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Propyne → Ddsa thpa

HRID 1976282
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HRID 1976282 반응식
CC#C.C1(=O)OC(=O)C=C1.C=CC=C.[CH3:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]/[CH:27]1[C:32](=[O:33])[O:31][C:29](=[O:30])[CH2:28]1.[CH2:34]1[CH:39]2[C:40]([O:42][C:43](=[O:44])[CH:38]2[CH2:37][CH:36]=[CH:35]1)=[O:41]>>[CH3:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]/[CH:27]1[C:32](=[O:33])[O:31][C:29](=[O:30])[CH2:28]1.[CH2:37]1[CH:38]2[C:43]([O:42][C:40](=[O:41])[CH:39]2[CH2:34][CH:35]=[CH:36]1)=[O:44]
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참가 물질

6

반응물 5

HCID 6335Propyne2회HCID 6810Tetrahydrophthalic anhydride2회HCID 78451,3-Butadiene2회HCID 7923Maleic Anhydride4회HCID 6433892Dodecenylsuccinic anhydride2회

생성물 1

HCID 131722535Ddsa thpa

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온도
227.5 °C

실험 절차

A 5 L-nitrogen-dried Büchi reactor, fitted with a mechanical stirrer, a sampling dip-leg, a vent, a rupture disk, a pressure sensor, a thermocouple well and a nitrogen inlet tube, was charged with propylene tetramer (2000 g, 1.75 eq.) and maleic anhydride (677 g, 1.0 eq.). The maleic anhydride was added as a solid (crushed briquettes from Aldrich) at room temperature. The reactor was then sealed and flushed with nitrogen for 5-10 min (5 psi of nitrogen was left in the reactor) before heat was applied. The mixture was heated up to 225-230° C. while stirring at 1000 rpm, the stirring being initiated when the reaction temperature had reached 55-60° C. The pressure built-up in the reactor was monitored with time and temperature (Pmax=54 psi). Sampling was performed during the course of the reaction until the desired conversion (followed by GC) with respect to maleic anhydride was achieved. After 4.5 hours of reaction, the reaction mass was cooled to 95° C. Butadiene (162 g; supplied by Matheson) was fed into the cooled reaction mixture through the inlet tube. After the butadiene addition, stirring was resumed without applying any additional heat. After two hours of reaction GC analysis showed that the maleic anhydride had been completely reacted. The contents of the reactor at a temperature of 55° C. were then discharged to a nitrogen-padded sample bottle while venting it with nitrogen. Analysis of the crude reaction mixture showed that it contained 54.96 wt % of DDSA, 5.68 wt % of THPA, 39.35 wt % of propylene tetramer and 0.01 wt % of maleic anhydride. Thus the weight ratio of the DDSA to THPA in this crude product was approximately 9.7:1. Unreacted starting materials (mostly residual olefin) were removed by flash distillation under reduced pressure using Kügelrohr equipment at an applied vacuum of 14.8 mmHg. After this purification, the product was a light yellow colored liquid.

후처리

  1. customA 5 L-nitrogen-dried Büchi reactor
  2. customfitted with a mechanical stirrer
  3. customThe reactor was then sealed
  4. customflushed with nitrogen for 5-10 min (5 psi of nitrogen
  5. waitwas left in the reactor)
  6. temperaturebefore heat
  7. customhad reached 55-60° C
  8. aliquotSampling
  9. customwas performed during the course of the reaction until the desired conversion (followed by GC) with respect to maleic anhydride
  10. customAfter 4.5 hours of reaction
  11. temperaturethe reaction mass was cooled to 95° C
  12. stirringstirring
  13. customAfter two hours of reaction GC analysis
  14. customhad been completely reacted
  15. customat a temperature of 55° C.
  16. customAnalysis of the crude reaction mixture
  17. customwere removed by flash distillation under reduced pressure
  18. customAfter this purification

출처 및 근거

ORD 기록
ord-2b5ada3b67e4425a9b78c120b9023db3
출처 데이터셋
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06225475B1

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