cis-1,2,3,6-테트라히드로프탈산무수물
cis-1,2,3,6-테트라히드로프탈산무수물 · THPA · CIS-4-CYCLOHEXENE-1,2-DICARBOXYLIC ANHYDRIDE · (3aR,7aS)-3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione · CIS-DELTA4-TETRAHYDROPHTHALIC ANHYDRIDE · CIS-4-CYCLOHEXENEDICARBOXYLIC ANHYDRIDE: 1,2,3,6-THPA: THPA · CIS-4-TETRAHYDROPHTHALIC ANHYDRIDE · 4-CYCLOHEXENE-1,2-DICARBOXYLIC ANHYDRIDE
식별자 및 물리적 특성
| CAS No. | 935-79-5 |
|---|---|
| 분자식 | C8H8O3 |
| 평균 분자량 | 152.15 g/mol |
| 단동위원소 질량 | 152.04734412 g/mol |
| SMILES | O=C1OC(=O)[C@@H]2CC=CC[C@H]12 |
| InChIKey | KMOUUZVZFBCRAM-OLQVQODUSA-N |
| PubChem CID | 98495 |
| ChEMBL | CHEMBL2228342 |
| EC No. | 213-308-7 |
| DTXSID | DTXSID80883570 |
| 현지명 | cis-1,2,3,6-테트라히드로프탈산무수물 |
화학 및 물리적 성질
| XLogP | 0.8 |
|---|---|
| 극성 표면적 | 43.4 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 11 |
| 형식 전하 | 0 |
| 복잡도 | 218 |
| Polymers | Plastics & Rubber -> Acid Anhydrides, Cyclic |
| SpringerMaterials Properties | Chemical shift |
| Physical Description | White chips[Alfa Aesar MSDS] |
| 녹는점 | 98 °C |
| 끓는 점 | 234.6°C (rough estimate) |
| 밀도 | 1.2143 (rough estimate) |
| 증기 밀도 | 5.2 (vs air) |
| 증기압 | <0.01 mm Hg ( 20 °C) |
| 굴절률 | 1.4447 (estimate) |
| 인화점 | 156 °C |
| 저장 조건 | under inert gas (nitrogen or Argon) at 2-8°C |
| 용해도 | soluble in Toluene,Benzene |
| 물리적 상태 | powder to crystal |
| 색상 | 흰색에서 거의 흰색 |
| 용해도 | 물과 반응 |
| BRN | 82341 |
| InChI | 1S/C8H8O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-2,5-6H,3-4H2/t5-,6+ |
| InChIKey | KMOUUZVZFBCRAM-OLQVQODUSA-N |
| SMILES | [H][C@@]12CC=CC[C@]1([H])C(=O)OC2=O |
| NIST | cis-1,2,3,6-Tetrahydrophthalic anhydride(935-79-5) |
| EPA | 1,3-Isobenzofurandione, 3a,4,7,7a-tetrahydro-, (3aR,7aS)-rel- (935-79-5) |
화학적 성질
Tetrahydrophthalic Anhydride (THPA) is a white crystalline powder or FLAKES. It is slightly soluble in benzene and acetone and it is also sensitive to moisture.
안전 및 규제
| GHS 분류 | DangerH317: May cause an allergic skin reaction [Warning Sensitization, Skin]P233, P260, P261, P264+P265, P271, P272, P273, P280, P284, P302+P352, P304+P340, P305+P354+P338, P317, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin] |
|---|---|
| 규제 정보 | Hazard Traits - Respiratory Toxicity |
| 유해성 요약 | May cause serious eye injuryMay cause skin and respiratory sensitization[Alfa Aesar MSDS] See ACID ANHYDRIDES. |
| Hazard Classes and Categories | Skin Sens. 1 (100%)Eye damage - category 1Eye Dam. 1 |
| 유해 작용 | Asthma - Reversible bronchoconstriction (narrowing of bronchioles) initiated by the inhalation of irritating or allergenic agents. |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | GW5775000 |
| 운송 번호(UN) | UN 2698 8/PG 3 |
| 관세 코드 | 29173990 |
| 위험 문구(R) | 41-42/43-52/53 |
| 위험 표시 | Xn |
| 안전 문구(S) | 22-24-26-37/39-61-52/53-42/43-41 |
| 포장분류 | III |
| 위험 등급 | 8Aquatic Chronic 3Eye Dam. 1Resp. Sens. 1Skin Sens. 1 |
| 저장 분류 | 8A - Combustible corrosive hazardous materials |
용도
개요
Tetrahydrophthalic anhydride is an organic compound with the formula C6H8C2O3. The compound exists as two isomers, this article being focused on the more common cis isomer. It is a precursor to other compounds including the dicarboxylic acid tetrahydrophthalic acid as well the tetrahydrophthalimide, which is a precursor to the fungicide Captan. It is a white solid that is soluble in organic solvents.Tetrahydrophthalic anhydride, the cis isomer, is prepared by the Diels-Alder reaction of butadiene and maleic anhydride.
용도
Tetrahydrophthalic Anhydride is an anhydride hardener mainly used in the fields of coatings, epoxy resin curing agents, polyester resins, adhesives, plasticizers, pesticides, etc. It is also used as a chemical intermediate for light colored alkyds.Tetrahydrophthalic Anhydride is an organic compound obtained from the reaction of Maleic Anhydride and Butadiene.
제조 및 합성 방법
제조 방법
A flask containing 500 ml of dry benzene and 196 gm (2 moles) of maleic anhydride is heated with a pan of hot water while butadiene is introduced rapidly (0.6-0.8 liter/min) from a commercial cylinder. The solution is stirred rapidly and the heating is stopped after 3-5 min when the temperature reaches 50°C. In 15-25 min the reaction causes the temperature of the solution to reach 70-75°C. The absorption of the rapid stream of butadiene is nearly complete in 30-40 min. The addition of butadiene is continued at a slower rate for a total of 2\ hr. The solution is poured into a 1-liter beaker which is covered and kept at 0-5°C overnight. The product is collected on a large Buchner funnel and washed with 250 ml of b.p. 35-60°C petroleum ether. A second crop is obtained by diluting the filtrate with an additional 250 ml of petroleum ether. Both crops are dried to constant weight in an oven at 70-80°C to yield 281.5-294.5 gm (96- 97%, m.p. 99-102°C). Recrystallization from ligroin or ether raises the melting point to 103-104°C.