메틸렌 비스(4-사이클로헥실아아이소사이안산)(메틸렌 비스(4-사이클로헥실아이소시안산))

Hydrogenated mdi

HCID 21202CAS 13622-90-7

기본 정보

표준 SMILES
O=C=NC1CCC(CC2CCC(N=C=O)CC2)CC1
InChIKey
KORSJDCBLAPZEQ-UHFFFAOYSA-N
분자식
C15H22N2O2
평균 분자량
262.35 g/mol
단동위원소 질량
262.16812794

개요

1,1-methylene bis(4-isocyanatocyclohexane) is a clear, colorless to light-yellow liquid. (NIOSH, 2024)

이름 및 식별자

우선 이름
Hydrogenated mdi
IUPAC
1-isocyanato-4-[(4-isocyanatocyclohexyl)methyl]cyclohexane
현지명
메틸렌 비스(4-사이클로헥실아아이소사이안산)(메틸렌 비스(4-사이클로헥실아이소시안산))
영어명
Methylene-bis(4-cyclohexylisocyanate)
분자식
C15H22N2O2
분자량
262.35

이름 및 동의어

5124-30-1Bis(4-isocyanatocyclohexyl)methaneNacconate H 12Methylene bis(4-cyclohexylisocyanate)1-isocyanato-4-[(4-isocyanatocyclohexyl)methyl]cyclohexaneMethylene bis-(4-cyclohexylisocyanate)Cyclohexane, 1,1'-methylenebis[4-isocyanato-4,4'-Methylenedicyclohexyl diisocyanate4,4'-Methylenedi(cyclohexyl isocyanate)Cyclohexane, 1,1'-methylenebis(4-isocyanato-Methylenebis(4-cyclohexylisocyanate)Dicyclohexylmethane-4,4'-di-isocyanate
이름 더 보기
1,1""-메틸렌비스메틸렌비스(4-사이클로헥실아아이소사이안산)(메틸렌비스(4-사이클로헥실아이소시안산))1,1'-메틸렌비스[4-이소시아나토시클로헥산]메틸렌 비스(4-사이클로헥실아이소사이안산)1,1'-메틸렌비스(4-이소시아나토시클로헥산)rmdismdiisocyanicacid,methylenedi-4,1-cyclohexyleneesterpicmH12MDI HMDI4,4'-METHYLENEBIS(CYCLOHEXYL ISOCYANATE)4,4-Methylenebis(cyclohexyl isocyanate),mixture of isomerscp99173
4CT385M7K2Saturated MDIReduced MDIHMDI cpdDMDI1-isocyanato-4-((4-isocyanatocyclohexyl)methyl)cyclohexane4,4-methylene biscyclohexyl diisocyanateRefChem:789184

데이터베이스 식별자

CAS
13622-90-7、17901-48-3、18937-00-3、28605-81-4、5124-30-1
PubChem CID
21202
DTXSID
DTXSID3027588
ChEMBL
CHEMBL1878565
ChEBI
CHEBI:53216
UNII
6Y80AJA84R、P815VNF99I、Z717ID22KX
EC Number
225-863-2
Nikkaji
J1.045.774B、J2.677.296F、J68.774J、J755.561J、J841.287A

물성

구조 계산 물성

XLogP
5.3
극성 표면적
58.9 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
4
회전 가능 결합 수
4
무거운 원자 수
19

실험 및 물리화학적 성질

PolymersPlastics & Rubber -> Diisocyanates
SpringerMaterials PropertiesBoiling point
Density · 4건

1.07 at 77 °F (NIOSH, 2024) - Denser than water; will sink

1.066 g/cu cm

1.07 at 77 °F

(77 °F): 1.07

Color/FormClear, colorless to light-yellow liquid
Solubility · 3건

Reacts with water (NIOSH, 2024)

Soluble in acetone

Reacts

Flash Point · 3건

greater than 395 °F (NIOSH, 2024)

>395 °F

>395 °F

물리화학적 성질

녹는점
25 °C · 25°C
끓는 점
168 °C · 168 °C / 1.5mmHg
밀도
1.066 g/mL · 1.066 g/mL at 25 °C(lit.)
증기압
0.001 Pa · 0.001Pa at 20℃
굴절률
20 · n20/D 1.497(lit.)
인화점
230 °F · >230 °F

화학적 성질

Liquid.Soluble in acetone;reacts with water or ethanol.

안전 및 규제

GHS 분류

GHS Classification · 6건

Danger

H315: Causes skin irritation [Warning Skin corrosion/irritation]

P233, P260, P261, P264, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 3.6% (37 of 1034) of reports.

Danger

H315 (96.4%): Causes skin irritation [Warning Skin corrosion/irritation]

유해성 정보

Regulatory Information · 6건

Chemical: Cyclohexane, 1,1'-methylenebis[4-isocyanato-

Hazard Traits - Respiratory Toxicity

Cyclohexane, 1,1'-methylenebis[4-isocyanato- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclohexane, 1,1'-methylenebis[4-isocyanato- 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)

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Status: Active Update: 16-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13842

Restricted substance: 4,4'-methylenedicyclohexyl diisocyanate

DOT LabelPoison
Fire HazardsFlash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Health HazardsExcerpt from NIOSH Pocket Guide for Methylene bis(4-cyclohexylisocyanate):
Hazards SummarySee ISOCYANATES.
Reactive GroupIsocyanates and Isothiocyanates

안전 및 보호

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 2건

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

(General first aid procedures)

Nonfire Spill ResponseSTORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)
Disposal Methods · 1건

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Preventive Measures · 4건

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Isolation and EvacuationExcerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

독성 정보

Treatment · 1건

Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)

Target OrgansEyes, skin, respiratory system
Health Effects · 1건

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)

Ecotoxicity ValuesLC50; Species: Brachydanio rerio (Zebra fish); Concentration: 1.2 mg/L for 96 hr /91.6% a.i./ /Conditions of bioassay not specified in source examined/
Environmental Fate · 3건

TERRESTRIAL FATE: Isocyanates hydrolyze readily in moist soil(1); therefore, adsorption and volatilization of methylene bis(4-cyclohexylisocyanate) are not expected to be an important environmental fate process(SRC). Methylene bis(4-cyclohexylisocyanate) is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). A 0% of theoretical BOD using activated sludge in the Japanese MITI test(3) suggests that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Isocyanates hydrolyze readily in water(1); therefore, adsorption to solids and sediment, volatilization and bioconcentration of methylene bis(4-cyclohexylisocyanate) are not expected to be an important environmental fate process(SRC). A 0% of theoretical BOD using activated sludge in the Japanese MITI test(2) suggests that biodegradation is an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methylene bis(4-cyclohexylisocyanate), which has an estimated vapor pressure of 2.3X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase methylene bis(4-cyclohexylisocyanate) is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 5 hours(SRC), calculated from its rate constant of 2.6X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase methylene bis(4-cyclohexylisocyanate) may be removed from the air by wet or dry deposition(SRC). Methylene bis(4-cyclohexylisocyanate) does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.

규제 정보

TSCA Requirements · 2건

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 10/29/90; Reporting date: 12/27/90.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Cyclohexane, 1,1'-methylenebis(4-isocyanato)- is included on this list. Effective date: 6/1/87; Sunset date: 6/1/97.

안전 데이터

OEL
Ceiling: 0.01 ppm (0.11 mg/m3)
wgk
1
tsca
TSCA listed
rtecs
NQ9250000
ridadr
UN 2206 6.1/PG 2
HS 번호
2929.10.8090

화학 및 산업

약리 정보

Mechanism of Action · 1건

Skin sensitization with chemical allergens is associated with the activation and proliferation of lymphocytes in lymph nodes draining the site of exposure. As lymphocyte activation is regulated by the action of cytokines, /the authors have/ investigated the nature and kinetics of cytokine production by draining lymph node cells (LNC) from mice, following their primary exposure to chemical allergens. Both interleukin-1 (IL-1) and IL-6 were induced in a biphasic manner following primary exposure of mice to oxazolone or to dicyclohexylmethane-4,4'-diisocyanate (HMDI). ...Increased IL-4 production was observed only when LNC were prepared 96 hr following sensitization. Despite vigorous lymphocyte proliferation there was no evidence for IL-2 production by draining LNC.

Metabolism/Metabolites · 1건

Cyanide is rapidly alsorbed through oral, inhalation, and dermal routes and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

용도 및 제조

Uses · 5건

Methylene bis(4-cyclohexylisocyanate) is used primarily to produce urethane products that will not yellow on exposure to light. [ACGIH]

Plastic Composites Manufacturing [Category: Industry]

... Hydrogenated MDI (HMDI) /is/ used in the formulation of flexible coatings and polyurethane elastomers.

Methylene bis(4-cyclohexylisocyanate) has been used primarily to produce urethane products that will not yellow on exposure to light.

... Automotive safety glass and biomedical applications

U.S. Production · 4건

2023: 25,000,000 - <40,000,000 lb

Methylene bis(4-cyclohexylisocyanate) is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#6809]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Cyclohexane, 1,1'-methylenebis(4-isocyanato)-. Aggregated National Production Volume: 10 to < 50 million pounds.

Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesOther
General Manufacturing Information · 3건

Mining (except Oil and Gas) and support activities

Cyclohexane, 1,1'-methylenebis[4-isocyanato-: ACTIVE

Cyclohexane, 1,1'-methylenebis[4-isocyanato-, (trans,trans)-: INACTIVE

응용 분야 · 3건

개요Methylene bis (4-cyclohexylisocyanate) (HMDI) (CAS No. 5124-30-1) is a clear to pale yellow liquid, which is soluble in acetone water and is incompatible with alcohols, amines, bases, acids, and may slowly polymerize if heated above 50 ℃. HMDI reacts with water and alcohol.

용도HMDI has excellent light stability and the stability of the six membered ring structure, has excellent weather resistance and excellent mechanical properties of polyurethane material, and is especially suitable for the production of high performance elastic body, a water polyurethane resin and UV resin.

일반 설명Clear colorless to light-yellow liquid.

공급사50 곳

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
苏州道澜生物医药科技有限公司15952404857 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]

추가 설명

정의ChEBI: A diisocyanate consisting of dicyclohexylmethane with two isocyanate groups at the 4- and 4'-positions.

관련 반응

13건

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