2-氯-1,3-丙二醇

2-氯-1,3-丙二醇
別名	2-MCPD; β-MCP
識別
CAS號	497-04-1
PubChem	10337
SMILES	ClC(CO)CO;
InChI	InChI=1S/C3H7ClO2/c4-3(1-5)2-6/h3,5-6H,1-2H2;
InChIKey	DYPJJAAKPQKWTM-UHFFFAOYSA-N
性質
化學式	C3H7ClO2
摩爾質量	110.54 g·mol−1
外觀	無色粘稠液體
密度	1.3416 g·cm−3（0 °C，真空）; 1.3241 g·cm−3（20 °C，真空）
沸點	96~98 °C（3 mmHg）; 122.5~123.5 °C（13.5 mmHg）
折光度n; D	1.4817（25 °C）
危險性
	GHS危險性符號;
GHS提示詞	危險
H-術語	H301
P-術語	P264, P270, P301+310, P405, P501
主要危害	急性毒性3級（經口）
閃點	N.A.
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

2-氯-1,3-丙二醇是一種有機氯化合物，化學式為C₃H₇ClO₂。它和其同分異構體 3-氯-1,2-丙二醇一樣，是一種食品污染物，具有細胞毒性。^[4]

合成

2-氯-1,3-丙二醇可由烯丙醇和氯水反應製得。^[1]

它也可在丙三醇和鹽酸在羧酸催化下以副產物的形式伴隨1,3-二氯-2-丙醇和3-氯-1,2-丙二醇生成。^[5]

反應

2-氯-1,3-丙二醇在超聲下和吡啶加熱反應，可以生成N-(1,3-二羥基-2-丙基)吡啶鎓氯化物。^[6]

它和氫氧化鉀反應，可以得到縮水甘油。^[7]它和氯化亞碸在乙醚中反應，可以得到2-氯-1,3-丙二醇環亞硫酸酯。^[8]

它和羧酸酐反應，可以得到相應的羧酸酯：^[9]

參考文獻

^ ^1.0 ^1.1 ^1.2 ^1.3 Read, John; Hurst, Eric. Conversion of allyl alcohol to glyceryl chloro- and bromohydrins. Journal of the Chemical Society, Transactions. 1922, 121: 989-999. ISSN 0368-1645. doi:10.1039/ct9222100989.
^ ^2.0 ^2.1 Ben-Ishay, D. A Novel Rearrangement of Substituted Cyclic Sulfites. The Journal of Organic Chemistry. 1958, 23 (12): 2013-2014. doi:10.1021/jo01106a619.
^ 2-Chloro-1,3-propanediol. SigmaAldrich. [2024-07-09].
^ Thorsten Buhrke, Falko Frenzel, Jan Kuhlmann & Alfonso Lampen. 2-Chloro-1,3-propanediol (2-MCPD) and its fatty acid esters: cytotoxicity, metabolism, and transport by human intestinal Caco-2 cells. Toxicokinetics and Metabolism. 2015, 89: 2243-2251. doi:10.1007/s00204-014-1395-3.
^ R. Tesser, E. Santacesaria, M. Di Serio, G. Di Nuzzi, and V. Fiandra. Kinetics of Glycerol Chlorination with Hydrochloric Acid: A New Route to α,γ-Dichlorohydrin. Industrial & Engineering Chemistry Research. 2007, 46 (20): 6456–6465. doi:10.1021/ie070708n.
^ Nayl, AbdElAziz A. ; Arafa, Wael A. A.; Ahmed, Ismail M.; Abd-Elhamid, Ahmed I.; El-Fakharany, Esmail M.; Abdelgawad, Mohamed A.; Gomha, Sobhi M.; Ibrahim, Hamada M.; Aly, Ashraf A.; Brase, Stefan; Mourad, Asmaa K. Novel Pyridinium Based Ionic Liquid Promoter for Aqueous Knoevenagel Condensation: Green and Efficient Synthesis of New Derivatives with Their Anticancer Evaluation. Molecules. 2022, 27 (9): 2940. ISSN 1420-3049. doi:10.3390/molecules27092940.
^ Cespi, D.; Cucciniello, R.; Ricciardi, M.; Capacchione, C.; Vassura, I.; Passarini, F.; Proto, A. A simplified early stage assessment of process intensification: glycidol as a value-added product from epichlorohydrin industry wastes. Green Chemistry. 2016, 18 (16): 4559-4570. ISSN 1463-9262.
^ P. B. D. de la Mare; W. Klyne; D. J. Millen; J. G. Pritchard and D. Watson. Cyclic sulphites derived from the chloropropanediols. Journal of the Chemical Society (Resumed). 1956: 1813-1817.
^ Rahn, Anja K. K.; Yaylayan, Varoujan A. Characterization of electron ionization mass spectral (EIMS) fragmentation patterns of chloropropanol esters of palmitic acid using isotope labeling technique. Journal of Oleo Science. 2014, 63 (10): 1045-1055. ISSN 1345-8957. doi:10.5650/jos.ess14117.

延伸閱讀

Ananias Medina, Javier Ibáñez Abad, Pasi Tolvanen, Johan Wärnå, Kari Eränen, Tapio Salmi. Recent advances in glycerol hydrochlorination: Impact of reaction temperature, hydrogen chloride solubility and reaction intermediates. Chemical Engineering Science. 2022, 263: 118064. doi:10.1016/j.ces.2022.118064.
Hassanein, Salah Mohamed; Burmakov, A. I.; Bloshchina, F. A.; Yagupollskii, L. M. Reaction of hydroxy and carboxyl compounds with sulfur tetrafluoride. XX. Reactions of glycols with sulfur tetrafluoride. Zhurnal Organicheskoi Khimii. 1988, 24 (8): 1633-1638. ISSN 0514-7492. CODEN ZORKAE.

[Read-1] 1.0 ^1.1 ^1.2 ^1.3 Read, John; Hurst, Eric. Conversion of allyl alcohol to glyceryl chloro- and bromohydrins. Journal of the Chemical Society, Transactions. 1922, 121: 989-999. ISSN 0368-1645. doi:10.1039/ct9222100989.

[Ben-2] 2.0 ^2.1 Ben-Ishay, D. A Novel Rearrangement of Substituted Cyclic Sulfites. The Journal of Organic Chemistry. 1958, 23 (12): 2013-2014. doi:10.1021/jo01106a619.

[3] 2-Chloro-1,3-propanediol. SigmaAldrich. [2024-07-09].

[4] Thorsten Buhrke, Falko Frenzel, Jan Kuhlmann & Alfonso Lampen. 2-Chloro-1,3-propanediol (2-MCPD) and its fatty acid esters: cytotoxicity, metabolism, and transport by human intestinal Caco-2 cells. Toxicokinetics and Metabolism. 2015, 89: 2243-2251. doi:10.1007/s00204-014-1395-3.

[5] R. Tesser, E. Santacesaria, M. Di Serio, G. Di Nuzzi, and V. Fiandra. Kinetics of Glycerol Chlorination with Hydrochloric Acid: A New Route to α,γ-Dichlorohydrin. Industrial & Engineering Chemistry Research. 2007, 46 (20): 6456–6465. doi:10.1021/ie070708n.

[6] Nayl, AbdElAziz A. ; Arafa, Wael A. A.; Ahmed, Ismail M.; Abd-Elhamid, Ahmed I.; El-Fakharany, Esmail M.; Abdelgawad, Mohamed A.; Gomha, Sobhi M.; Ibrahim, Hamada M.; Aly, Ashraf A.; Brase, Stefan; Mourad, Asmaa K. Novel Pyridinium Based Ionic Liquid Promoter for Aqueous Knoevenagel Condensation: Green and Efficient Synthesis of New Derivatives with Their Anticancer Evaluation. Molecules. 2022, 27 (9): 2940. ISSN 1420-3049. doi:10.3390/molecules27092940.

[7] Cespi, D.; Cucciniello, R.; Ricciardi, M.; Capacchione, C.; Vassura, I.; Passarini, F.; Proto, A. A simplified early stage assessment of process intensification: glycidol as a value-added product from epichlorohydrin industry wastes. Green Chemistry. 2016, 18 (16): 4559-4570. ISSN 1463-9262.

[8] P. B. D. de la Mare; W. Klyne; D. J. Millen; J. G. Pritchard and D. Watson. Cyclic sulphites derived from the chloropropanediols. Journal of the Chemical Society (Resumed). 1956: 1813-1817.

[9] Rahn, Anja K. K.; Yaylayan, Varoujan A. Characterization of electron ionization mass spectral (EIMS) fragmentation patterns of chloropropanol esters of palmitic acid using isotope labeling technique. Journal of Oleo Science. 2014, 63 (10): 1045-1055. ISSN 1345-8957. doi:10.5650/jos.ess14117.

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