CN114634396A - Pentachloropropane and preparation method thereof - Google Patents
Pentachloropropane and preparation method thereof Download PDFInfo
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- CN114634396A CN114634396A CN202111638534.3A CN202111638534A CN114634396A CN 114634396 A CN114634396 A CN 114634396A CN 202111638534 A CN202111638534 A CN 202111638534A CN 114634396 A CN114634396 A CN 114634396A
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- Prior art keywords
- pentachloropropane
- preparation
- solid catalyst
- carbon
- active carbon
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- FTCVHAQNWWBTIV-UHFFFAOYSA-N 1,1,1,2,2-pentachloropropane Chemical compound CC(Cl)(Cl)C(Cl)(Cl)Cl FTCVHAQNWWBTIV-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000011949 solid catalyst Substances 0.000 claims abstract description 21
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000001412 amines Chemical class 0.000 claims abstract description 9
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims abstract description 8
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical group [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims abstract description 8
- 229940045803 cuprous chloride Drugs 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 17
- 238000003756 stirring Methods 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 3
- 239000004570 mortar (masonry) Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical group CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 235000013162 Cocos nucifera Nutrition 0.000 claims 1
- 244000060011 Cocos nucifera Species 0.000 claims 1
- 239000003245 coal Substances 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 13
- 230000009286 beneficial effect Effects 0.000 abstract description 5
- 238000004064 recycling Methods 0.000 abstract description 5
- 238000010924 continuous production Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 description 11
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 description 4
- 238000005187 foaming Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VVWFZKBKXPXGBH-UHFFFAOYSA-N 1,1,1,3,3-pentachloropropane Chemical compound ClC(Cl)CC(Cl)(Cl)Cl VVWFZKBKXPXGBH-UHFFFAOYSA-N 0.000 description 2
- FRCHKSNAZZFGCA-UHFFFAOYSA-N 1,1-dichloro-1-fluoroethane Chemical compound CC(F)(Cl)Cl FRCHKSNAZZFGCA-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to pentachloropropane and a preparation method thereof, belonging to the technical field of organic synthesis. The preparation method of pentachloropropane takes carbon tetrachloride and chloroethylene as raw materials, and adds solid catalyst and solvent to react to prepare the pentachloropropane; the active component of the solid catalyst is cuprous chloride, and the auxiliary active component is-NH2Organic amines of the group. The preparation method of pentachloropropane provided by the invention is convenient for recycling the catalyst, is energy-saving and environment-friendly, is beneficial to realizing continuous production, and improves the productivity.
Description
Technical Field
The invention relates to pentachloropropane and a preparation method thereof, belonging to the technical field of organic synthesis.
Background
1,1,1,3, 3-pentachloropropane, HCC-240fa for short, is an important chemical intermediate, can prepare HFC-245fa and HCFO-1233zd, and the two substances are important choices for replacing CFCs and HCFCs, and can be applied to the fields of cleaning, foaming, refrigeration and the like. The ODP of the HCFO-1233zd (E) is 0.00024, the GWP is 7.0, the environment-friendly performance is excellent, the toxicity is low, the HCFO-1233zd (E) foaming system is non-inflammable in normal state, the use is safe, the comprehensive performance of the hard foam synthesized by the HCFO-1233zd (E) foaming system is good, the heat insulation performance is excellent, and the requirements of the heat insulation industry can be met.
1,1,1,3, 3-pentachloropropane has similar physical and chemical properties to CFC-11 and HCFC-141b, has zero ODP, is the best substitute of CFC-11 and HCFC-141b, and has become a third generation foaming agent. In addition, HFC-245fa may also be used as refrigerants, cleaning agents, sprays, and heat transfer fluids. Therefore, the synthesis method thereof becomes a hot spot in the research of CFCs substitutes in recent years.
HCC-240fa is currently produced by telomerization of vinyl chloride and carbon tetrachloride, and widely used catalysts are iron-based catalysts as well as copper-based catalysts. Patent CN101913980 describes a preparation method of pentachloropropane, however, the telomerization metal salt catalyst is difficult to recover and has great loss in the post-treatment process because of small investment, and is really little recyclable, which will inevitably affect the improvement of production cost in the industrial production. In addition, the loss of heavy metal salts can cause serious environmental pollution problems.
Disclosure of Invention
The invention aims to provide pentachloropropane and a preparation method, which are convenient for recycling the catalyst, energy-saving and environment-friendly, are beneficial to realizing continuous production and improve the productivity.
The preparation method of pentachloropropane takes carbon tetrachloride and chloroethylene as raw materials, and adds solid catalyst and solvent to react to prepare the pentachloropropane;
preferably, the active component of the solid catalyst is cuprous chloride, and the auxiliary active component is a catalyst containing-NH2Organic amines of the group.
Preferably, the carrier of the solid catalyst is activated carbon; the particle size of the active carbon is 10-150 meshes.
Preferably, the organic amine is tert-butylamine, monoethanolamine, diethanolamine or triethanolamine.
Preferably, the mass ratio of the carrier, the active component and the auxiliary active component of the solid catalyst is 1: 0.025-0.2: 0.01-0.2.
Preferably, the preparation method of the solid catalyst comprises the following steps:
putting a certain amount of activated carbon into a mortar, grinding to the required particle size, adding into an organic solvent, stirring with a magnetic stirrer, and gradually adding a certain amount of dried cuprous chloride powder and organic amine cocatalyst during stirring. Stirring was continued for 1h, stirring was stopped and filtration was carried out.
Preferably, the mass ratio of the activated carbon carrier to the organic solvent is as follows: 1: 5-20.
Preferably, the organic solvent is acetonitrile, dimethylsulfoxide or tetrahydrofuran.
Preferably, the preparation method of pentachloropropane comprises the following steps:
dissolving chloroethylene in carbon tetrachloride, adding a solvent, and then carrying out reaction in a batch type reaction kettle or a continuous type reaction tube filled with a solid catalyst. After the reaction was completed, the solid catalyst was collected.
Preferably, the molar ratio of carbon tetrachloride to chloroethylene is 1: 1-10, the reaction pressure is 0.3-1.5MPa, the reaction temperature is 100-; the batch reaction time is 5-10h, and the residence time of the continuous reaction is 0.1-3 h.
Pentachloropropane prepared by the preparation method.
The invention prepares HCC-240fa by telomerizing carbon tetrachloride and chloroethylene through a solid catalyst. The method can facilitate the recycling of the catalyst, reduce the environmental pollution and the production cost, and can be applied to batch reaction and continuous reaction.
Compared with the prior art, the invention has the following beneficial effects:
(1) the invention adopts the solid supported catalyst, which is beneficial to the recycling of the catalyst;
(2) the catalyst is used for batch reaction, can realize the recycling of the catalyst, reduces pollution and cost, and is beneficial to realizing continuous production.
Detailed Description
The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. Any obvious modifications or alterations to the present invention, based on the teachings of the present invention, which are obvious to those skilled in the art, should also be considered as the scope of the present invention.
Example 1
A method for producing pentachloropropane, comprising the steps of:
(1) the preparation process of the solid catalyst is as follows:
putting a certain amount of activated carbon into a mortar, grinding to 100-150 meshes, adding the activated carbon into an acetonitrile organic solvent, stirring by using a magnetic stirrer, and gradually adding a certain amount of dried cuprous chloride powder and triethanolamine cocatalyst in the stirring process. Stirring was continued for 1h, stirring was stopped and filtration was carried out. Wherein the mass ratio of the activated carbon to the acetonitrile solvent is 1:10, and the mass ratio of the activated carbon to the acetonitrile solvent is as follows: cuprous chloride: the triethanolamine mass ratio is as follows: 1:0.05:0.05.
(2) Placing the prepared solid catalyst in a batch type reaction kettle, and introducing the mixed carbon tetrachloride, chloroethylene and acetonitrile. The telomerization is carried out at elevated temperature and pressure. After the reaction was completed, the solid catalyst was collected. Wherein the reaction pressure is 0.5MPa, the reaction temperature is 130 ℃, the mass ratio of carbon tetrachloride to the solid catalyst is 20:1, the mass ratio of carbon tetrachloride to chloroethylene is 10:1, the volume ratio of carbon tetrachloride to acetonitrile is 6:1, and the reaction time is 6 hours.
Example 2
A process for the production of pentachloropropane carried out as in example 1, except that:
the catalyst was placed in a fixed bed reactor with a residence time of 0.1 h.
Example 3
A process for the production of pentachloropropane carried out as in example 1, except that:
dimethyl sulfoxide is adopted as the organic solvent.
Example 4
A process for the production of pentachloropropane carried out as in example 1, except that:
diethanolamine is used as the organic amine.
Example 5
A process for the production of pentachloropropane carried out as in example 1, except that:
the reaction temperature was 120 ℃.
Example 6
A process for the production of pentachloropropane carried out as in example 1, except that:
the reaction time was 3 hours.
Example 7
A process for the production of pentachloropropane carried out as in example 1, except that:
activated carbon: cuprous chloride: the triethanolamine comprises the following components in percentage by mass: 1:0.08:0.08.
Example 8
A process for the production of pentachloropropane carried out as in example 1, except that:
the mass ratio of the activated carbon to the acetonitrile solvent is 1: 20.
Comparative example 1
A process for the production of pentachloropropane carried out as in example 1, except that:
no organic amine is added in the preparation process of the solid catalyst.
Table 1 results of the different embodiments of the reaction
The foregoing is merely an example of the present invention and common general knowledge of known specific structures and features of the embodiments is not described herein in any greater detail. It should be noted that, for those skilled in the art, without departing from the structure of the present invention, several changes and modifications can be made, which should also be regarded as the protection scope of the present invention, and these will not affect the effect of the implementation of the present invention and the practicability of the patent. The scope of the claims of the present application shall be determined by the contents of the claims, and the description of the embodiments and the like in the specification shall be used to explain the contents of the claims.
Claims (10)
1. A preparation method of pentachloropropane is characterized in that: adding a solid catalyst and a solvent into carbon tetrachloride and chloroethylene serving as raw materials to react to prepare the pentachloropropane;
the active component of the solid catalyst is cuprous chloride, and the auxiliary active component is-NH2Organic amines of the group.
2. The preparation method of pentachloropropane according to claim 1, characterized in that: the carrier of the solid catalyst is active carbon; the particle size of the active carbon is 10-150 meshes; the active carbon is coconut shell active carbon, wood active carbon, coal active carbon or shell active carbon.
3. The process for the preparation of pentachloropropane according to claim 1, characterized in that: the organic amine is tert-butylamine, monoethanolamine, diethanolamine or triethanolamine.
4. The process for the preparation of pentachloropropane according to claim 1, characterized in that: the mass ratio of the carrier, the active component and the auxiliary active component of the solid catalyst is 1: 0.025-0.2: 0.01-0.2.
5. The preparation method of pentachloropropane according to claim 1, characterized in that: the preparation method of the solid catalyst comprises the following steps:
putting the activated carbon into a mortar, grinding to the required particle size, adding the activated carbon into the organic solvent, stirring, gradually adding the dried cuprous chloride powder and the organic amine cocatalyst during stirring, continuing stirring, and filtering.
6. The method for preparing pentachloropropane according to claim 5, characterized in that: the mass ratio of the activated carbon carrier to the organic solvent is as follows: 1: 5-20.
7. The method for preparing pentachloropropane according to claim 5, characterized in that: the organic solvent is acetonitrile, dimethyl sulfoxide or tetrahydrofuran.
8. The preparation method of pentachloropropane according to claim 1, characterized in that: the method comprises the following steps:
dissolving chloroethylene in carbon tetrachloride, adding a solvent, and reacting in a batch reactor or a continuous reaction tube filled with a solid catalyst.
9. The method for preparing pentachloropropane according to claim 8, characterized in that: the molar ratio of carbon tetrachloride to chloroethylene is 1: 1-10, the reaction pressure is 0.3-1.5MPa, the reaction temperature is 100-; the batch reaction time is 5-10h, and the residence time of the continuous reaction is 0.1-3 h.
10. A pentachloropropane characterized by: prepared by the preparation method of claims 1-9.
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CN202111638534.3A CN114634396A (en) | 2021-12-29 | 2021-12-29 | Pentachloropropane and preparation method thereof |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116535287A (en) * | 2023-07-04 | 2023-08-04 | 山东澳帆新材料有限公司 | Synthesis method of 1, 3-pentachloropropane |
CN116986966A (en) * | 2023-09-21 | 2023-11-03 | 淄博澳帆化工有限公司 | Method for continuously preparing 1, 3-pentachloropropane |
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Cited By (4)
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CN116535287A (en) * | 2023-07-04 | 2023-08-04 | 山东澳帆新材料有限公司 | Synthesis method of 1, 3-pentachloropropane |
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CN116986966A (en) * | 2023-09-21 | 2023-11-03 | 淄博澳帆化工有限公司 | Method for continuously preparing 1, 3-pentachloropropane |
CN116986966B (en) * | 2023-09-21 | 2023-12-12 | 淄博澳帆化工有限公司 | Method for continuously preparing 1, 3-pentachloropropane |
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