1,2-벤젠다이카보나이트릴

1,2-벤젠다이카보나이트릴 · o-프탈로디니트릴 · 오쏘-프탈로다이나이트릴 · 1,2-다이사이아노벤젠 · 1,2-벤젠디카르보나이트릴 · 1,2-벤조디나이트릴 · 1,2-비스(사이아노)벤젠 · 오쏘-다이사이아노벤젠

식별자 및 물리적 특성

CAS No.	91-15-6
분자식	C8H4N2
평균 분자량	128.13 g/mol
단동위원소 질량	128.03744813 g/mol
SMILES	N#Cc1ccccc1C#N
InChIKey	XQZYPMVTSDWCCE-UHFFFAOYSA-N
PubChem CID	7042
ChEMBL	CHEMBL3185350
ChEBI	CHEBI:232056
EC No.	202-044-8
DTXSID	DTXSID8029604
현지명	1,2-벤젠다이카보나이트릴

화학 및 물리적 성질

XLogP	1
극성 표면적	47.6
수소 결합 공여자 수	0
수소 결합 수용자 수	2
회전 가능 결합 수	0
무거운 원자 수	10
형식 전하	0
복잡도	178
물질 분류	Nitrogen Compounds -> Nitriles
SpringerMaterials Properties	Schoenflies notation
LogP(분배 계수)	log Kow = 0.990.58
냄새	Slightly aromatic
밀도	1.238 g/cu cm1.24 g/cm³
Color/Form	NEEDLES FROM WATER OR PETROLEUM ETHERBuff-colored crystalsFaint grayish yellow
용해도	Soluble in alcohol and etherSoluble in acetone and benzene.In water, 395 mg/l @ 25 °C.Solubility in water, g/100ml at 25 °C: 0.06벤젠: 50mg/mL, 투명
인화점	162 °C162°C
끓는 점	304.5 °C227.54°C (rough estimate)
Decomposition	When heated to decomposition it emits toxic fumes of CN- and NOx /cyanides and nitrogen oxides/.
녹는점	138 °C141 °C137-139 °C (lit.)
증기압	0.00569 [mmHg]0.05 millibar @ 20 °C (3.75X10-2 mm Hg)Vapor pressure, Pa at 20 °C: 4<1 Pa (25 °C)
굴절률	1.6231 (estimate)
저장 조건	Store below +30°C.
물리적 상태	결정 또는 결정성 분말
색상	흰색에서 베이지색
pH	7 (H2O)
용해도	0.56g/L(25℃)
BRN	775028
헨리 상수	2.0×101 mol/(m3Pa) at 25℃, HSDB (2015)
안정성	안정적인. 강염기, 강산, 강산화제, 강환원제와 호환되지 않습니다.
InChI	1S/C8H4N2/c9-5-7-3-1-2-4-8(7)6-10/h1-4H
InChIKey	XQZYPMVTSDWCCE-UHFFFAOYSA-N
SMILES	N#Cc1ccccc1C#N
NIST	Phthalonitrile(91-15-6)
EPA	1,2-Benzenedicarbonitrile (91-15-6)

화학적 성질

Phthalonitrile is a crystalline powder having a faint grayish yellow color and a slighty aromatic odor, similar to benzonitrile. Phthalonitrile was first described in 1896 when it was isolated during the diazotization of 2-aminobenzonitrile. The compound is sparingly soluble in water (ca. 1 g/L) and soluble in acetone, nitrobenzene, and benzonitrile. It cannot be distilled and polymerizes if heated above the melting point. It is not explosive and is difficult to ignite, but the dust can explode.

안전 및 규제

GHS 분류	DangerH300 (28.4%): Fatal if swallowed [Danger Acute toxicity, oral]P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 162 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H301: Toxic if swallowed [Danger Acute toxicity, oral]
규제 정보	Status: Active Update: 31-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/1983Phthalonitrile: Does not have an individual approval but may be used under an appropriate group standard
화재 위험	Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.
유해성 요약	Inhalation of high concentrations may cause CNS effects[ICSC] Emergency treatment: Benzyl cyanide[HSDB] Lethal doses cause tremor and convulsions in rats[RTECS] TLV Basis = convulsions and decreased body weightUnlike the aliphatic nitriles, aromatic nitriles such as m-phthalodinitrile do not liberate cyanide in the body. [ACGIH] An acute neurotoxinNot irritating to skin or eyes[Reference #1] See m-Phthalodinitrile. See NITRILES.
UN 분류	UN Hazard Class: 6.1UN Pack Group: III
Chemical Dangers	Decomposes on heating. This produces toxic fumes including cyanide. On combustion, forms nitrogen oxides. Reacts with strong oxidants.
Packaging and Labelling	Do not transport with food and feedstuffs.
Toxic Combustion Products	When heated to decomposition it emits toxic fumes of hydrogen cyanide and NOx /cyanides and nitrogen oxides/.
Hazard Classes and Categories	Acute Tox. 2 (28.4%)Acute toxicity (Oral) - Category 3
소화	Use dry powder, carbon dioxide, foam.

용도

Phthalonitrile is used as an intermediate for chemical synthesis in the production of building blocks for colorants and coatings, life science and agricultural chemicals. It is also used as a precursor to phthalocyanine pigments (which are precursors to the blue dye in jeans), fluorescent brighteners, and photographic sensitizers.

제조 및 합성 방법

제조 방법

Phthalonitrile can be produced from phthalic acid, phthalic anhydride, phthalamide, or phthalimide by reaction with ammonia and elimination of water at 300–500°C in the gas phase in the presence of a catalyst. In a single-stage continuous process, o-xylene is converted to phthalonitrile by reaction with ammonia and oxygen in the gas phase in a fluidized-bed reactor. Generally, metal oxide mixtures containing vanadium, antimony, chromium, and molybdenum, with further active components such as iron, tungsten, and alkali-metal oxides, on an alumina or silica support are used as catalysts.