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クロトン酸

Crotonic Acid

HCID 637090
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
107-93-7
標準SMILES
C/C=C/C(=O)O
InChIKey
LDHQCZJRKDOVOX-NSCUHMNNSA-N
分子式
C4H6O2
平均分子量
86.09 g/mol
単同位体質量
86.03677943

概要

Crotonic acid appears as a white crystalline solid. Shipped as either a solid or liquid. Soluble in water and less dense than water. Corrosive to metals and tissue.

名称と識別子

優先名称
Crotonic Acid
IUPAC
(E)-but-2-enoic acid
現地名
クロトン酸
英語名
Crotonic acid
分子式
C4H6O2
分子量
86.09

名称と別名

CROTONIC ACID(E)-but-2-enoic acidtrans-2-Butenoic acid3-Methylacrylic acid(2E)-but-2-enoic acid3724-65-0beta-Methylacrylic acidalpha-Butenoic acidalpha-Crotonic acidSolid crotonic acidbeta-Methacrylic acidKyselina krotonova
名称をさらに表示
クロトン酸トランス-2-ブテン酸TRANS-クロトン酸(E)-2-ブテン酸(2E)-ブタ-2-エン酸(2E)-2-ブテン酸(E)-クロトン酸CrotonateBUTENOIC ACIDBUT-2-ENOIC ACIDTRANS-CROTONIC ACID(E)-2-BUTENOIC ACID2-Butenoic acid, (E)-FEMA 3908(2E)-2-Butenoic acidNSC 8751
Acrylic acid, 3-methyl-2E-butenoic acidYW5WZZ4O5QNSC-8751FEMA NO. 3908CHEBI:41131NSC-206946RefChem:919215

データベース識別子

CAS
107-93-7、3724-65-0
PubChem CID
637090
DTXSID
DTXSID30880973
ChEMBL
CHEMBL1213528
ChEBI
CHEBI:41131
UNII
YW5WZZ4O5Q
EC Number
203-533-9、223-077-4
Nikkaji
J109.464E、J367K

物性

構造計算による物性

XLogP
0.7
極性表面積
37.3 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
1
重原子数
6
形式電荷
0
複雑度
73.6

実験および物理化学的性質

Chemical Classes · 2 件

Other Classes -> Organic Acids

Corrosives

DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]
CosmeticsStabilizing
SpringerMaterials PropertiesCoriolis coupling
LogP · 4 件

Log Kow = 0.72 /isomer not specified/

0.72

0.72

0.71

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 5 件

Density = 1.018 at 15 °C/4 °C

Density = 0.9604 g/ cu cm at 77 °C /TRANS ISOMER/

Density = 1.0267 g/ cu cm at 20 °C /CIS ISOMER/

Relative density (water = 1): 1.02

1.018 @ 15°C

Flavoring AgentsEU Flavoring substances
Color/Form · 3 件

MONOCLINIC NEEDLES OR PRISMS (FROM WATER OR PETROLEUM ETHER)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 0.3% (5 of 1826) of reports.

Danger

H302 (95.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1826 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

This chemical does not meet GHS hazard criteria for 0.4% (1 of 227) of reports.

危険有害性情報

Regulatory Information · 6 件

Chemical: 2-Butenoic acid

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

2-Butenoic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Butenoic acid 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)

2-Butenoic acid, (2E)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Butenoic acid, (2E)- 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)

REACH registered substance: trans-crotonic acid (EC: 203-533-9)

2-Butenoic acid, (2E)-: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelCorrosive
Fire Hazards · 4 件

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· Combustible material: may burn but does not ignite readily.

· Combustible material: may burn but does not ignite readily.

Combustible. Risk of fire and explosion on contact with incompatible substances. See Chemical Dangers. Above 88 °C explosive vapour/air mixtures may be formed.

化学と産業

薬理情報

Metabolism/Metabolites...IT /CROTONIC ACID/ IS KNOWN TO BE CONVERTED TO BETA-HYDROXYBUTYRYL-COA BY THE ENZYME KNOWN AS CROTONASE ENOYL CoA HYDRATE PRESENT IN LIVER & OTHER TISSUES.
Cellular LocationsExtracellular
Metabolite PathwaysFatty Acid Biosynthesis

用途と製造

Uses · 6 件

Used to make copolymers (for lacquers, paper sizing, resins, plasticizers, and drugs) and softening agents for synthetic rubber; Also used as a coating, fungicide, and corrosion-resistant additive; [HSDB]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

MFR OF COPOLYMERS WITH VINYL ACETATE USED IN LACQUERS & PAPER SIZING; MFR OF SOFTENING AGENTS FOR SYNTHETIC RUBBER; IN MEDICINAL CHEMISTRY, EG, MFR OF DL-THREONINE, VIT A

Coating, resins, fungicide, corrosion resistance improvement additive. Water-soluble resins and copolymers are suitable for pharmaceuticals, binders, and film

Chemical modifications rendering the surface layers of silicone rubber contact lenses hydrophilic property.

Carboxylated comonomer (polyvinyl acetate latex).

U.S. Production · 2 件

2023: 224,869 lb

2023: 7,040 lb

Consumer UsesDye
Industry Uses · 2 件

Monomers

Not Known or Reasonably Ascertainable

Methods of Manufacturing · 3 件

Obtained on a commercial scale exclusively by oxygen-air-oxidation of crotonaldehyde.

LAB PROCEDURE USING ALKALINE SILVER OXIDE; FROM ACETALDEHYDE & MALONIC ACID IN PYRIDINE.

Isomerization of vinylacetic acid by warming with 50% sulfuric acid.

関連反応

85 件
反応記録を作成
HRID 34445 の反応式
HRID 34445反応物としてuspto-grants-1988_08
HRID 54886 の反応式
HRID 54886反応物としてuspto-grants-1997_04
HRID 129981 の反応式
HRID 129981反応物としてuspto-grants-1995_11
HRID 249533 の反応式
HRID 249533反応物としてuspto-grants-1993_05
HRID 280005 の反応式
HRID 280005反応物としてuspto-grants-1986_05
HRID 327270 の反応式
HRID 327270生成物としてuspto-grants-1993_12
HRID 327271 の反応式
HRID 327271生成物としてuspto-grants-1993_12
HRID 355431 の反応式
HRID 355431反応物としてuspto-grants-1998_11
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化合物ノート

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COLORLESS NEEDLE-LIKE CRYSTALS

WHITE CRYSTALLINE SOLID

Solubility · 5 件

VERY SOL IN WATER; SOL IN ETHER, ACETONE & IN HOT PETROLEUM ETHER

IN ETHANOL @ 25 °C: 52.5% WT/WT; ACETONE @ 25 °C: 53.0% W/W; IN TOLUENE @ 25 °C: 37.5% WT/WT

Water solubility: 8.6X10+4 mg/l at 25 °C

555 g/l in water at 20 °C

8.60E+04 mg/L @ 25 °C (exp)

Flash Point · 3 件

190 °F (NFPA, 2010)

190 °F (OPEN CUP)

88 °C o.c.

物理化学的性質

融点
70 · 70-72 °C (lit.)
沸点
180 · 180-181 °C (lit.)
比重(密度)
1.027 g/mL · 1.027 g/mL at 25 °C (lit.)
蒸気密度
2.97 · 2.97 (vs air)
蒸気圧
0.19 mm · 0.19 mm Hg ( 20 °C)
屈折率
1.4228 · 1.4228
FEMA
3908 · 3908 | (E)-2-BUTENOIC ACID
闪点
190 °F · 190 °F
貯蔵温度
30 °C · Store below +30°C.
溶解性
2 O: · H2O: 可溶
酸解離定数(Pka)
4.69 · 4.69(at 25℃)
外見
結晶フレーク
色
白色~淡黄色
PH
3 · 3 (10g/l, H2O, 20℃)
臭い (Odor)
1 %で。乳白色の · 1.00%で。乳白色の
においのタイプ
乳白色の
爆発限界(explosive limit)
15.1 %, · 15.1%, 171°F
水溶解度
94 g/L · 94g/L(25℃)
Merck
14 · 14,2597
JECFA Number
1371 · 1371
BRN
1719943 · 1719943
Henry's Law Constant
4.1 · 4.1×101 mol/(m3Pa) at 25℃, HSDB (2015)
InChI
1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2+
InChIKey
LDHQCZJRKDOVOX-NSCUHMNNSA-N
SMILES
[H]\C(C)=C(\[H])C(O)=O
LogP
0.85 at · 0.85 at 25℃
CAS データベース
107 · 107-93-7(CAS DataBase Reference)
NISTの化学物質情報
Crotonic acid(107-93-7)
EPAの化学物質情報
2 · 2-Butenoic acid, (2E)- (107-93-7)
Fire PotentialMODERATE, WHEN EXPOSED TO HEAT OR FLAME
Health Hazards · 3 件

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

Hazards Summary · 1 件

A strong tissue irritant; [Hawley] May polymerize on exposure to UV light or moisture; A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause pulmonary edema; [ICSC] Emergency treatment: acids; [HSDB]

DOT ID and Guide · 2 件

2823 153

3472 153

Reactive GroupAcids, Carboxylic
UN ClassificationUN Hazard Class: 8; UN Pack Group: III
Reactivity Profile · 1 件

CROTONIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

Chemical Dangers · 1 件

The substance may polymerize under the influence of UV light or moisture. This generates fire and explosion hazard. The solution in water is a weak acid. Reacts violently with strong bases and peroxides. This generates fire and explosion hazard.

Physical DangersThe vapour is heavier than air.

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use water spray, foam, dry powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 件

Fresh air, rest. Seek medical attention if you feel unwell.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention if skin irritation occurs.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Seek medical attention if you feel unwell.

Accidental Release Measures · 4 件

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 3 件

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

General First Aid:

General First Aid:

Safe StorageStore only in original container. Store only if stabilized. Separated from food and feedstuffs, strong bases and peroxides. Well closed. Dry. Keep in the dark. Ventilation along the floor. Store in an area without drain or sewer access.
Exposure Control and Personal Protection · 2 件

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

Fire Fighting Procedures · 1 件

If material on fire or involved in fire: Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.

Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Disposal Methods · 1 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Spillage Disposal · 1 件

Evacuate danger area! Remove all ignition sources. Consult an expert! Personal protection: face shield. Do NOT let this chemical enter the environment. Let solidify. Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations.

Preventive Measures · 3 件

If material not on fire and not involved in fire: Keep material out of water sources and sewers. Neutralize spilled material with crushed limestone, soda ash, or lime.

Personnel protection: Avoid breathing vapors. Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. If contact with the material anticipated, wear appropriate chemical protective clothing.

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.

Isolation and Evacuation · 3 件

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Immediate precautionary measure

Immediate precautionary measure

毒性情報

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 59(SRC), determined from a measured log Kow of 0.72(2) and a regression-derived equation(3), indicates that crotonic acid is expected to have high mobility in soil(SRC). Volatilization of trans-crotonic acid is not expected to be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 2.4X10-7 atm-cu m/mole(SRC), determined from a vapor pressure of 0.18 mm Hg at 20 °C(4) and a measured water solubility of 8.6X10+4 mg/l at 25 °C(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 59(SRC), determined from a measured log Kow of 0.72(2) and a regression-derived equation(3), indicates that crotonic acid is not expected to adsorb to suspended solids and sediment in water(SRC). trans-Crotonic acid is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 2.4X10-7 atm-cu m/mole(SRC), determined from a vapor pressure of 0.18 mm Hg at 20 °C(4) and a measured water solubility of 8.6X10+4 mg/l at 25 °C(5). According to a classification scheme(6), an estimated BCF value of 2.1(3,SRC), from a measured log Kow(2), suggests that bioconcentration in aquatic organisms is low(SRC). Crotonic acid was biodegraded by anaerobic bacteria to butyrate and acetate(7-9). After a lag period of 2 days, crotonic acid was metabolized, at a rate of 200 mg/l day, by anaerobic bacteria acclimated to acetate culture(9). Crotonic acid reached 44% of its theoretical BOD in 5 days using a sewage inoculum(10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trans-crotonic acid, which has a vapor pressure of 0.18 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase trans-crotonic acid 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 17 hours(3,SRC).

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
Signs and Symptoms · 4 件

Cough. Sore throat.

Redness.

Redness. Pain. Burning sensation. Burns.

Sore throat.

Effluent Concentrations · 1 件

Crotonic acid was identified as an oxygenated organic emission from bench-scale fires using individual components derived from ponderosa pine as fuel(1). Smoldering wood fires emitted crotonic acid at a mean concentration of 0.068 g/kg; smoldering needle fires emitted crotonic acid at a mean concentration of 0.037 g/kg; smoldering bark fires emitted a mean crotonic acid concentration of 0.039 g/kg; self-sustained smoldering bark fires emitted 0.03 g/kg crotonic acid; and smoldering litter (consisting primarily of loose brown needles, with lesser amounts of cones, bark, grass) fires emitted a mean concentration of 0.04 g/kg crotonic acid(1).

ICSC Environmental DataThe substance is harmful to aquatic organisms.
Soil Adsorption/Mobility · 1 件

The Koc of crotonic acid is estimated as approximately 59(SRC), using a measured log Kow of 0.72(1) and a regression-derived equation(2,SRC). According to a classification scheme(3), this estimated Koc value suggests that crotonic acid is expected to have high mobility in soil(SRC).

Human Toxicity ExcerptsNO CUMULATIVE EFFECTS WOULD BE EXPECTED @ NONIRRITATING EXPOSURE LEVELS... CROTONIC ACID SHOULD BE REGARDED AS HAVING SAME HAZARDS AS OTHER STRONG ACIDS.
Fish/Seafood ConcentrationsCrotonic acid was detected in fresh mussels collected at the Oarai coast in Ibaraki, Japan, on July 31, 1985, at a concentration of 0.16 ug/g fresh weight(1).
Artificial Pollution Sources · 1 件

Crotonic acid's production and use in the synthesis of resins, polymers, plasticizers, and drugs(1) may result in its release to the environment(SRC). Only the trans form of crotonic acid and its derivatives have industrial importance as monomers in copolymerization reactions and as intermediates in the synthesis of pharmaceuticals or fungicides(2).

Environmental Biodegradation · 1 件

Crotonic acid (mixture) was identified as being amenable to anaerobic biodegradation(1). Anaerobic bacteria isolated from mesophilic digester sludge acclimatized with 4-chlorobutyrate tentatively classified in the genus Clostridium, degraded crotonate to butyrate, acetate, and hydrogen(2). Ilyobacter polytropus anaerobically degraded crotonate to butyrate and acetate(2). Crotonate was degraded by an anaerobic bacterium to butyrate and acetate(3). After a lag period of 2 days, crotonic acid (isomer not specified) was metabolized, at a rate of 200 mg/l day, by anaerobic bacteria acclimated to acetate culture(4). Crotonic acid (isomer not specifed) reached 44% of its theoretical BOD in 5 days using a sewage inoculum(5).

Environmental Bioconcentration · 1 件

An estimated BCF value of 2.1 was calculated for crotonic acid(SRC), using a measured log Kow of 0.72(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).

安全データ

wgk
3
rtecs
GQ2900000
ridadr
UN 3472 8/PG III (CROTONIC ACID, LIQUID)
毒性
LD50 orally in rats: 1.0 g/kg (Smyth, Carpenter)
hs_code
29161940
risk_code
21/22-34-50/53-36/37/38
化審法
(2)-963
hazard_code
C,N,Xi
safety_code
26-36/37/39-45-61-37/39
hazard_class
8
packing_group
III
自然発火温度
744 °F
Hazard Classifications
Eye Dam. 1
ストレージクラス
8A - Combustible corrosive hazardous materials
Formulations/Preparations · 2 件

GRADE: 97%

Technical grade, 98.5% min

Use Classification · 4 件

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Cosmetics -> Stabilizing

General Manufacturing Information · 5 件

All Other Basic Organic Chemical Manufacturing

Not Known or Reasonably Ascertainable

2-Butenoic acid: ACTIVE

IT /CROTONIC ACID/ IS PRESENT AS CONSTITUENT OF CROTON OIL.

Only the trans form of crotonic acid and its derivatives have industrial importance as monomers in copolymerization reactions and as intermediates in the synthesis of pharmaceuticals or fungicides.

応用分野 · 4 件

解説trans-2-butenoic acid.C4H6O2(86.09).塩基の存在下でアセトアルデヒドとマロン酸を縮合させるか,クロトンアルデヒドを酸化すると得られる."無色の斜状結晶.融点72 ℃,沸点189 ℃.d1541.018.水に可溶.cis-2-グデン酸はイソクロトン酸とよばれる.イソクロトン酸は無色の針状結晶.融点13.5~14.5 ℃,沸点169 ℃.d154"1.0312, n14D1.4483.水に可溶.トランス形のほうが安定である.180 ℃ に加熱するとクロトン酸にかわる.森北出版「化学辞典(第2版)

使用trans-Crotonic acid is used in the copolymerization of crotonic acid hydrogel systems by using gamma-rays. The crosslinked copolymeric crotonic acid hydrogels release fertilizers and drugs that help to prevent environmental pollution.

一般的な説明Crotonic acid undergoes esterification with butan-2-ol by following second order reaction kinetics.

使用用途クロトン酸の主な用途は、他の物質と共重合させて形成するコポリマー (copolymer) の原料です。主な共重合モノマーにはなどのビニル系化合物があります。合成された共重合化合物は、皮膜形成材や、ヘアスタイリング剤として使用されています。 また、クロトン酸はガンマ線を用いたクロトン酸ハイドロゲルシステムの共重合にも用いられています。架橋共重合体クロトン酸ハイドロゲルは、肥料や薬剤を徐放し、環境汚染の防止に効果があるとされている物質です。 その他にも、医薬、香料、農薬など各種有機合成の原料としての用途が挙げられます。

調製方法

製造方法(E)-2-Butenoic acid may be formed by oxidation of crotonaldehyde, 2-butenal. If (Z)-butenoic acid is heated at 180°C, it is converted to (E)-2-butenoid acid.

純化方法Distil the acid under reduced pressure and/or recrystallise it from pet ether (b 60-80o) or water, or by partial freezing of the melt. [Beilstein 2 IV 1498.]

上流・下流製品情報

上流原料

ビス酢酸コバルト(II)クロトンアルデヒド(トランス)ビス酢酸銅(II)·水和物3-メチルアクリル酸マロン酸

下流製品

3-フェニル酪酸3-ヒドロキシ酪酸ナトリウムクロタミトンDL-3-ヒドロキシ酪酸ナトリウム4-ブロモクロトン酸β-メチルレブリン酸2,3-ジブロモ酪酸3-Mercaptobutyric acidrac-(R*)-3-アミノ酪酸(E)-2-ブテン酸シクロヘキシル2-ブテン酸ヘプチル(E)-2-ブテン酸ヘキシル