparation of halogenated bicyclo- [2, 2, 1] -hepten- (2) - and bicyclo- [2, 2, 1] -heptadiene- (2, 5) -bis-oxyalkylene- (5, 6) - links |
| DE1037445B (en) * | 1955-04-01 | 1958-08-28 | Exxon Research Engineering Co | Process for the preparation of bicyclo- [2, 2, 1] -5-heptenecarboxylic acids and their derivatives |
| US3453293A (en) * | 1967-01-23 | 1969-07-01 | Ciba Geigy Corp | Process for the preparation of bicyclo-(2:2:1) hept-5-ene dicarboxylic acid anhydrides |
| US3370027A (en) * | 1967-03-21 | 1968-02-20 | Velsicol Chemical Corp | Polymeric compositions prepared from a hydrocarbon fraction composed substantially of dimers and codimers of conjugated dienes |
| EP0081888B1 (en) * | 1981-12-17 | 1986-08-27 | Dsm Resins B.V. | Resins and their use in coating compositions |
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