3차부틸 하이드로 퍼옥사이드

3차부틸하이드로퍼옥사이드 · TERT-뷰틸하이드로퍼옥사이드 · 1,1-다이메틸 히드로과산화물 · Cadox TBH · Perbutyl H · T 히드로 · TBHP · Trigonox AW70

식별자 및 물리적 특성

CAS No.	75-91-2
분자식	C4H10O2
평균 분자량	90.12 g/mol
단동위원소 질량	90.06807956 g/mol
SMILES	CC(C)(C)OO
InChIKey	CIHOLLKRGTVIJN-UHFFFAOYSA-N
PubChem CID	6410
ChEMBL	CHEMBL348399
ChEBI	CHEBI:64090
EC No.	200-915-7
DTXSID	DTXSID9024693
현지명	3차부틸 하이드로 퍼옥사이드

화학 및 물리적 성질

XLogP	0.6
극성 표면적	29.5
수소 결합 공여자 수	1
수소 결합 수용자 수	2
회전 가능 결합 수	1
무거운 원자 수	6
형식 전하	0
복잡도	35
LogP(분배 계수)	-1.3 (calculated)
밀도	0.88 at 77 °F (USCG, 1999) - Less dense than waterwill float0.8960 g/cu cm at 20 °CRelative density (water = 1): 0.930.86 @25 °C0.937 g/mL at 20 °C
Color/Form	LiquidWater-white liquid
용해도	greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)Soluble in waterModerately soluble in waterSlightly soluble in waterSoluble in ethanol, ethyl ether, carbon tetrachloride, chloroformFor more Solubility (Complete) data for tert-Butyl hydroperoxide (7 total), please visit the HSDB record page.
인화점	80 °F (NTP, 1992)43 °(may explode on heating)Less than 80 °F (less than 27 °C) /closed cup/43 °C85 °F
끓는 점	192 °F at 760 mmHg (decomposes)104 °F at 23 mmHg (NTP, 1992)BP: 89 °C (decomposes)BP: 35 °C at 20 mm HgBP: 40 °C at 23 mm Hg37 °C (15 mmHg)
Decomposition	When heated to decomposition it emits acrid smoke and fumes.89 °C
녹는점	18 °F (NTP, 1992)-8 °CMP: 6 °C-3 °C-2.8 °C
증기 밀도	2.07 (NTP, 1992) - Heavier than airwill sink (Relative to Air)2.07 (Air = 1)Relative vapor density (air = 1): 3.1
후각 역치	Odor Threshold Low: 0.05 [ppm]
증기압	5.46 [mmHg]5.46 mm Hg at 25 °CVapor pressure, kPa at 20 °C: 3.07 (calculated)3.07 [mm Hg] @20 °C62 mmHg at 45 °C
굴절률	Index of refraction = 1.4015 at 20 °C/Dn20/D 1.403
저장 조건	2-8°C
pKa(산도 계수)	pK1: 12.80 (25°C)
물리적 상태	액체
색상	무색의
pH	4.3
용해도	혼용 가능
Merck	14,1570
BRN	1098280
헨리 상수	4.2×100 mol/(m3Pa) at 25℃, Wang et al. (2017)
안정성	안정적이지만 밀폐된 상태에서 가열하면 폭발할 수 있습니다. 미량의 금속, 분자체 또는 기타 오염물질에 의해 분해가 가속화될 수 있습니다. 환원제, 가연성 물질, 산과 호환되지 않습니다.
InChI	1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3
InChIKey	CIHOLLKRGTVIJN-UHFFFAOYSA-N
SMILES	CC(C)(C)OO
LogP(분배 계수)	1.230 (est)
NIST	Tert-butyl hydroperoxide(75-91-2)
EPA	tert-Butyl hydroperoxide (75-91-2)

화학적 성질

tert-Butyl hydroperoxide (TBHP) is a water-white liquid commonly commercially available as a 70% solution in water; 80% solutions are also available. It is used to initiate polymerization reactions and in organic syntheses to introduce peroxy groups into the molecule.

안전 및 규제

GHS 분류	WarningH341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 17.3% (234 of 1351) of reports.
규제 정보	Chemical: Hydroperoxide, 1,1-dimethylethylHydroperoxide, 1,1-dimethylethyl is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Hydroperoxide, 1,1-dimethylethyl are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 10-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13623Hydroperoxide, 1,1-dimethylethyl: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
기타 안전 정보	IMAP assessments - Selected organic hydroperoxides: Human health tier II assessment
운송 라벨(DOT)	Organic Peroxide
화재 위험	Behavior in Fire: May explode in fire (USCG, 1999)Excerpt from ERG Guide 145 [Organic Peroxides (Heat and Contamination Sensitive)]:May explode from heat or contamination. May ignite combustibles (wood, paper, oil, clothing, etc.). May be ignited by heat, sparks or flames. May burn rapidly with flare-burning effect. Containers may explode when heated. Runoff may create fire or explosion hazard. (ERG, 2024)Excerpt from ERG Guide 146 [Organic Peroxides (Heat, Contamination and Friction Sensitive)]:May explode from heat, shock, friction or contamination. May ignite combustibles (wood, paper, oil, clothing, etc.). May be ignited by heat, sparks or flames. May burn rapidly with flare-burning effect. Containers may explode when heated. Runoff may create fire or explosion hazard. (ERG, 2024)Flammable. Many reactions may cause fire or explosion. Risk of fire and explosion on heating. Above 43 °C explosive vapour/air mixtures may be formed.
화재 가능성	Very dangerous fire hazard when exposed to heat or flame, or by spontaneous chemical reaction such as with reducing materials.

용도

tert-Butyl hydroperoxide is used as an initiator for radical polymerization and in various oxidation process such as sharpless epoxidation. It is involved in osmium catalyzed vicinal hydroxylation of olefins under alkaline conditions. Furthermore, it is used in catalytic asymmetric oxidation of sulfides to sulfoxides using binaphthol as a chiral auxiliary and in the oxidation of dibenzothiophenes. It plays an important role for the introduction of peroxy groups in organic synthesis.

개요

Tert-butyl hydroperoxide is an alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes. It has a role as an antibacterial agent and an oxidising agent.

일반 설명

Watery odorless colorless liquid. Floats and mixes slowly with water.

제조 및 합성 방법

생산 방법

TBHP is produced by the liquid-phase reaction of isobutane and molecular oxygen or by mixing equimolar amounts of t-butyl alcohol and 30–50% hydrogen peroxide. TBHP can also be prepared from t-butyl alcohol and 30% hydrogen peroxide in the presence of sulfuric acid or by oxidation of tert-butylmagnesium chloride. The manufacturing process of TBHP is in a closed system.