CN110372473A - A kind of preparation method of the chloro- 4,4,4- trifluorobutane of 1,1,1,3,3- five - Google Patents

A kind of preparation method of the chloro- 4,4,4- trifluorobutane of 1,1,1,3,3- five Download PDF

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CN110372473A
CN110372473A CN201910682328.9A CN201910682328A CN110372473A CN 110372473 A CN110372473 A CN 110372473A CN 201910682328 A CN201910682328 A CN 201910682328A CN 110372473 A CN110372473 A CN 110372473A
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chloro
molar ratio
trifluoropropene
preparation
trifluorobutanes
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吕剑
赵波
曾纪珺
韩升
杨志强
唐晓博
郝志军
亢建平
李凤仙
张伟
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Xian Modern Chemistry Research Institute
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
    • B01J27/053—Sulfates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
    • B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/842—Iron

Abstract

The invention discloses one kind 1,1,1,3,3- five chloro- 4,4, the preparation method of 4- trifluorobutane, using 2- chloro-3,3,3 ,-trifluoropropene and carbon tetrachloride as raw material, in the presence of telomerization catalyst, catalyst aid and reducing agent, synthesis obtains 1,1,1,3,3- five chloro- 4,4,4- trifluorobutanes.The present invention provides the high-efficient synthetic route of a telomerisation, mainly for the preparation of 1,1,1,3,3- five chloro- 4,4,4- trifluorobutanes.

Description

A kind of preparation method of the chloro- 4,4,4- trifluorobutane of 1,1,1,3,3- five
Technical field
The present invention relates to a kind of preparation methods of hydrogen fluorochloroparaffins, more particularly to one kind 1,1,1,3,3- five chloro- 4,4,4- The preparation method of trifluorobutane.
Background technique
Since the first and second generation foaming agent (fluoro trichloromethane CFC-11, a fluorine dichloroethanes HCFC-141b etc.) destruction is smelly Oxygen layer has been prohibited from using, and third generation blowing agents (1,1,1,3,3- pentafluoropropane HFC-245fa etc.) can generate it is stronger Greenhouse effects.As global warming increasingly sharpens to earth ecology influence, there is an urgent need to find environmentally protective foaming agent.
1,1, Isosorbide-5-Nitrae, 4,4- hexafluoro -2- butylene (HFO-1336) are discharged into after atmosphere quickly because of the double bond contained in its molecule Just it can be degraded with OH free radical addition by oxidation, atmosphere is short (20 days) there are the service life, and greenhouse effect value (GWP ≈ 9) is low. Its boiling point and room temperature are close, and foaming, heat-proof quality are excellent, become optimum substituent.Therefore 1,1,1,4,4,4- hexafluoro -2- butylene Study of synthesis method show importance increasingly.And using the chloro- 3,3,3- trifluoro propene of 2- and carbon tetrachloride as Material synthesis HFO- The advantages of 1336 have step short, high income is one of best route.
The chloro- 3,3,3- trifluoro propene of 2- and carbon tetrachloride telomerisation are a passes of synthesizing new blowing agent H FO-1336 Key step, patent CN102884030B report the telomerization method of a kind of 2- chloro-3,3,3 ,-trifluoropropene and carbon tetrachloride, metal Dosage is 1.5wt%~2.5wt%, and metal consumption is larger, and the telomerization ratio of carbon tetrachloride and 2- chloro-3,3,3 ,-trifluoropropene is 50:50mol%, in fact, 2- chloro-3,3,3 ,-trifluoropropene can not be dissolved completely in carbon tetrachloride under this High Concentration Situation, Cause the chloro- 3,3,3- trifluoro propene loss of 2-, waste.
Summary of the invention
The technical problem to be solved by the present invention is in view of the deficiencies of the prior art, provide a kind of telomerisation 2- chloro- 3,3, The preparation of 3- trifluoro propene high conversion rate, the chloro- 4,4,4- trifluorobutane of 1,1,1,3,3- five that metal consumption is low, telomerization ratio is high Method.
Of the invention 1,1,1,3,3- five chloro- 4, the preparation method of 4,4- trifluorobutanes, using 2- chloro- 3,3,3- trifluoropropyls Alkene and carbon tetrachloride are raw material, and in the presence of telomerization catalyst, catalyst aid and reducing agent, synthesis obtains 1,1,1,3,3- five Chloro- 4,4,4- trifluorobutane.Reaction equation is as follows:
Of the invention 1,1,1,3,3- five chloro- 4, the preparation method of 4,4- trifluorobutanes, with 2- chloro-3,3,3 ,-trifluoropropene It is raw material with carbon tetrachloride, in the presence of telomerization catalyst, catalyst aid and reducing agent, it is chloro- that synthesis obtains 1,1,1,3,3- five 4,4,4- trifluorobutanes, wherein telomerization catalyst is the molysite of divalent or trivalent, and catalyst aid is organic amine, organic phosphorus or phosphorus Esters of gallic acid ligand, reducing agent are metal or organic reducing agent；Reaction condition are as follows: carbon tetrachloride and the chloro- 3,3,3- trifluoro propene of 2- Molar ratio is 1~10:1, and telomerization catalyst and the molar ratio of 2- chloro-3,3,3 ,-trifluoropropene are 0.001~0.1:1, and catalysis helps The molar ratio of agent and 2- chloro-3,3,3 ,-trifluoropropene is 0.001~0.1:1, and reducing agent rubs with 2- chloro-3,3,3 ,-trifluoropropene You than be 0.001~0.1:1, reaction temperature be 50~180 DEG C, the reaction time be 1~for 24 hours.
The telomerization catalyst is the molysite of divalent or trivalent, including iron chloride, ferric bromide, frerrous chloride, sulfuric acid Iron or ferric acetyl acetonade, preferably iron chloride or frerrous chloride.
The catalyst aid is organic amine, organic phosphorus or phosphoric acid ester ligand, including 2,2- bipyridyl, three (2- pyridines Ylmethyl) amine, three (2- dimethylaminoethyl) amine, triphenyl phosphorus, tributyl phosphate or tributyl phosphites, preferably three (2- pyrroles Piperidinyl methyl) amine or tributyl phosphate.
The reducing agent is metal or organic reducing agent, including iron powder, azodiisobutyronitrile or ascorbic acid are excellent Select iron powder or azodiisobutyronitrile.
Preferred reaction condition is carbon tetrachloride and 2- chloro-3,3,3 ,-trifluoropropene molar ratio is 2~5:1, telomerization catalysis 0.005~0.1:1 of molar ratio of agent and 2- chloro-3,3,3 ,-trifluoropropene, catalyst aid rub with 2- chloro-3,3,3 ,-trifluoropropene , than being 0.01~0.2:1, the molar ratio of reducing agent and 2- chloro-3,3,3 ,-trifluoropropene is 0.03~0.3:1, reaction temperature 80 for you ~150 DEG C, 2~10h of reaction time.
The present invention has the advantages that
(1) boiling point of 2- chloro-3,3,3 ,-trifluoropropene be 15 DEG C, carry out telomerisation when, conversion ratio need to be higher than 95% with Upper just to have industrial application value, otherwise, raw material is difficult to recycle, and will increase production, separation costs, in optimum condition of the present invention Under, 2- chloro-3,3,3 ,-trifluoropropene can reach close to 100% conversion, therefore, present invention prospects for commercial application with higher； (2) commercial synthesis catalyst, metal consumption should be as low as possible, and the telomerization catalyst system that the present invention uses, metal consumption is most It is no more than 0.4wt%~1.3wt% greatly, compares traditional system metal consumption (CN102884030B) 1.5wt~2.5wt%, urge Change efficiency to significantly improve；(3) the telomerization ratio of carbon tetrachloride and the chloro- 3,3,3- trifluoro propene of 2- is also commercial synthesis 1,1,1,3, 3- five chloro- 4, one of the key parameter of 4,4- trifluorobutanes, if telomerization ratio is too small, it will cause energy consumption of reaction increase, four chlorinations Carbon flow is lost, and under optimum condition of the present invention, the telomerization ratio of carbon tetrachloride and 2- chloro-3,3,3 ,-trifluoropropene is up to 2:1.
Specific embodiment
Below by specific embodiment, invention is further described in detail, but not does in any form to the present invention Limitation.
Embodiment 1:
2.14 grams of iron chloride, 13.16 grams of tributyl phosphates and 50 are added into 1.5L stainless steel band stirring autoclave The solution of gram carbon tetrachloride, solid feed inlet are added 4.39 grams of iron powders and 450 grams of carbon tetrachloride, are passed through 2- chloro- 3,3,3- tri- in advance After 26 grams of fluoropropene, 115 DEG C of reaction temperature are warming up to, gas phase is continuously passed through 2- chloro-3,3,3 ,-trifluoropropene, to 2- chloro- 3,3, 3- trifluoro propene intake stops being passed through after reaching 100 grams, continues to be stirred to react to pressure 0.3MPa, cooling stops reaction, takes Sample carries out GC analysis, after vacuum distillation, obtains product.
Product is detected through nuclear-magnetism, and data are as follows:
1H NMR(500MHz,CDCl3)δ3.72(s,2H)；
13C NMR(500MHz,CDCl3) δ 121.8 (q, J=281.3Hz), 92.6,79.7 (q, J=34.8Hz), 59.1；
19F NMR(470MHz,CDCl3)δ-80.2(s,CF3).
Above-mentioned data prove that it is exactly the chloro- 4,4,4- trifluorobutane of 1,1,1,3,3- five that product, which is made,.
Embodiment 2~6
Embodiment 2~6 prepares the chloro- 4,4,4- trifluoro fourth of 1,1,1,3,3- five according to preparation method identical in embodiment 1 Alkane, except that the reaction carbon tetrachloride in embodiment 1: 2- chloro-3,3,3 ,-trifluoropropene ratio is 2.5:1, and embodiment 2 Telomerization ratio is respectively 1:1,2:1,5:1,7:1,10:1 in~6.The reaction result of embodiment 2~6 is as shown in table 1.
The screening of 1 telomerization ratio of table
Embodiment Molar ratio Conversion ratio (%) Selectivity (%)
2 1:1 90.5 84.1
3 2:1 93.3 96.1
4 5:1 94.5 95.0
5 7:1 95.6 94.3
6 10:1 96.8 96.2
Embodiment 7~10:
Embodiment 7~10 prepares the chloro- 4,4,4- trifluoro fourth of 1,1,1,3,3- five according to preparation method identical in embodiment 1 Alkane except that the catalysts in embodiment 1 are iron chloride, and is respectively ferric bromide, protochloride in embodiment 7~10 Iron, ferric sulfate or ferric acetyl acetonade.The reaction result of embodiment 7~10 is as shown in table 2.
2 catalyst screening of table
Embodiment 11~15:
Embodiment 11~15 prepares the chloro- 4,4,4- trifluoro of 1,1,1,3,3- five according to preparation method identical in embodiment 1 Butane except that the catalysts in embodiment 1 are tributyl phosphate, and is respectively 2,2- connection in embodiment 11~15 Pyridine, three (2- pyridylmethyl) amine, three (2- dimethylaminoethyl) amine, triphenyl phosphorus or tributyl phosphites.Embodiment 11 ~15 reaction result is as shown in table 3.
Influence of 3 ligand of table to reaction
Embodiment 16~17:
Embodiment 16~17 prepares the chloro- 4,4,4- trifluoro of 1,1,1,3,3- five according to preparation method identical in embodiment 1 Butane except that the reducing agent in embodiment 1 is iron powder, and is respectively azodiisobutyronitrile or anti-in embodiment 16~17 Bad hematic acid.The reaction result of embodiment 16~17 is as shown in table 4.
Influence of 4 reducing agent of table to reaction
Embodiment Reducing agent Conversion ratio (%) Selectivity (%)
16 Azodiisobutyronitrile 93.2 94.6
17 Ascorbic acid 83.7 88.2
Embodiment 18~22:
Embodiment 18~22 prepares the chloro- 4,4,4- trifluoro of 1,1,1,3,3- five according to preparation method identical in embodiment 1 Butane except that the reaction temperature in embodiment 1 is 115 DEG C, and is respectively 50 DEG C, 80 DEG C, 100 in embodiment 18~22 ℃,150℃,180℃.The reaction result of embodiment 18~22 is as shown in table 5.
5 reaction temperatures affect of table
Embodiment 23~27:
Embodiment 23~27 prepares the chloro- 4,4,4- trifluoro of 1,1,1,3,3- five according to preparation method identical in embodiment 1 Butane, except that reaction time in embodiment 1 is 5h, and be respectively in embodiment 23~27 5h, 8h, 10h, 16h, 24h.The reaction result of embodiment 23~27 is as shown in table 6.
6 reaction time of table influences reaction
Embodiment Reaction time (h) Conversion ratio (%) Selectivity (%)
23 5 92.7 94.1
24 8 95.0 93.2
25 10 96.0 91.5
26 16 97.2 92.4
27 24 94.1 88.7

Claims (5)

1. one kind 1,1,1,3,3- five chloro- 4, the preparation method of 4,4- trifluorobutanes, it is characterised in that with 2- chloro- 3,3,3- trifluoros Propylene and carbon tetrachloride are raw material, and in the presence of telomerization catalyst, catalyst aid and reducing agent, synthesis obtains 1,1,1,3,3- five Chloro- 4,4,4- trifluorobutanes, wherein telomerization catalyst is the molysite of divalent or trivalent, catalyst aid is organic amine, it is organic phosphorus or Phosphoric acid ester ligand, reducing agent are metal or organic reducing agent；Reaction condition are as follows: carbon tetrachloride and the chloro- 3,3,3- trifluoropropyl of 2- Alkene molar ratio is 1~10:1, and the molar ratio of telomerization catalyst and 2- chloro-3,3,3 ,-trifluoropropene is 0.001~0.1:1, catalysis The molar ratio of auxiliary agent and 2- chloro-3,3,3 ,-trifluoropropene is 0.001~0.1:1, reducing agent and 2- chloro-3,3,3 ,-trifluoropropene Molar ratio be 0.001~0.1:1, reaction temperature be 50~180 DEG C, the reaction time be 1~for 24 hours.
2. according to claim 11,1,1,3,3- five chloro- 4, the preparation method of 4,4- trifluorobutanes, it is characterised in that institute Stating telomerization catalyst is iron chloride, ferric bromide, frerrous chloride, ferric sulfate or ferric acetyl acetonade.
3. according to claim 11,1,1,3,3- five chloro- 4, the preparation method of 4,4- trifluorobutanes, it is characterised in that urge Change auxiliary agent is 2,2- bipyridyl, three (2- pyridylmethyl) amine, three (2- dimethylaminoethyl) amine, triphenyl phosphorus, tricresyl phosphate fourth Ester or tributyl phosphite.
4. according to claim 11,1,1,3,3- five chloro- 4, the preparation method of 4,4- trifluorobutanes, it is characterised in that also Former agent is iron powder, azodiisobutyronitrile or ascorbic acid.
5. according to claim 11,1,1,3,3- five chloro- 4, the preparation method of 4,4- trifluorobutanes, it is characterised in that anti- Answer that condition is carbon tetrachloride and 2- chloro-3,3,3 ,-trifluoropropene molar ratio is 2~5:1, telomerization catalyst and 2- chloro- 3,3,3- tri- The molar ratio of 0.005~0.1:1 of molar ratio of fluoropropene, catalyst aid and 2- chloro-3,3,3 ,-trifluoropropene is 0.01~0.2: 1, the molar ratio of reducing agent and 2- chloro-3,3,3 ,-trifluoropropene is 0.03~0.3:1,80~150 DEG C of reaction temperature, the reaction time 5~10h.
CN201910682328.9A 2019-07-26 2019-07-26 A kind of preparation method of the chloro- 4,4,4- trifluorobutane of 1,1,1,3,3- five Pending CN110372473A (en)

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Publication number Priority date Publication date Assignee Title
WO2021178507A1 (en) * 2020-03-04 2021-09-10 The Chemours Company Fc, Llc Process to produce (z)-1,1,1,4,4,4-hexafluoro-2-butene and intermediates

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CN105418360A (en) * 2015-11-11 2016-03-23 西安近代化学研究所 Method for preparing 1,1,1,3,3-pentachlorobutane
CN109678650A (en) * 2018-12-25 2019-04-26 西安近代化学研究所 A kind of preparation method of the chloro- 4,4,4- trifluorobutane of 1,1,1,3- tetra-

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CN101016223A (en) * 2007-02-25 2007-08-15 常熟三爱富中昊化工新材料有限公司 Preparing method of pentafluorodichloropropane
US20130211156A1 (en) * 2012-02-14 2013-08-15 Honeywell International Inc. Process for 1,3,3,3-tetrafluoropropene
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CN105418360A (en) * 2015-11-11 2016-03-23 西安近代化学研究所 Method for preparing 1,1,1,3,3-pentachlorobutane
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021178507A1 (en) * 2020-03-04 2021-09-10 The Chemours Company Fc, Llc Process to produce (z)-1,1,1,4,4,4-hexafluoro-2-butene and intermediates
CN115210202A (en) * 2020-03-04 2022-10-18 科慕埃弗西有限公司 Process for preparing (Z) -1,1,1,4,4,4-hexafluoro-2-butene and intermediates

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