Kiến thức

Hydroquinone-Wikipedia

Hydroquinone

From Wikipedia, the free encyclopedia

Jump to navigation

Jump to search

Chemical compound
Hydroquinone

Hydroquinone

Trans-hydroquinone-from-xtal-3D-balls.png

Hydroquinone crystal.jpg

Names

Preferred IUPAC name

Benzene-1,4-diol

[1]

Other names

Hydroquinone

[1]


Idrochinone
Quinol
1,4-Dihydroxybenzene
1,4-Hydroxy benzene

Identifiers

CAS Number

  • 123-31-9

     checkY

3D model (

JSmol

)

  • Interactive image

Beilstein Reference

605970

ChEBI

  • CHEBI:17594

     checkY

ChEMBL

  • ChEMBL537

     checkY

ChemSpider

  • 764

     checkY

ECHA InfoCard

100.004.199

Edit this at Wikidata

EC Number

  • 204-617-8

Gmelin Reference

2742

KEGG

  • D00073

     checkY

PubChem

CID

  • 785

RTECS number

  • MX3500000

UNII

  • XV74C1N1AE

     checkY

UN number

3077, 2662

CompTox Dashboard

(EPA)

  • DTXSID7020716

    Edit this at Wikidata

InChI

  • InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H checkY
    Key: QIGBRXMKCJKVMJ-UHFFFAOYSA-N checkY
  • InChI=1/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H
    Key: QIGBRXMKCJKVMJ-UHFFFAOYAX

SMILES

  • c1cc(ccc1O)O
Properties

Chemical formula

C6H6O2

Molar mass

110.112 g·mol−1
Appearance white solid

Density

1.3 g cm−3, solid

Melting point

172 °C (342 °F; 445 K)

Boiling point

287 °C (549 °F; 560 K)

Solubility in water

5.9 g/100 mL (15 °C)

Vapor pressure

10−5 mmHg (20 °C)

[2]

Acidity

(pKa)

9.9

[3]

Magnetic susceptibility

(χ)

−64.63×10−6 cm3/mol
Structure

Dipole moment

1.4±0.1 

D

[4]

Pharmacology

ATC code

D11AX11

(

WHO

)

Hazards

EU classification

(DSD)

(outdated)

Harmful (Xn)

Carc. Cat. 3

Muta. Cat. 3

Dangerous for
the environment (N)

R-phrases

(outdated)

R22

R40

R41

R43

R50

R68

S-phrases

(outdated)

(S2)

S26

S36/37/39

S61

NFPA 704

(fire diamond)

[6]

2

1

Flash point

165 °C (329 °F; 438 K)
Lethal dose or concentration (LD, LC):
LD50 (

median dose

)

490 mg/kg (mammal, oral)
245 mg/kg (mouse, oral)
200 mg/kg (rabbit, oral)
320 mg/kg (rat, oral)
550 mg/kg (guinea pig, oral)
200 mg/kg (dog, oral)
70 mg/kg (cat, oral)

[5]

NIOSH

(US health exposure limits):

PEL

(Permissible)

TWA 2 mg/m3

[2]

REL

(Recommended)

C 2 mg/m3 [15-minute]

[2]

IDLH

(Immediate danger)

50 mg/m3

[2]

Related compounds
Related

benzenediols

Pyrocatechol

Resorcinol

Related compounds

1,4-benzoquinone

Except where otherwise noted, data are given for materials in their

standard state

(at 25 °C [77 °F], 100 kPa).

checkY 

verify

 (

what is

 checkY☒N ?)

Infobox references

Chemical compound

Hydroquinone, also known as benzene-1,4-diol or quinol, is an

aromatic

organic compound

that is a type of

phenol

, a derivative of

benzene

, having the

chemical formula

C6H4(OH)2. It has two

hydroxyl groups

bonded

to a

benzene ring

in a

para

position. It is a white granular

solid

. Substituted derivatives of this parent compound are also referred to as hydroquinones. The name “hydroquinone” was coined by

Friedrich Wöhler

in 1843.

[7]

Production[

edit

]

Hydroquinone is produced industrially by two main routes.

[8]

  • The most widely used route is similar to the

    cumene process

    in reaction mechanism and involves the dialkylation of

    benzene

    with

    propene

    to give 1,4-diisopropylbenzene. This compound reacts with air to afford the bis(hydroperoxide), which is structurally similar to

    cumene hydroperoxide

    and rearranges in acid to give

    acetone

    and hydroquinone.

    [9]

  • A second route involves

    hydroxylation

    of

    phenol

    over a catalyst. The conversion uses

    hydrogen peroxide

    and affords a mixture of hydroquinone and

    catechol

    (benzene-1,2-diol):

C6H5OH + H2O2 → C6H4(OH)2 + H2O

Other, less common methods include:

  • A potentially significant synthesis of hydroquinone from

    acetylene

    and

    iron pentacarbonyl

    has been proposed

    [10]

    [11]

    [12]

    [13]

    [14]

    [15]

    Iron pentacarbonyl serves as a

    catalyst

    , rather than as a

    reagent

    , in the presence of free

    carbon monoxide

    gas.

    Rhodium

    or

    ruthenium

    can substitute for iron as the catalyst with favorable chemical yields but are not typically used due to their cost of recovery from the reaction mixture.

    [10]

  • Hydroquinone and its

    derivatives

    can also be prepared by oxidation of various phenols. Examples include

    Elbs persulfate oxidation

    and

    Dakin oxidation

    :

  • Hydroquinone was first obtained in 1820 by the French chemists

    Pelletier

    and

    Caventou

    via the

    dry distillation

    of

    quinic acid

    .

    [16]

Xem thêm: Google Keep Là Gì? Cách Sử Dụng Keep Trên Điện Thoại ✔️

Reactions[

edit

]

The reactivity of hydroquinone’s

hydroxyl

groups resembles that of other

phenols

, being weakly acidic. The resulting

conjugate base

undergoes easy O-alkylation to give

mono- and diethers

. Similarly, hydroquinone is highly susceptible to ring substitution by

Friedel–Crafts reactions

such as alkylation. This reaction is exploited en route to popular antioxidants such as 2-tert-butyl-4-methoxyphenol (

BHA

). The useful dye

quinizarin

is produced by diacylation of hydroquinone with

phthalic anhydride

.

[8]

Redox[

edit

]

Hydroquinone undergoes

oxidation

under mild conditions to give

benzoquinone

. This process can be reversed. Some naturally occurring hydroquinone derivatives exhibit this sort of reactivity, one example being

coenzyme Q

. Industrially this reaction is exploited both with hydroquinone itself but more often with its derivatives where one OH has been replaced by an amine.

When colorless hydroquinone and benzoquinone, a bright yellow solid, are

cocrystallized

in a 1:1 ratio, a dark-green crystalline

charge-transfer complex

(

melting point

171 °C) called

quinhydrone

(C6H6O2·C6H4O2) is formed. This complex dissolves in hot water, where the two molecules dissociate in solution.

[17]

Amination[

edit

]

An important reaction is the conversion of hydroquinone to the mono- and diamine derivatives.

Methylaminophenol

, used in photography, is produced in this way:

[8]

C6H4(OH)2 +

CH3NH2

→ HOC6H4NHCH3 + H2O

Similarly diamines, useful in the rubber industry as antiozone agents, are produced similarly from

aniline

:

C6H4(OH)2 + 2 C6H5NH2 → C6H4(N(H)C6H5)2 + 2 H2O

Uses[

edit

]

Hydroquinone has a variety of uses principally associated with its action as a reducing agent that is

soluble

in water. It is a major component in most black and white

photographic developers

for film and paper where, with the compound

metol

, it reduces silver

halides

to elemental

silver

.

There are various other uses associated with its

reducing power

. As a

polymerisation inhibitor

, exploiting its

antioxidant

properties, hydroquinone prevents polymerization of

acrylic acid

,

methyl methacrylate

,

cyanoacrylate

, and other monomers that are susceptible to radical-initiated

polymerization

. By acting as a free radical scavenger, hydroquinone serves to prolong the shelflife of light-sensitive resins such as

preceramic polymers

.

[18]

Hydroquinone can lose a hydrogen cation from both hydroxyl groups to form a diphenolate ion. The di

sodium

diphenolate

salt

of hydroquinone is used as an alternating co

monomer

unit in the production of the

polymer

PEEK

.

Skin depigmentation[

edit

]

Hydroquinone is used as a topical application in

skin whitening

to reduce the

color

of skin. It does not have the same predisposition to cause

dermatitis

as

metol

does. This is a prescription-only ingredient in some countries, including the member states of the European Union under

Directives

76/768/EEC:1976.

[19]

[20]

In 2006, the United States

Food and Drug Administration

revoked its previous approval of hydroquinone and proposed a ban on all

over-the-counter

preparations.

[21]

The FDA stated that hydroquinone cannot be ruled out as a potential

carcinogen

.

[22]

This conclusion was reached based on the extent of

absorption

in humans and the incidence of

neoplasms

in rats in several studies where adult rats were found to have increased rates of tumours, including

thyroid follicular cell hyperplasias

, anisokaryosis (variation in nuclei sizes), mononuclear cell leukemia,

hepatocellular adenomas

and

renal tubule cell adenomas

. The Campaign for Safe Cosmetics has also highlighted concerns.

[23]

Numerous studies have revealed that hydroquinone, if taken orally, can cause exogenous

ochronosis

, a disfiguring disease in which blue-black pigments are deposited onto the skin; however, skin preparations containing the ingredient are administered topically. The FDA had classified hydroquinone in 1982 as a safe product – generally recognized as safe and effective (GRASE), however additional studies under the National Toxicology Program (NTP) were suggested in order to determine whether there is a risk to humans from the use of hydroquinone.

[21]

[24]

[22]

NTP evaluation showed some evidence of long-term carcinogenic and genotoxic effects

[25]

While using hydroquinone as a lightening agent can be effective with proper use, it can also cause skin sensitivity. Using a daily sunscreen with a high

PPD (persistent pigment darkening)

rating reduces the risk of further damage. Hydroquinone is sometimes combined with

alpha-hydroxy acids

that exfoliate the skin to quicken the lightening process. In the United States, topical treatments usually contain up to 2% in hydroquinone. Otherwise, higher concentrations (up to 4%) should be prescribed and used with caution.

While hydroquinone remains widely prescribed for treatment of

hyperpigmentation

, questions raised about its safety profile by regulatory agencies in the EU, Japan, and USA encourage the search for other agents with comparable efficacy.

[26]

Several such agents are already available or under research,

[27]

including

azelaic acid

,

[28]

kojic acid

, retinoids, cysteamine,

[29]

topical steroids,

glycolic acid

, and other substances. One of these,

4-butylresorcinol

, has been proven to be more effective at treating melanin-related skin disorders by a wide margin, as well as safe enough to be made available over the counter.

[30]

Xem thêm: Tính chất hoá học của Crom (Cr), Crom oxit và hợp chất của Crom-hoá 12 bài 34

Natural occurrences[

edit

]

Hydroquinones are one of the two primary reagents in the defensive glands of

bombardier beetles

, along with

hydrogen peroxide

(and perhaps other compounds, depending on the species), which collect in a reservoir. The reservoir opens through a muscle-controlled valve onto a thick-walled reaction chamber. This chamber is lined with cells that secrete

catalases

and

peroxidases

. When the contents of the reservoir are forced into the reaction chamber, the catalases and peroxidases rapidly break down the hydrogen peroxide and

catalyze

the

oxidation

of the hydroquinones into

p-quinones

. These reactions release free oxygen and generate enough heat to bring the mixture to the boiling point and vaporize about a fifth of it, producing a hot spray from the beetle’s

abdomen

.

[31]

Farnesyl

hydroquinone derivatives are the principal irritants exuded by the

poodle-dog bush

, which can cause severe

contact dermatitis

in humans.

Hydroquinone is thought to be the active toxin in

Agaricus hondensis

mushrooms.

[32]

Hydroquinone has been shown to be one of the chemical constituents of the natural product

propolis

.

[33]

It is also one of the chemical compounds found in

castoreum

. This compound is gathered from the

beaver

‘s castor sacs.

[34]

In

bearberry

(Arctostaphylos uva-ursi), arbutin is converted to hydroquinone.

See also[

edit

]

  • Photographic developer

  • Semiquinone

  • Bombardier beetle

Xem thêm: 16 giới từ chỉ vị trí thông dụng trong tiếng Anh-Tiếng Anh ABC

References[

edit

]

  1. ^

    a

    b

    “Front Matter”. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge:

    The Royal Society of Chemistry

    . 2014. p. 691.

    doi

    :

    10.1039/9781849733069-FP001

    .

    ISBN

     

    978-0-85404-182-4

    .

  2. ^

    a

    b

    c

    d

    NIOSH Pocket Guide to Chemical Hazards.

    “#0338”

    .

    National Institute for Occupational Safety and Health

    (NIOSH).

  3. ^

    “Hydroquinone”

    (PDF).

    OECD SIDS

    . UNEP Publications.

  4. ^

    Lander, John J.; Svirbely, John J. Lander, W. J. (1945). “The Dipole Moments of Catechol, Resorcinol and Hydroquinone”. Journal of the American Chemical Society. 67 (2): 322–324.

    doi

    :

    10.1021/ja01218a051

    .

  5. ^

    “Hydroquinone”

    . Immediately Dangerous to Life or Health Concentrations (IDLH).

    National Institute for Occupational Safety and Health

    (NIOSH).

  6. ^

    “Archived copy”

    (PDF).

    Archived

    (PDF) from the original on 2014-02-02. Retrieved 2014-01-25.CS1 maint: archived copy as title (

    link

    )

  7. ^

    F. Wöhler (1844) “Untersuchungen über das Chinon” (Investigations of quinone), Annalen der Chemie und Pharmacie, 51 : 145-163.

    From page 146:

    “Das so erhaltene Destillat … enthält … einen neuen, krystallisierenden Körper, den ich unter dem Namen farbloses Hydrochinon weiter unten näher beschreiben werde.” (The distillate so obtained … contains … a new, crystallizable substance, that I will describe, under the name of colorless hydroquinone, further below in more detail.) [Note: Wöhler’s empirical formula for hydroquinone (p. 152) is incorrect because (1) he attributed 25 (instead of 24) carbon atoms to the molecule, and (2) as many chemists at the time did, he used the wrong atomic masses for carbon (6 instead of 12) and oxygen (8 instead of 16). With these corrections, his empirical formula becomes: C12H12O4. Dividing the subscripts by 2, the result is: C6H6O2, which is correct.]

  8. ^

    a

    b

    c

    Phillip M. Hudnall “Hydroquinone” in Ullmann’s Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. 2005 Wiley-VCH, Weinheim.

    doi

    :

    10.1002/14356007.a13_499

    .

  9. ^

    Gerhard Franz, Roger A. Sheldon “Oxidation” in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2000

    doi

    :

    10.1002/14356007.a18_261

  10. ^

    a

    b

    Reppe, Walter; Kutepow, N; Magin, A (1969). “Cyclization of Acetylenic Compounds”. Angewandte Chemie International Edition in English. 8 (10): 727–733.

    doi

    :

    10.1002/anie.196907271

    .

  11. ^

    Hubel, Karl; Braye, Henri (1960).

    Process for the preparation of substituted cyclic compounds and products resulting therefrom US3149138 A

    (PDF). Union Carbide Corp.

  12. ^

    Pino, Piero; Braca, Giuseppe; Sbrana, Glauco (1964).

    Preparation of hydroquinone US3355503 A

    (PDF). Lonza Ag.

  13. ^

    Walter, Reppe; Magin, August (1966).

    Production of hydroquinones US3394193 A

    (PDF). Basf Ag.

  14. ^

    Piero, Pino; Giuseppe, Braca; Frediano, Settimo; Glauco, Sbrana (1967).

    Preparation of hydroquinone US3459812 A

    (PDF). Lonza Ag.

  15. ^

    Holmes, J.; Hagemeyer, H. (1971).

    Process for the production of hydroquinone US 3742071 A

    (PDF). Eastman Kodak Co.

  16. ^

    See:

    • Pelletier and Caventou (1820) “Recherches chimiques sur les quinquinas” (Chemical investigations of quinquinas [i.e., the bark of various

      Cinchona

      trees]), Annales de Chimie et de Physique, 2nd series, 15 : 289-318, 337-364.

      On pages 341-342

      , the preparation and properties of l’acide pyro-kinique (pyroquinic acid or hydroquinone) are discussed.

    • Roscoe, Henry (1891).

      A Treatise on Chemistry, Volume 3, Part 3

      . London: Macmillan & Co. p. 165.

  17. ^

    1927-, Streitwieser, Andrew (1992). Introduction to organic chemistry. Heathcock, Clayton H., 1936-, Kosower, Edward M. (4th ed.). Upper Saddle River, N.J.: Prentice Hall.

    ISBN

     

    978-0139738500

    .

    OCLC

     

    52836313

    .CS1 maint: numeric names: authors list (

    link

    )

  18. ^

    Additive manufacturing of ceramics from preceramic polymers

    Additive manufacturing 2019 vol. 27. pp 80-90

  19. ^

    76/768/EEC:1976 Council Directive 76/768/EEC of 27 July 1976 on the approximation of the laws of the Member States relating to cosmetic products :

    http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=CELEX:31976L0768:EN:HTML

  20. ^

    “Clear N Smooth Skin Toning Cream recalled”

    . 2011-10-04. Retrieved 4 April 2018.

  21. ^

    a

    b

    United States Food and Drug Administration (2006).

    Skin Bleaching Drug Products for Over-the-Counter Product Use; Proposed Rule

    (PDF) (Report). 1978N-0065.

    Archived

    (PDF) from the original on 2011-05-16.

  22. ^

    a

    b

    Research, Center for Drug Evaluation and.

    “About the Center for Drug Evaluation and Research – Hydroquinone Studies Under The National Toxicology Program (NTP)”

    . www.fda.gov.

    Archived

    from the original on 2017-01-22. Retrieved 2017-02-12.

  23. ^

    Campaign For Safe Cosmetics – Hydroquinone

    Archived

    2010-11-27 at the

    Wayback Machine

  24. ^

    Olumide, YM; Akinkugbe, AO; Altraide, D; Mohammed, T; Ahamefule, N; Ayanlowo, S; Onyekonwu, C; Essen, N (April 2008). “Complications of chronic use of skin lightening cosmetics”. International Journal of Dermatology. 47 (4): 344–53.

    doi

    :

    10.1111/j.1365-4632.2008.02719.x

    .

    PMID

     

    18377596

    .

  25. ^

    “Hydroquinone 10022-H”

    . ntp.niehs.nih.gov.

    Archived

    from the original on 2017-10-01. Retrieved 2017-02-12.

  26. ^

    Draelos, Zoe Diana (2007-09-01). “Skin lightening preparations and the hydroquinone controversy”. Dermatologic Therapy. 20 (5): 308–313.

    doi

    :

    10.1111/j.1529-8019.2007.00144.x

    .

    ISSN

     

    1529-8019

    .

    PMID

     

    18045355

    .

    S2CID

     

    24913995

    .

  27. ^

    Bandyopadhyay, Debabrata (2009-01-01).

    “Topical treatment of melasma”

    . Indian Journal of Dermatology. 54 (4): 303–309.

    doi

    :

    10.4103/0019-5154.57602

    .

    ISSN

     

    0019-5154

    .

    PMC

     

    2807702

    .

    PMID

     

    20101327

    .

  28. ^

    Mazurek, Klaudia; Pierzchała, Ewa (2016-09-01). “Comparison of efficacy of products containing azelaic acid in melasma treatment”. Journal of Cosmetic Dermatology. 15 (3): 269–282.

    doi

    :

    10.1111/jocd.12217

    .

    ISSN

     

    1473-2165

    .

    PMID

     

    27028014

    .

  29. ^

    Mansouri, P.; Farshi, S.; Hashemi, Z.; Kasraee, B. (2015-07-01). “Evaluation of the efficacy of cysteamine 5% cream in the treatment of epidermal melasma: a randomized double-blind placebo-controlled trial”. The British Journal of Dermatology. 173 (1): 209–217.

    doi

    :

    10.1111/bjd.13424

    .

    ISSN

     

    1365-2133

    .

    PMID

     

    25251767

    .

    S2CID

     

    21618233

    .

  30. ^

    “Hydroquinones”. Phenols—Advances in Research and Application: 2013 Edition. Scholastic. 2013. p. 76.

  31. ^

    Organic Chemistry, Solomon and Fryhle, 10th edition, Wiley Publishing, 2010.[

    page needed

    ]

  32. ^

    Joval, E; Kroeger, P; N (April 1996). “Hydroquinone: the toxic compound of Agaricus hondensis”. Planta Medica. 62 (2): 185.

    doi

    :

    10.1055/s-2006-957852

    .

    PMID

     

    17252436

    .

  33. ^

    Burdock, G.A. (1998). “Review of the biological properties and toxicity of bee propolis (propolis)”. Food and Chemical Toxicology. 36 (4): 347–363.

    doi

    :

    10.1016/S0278-6915(97)00145-2

    .

    PMID

     

    9651052

    .

  34. ^

    The Beaver: Its Life and Impact. Dietland Muller-Schwarze, 2003, page 43 (

    book at google books

    )

External links[

edit

]

  • International Chemical Safety Card 0166

  • NIOSH Pocket Guide to Chemical Hazards

  • IARC Monograph: “Hydroquinone”

Retrieved from “

https://en.wikipedia.org/w/index.php?title=Hydroquinone&oldid=1012702515

Chuyên mục: Kiến thức

Related Articles

Trả lời

Email của bạn sẽ không được hiển thị công khai. Các trường bắt buộc được đánh dấu *

Check Also
Close
Back to top button