COMPOSTO DE AMIDA

Abstract

The amide compound has a structure represented by formula (1). [In formula (1): C, C 1, and C2 are carbon atoms; N is a nitrogen atom; R1 and R2 are each a hydrocarbon group; R11 and R12 are each a hydrogen atom or a hydrocarbon group, at least one being a hydrocarbon group; R3 to R6 are each a hydrogen atom or a hydrocarbon group; R is a hydrogen atom; and m is an integer of 1-5.]

Description

1 / 29 AMIDE COMPOUND Technical Field

[0001] The present invention relates to a new amide compound. State of the Art

[0002] Amide compounds are known to be used not only in pharmaceutical intermediate applications, such as solvents, medicines and pesticides, but also, for example, in nylon raw materials. Amide compounds have also been reported to be used as titanium catalysts supported by Mg compounds, which are used in the polymerization of olefins.

[0003] A catalyst for olefin polymerization is one of the techniques widely developed to date, triggered by the discovery of the so-called Ziegler-Natta catalysts. Ziegler reported in 1953 that ethylene was polymerized even at low pressures using a combination of titanium tetrachloride and an organoaluminum compound, and Natta subsequently reported the first polymerization of propylene using a combination of titanium trichloride and a halogen-containing organoaluminum compound. Meanwhile, catalysts containing titanium tetrachloride, a magnesium compound, and a Lewis base, referred to as third-generation catalysts, were found to achieve high polymerization activity (high productivity) and high stereoregularity in propylene polymerization. This provided an opportunity to allow propylene polymers (polypropylene) to spread worldwide.

[0004] It has been discovered that a Lewis base (hereinafter also referred to as an internal donor), one of the main components of the above third-generation catalyst component (hereinafter also referred to as a solid titanium catalyst component), significantly affects the performance of Petition 870250084527, dated 09 / 19 / 2025, page 13 / 43 2 / 29 catalyst, and several Lewis bases have been developed to date.

[0005] As Lewis bases for use in ZieglerNatta catalysts, ethyl benzoate, phthalic esters, 1,3-diketone (Patent Literature 1), malonic ester (Patent Literature 2), succinic ester (Patent Literature 3), 2,4-pentanediol diester (Patent Literature 4), naphthalenediol diester (Patent Literature 5), and catechol diester (Patent Literature 6) have been reported. Even today, many companies are conducting intensive research and development in this field. It has also been reported that a diamide compound with a specific structure is suitable (Patent Literature 7, Patent Literature 8). List of citations Patent Literature

[0006] Patent Literature 1: JP2005-226076A Patent Literature 2: JP2000-516987A Patent Literature 3: JP2002-542347A Patent Literature 4: JP2005-517746A Patent Literature 5: JP2011-529888A Patent Literature 6: JP2014-500390A Patent Literature 7: Chinese Patent Publication No. 108570120 Patent Literature 8: Chinese Patent Publication No. 108570119. Summary of the invention Technical problem

[0007] Propylene polymers, although possessing heat resistance and rigidity similar to those of general-purpose engineering plastics, have the advantage of generating a smaller amount of toxic gas, even when subjected to combustion, because they are substantially composed only of carbon and hydrogen.

[0008] With recent advances in molding techniques, the Petition 870250084527, dated 09 / 19 / 2025, page 14 / 43 3 / 29 The use of a propylene polymer with greater stereoregularity than before has the potential to develop superior physical properties (such as stiffness and heat resistance). For this reason, the market has demanded propylene polymers with greater stereoregularity. From the point of view of resource economy and environmental protection, methods for producing a propylene polymer with high productivity have also been required. [ 0009]Therefore, an objective of the present invention is to provide a suitable internal donor compound for a solid titanium catalyst component capable of producing a propylene polymer with extremely high stereoregularity (which can be expected to exhibit a high melting point or high heat of fusion) with high productivity (high activity), when used primarily for the solid titanium catalyst component. Solution to the Problem

[0010] As a result of a diligent study to solve the above problems, the present inventors discovered that an amide compound with a specific structure is suitable as, for example, a Lewis base for a solid titanium catalyst component, and concluded the present invention. Examples of the present invention are shown below.

[0011] {1} An amide compound with a structure of the following formula (1): [Chemical Formula 1] (1) Petition 870250084527, dated 09 / 19 / 2025, page 15 / 43 4 / 29 in which C, C1 and C2 are carbon atoms. N is a nitrogen atom, R1 and R2 are each a hydrocarbon group. R11 and R12 are each either a hydrogen atom or a hydrocarbon group, and at least one of their groups is a hydrocarbon group. R3a and R6 are each a hydrogen atom or a hydrocarbon group. R is a hydrogen atom, and in is an integer from 1 to 5.

[0012] {2} The amide compound, according to {1}, wherein both R11 and R12 are hydrocarbon groups.

[0013] {3} The amide compound, according to {1} or {2}, where R1, R2, R4 and R5 are hydrocarbon groups composed of carbon and hydrogen. Advantageous Effects of the Invention

[0014] The amide compound of the present invention can be used as, for example, not only a raw material for a solvent, a pharmaceutical intermediate or nylon, but also a chelating agent or a raw material for a Ziegler-Natta catalyst. Description of the Modalities

[0015] Next, an amide compound according to the present invention will be described in detail. [Amide compound]

[0016] The amide compound according to the present invention (hereinafter also referred to as the amide compound (A)) is represented by the following general formula (1): [Chemical Formula 2] RR Petition 870250084527, dated 09 / 19 / 2025, p. 16 / 43 5 / 29

[0017] In formula (1), C, C1 and C2 are carbon atoms and N is a nitrogen atom. A line like - indicates a covalent bond. [00181R1e R2são, each one, is a hydrocarbon group. More specifically, R1e R2são, each one, is a substituted or unsubstituted hydrocarbon group with 1 to 20 carbon atoms. Examples of the hydrocarbon group may include not only aliphatic hydrocarbon groups and alicyclic hydrocarbon groups, but also substituted or unsubstituted hydrocarbon groups with an aryl group and 6 to 20 carbon atoms. Such a substituent may be a structure containing a heteroatom, as described below. Examples of the aryl group containing a heteroatom may include those with a basic skeleton with a structure in which the aryl structure itself contains a heteroatom, such as a pyrrole ring or a pyran ring, and those in which a substituent, such as a hydrocarbon group containing a heteroatom, for example, an alkoxy group, is attached to a benzene ring.] [00191R11e R12 are hydrogen atoms or hydrocarbon groups and at least one of them is a hydrocarbon group. Specific examples of hydrocarbon groups may include the same substituents as the substituents exemplified as R1e R2. R11e R12 are both preferably hydrocarbon groups.]

[0020] H in an amide compound with an NH-type structure, as described above, is termed active hydrogen and is expected to be highly reactive with, for example, titanium in a solid titanium catalyst component for olefin polymerization, and is therefore considered to have a high probability of being unsuitable as an electron donor component. However, the amide compound of the present invention exhibits the unexpected property of being suitable as an electron donor component in some cases. Petition 870250084527, dated 09 / 19 / 2025, page 17 / 43 6 / 29

[0021] R1e R2em R1a R12 are preferably substituted or unsubstituted hydrocarbon groups with an aryl group and 6 to 20 carbon atoms.

[0022] A representative example of a heteroatom-containing structure is a structure with a heteroatom-containing substituent, a preferred example of such a substituent is a heteroatom-containing aryl group and a particularly preferred example is an oxygen-containing aryl group.

[0023] R1 and R2 are preferably structures in which a carbon contained within them is covalently bonded to the adjacent carbonyl carbon.

[0024] R3, R4, R5 and R6 are each a hydrogen atom or a hydrocarbon group. The hydrocarbon group is a group that includes the aspect of having a heteroatom, as described above. The heteroatom is preferably a group containing an element selected from the elements of Groups 15, 16 and 17 of the periodic table. More specific examples of R3, R4, R5 and R6 may include groups selected from a hydrogen atom, substituted or unsubstituted hydrocarbon groups with 1 to 20 carbon atoms or halogen atoms.

[0025] The hydrocarbon group will be described in more detail. The hydrocarbon group of the present invention is a substituent that essentially contains a carbon atom and a hydrogen atom and can be partially substituted with an atom selected from the group consisting of elements from Groups 15 to 17 of the periodic table, such as a nitrogen atom, an oxygen atom, a phosphorus atom, and a halogen atom. The heteroatom can be substituted in one or multiple positions.

[0026] In the present invention, the term atom, as in, for example, a halogen atom or a hydrogen atom in the description of a substituent, may naturally refer to aspects with a bond such as H- or Cl- when expressed in a structural formula. Petition 870250084527, dated 09 / 19 / 2025, page 18 / 43 7 / 29

[0027] R is a hydrogen atom. In the present invention, a structure is included in which the Rs bonded to the carbon adjacent to -(CR2)m- in formula (1) are linked together to form a double bond.

[0028] The -(CR2)m- structure is preferably a methylene chain structure.

[0029] R1, R2, R3, R4, R5, R6, R11 and R12 can be linked together to form a ring structure. Preferred aspects of this will be described.

[0030] R1 and R2 can be linked together to form a ring structure. Substituents selected from R1, R3, R4 and R11 can be linked together to form a ring structure. Substituents selected from R2, R5, R6 and R12 can be linked together to form a ring structure.

[0031] A substituent selected from among the substituents of R3 and R4 and a substituent selected from among the substituents of R5 and R6 can also be linked to each other to form a ring structure.

[0032] A ring structure formed by selected substituents from R3 to R6, linked together, is preferably an alicyclic structure, such as a ring of five or more members, and more preferably a ring of six or more members, when the mobility at the periphery of carbon C1 or carbon C2 in formula (1), as described below, is taken into account. Incidentally, the upper limit of the number of members in the ring structure is arbitrary, but a ten-membered ring is preferred, and an eight-membered ring is more preferred.

[0033] In the case where R3 and R4 or R5 and R6 form a ring structure, aspects in which a carbon-carbon double bond is formed are also included (in this case, the carbon-carbon double bond is considered a two-membered ring). On the other hand, in the case where R3 and R6 are linked together to form a ring structure, this ring structure is preferably Petition 870250084527, dated 09 / 19 / 2025, page 19 / 43 8 / 29 an alicyclic structure. The reason why such a structure is suitable for the present invention will be described below.

[0034] R3a R6 are preferably relatively small volume substituents. In a solid titanium catalyst component containing an organic compound (which is generally called an internal donor in some cases), there is a tendency for many instances where a large volume compound is suitable. The reason for the tendency for such a low volume substituent to be suitable, as exhibited in the present invention, is not clear at present, but it is considered to be because, probably as described below, the amide compound of the present invention tends to easily and stably obtain a relatively suitable conformation as, for example, a component of an olefin polymerization catalyst and, conversely, perturbations in the coordination of an olefin with titanium in the solid titanium catalyst component are less likely to occur when R3a R6, which are substituents present on an opposite side to an amide group, are small volume structures.R3 and R6 are, more preferably, hydrogen atoms. [00351R11e R12 are hydrocarbon groups, and an aspect in which these substituents are linked together to form a ring structure is preferable in some cases. Although the structure of the -(CR2)m- portion in formula (1) exhibits a relatively flexible structure, it is considered that such a structure suppresses the rotation of the amide group, has the effect of facilitating the attainment of a conformation in which a relatively large movement occurs, for example, a relatively large twist, and therefore has an appropriate interaction with the titanium in the solid titanium catalyst component and probably readily forms a highly stereoregular active point. [00361M in the amide compound of the present invention is an integer from 1 to 5. A preferred lower limit value is 2, although Petition 870250084527, dated 09 / 19 / 2025, p. 20 / 43 9 / 29 also depends on the structure of A. On the other hand, a preferable upper limit value is 4. Within this range, the distance between at least two amide groups is in an appropriate range, and adequate olefin polymerization performance can be expected.

[0037] The hydrocarbon groups contained in R1a R12 are monovalent hydrocarbon groups with 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 2 to 8 carbon atoms, even more preferably 3 to 8 carbon atoms, even more preferably 4 to 8 carbon atoms and particularly preferably 4 to 6 carbon atoms. Examples of such hydrocarbon groups include aliphatic hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a hexyl group, a heptyl group, an octyl group, a 2-ethylhexyl group, a decyl group, a dodecyl group, a tetradecyl group, a hexadecyl group, an octadecyl group, an eicosyl group, a cyclohexyl group, a substituted or unsubstituted aryl group, such as a phenyl group, and a substituted or unsubstituted cycloalkenyl group.Alicyclic hydrocarbon groups and aromatic hydrocarbon groups may contain a substituent. Among such substituents, preferable are, for example, an n-butyl group, an isobutyl group, a hexyl group, an octyl group, and a phenyl group, and more preferable are an n-butyl group, an isobutyl group, and a phenyl group.

[0038] In the case of hydrocarbon groups containing elements from Groups 15 to 17 of the periodic table, such as nitrogen, oxygen and halogens, specifically suitable examples may include a group containing a carbonyl structure, such as a carboxylic acid ester group, an aldehyde group, an acetyl group or an oxycarbonylalkyl group, an alkoxy group, a substituted alkoxy group. Petition 870250084527, dated 09 / 19 / 2025, page 21 / 43 10 / 29 or unsubstituted, a substituted or unsubstituted alkenyloxy group, a substituted or unsubstituted cycloalkyloxy group, a substituted or unsubstituted cycloalkenyloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryloxy group, and a siloxy group. The heteroatom is preferably nitrogen and oxygen, and more preferably oxygen.

[0039] The heteroatom-containing substituent is preferably an aryl group containing an oxygen-containing substituent, and a preferred example is specifically a structure in which an oxygen-containing substituent, such as an alkoxy group, an aryloxy group, an alkoxyalkyl group, an aryloxyalkyl group, and a substituent in which the oxygen of the above substituent is replaced by a carbonyl group or a carboxyl group, is attached to an aromatic skeleton. Among such substituents, a substituent in which an alkoxy group or an aryloxy group is attached to an aromatic skeleton is preferred, and a substituent in which an alkoxy group is attached to an aromatic skeleton is more preferred. The number of carbon atoms in the oxygen-containing substituent is preferably from 1 to 10, more preferably from 1 to 8, and even more preferably from 1 to 6.More specifically, examples in addition to the methoxyphenyl group preferably include an ethoxyphenyl group, a propyloxyphenyl group, an isopropyloxyphenyl group, a butoxyphenyl group, and a phenoxyphenyl group.

[0040] In the present invention, R1, R2, R3, R4 and R5 are preferably hydrocarbon groups and, more preferably, hydrocarbon groups composed of carbon and hydrogen. In the present invention, the hydrocarbon group composed of carbon and hydrogen refers to a hydrocarbon group that substantially does not contain heteroatoms and consists of carbon and hydrogen. In such a hydrocarbon group, Petition 870250084527, dated 09 / 19 / 2025, page 22 / 43 11 / 29 R1 and R2 are preferably substituents selected from alkyl groups and aromatic hydrocarbon groups. Meanwhile, R4 and R5 are preferably aliphatic hydrocarbon groups and, more preferably, alkyl groups.

[0041] Furthermore, R1, R2, R3, R4, R5, R6, R11 and R12 are preferably independent groups (substituents) that are not linked to each other in some cases.

[0042] In the case where one of R11 and R12 is a hydrogen atom, the other substituent is preferably a hydrocarbon group including an aromatic structure. More specific examples may include aliphatic hydrocarbon groups, substituents with a structure in which a hydrogen atom in an alicyclic hydrocarbon group is replaced by an aryl group, or aromatic hydrocarbon groups. Examples of such substituents may include substituents with a structure in which some of the aliphatic hydrocarbon groups, such as benzyl groups, 2-phenylethyl groups, 3-phenylpropyl groups, 2-phenylpropyl groups, or 4-phenylbutyl groups, have been replaced with an aryl group, such as a phenyl group. Examples may include hydrocarbon groups with an aromatic structure and an alicyclic structure, such as a (phenylcyclohexyl)methyl group, a 2-(phenylcyclohexyl)ethyl group, and a 3-(phenylcyclohexyl)propyl group.Examples of aromatic hydrocarbon groups may include a phenyl group, a naphthalyl group, an indenyl group, a fluorenyl group, and substituents with a structure obtained by adding hydrogen to the aromatic fraction of a part of the structure.

[0043] Examples of such an amide compound include the following structures. Some structural formulas of the following exemplary compounds have stereoisomers, and even isomeric structures are clearly represented for some exemplary compounds, but there may be isomeric structures that are not exemplified. [Chemical Formula 3] Petition 870250084527, dated 09 / 19 / 2025, p. 23 / 43 12 / 29 Α-4 'Pr^NN 'Pr Π Me Me Π Ο Ο Bu Me Me 'Bu N N. ?Bu A-6 Cy^ / NN Cy Π Me Me Π OO A-8 Me NN\ / PhYΥμθ MeY oo A-10 Ph^NN^,Ph YnBunBuY oo A-14 Ph. ,N N. ,Ph Yèn B'nY O o A-15 A-16 Ph^ / N N Ph P Me Me P O O A-18nBux^^!Bu Ph. . N N Ph P Me Me P The The A-19 A-21 A-22 Ph^-\^Me Ph NN\ / PhY Me Me Y The The A-23 Me Me Me \|^\| / Me Phv / NN,,Ph Y Me Me Y O.O A-24 Me Me \| / \^-Me Ph / ,Ν N^ / Ph Y Me Me Y O.O A-25 A-30 A-31 A-32 A-33 Petition 870250084527, de 19 / 09 / 2025, pág. 24 / 43 13 / 29 [Chemical Formula 4] Et A-39 A-40 A-41 'Bu A-43 'Bu OMe A-52 A-53 Petition 870250084527, dated 09 / 19 / 2025, page 25 / 43 14 / 29 [Chemical Formula 5] A-54 A-55 A-56 A-57 'Bu A-58 A-59 Me Me Me A-67 A-68 A-69 A-74 Petition 870250084527, dated 09 / 19 / 2025, page 26 / 43 15 / 29 [Chemical Formula 6] Me Me O B-1 Me Me Me Me O And B-2 Me Me O B-3 Me Me Me Me O B-4 Me Me 0 B-6 Me Me O B-8 B-10 B-12 O Me Bη B-13 Me Me Me Me Me O Me Me Me Me Me Me o pH [Chemical Formula 7] B14 B-15 Petition 870250084527, dated 09 / 19 / 2025, page 27 / 43 16 / 29 Me. .N. .N. Me Y Me Me Me Me Et. N N. Et OO C-1 Me. / x. .Me 'Ρι-χ^ ,NN / Pr Me Me 0 O C-4 x^N.Λ Y Me Me Y C-2 O C-6Bu^-N·,. ., -N 'Bu Y Me Me O O C-5 ., -N^cy >< Me Me γ O O C-8 . .N. ^N. .Ph Y Me Me Y O O C-9 . .N. ^N. .Ph ¥Et Et¥ O 0 C-10 O C-7 Ph._ΝχΝύΡΙί ΠnPr Pr 11 O 0 C-11 O 0 C-12 . .N.XN Ph Me Me Y Ph. .N. .N Ph Me Me . .N.XN Ph Me Me C-13 O O C-14 O O C-15 O O C-16 Ph. .N. ,_N .Ph Me Me O O C-17 Ph. _N. ,.N. Ph y Me Me O 0 Ph. .N. .. N Ph yy Me Me OO Ph. .N. ^N. .Ph Me Me OO C-20 .. ^N. Ph Y Me Me C-18 Ph-^N„„ M -N^Ph>< Me Me >< C-19 PhX / N'r„ m -N^ / Ph>< Me Me OO C-21 OO C-22 OO C-23 Petition 870250084527, dated 09 / 19 / 2025, page 28 / 43 17 / 29 [Chemical Formula 8] D-1 D-2 Me Me Me Me O D-6 Me Me Me Me O D-7 Me Me O D-8 D-10 D-12 D-13 D-14 D-15 Me Cy O D-16 D-17 Me Me D-18 Me Me D-19 D-20 D-21 D-22 Me Bn pH D-23 Petition 870250084527, dated 09 / 19 / 2025, p. 29 / 43 18 / 29 [Chemical Formula 9] H-27 H-28

[0044] In addition to the compounds shown above, compounds that have an NH-type amide structure to be revealed in the Examples below can also be exemplified.

[0045] In the structural formulas described above, a methyl group is denoted as Me, an ethyl group is denoted as Et, a propyl group is denoted as Pr, a butyl group is denoted as Bu, a phenyl group is denoted as Ph, a cyclohexyl group is denoted as Cy, and a benzyl group is denoted as Bn. n represents normal, i represents iso, and et represents tertiary.

[0046] In structural formulas, a carbon atom is present in the upper or final portion of them, and represents a covalent bond. The form of these compound structural formulas is well known to those skilled in the art.

[0047] Such compounds can be used in a variety of applications and, in particular, an application as an internal donor of a solid titanium catalyst component used in a catalyst for olefin polymerization is suitable. If used as internal donors, these compounds can be used alone or two or more of them can be used in combination. Provided that the objective of the present invention is not impaired, this amide compound can be used in conjunction with a known internal donor component, such as a diamide compound or a different known ester compound. Amide compound can also be formed in a process for preparing the solid titanium catalyst component.

[0048] When the polymerization of an α-olefin, such as propene, is carried out in the presence of a catalyst of Petition 870250084527, dated 09 / 19 / 2025, pp. 30 / 43 19 / 29 Polymerization of olefins for which the solid titanium catalyst component described above is used, there is a tendency for a polymer with a wide molecular weight distribution and high melting point and heat of fusion to be highly active.Although the reason for this is unknown at present, the present inventors believe that, including the contents described above, the amide portion in the amide compound of the present invention tends to be relatively tightly coordinated with the titanium and magnesium in the solid titanium catalyst component, while, especially from the point of view of rigidity, centered around carbon C1 and carbon C2, which are linked to the nitrogen of the amide groups in the structural formula (1), the amide compound of the present invention is considered to have a loose structure, thus assuming a conformation with movement in a limited range and, therefore, an olefinic polymer with high stereoregularity and wide molecular weight distribution (with a dispersion on the high molecular weight side) is easily obtained.In this case, the stereoregularity of the polymers, especially those on the high molecular weight side, is high, making them easily crystallizable despite their molecular weight, and since the effect of the nucleating agent is also expressed, it is assumed that a polymer with a high melting point and heat of fusion is easily obtained.

[0049] The olefinic polymer obtained by the method of the present invention is a polymer obtained using a catalyst that can assume a conformation with a certain degree of dispersion and, therefore, can be a polymer with dispersion also on the low molecular weight side. This can result in the dissolution of more components in a hydrocarbon solvent, such as decane. It is feared that such dissolved components weaken the crystalline structure of the olefinic polymers, but the heat of fusion of the olefinic polymer of the present invention tends to be high. This is probably due to the effect of the nucleating agent on the high molecular weight components. Petition 870250084527, dated 09 / 19 / 2025, pp. 31 / 43 20 / 29 molecular described above. <Método para produção de composto de amida>

[0050] A method for producing the amide compound is not particularly limited, it being possible to use, for example, the synthesis example in the Examples to be described below. The amide compound can also be synthesized using a known reaction. The amide compound can also be synthesized by synthesizing each fraction by a known synthesis method and combining them by a known method. More specifically, the amide compound can be produced using a reaction as described below.

[0051] A diamine compound with the following reaction formula (2) can be synthesized by a reaction between an N,N'-dialkyldiamine compound and an acid chloride in the presence of, for example, a base. The diamine compound used can be a corresponding hydrochloride. Examples of the base used may include, but are not limited to, sodium hydroxide, potassium hydroxide, pyridine, N,N-dimethyl-4-aminopyridine (DMAP) and triethylamine. [Chemical Formula 10]

[0052] The diamide compound shown in reaction formula (2) can also be synthesized by the method involving the reaction of an N,N'-dialkyldiamine compound with carboxylic acid in the presence of an acid catalyst or the method using a condensation reagent such as N,N'-dicyclohexylcarbodiimide (DCC), as shown in the following reaction formula (3). [Chemical Formula 11] Acid catalyst or θ condensation reagent ^NH HN. RR' HO R ^n^^nT / R rr' r'Y , , oo (3) Petition 870250084527, dated 09 / 19 / 2025, pp. 32 / 43 21 / 29

[0053] Furthermore, the diamide compound shown in reaction formula (3) can also be synthesized by reacting a diamide compound and a base that correspond to each other, as shown in reaction formula (4) below, and then by reacting the reaction product with an alkyl halide. The base used is not particularly limited, and examples include organolithium reagents, sodium hydride and potassium hydride. [Chemical Formula 12] OO OO (4)

[0054] As described above, the amide compound of the present invention can be used in various applications. In particular, the amide compound is suitable as an internal donor component of a solid titanium catalyst component contained in a catalyst for olefin polymerization, as described above. In addition to the applications described above, the amide compound is expected to be used as a special solvent, an intermediate for pharmaceuticals or pesticides, and a raw material for a special polyamide. Examples (Method for compound analysis)

[0055] A ^-H-NMR spectrum (400 MHz, manufactured by JEOL Ltd., measuring instrument type JNM-ECZ400S / L 1) was measured, the peaks were assigned by a routine method to determine a structure. [Example 1]<Síntese do composto 1>

[0056] A compound 1 shown below was synthesized by a method described below. [Chemical Formula 13] Petition 870250084527, dated 09 / 19 / 2025, pp. 33 / 43 22 / 29

[0057] 5.05 g of N,N'-dimethyl-2,4-pentanediamine (38.8 mmol, 1 eq) and 39 mL of pyridine (dehydrated) were added to a 100 mL three-necked flask, dried in an oven, containing a magnetic stirring bar, under a nitrogen atmosphere. After cooling the reaction solution in an ice bath, 11.7 g of benzoyl chloride (83.0 mmol, 2.1 eq) were added slowly, dropwise. After the dropwise addition was complete, the reaction temperature was slowly raised to room temperature, and the reaction solution was stirred continuously for 22 hours. After the reaction was complete, the reaction solution was cooled again in an ice bath, and 5 mL of methanol were added. Water and ethyl acetate were added to the resulting reaction solution, and the resulting aqueous layer was extracted with ethyl acetate three times. The combined organic layers were washed once with water and brine, dried over magnesium sulfate, and then concentrated in a rotary evaporator.The crude product obtained was purified by NH3 (hexane:ethyl acetate = gradient 90:10 to 40:60) gel column chromatography to obtain 11.7 g of compound 1 (35.1 mmol, 90% yield). The α-H-NMR data of compound 1 obtained are shown below. [0058PH-NMR (400 MHz, CDCls, TMS as internal standard) : δ 0.94-1.32 (m, 6H) , 1.57-1.90 (m, 2H, superimposed with the H2O signal) , 2.37-3.00 (m, 6H) , 3.63-4.96 (m, 2H) , 6.87-7.46 (m, 10H, superimposed with the residual CHCl3 signal). <Preparação do componente de catalisador de titânio sólido [al]>

[0059] After a 1-liter glass container has been sufficiently purged with nitrogen, 85.8 g of chloride Petition 870250084527, dated 09 / 19 / 2025, pp. 34 / 43 23 / 29 g of anhydrous magnesium, 321 g of decane, and 352 g of 2-ethylhexyl alcohol were added and subjected to thermal reactions at 130°C for 3 hours to obtain a homogeneous solution. Then, 241 g of this solution and 6.43 g of ethyl benzoate were added to the glass container and mixed under stirring at 50°C for 1 hour.

[0060] After the homogeneous solution thus obtained had been cooled to room temperature, 38.3 ml of the homogeneous solution were added dropwise over 45 minutes to 100 ml of titanium tetrachloride, maintained at -20°C under stirring. After the addition was complete, the temperature of this mixture was raised to 80°C for 3.8 hours. When the temperature reached 80°C, 1.71 g of compound 1 was added to the mixture. The temperature was again raised to 120°C for 40 minutes, and the mixture was maintained at the same temperature for 35 minutes, under stirring. After the reaction was complete, the solid portion was recovered by hot filtration, resuspended in 100 ml of titanium tetrachloride and again subjected to thermal reaction at 120°C for 35 minutes, under stirring. After the reaction was complete, the solid portion was recovered again by hot filtration and thoroughly washed with decane at 100°C and decane at room temperature until no free titanium compounds were detected in the washing fluid.The solid titanium catalyst component [α1] prepared by the above operations was preserved as a decane suspension, and a portion of the suspension was dried to verify the catalyst composition. The composition of the solid titanium catalyst component [α1] thus obtained included 0.66 wt% titanium, 1.3 wt% magnesium, and 0.05 wt% residual 2-ethylhexyl alcohol. <Polimerização principal>

[0061] After adding 500 g of propylene and 1 NL of hydrogen at room temperature to a polymerization vessel with an internal capacity of 2 L, a mixture obtained by mixing 7 mL of heptane, 0.50 mmol of triethyl aluminum, 0.10 Petition 870250084527, dated 09 / 19 / 2025, pages 35 / 43 24 / 29 mmol of cyclohexylmethyldimethoxysilane and 0.0040 mmol of the solid titanium catalyst component [α1] (in terms of titanium atoms) were mixed at 25°C for 10 minutes, and the temperature inside the polymerization vessel was rapidly raised to 70°C under stirring. After polymerization at 70°C for 1.5 hours, the reaction was stopped with a small amount of ethanol, and the propylene was purged. Furthermore, the resulting polymer particles were dried under reduced pressure at 80°C overnight. A variety of polymerization results are described below.

[0062] Activity: 13.4 kg-PP / g-catalyst Specific gravity by mass: 380 kg / m3 MFR: 10.1 g / 10 min Decane insoluble fraction: 9.0% by mass Tm: 163.0°C, 157.6°C Tc: 112.6°C Tmf: 169.0°C ΔH: 89.7 J / g Mw / Mn: 9.1 Mz / Mw: 8.8

[0063] A variety of analytical methods are described below. (1) Specific gravity by mass:

[0064] The specific gravity by mass was measured in accordance with JIS K-6721. (2) Melt flow rate (MFR):

[0065] According to ASTM D1238E, the measurement temperature for a propylene polymer was defined as 230°C with a load of 2.16 kg. (3) Amount of decane-soluble (insoluble) portion:

[0066] A glass measuring container was loaded with approximately 3 g of propylene polymer (measured with an accuracy of 10-4 g; the weight indicated by b (gram) in the following formula), 500 ml of decane and a small amount of a heat-resistant decane-soluble stabilizer, and the propylene polymer. Petition 870250084527, dated 09 / 19 / 2025, pages 36 / 43 25 / 29 was dissolved by heating to 150°C for two hours while being stirred with a stirrer in a nitrogen atmosphere, left to stand at 150°C for two hours, and gradually cooled to 23°C for eight hours. A liquid containing a precipitate obtained from the propylene polymer was filtered under reduced pressure with a standard 25G-4 glass filter manufactured by Tokyo Garasu Kikai Co., Ltd. 100 ml of filtrate were recovered and dried under reduced pressure to obtain a portion of a decane-soluble fraction, and this weight was measured with an accuracy of 10⁻⁴ g (this weight was indicated by a (g) in the following formula). After this operation, the amount of the decane-soluble fraction was determined by the following formula.

[0067] Content of the soluble part in decane = 100 x (500 xa) / (100 xb) Content of the insoluble part in decane = 100 - 100 x (500 xa) / (100 xb) (4) Molecular weight distribution (MWD):

[0068] Gel permeation chromatograph: HLC-8321 type GPC / HT manufactured by Tosoh Corporation Detector: Differential refractometer Column: Two TSKgel GMH6-HTs and two TSKgel GMH6-HTLs manufactured by Tosoh Corporation were connected in series. Mobile phase medium: o-Dichlorobenzene Flow rate: 1.0 ml / minute. Measurement temperature: 140°C. Calibration curve creation method: A standard polystyrene sample was used. Sample concentration: 0.1% (w / w) Sample solution quantity: 0.4 ml

[0069] The measurement was performed under the conditions described above, and the resulting chromatogram was analyzed by a known method to calculate the weight-average molecular weight (Mw), the number-average molecular weight (Mn), and the Z-average molecular weight. Petition 870250084527, dated 09 / 19 / 2025, pp. 37 / 43 26 / 29 (Mz), the Mw / Mn value and the Mz / Mw value, which are molecular weight distribution (MWD) indices. The measurement time per sample was 60 minutes. (5) Melting point (Tm) of the polymer:

[0070] The melting point (Tm), crystallization temperature (Tc), and heat of fusion (ΔH) of the polymer of the present invention were measured using a differential scanning calorimeter (DSC), a DSC 8000 device manufactured by PerkinElmer Co., Ltd. 3 to 10 mg of a sample were sealed in an aluminum crucible and heated from room temperature to 200°C at 100°C / minute. This sample was held at 200°C for five minutes and then cooled to 30°C at 10°C / minute. The maximum temperature observed in this cooling test was considered the crystallization temperature (Tc), and the amount of heat generated, specified by the peak area, was considered ΔH. Subsequently, the sample was held at 30°C for five minutes and then heated a second time to 200°C at 10°C / minute. The maximum temperature observed in this second heating test was considered the melting point (Tm).

[0071] The final melting point (Tmf) of the polymer of the present invention was measured using a differential scanning calorimeter (DSC), the DSC 8000 device manufactured by PerkinElmer Co., Ltd. 3 to 10 mg of a sample were sealed in an aluminum crucible and heated from room temperature to 240°C at 80°C / minute. The sample was held at 240°C for one minute and then cooled to 0°C at 80°C / minute. The sample was held at 0°C for one minute, then heated to 150°C at 80°C / minute and held for five minutes. Finally, the sample was heated to 180°C at 1.35°C / minute, and the intersection between the tangent of the inflection point on the high-temperature side of a peak obtained in this final heating test and the baseline was used as the final melting point (Tmf).

[0072] Tmf can be considered one of the parameters for Petition 870250084527, dated 09 / 19 / 2025, pp. 38 / 43 27 / 29 evaluate, for example, the crystalline structure of a component that exhibits extremely high stereoregularity, or the ease of crystallization, or the crystalline structure of a polymer in an ultra-high molecular weight region, which is considered to have a lower probability of crystallization. More specifically, it can be considered that the higher the value of this Tmf, the greater the probability of an ultra-high molecular weight polymeric component forming highly heat-resistant crystals. [Example 2]<Sintese do composto 2>

[0073] A compound 2 shown below was synthesized by a method described below. [Chemical Formula 14]

[0074] 4.90 g (18.1 mmol, 79% yield) of compound 2 were obtained according to the operation and equivalence relationship described in<Sintese do composto 1> , except that butyryl chloride was used instead of benzoyl chloride in<Sintese do composto 1> , as described above. The P-NMR data for compound 2 obtained are shown below. [0075PH-NMR (400MHz, CDCls, TMS as internal standard): 0.911.00 (m, 6H), 1.04-1.28 (m, 6H), 1.38-1.83 (m, 6H, superimposed with the H2O signal), 2.05-2.35 (m, 4H), 2.75-2.84 (m, 6H), 3.664.85 (m, 2H). <Preparação do componente de catalisador de titânio sólido [a2]>

[0076] A solid titanium catalyst component [a2] was obtained in the same manner as Example 1, except that 1.37 g of compound 2 was used instead of 1.77 g of compound 1. The composition of the solid titanium catalyst component [a2] Petition 870250084527, dated 09 / 19 / 2025, pp. 39 / 43 The 28 / 29 thus obtained consisted of 0.64% by mass of titanium, 1.4% by mass of magnesium, and 0.07% by mass of a residue of 2-ethylhexyl alcohol. <Polimerização principal>

[0077] The polymerization of propylene was carried out in the same manner as in Example 1, except that the solid titanium catalyst component [a2] was used in place of the solid titanium catalyst component [al]. A variety of polymerization results are described below.

[0078] Activity: 14.6 kg-PP / g-catalyst Specific gravity by mass: 470 kg / m³ MFR: 13.0 g / 10 min Content of the insoluble portion in decane: 8.0% by mass Tm: 158.7°C Tc: 114.4°C Tmf: 169.2°C ΔH: 90.3 J / g Mw / Mn: 8.8 Mz / Mw: 8.3 [Example 3]<Sintese do composto 3>

[0079] A compound 3 shown below was synthesized by a method described below. [Chemical Formula 15] (Compound 3)

[0080] A 100 mL three-necked flask, dried in an oven, containing a magnetic stirring bar, was prepared and the internal atmosphere was replaced with nitrogen. 0.99 g of N-benzyl-1,3-propanediamine (12.1 mmol, 1 eq) and 24 mL of pyridine (dehydrated) were added in the same nitrogen atmosphere, and the reaction solution was cooled in an ice bath. Petition 870250084527, dated 09 / 19 / 2025, pages 40 / 43 29 / 29 After confirming that the reaction solution had been sufficiently cooled, 3.56 g of benzoyl chloride (25.3 mmol, 2.1 eq) were added slowly, dropwise. After the dropwise addition was complete, the reaction temperature was slowly raised to room temperature and the reaction solution was stirred continuously for 20 hours. After monitoring the reaction by GC-MS analysis, the reaction solution was cooled again in an ice bath and stopped by the addition of 2 mL of methanol. Ethyl acetate and water were added to the stopped reaction solution, and the reaction solution was extracted with ethyl acetate three times. The combined organic layers were washed once with water, a saturated aqueous solution of sodium bicarbonate, and brine, and the resulting organic layer was dried over magnesium sulfate and then concentrated in a rotary evaporator.The crude product obtained was purified by NH3 (hexane:ethyl acetate = gradient from 100:0 to 60:40) gel column chromatography to obtain 4.34 g of TKN-040 (compound 3) (11.7 mmol, 97% yield). The product was highly viscous and a small amount of ethyl acetate remained. The 1H-NMR data of the obtained compound 3 are shown below. [0081PH-NMR (500 MHz, CDCp, TMS as internal standard): δ 1.80-1.85 (m, 2H), 3.51-3.55 (m, 2H), 3.65-3.68 (m, 2H), 4.54 (s, 2H), 7.17-7.19 (m, 2H), 7.29-7.49 (m, 10H), 7.87 (br s, 1H), 7.94-7.96 (m, 2H). Petition 870250084527, dated 09 / 19 / 2025, pages 41 / 43

Claims

1 / 1 CLAIMS 1. Amide compound characterized by having a structure of the following formula (1): [Chemical Formula 1] wherein C, C1 and C2 are carbon atoms, N is a nitrogen atom, R1 and R2 are each a hydrocarbon group, R11 and R12 are each a hydrogen atom or a hydrocarbon group, and at least one group of them is a hydrocarbon group, R3 to R6 are each a hydrogen atom or a hydrocarbon group, R is a hydrogen atom, in is an integer from 1 to 5.

2. Amide compound according to claim 1, characterized in that both R11 and R12 are hydrocarbon groups.

3. Amide compound according to claim 1, characterized in that R1, R2, R4 and R5 are hydrocarbon groups composed of carbon and hydrogen. Petition 870250084527, dated 09 / 19 / 2025, pp. 42 / 43