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1.4-다이옥세인

1.4-다이옥세인
1.4-다이옥세인 구조식 이미지
카스 번호:
123-91-1
한글명:
1.4-다이옥세인
동의어(한글):
1,4-다이옥산;1,4-디옥산;1.4-다이옥세인;P-다이옥세인;디옥산;1/4-디옥산
상품명:
1,4-Dioxane
동의어(영문):
DIOX;AAAAA;Diokan;Dioxan;Dioksan;Dioxanne;p-Dioxan;AROSE IEF;P-DIOXANE;4-Dioxane
CBNumber:
CB6240532
분자식:
C4H8O2
포뮬러 무게:
88.11
MOL 파일:
123-91-1.mol

1.4-다이옥세인 속성

녹는점
12 °C
끓는 점
101 °C
밀도
1.034 g/mL at 25 °C(lit.)
증기 밀도
3 (vs air)
증기압
27 mm Hg ( 20 °C)
굴절률
n20/D 1.422(lit.)
인화점
54 °F
저장 조건
Flammables area
용해도
Soluble in acetone, alcohol, benzene, and ether (Weast, 1986). Miscible with most organic solvents (Huntress and Mulliken, 1941) including 2-methylpropanol, toluene, cychexanone, and cyclopentanone.
물리적 상태
Solution
색상
APHA: ≤20
냄새
Mild ether-like odor detectable at 0.8 to 172 ppm (mean = 12 ppm)
수소이온지수(pH)
6-8 (500g/l, H2O, 20℃)
폭발한계
1.7-25.2%(V)
수용성
SOLUBLE
감도
Hygroscopic
최대 파장(λmax)
λ: 220 nm Amax: ≤0.70
λ: 235 nm Amax: ≤0.50
λ: 250 nm Amax: ≤0.20
λ: 270 nm Amax: ≤0.10
λ: 295-400 nm Amax: ≤0.01
Merck
14,3300
BRN
102551
Henry's Law Constant
4.89(x 10-6 atm?m3/mol) (static headspace-GC, Welke et al., 1998)
노출 한도
TLV-TWA 25 ppm (≈90 mg/m3) (ACGIH), 100 ppm (MSHA and OSHA); carcinogenicity: Animal Sufficient Evidence (IARC).
안정성
Stable. Incompatible with oxidizing agents, oxygen, halogens, reducing agents, moisture. Highly flammable - note wide explosive range. May form explosive peroxides in storage (rate of formation increased by heating, evaporation or exposure to light).
CAS 데이터베이스
123-91-1(CAS DataBase Reference)
NIST
1,4-Dioxane(123-91-1)
EPA
1,4-Dioxane(123-91-1)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn,F,T
위험 카페고리 넘버 45-46-11-36/38-48/23/24/25-65-66-40-36/37-19-41-37/38-39/23/24/25-23/24/25-48/20/22-38-22-36/37/38-10
안전지침서 9-16-36/37-46-45-53-7-62-26-24/25-23-S9-S46-S36/37-S16
유엔번호(UN No.) UN 1993 3/PG 2
WGK 독일 3
RTECS 번호 JG8225000
F 고인화성물질 8
자연 발화 온도 180 °C
TSCA Yes
위험 등급 3
포장분류 II
HS 번호 29329990
유해 물질 데이터 123-91-1(Hazardous Substances Data)
독성 LD50 in mice, rats (ml/kg): 5.7, 5.2 orally (Laug)
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H225 고인화성 액체 및 증기 인화성 액체 구분 2 위험 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 P264, P270, P301+P312, P330, P501
H304 삼켜서 기도로 유입되면 치명적일 수 있음 흡인 유해성물질 구분 1 위험
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H331 흡입하면 유독함 급성 독성 물질 흡입 구분 3 위험 P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
H336 졸음 또는 현기증을 일으킬 수 있음 특정표적장기 독성 물질(1회 노출);마취작용 구분 3 경고 P261, P271, P304+P340, P312,P403+P233, P405, P501
H340 유전적인 결함을 일으킬 수 있음 (노출되어도 생식세포 유전독성을 일으키지 않는다는 결정적인 증거가 있는 노출경로가 있다면 노출경로 기재) 생식세포 변이원성 물질 구분 1A, 1B 위험
H350 암을 일으킬 수 있음 (노출되어도 암을 일으키지 않는다는 결정적인 증거가 있는 노출경로가 있다면 노출경로 기재) 발암성 물질 구분 1A, 1B 위험
H351 암을 일으킬 것으로 의심됨 (노출되어도 암을 일으키지 않는다는 결정적인 증거가 있는 노출경로가 있다면 노출경로 기재) 발암성 물질 구분 2 경고 P201, P202, P281, P308+P313, P405,P501
H370 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킴(노출되어도 특정 표적장기 독성을 일으키지 않는다는 결정적인 노출경로가 있다면 노출경로를 기재) 특정 표적장기 독성 - 1회 노출 구분 1 위험 P260, P264, P270, P307+P311, P321,P405, P501
H372 장기간 또는 반복 노출되면 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킴 특정 표적장기 독성 - 반복 노출 구분 1 위험 P260, P264, P270, P314, P501
H373 장기간 또는 반복 노출되면 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킬 수 있음 특정 표적장기 독성 - 반복 노출 구분 2 경고 P260, P314, P501
H412 장기적 영향에 의해 수생생물에 유해함 수생 환경유해성 물질 - 만성 구분 3 P273, P501
예방조치문구:
P201 사용 전 취급 설명서를 확보하시오.
P202 모든 안전 조치 문구를 읽고 이해하기 전에는 취급하지 마시오.
P210 열·스파크·화염·고열로부터 멀리하시오 - 금연 하시오.
P233 용기를 단단히 밀폐하시오. 용기는 환기가 잘 되는 곳에 단단히 밀폐하여 보관하시오.
P240 용기와 수용설비를 접지 및 접합시키시오.
P260 분진·흄·가스·미스트·증기·...·스프레이를 흡입하지 마시오.
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P270 이 제품을 사용할 때에는 먹거나, 마시거나 흡연하지 마시오.
P271 옥외 또는 환기가 잘 되는 곳에서만 취급하시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P281 요구되는 개인 보호구를 착용하시오
P311 의료기관(의사)의 진찰을 받으시오.
P301+P310 삼켰다면 즉시 의료기관(의사)의 진찰을 받으시오.
P303+P361+P353 피부(또는 머리카락)에 묻으면 오염된 모든 의복은 벗거나 제거하시오 피부를 물로 씻으시오/샤워하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P307+P311 노출된 경우,독성 물질 센터 또는 의사에게 전화하기
P308+P313 노출 또는 접촉이 우려되면 의학적인 조치· 조언를 구하시오.
P370+P378 화재 시 불을 끄기 위해 (Section 5. 폭발, 화재시 대처방법의 적절한 소화제)을(를) 사용하시오.
P405 밀봉하여 저장하시오.
P403+P233 용기는 환기가 잘 되는 곳에 단단히 밀폐하여 저장하시오.
P403+P235 환기가 잘 되는 곳에 보관하고 저온으로 유지하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.

1.4-다이옥세인 C화학적 특성, 용도, 생산

용도

유기용매에 모두 잘 녹는 우수한 용제이며, 공업적으로 아세틸셀룰로스나 에틸셀룰로스의 용제, 또 도료용 용제 등으로 널리 쓰이고 있다.

개요

1,4-dioxane is a clear liquid with ether-like odour. It is highly flammable and forms explosive peroxides in storage (rate of formation increased by heating, evaporation, or exposure to light). 1,4-Dioxane is incompatible with oxidising agents, oxygen, halogens, reducing agents, and moisture. Industrial applications of 1,4-dioxane are extensive, for instance, as solvent for cellulose acetate, ethyl cellulose, benzyl cellulose, resins, oils, waxes, and some dyes; as a solvent for paper, cotton, and textile processing; and for various organic and inorganic compounds and products. It is also used in automotive coolant liquid and in shampoos and other cosmetics as a degreasing agent and as a component of paint and varnish. Human exposures to 1,4-dioxane have been traced to multiple occupations and breathing of contaminated workplace air and drinking polluted water. Industrial uses of 1,4-dioxane are very many. For instance, it is used as solvent for celluloses, resins, lacquers, synthetic rubbers, adhesives, sealants, fats, oils, dyes, and protective coatings; as a stabiliser for chlorinated solvents and printing inks; and as a wetting and dispersing agent in textile processing agrochemicals and pharmaceuticals, in different processing of solvent-extraction processes, and in the preparation and manufacture of detergents.

화학적 성질

1,4-Dioxane is a colorless, stable liquid with a faint, pleasant odor. Although it has been known as far back as 1863, it was not until 1929 that is became commercially available. It is chemically a di-ether obtained by the loss of water from two molecules of ethylene glycol. It is completely soluble in water, as well as most organic solvents. It is freely soluble in mineral, vegetable, blown and heat-bodied oils, and oil soluble dyes. Most waxes are more readily soluble in dioxane when heated and examples of these are beeswax, carnauba, montan, paraffin, gilsonite, and Japan wax.

물리적 성질

Clear, colorless, very flammable, volatile liquid with a faint pleasant, ether-like odor. Experimentally determined detection and recognition odor threshold concentrations were 2.9 mg/m3 (800 ppbv) and 6.5 mg/m3 (1.8 ppmv), respectively (Hellman and Small, 1974).

용도

1,4-Dioxane, the six-member cyclic diether, is used as an aluminum inhibitor in chlorinated solvents like 1,1,1-trichloroethane and as a solvent for certain resins and polymers.

용도

1,4-Dioxane is used as a solvent for celluloseesters, oils, waxes, resins, and numerousorganic and inorganic substances. It is alsoused in coatings and as a stabilizer in chlorinatedsolvents.

용도

Suitable for HPLC, spectrophotometry, environmental testing

용도

Stabilizer in chlorinated solvents. Solvent for cellulose acetate, ethyl cellulose, benzyl cellulose, resins, oils, waxes, oil and spirit-sol dyes, and many other organic as well as some inorganic Compounds.

정의

ChEBI: A dioxane with oxygen atoms at positions 1 and 4.

정의

dioxan: A colourless toxic liquid,C4H8O2; r.d. 1.03; m.p. 11°C; b.p.101.5°C. The molecule has a sixmemberedring containing fourCH2groups and two oxygen atoms at oppositecorners. It can be made fromethane-1,2-diol and is used as a solvent.

일반 설명

A clear colorless liquid with a faint ethereal odor. Flash point 55°F. Slightly denser than water and soluble in water. Vapors heavier than air. Susceptible to autooxidation to form peroxides.

공기와 물의 반응

Highly flammable. When exposed to air 1,4-Dioxane undergoes autooxidation with formation of peroxides. In the distillation process peroxides will concentrate causing violent explosion. Water soluble.

반응 프로필

1,4-Dioxane is a flammable liquid; when exposed to air 1,4-Dioxane undergoes autooxidation with formation of peroxides. In the distillation process peroxides will concentrate causing violent explosion. The addition complex with sulfur trioxide (1:1) sometimes decomposes violently on storing at room temperature [Sisler, H. H. et al., Inorg. Synth., 1947, 2, p. 174]. Evaporation of boron trifluoride in aqueous 1,4-Dioxane with nitric acid led to an explosion upon addition of perchloric acid [MCA Guide, 1972, p. 312]. Explosive reaction with Raney nickel catalyst above 210° C {Mozingo R., Org. Synth., 1955, Coll. Vol. 3, p. 182].

건강위험

The toxicity of 1,4-dioxane is low in testanimals by all routes of exposure. However,in humans the toxicity of this compoundis severe. The target organs are theliver, kidneys, lungs, skin, and eyes. Exposureto its vapors as well as the absorptionthrough the skin or ingestion can cause poisoning,the symptoms of which include drowsiness,headache, respiratory distress, nausea,and vomiting. It causes depression of centralnervous system. There are reports of humandeaths from subacute and chronic exposures todioxane vapors at concentration levels rangingbetween 500 and 1000 ppm. Serious healthhazards may arise from its injurious effects onthe liver, kidneys, and brain. Rabbits died ofkidney injury resulting from repeated inhalationof 1,4-dioxane vapors for 30 days (Smyth1956). It is an irritant to the eyes, nose, skin,and lungs. In humans, a 1-minute exposure to5000-ppm vapors can cause lacrimation.
LC50 value, inhalation (rats): 13,000 ppm/2 h
LD50 value, oral (mice): 5700 mg/kg
1,4-Dioxane is an animal carcinogen oflow potential. Ingestion of high concentrationsof this compound at a level of7000–18,000 ppm in drinking water for14–23 months caused nasal and liver tumorsin rats (ACGIH 1986). Guinea pigs developedlung tumors.

인화성 및 폭발성

Dioxane is a highly flammable liquid (NFPA rating = 3). Its vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. Dioxane vapor forms explosive mixtures with air at concentrations of 2 to 22% (by volume). Fires involving dioxane should be extinguished with carbon dioxide or dry powder extinguishers.
Dioxane can form shock- and heat-sensitive peroxides that may explode on concentration by distillation or evaporation. Samples of this substance should always be tested for the presence of peroxides before distilling or allowing to evaporate. Dioxane should never be distilled to dryness.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenicdata. Poison by intraperitoneal route. Moderately toxic by ingestion and inhalation. Mildly toxic by skin contact. Human systemic effects by inhalation: lachrymation, conjunctiva irritation, convulsions, hgh blood pressure, unspecified respiratory and gastrointestinal system effects. Mutation data reported. An eye and slun irritant. The irritant effects probably provide sufficient warning, in acute exposures, to enable a worker to leave exposure before being seriously affected. Repeated exposure to low concentrations has resulted in human fatahties, the organs chefly affected being the liver and kidneys. A very dangerous fire and explosion hazard when exposed to heat or flame; can react vigorously with oxidizing materials. Violent reaction with (H2 + Raney Ni), AgClO4. Can form dangerous peroxides when exposed to air. Potentially explosive reaction with nitric acid + perchloric acid, Raney nickel catalyst (above 210°C). Forms explosive mixtures with decaborane (impactsensitive), triethynylaluminum (sensitive to heating or drying). Violent reaction with sulfur trioxide. Incompatible with sulfur trioxide. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also GLYCOL ETHERS.

Carcinogenicity

1,4-Dioxane is reasonably anticipated to be a human carcinogen basedon sufficient evidence of carcinogenicity from studies in experimental animals.

Source

Improper disposal of products listed below may result in 1,4-dioxane leaching into groundwater.

환경귀착

Biological. Heukelekian and Rand (1955) reported a 10-d BOD value of 0.00 g/g which is 0.0% of the ThOD value of 1.89 g/g.
Photolytic. Irradiation of pure 1,4-dioxane through quartz using a 450-W medium-pressure mercury lamp gave meso and racemic forms of 1-hydroxyethyldioxane, a pair of diastereomeric dioxane dimers (Mazzocchi and Bowen, 1975), dioxanone, dioxanol, hydroxymethyldioxane, and hydroxyethylidenedioxane (Houser and Sibbio, 1977). When 1,4-dioxane is subjected to a megawatt ruby laser, 4% was decomposed yielding ethylene, carbon monoxide, hydrogen, and a trace of formaldehyde (Watson and Parrish, 1971).
Chemical/Physical. Anticipated products from the reaction of 1,4-dioxane with ozone or OH radicals in the atmosphere are glyoxylic acid, oxygenated formates, and OHCOCH2CH2OCHO (Cupitt, 1980). Storage of 1,4-dioxane in the presence of air resulted in the formation of 1,2- ethanediol monoformate and 1,2-ethane diformate (Jewett and Lawless, 1980). Stefan and Bolton (1998) studied the degradation of 1,4-dioxane in dilute aqueous solution by OH radicals. Degradation follows pseudo-first-order kinetics at a rate of 8.7 x 10-3/sec. Within 5 min of direct photolysis of hydrogen peroxide to generate OH radicals, almost 90% of the 1,4-dioxane reacted. Four primary intermediate formed were 1,2-ethanediol monoformate, 1,2-ethanediol diformate, formic acid, and methoxyacetic acid. These compounds were attacked by OH radicals yielding glycolic, glyoxylic, and acetic acids which led to oxalic acid as the last intermediate. Malonic acid was also identified as a minor intermediate. Twelve minutes into the reaction, the pH decreased rapidly to 3.25 from 5.0, then less rapidly to 3.25 after 23 min. After 1 h, the pH rose to 4.2 min. The decrease of pH during the initial stages of reaction is consistent with the formation of organic acids. Oxidation of organic acid by OH radicals led to an increase of pH. The investigators reported that the lower pH at the end of the experiment was due to carbonic acid formed during the mineralization process.

저장

dioxane should be used only in areas free of ignition sources, and quantities greater than 1 liter should be stored in tightly sealed metal containers in areas separate from oxidizers. Containers of dioxane should be dated when opened and tested periodically for the presence of peroxides.

Purification Methods

It is prepared commercially either by dehydration of ethylene glycol with H2SO4 and heating ethylene oxide or bis(.-chloroethyl)ether with NaOH. The usual impurities are acetaldehyde, ethylene acetal, acetic acid, water and peroxides. Peroxides can be removed (and the aldehyde content decreased) by percolation through a column of activated alumina (80g per 100-200mL solvent), by refluxing with NaBH4 or anhydrous stannous chloride and distilling, or by acidification with conc HCl, shaking with ferrous sulfate and leaving in contact with it for 24hours before filtering and purifying further. Hess and Frahm [Chem Ber 71 2627 1938] refluxed 2L of dioxane with 27mL conc HCl and 200mL water for 12hours with slow passage of nitrogen to remove acetaldehyde. After cooling the solution, KOH pellets were added slowly and with shaking until no more would dissolve and a second layer had separated. The dioxane was decanted, treated with fresh KOH pellets to remove any aqueous phase, then transferred to a clean flask where it was refluxed for 6-12hours with sodium, then distilled from it. Alternatively, Kraus and Vingee [J Am Chem Soc 56 511 1934] heated it on a steam bath with solid KOH until fresh addition of KOH gave no more resin (due to acetaldehyde). After filtering through paper, the dioxane was refluxed over sodium until the surface of the metal was not further discoloured during several hours. It was then distilled from sodium. The acetal (b 82.5o) is removed during fractional distillation. Traces of *benzene, if present, can be removed as the *benzene/MeOH azeotrope by distillation in the presence of MeOH. Distillation from LiAlH4 removes aldehydes, peroxides and water. Dioxane can be dried using Linde type 4X molecular sieves. Other purification procedures include distillation from excess C2H5MgBr, refluxing with PbO2 to remove peroxides, fractional crystallisation by partial freezing and the addition of KI to dioxane acidified with aqueous HCl. Dioxane should be stored out of contact with air, preferably under N2. A detailed purification procedure is as follows: Dioxane is stood over ferrous sulfate for at least 2 days, under nitrogen. Then water (100mL) and conc HCl (14mL)/ litre of dioxane are added (giving a pale yellow colour). After refluxing for 8-12hours with vigorous N2 bubbling, pellets of KOH are added to the warm solution to form two layers and to discharge the colour. The solution is cooled rapidly with more KOH pellets being added (magnetic stirring) until no more dissolved in the cooled solution. After 4-12hours, if the lower phase is not black, the upper phase is decanted rapidly into a clean flask containing sodium, and refluxed over sodium (until freshly added sodium remained bright) for 1hour. The middle fraction is collected (and checked for minimum absorbency below 250nm). The distillate is fractionally frozen three times by cooling in a refrigerator, with occasional shaking or stirring. This material is stored in a refrigerator. Before use it is thawed, refluxed over sodium for 48hours, and distilled into a container. All joints are clad with Teflon tape. Coetzee and Chang [Pure Appl Chem 57 633 1985] dried the solvent by passing it slowly through a column (20g/L) of 3A molecular sieves activated by heating at 250o for 24hours. Impurities (including peroxides) are removed by passing the effluent slowly through a column packed with type NaX zeolite (pellets ground to 0.1mm size) activated by heating at 400o for 24hours or chromatographic grade basic Al2O3 activated by heating at 250o for 24hours. After removal of peroxides the effluent is refluxed for several hours over sodium wire, excluding moisture, distilled under nitrogen or argon and stored in the dark. One of the best tests of purity of dioxane is the formation of the purple disodium benzophenone complex during reflux and its persistence on cooling. (Benzophenone is better than fluorenone for this purpose and for the storing of the solvent.) [Carter et al. Trans Faraday Soc 56 343 1960, Beilstein 19 V 16.] TOXIC. Rapid purification: Check for peroxides (see Chapter 1 and Chapter 2 for test under ethers). Pre-dry with CaCl2 or better over Na wire. Then reflux the pre-dried solvent over Na (1% w/v) and benzophenone (0.2% w/v) under an inert atmosphere until the blue colour of the benzophenone ketyl radical anion persists. Distil, and store it over 4A molecular sieves in the dark.

비 호환성

Dioxane can form potentially explosive peroxides upon long exposure to air. Dioxane may react violently with Raney nickel catalyst, nitric and perchloric acids, sulfur trioxide, and strong oxidizing reagents.

폐기물 처리

Excess dioxane and waste material containing this substance should be placed in an appropriate container, clearly labeled, and handled according to your institution's waste disposal guidelines.

주의 사항

Workers Should be careful during handling of 1,4-Dioxane and avoid open flames, sparks and smoking. Workers should wear proper protectives since 1,4-Dioxane in known as hazardous, cause damage to eyes, respiratory tract, liver and kidney.

법규

Coast Guard, Department of Homeland Security
Minimum requirements have been established for safe transport of 1,4-dioxane on ships and barges.
Department of Transportation (DOT)
1,4-Dioxane is considered a hazardous material, and special requirements have been set for marking, labeling, and transporting this material.
Environmental Protection Agency (EPA)
Clean Air Act
National Emissions Standards for Hazardous Air Pollutants: Listed as a hazardous air pollutant.
New Source Performance Standards: Manufacture or use is subject to certain provisions for the control of volatile organic compound emissions.
Comprehensive Environmental Response, Compensation, and Liability Act
Reportable quantity (RQ) = 100 lb.
Emergency Planning and Community Right-To-Know Act
Toxics Release Inventory: Listed substance subject to reporting requirements.
Resource Conservation and Recovery Act
Listed Hazardous Waste: Waste code for which the listing is based wholly or partly on the presence of 1,4-dioxane = U108. Listed as a hazardous constituent of waste.
Food and Drug Administration (FDA)
1,4-Dioxane levels shall not exceed 10 mg/kg in glycerides and polyglycides of hydrogenated vegetable oils when used as a food additive.
Occupational Safety and Health Administration (OSHA)
While this section accurately identifies OSHA’s legally enforceable PELs for this substance in 2010, specific PELs may not reflect the more current studies and may not adequately protect workers. Permissible exposure limit (PEL) = 100 ppm (360 mg/m3).

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