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My limited research on the topic suggests the only reason Sirach (or Ecclesiasticus or Ben Sira, etc.) was put in the Apocrypha was because the Jewish canon excluded it. As for why the Jewish canon did not include it, I couldn't find any reasoning that involved the content of the book.
Is there something theologically problematic in Sirach that prevents it from being classified as Scripture (from a Protestant view)?
William Whitaker's Disputations on Holy Scripture is a classic Reformation-era work that goes into great depth regarding the reasons that the apocrypha were rejected. He deals with Sirach (Ecclesiasticus) beginning on page 90.
He begins by arguing that the "common" reasons for rejecting the apocrypha also apply to this book, such as not being part of the Jewish canon, lack of early acceptance, and a lack of an original Hebrew version. He also notes a number of deficiencies, such as the author seeking pardon for his translation:
He asks pardon, if he should seem in some places to fail of an adequate power of expression. By all which he sufficiently proves that he is neither a prophet nor endowed with a prophetic spirit. For the Holy Spirit asks pardon of no one, hesitates not in the choice of words, and ever reaches the mark he aims at.
But Whitaker focuses on the book's explanation of the events of 1 Samuel 28, in which Saul, following Samuel's death, goes to a medium in an attempt to speak to Samuel's spirit. Sirach 46:20 reads:
Even after he had fallen asleep, he prophesied
and made known to the king his death,
and lifted up his voice from the ground
in prophecy, to blot out the wickedness of the people. (NRSV)
Whitaker contends that "the souls of the saints cannot be evoked by magical arts or incantations," and notes that in several places Augustine argued that Saul rather spoke with a mere "phantom and imaginary illusion produced by diabolical devices." Thus Sirach 46:20 is in error and cannot be scripture.
Other Protestants have raised issues with other portions of the text, such as Sirach 15's discussion of free will. E. J. Young also writes:
Ecclesiasticus and the Wisdom of Solomon inculcate a morality based upon expediency. [...] Ecclesiasticus teaches that the giving of alms makes atonement for sin (3:30). ("The Canon of the Old Testament" in Revelation and the Bible Contemporary Evangelical Thought)
It's not clear to me, however, if such issues with the text were raised during the Reformation. Martin Luther did deal with Sirach 15 is his Bondage of the Will, and, though not accepting the book as canonical, nonetheless contended that it did not say what Erasmus argued. (see §46ff. of Bondage of the Will, and The Reception of the Church Fathers in the West, 584 for a summary)
So we can safely conclude that while Sirach was excluded primarily for the more general reasons the apocrypha was rejected, it was nonetheless found to have at least some theological issues in itself.
Sirach 2:1 (1611 KJV)
My sonne, if thou come to serue the Lorde, prepare thy soule for temptation.
Despite being tagged as "apocryphal", I don't think there was widespread condemnation by some Protestants of Sirach and other books of the deuterocanon in earnest until early in the 19th century. For the reasons given below, I don't think that there is anything seen as theologically problematic in Sirach (Ecclesiasticus) from a Protestant point of view, other than perhaps the issue of authority over the Bible canon itself.
Background
Apocrypha is a (Greek) term that Jerome seems to have applied to the book, even though he himself elected to include it in his Latin translation of the Old Testament Scriptures. It is related to the Greek word ἀπόκρυφος (apokryphos), meaning secret or stored away. The Greek Church Fathers never referred to Sirach or any of the other books in the deuterocanon as apocrypha. That term was usually reserved for spurious post-Apostolic gnostic works like the Gospel of Judas or the Gospel of Thomas.
Every Old Testament canon officially enumerated by the Church in the first millennium included Sirach (Ecclesiasticus in Latin) and other books of the deuterocanon (e.g. Tobit, Judith, Wisdom, Maccabees). A description of the formalization of the Bible canon by the Church - Old Testament and New - can be found here. While it is true that prior to the Council of Carthage in 397 (perhaps the earliest Church Council setting a Bible canon) some early Christian writers (including Church Fathers) seemed not to have included it and other deuterocanonical books in what they considered the Old Testament, or at least questioned whether it should have been included, a great many others did and none of them objected to its inclusion after the Church had ruled on the canon (Jerome being a prime example of this). A discussion of this can be found here.
Sirach is found in both the Codex Sinaiticus and the Codex Vaticanus, the two oldest complete Christian Bibles in existence. (Both of these codices are bases for the Nestle-Aland Critical Text, upon which most modern Protestant Bible translations are based). Sirach was included not only in the original 1611 King James Bible, but even in Calvin's 1560 Geneva Bible. The book was not expurgated from the King James Bible (along with the other deuterocanonical books) until the early 19th century. It can still be found, however, today in all Catholic and Orthodox Christian Bibles, along with a handful of Bibles that are considered to be more or less Protestant (e.g. RSV), albeit in special editions.
Reasons given for excluding the deuterocanon in general
There are lots of reasons floated why the deuterocanon was excised. Lists like this one from www.jesus-is-lord.com can be found all over the Internet. A more solid source, Protestant theologian Norman Geisler, makes a dozen or so points that I think are typical of the more thoughtful objections against its inclusion in the Bible. He is referring to the deuterocanon in general here, and not Sirach, but I think his arguments largely transfer:
(1) There are no clear quotations of deuterocanonical books in the New Testament
(2) The fact that the New Testament quotes largely from the Greek Septuagint version of the Old Testament - which includes the deuterocanon - rather than the Hebrew version does not convey legitimacy on the deuterocanonical books by virtue of their having been included in all extant copies of the Septuagint.
(3) Citations of Church Fathers quoting from the deuterocanon are "selective and misleading".
(4) Although some early Church Fathers accepted the deuterocanon, others did not.
(5) Scenes depicting episodes from the deuterocanon in early Christian catacombs does not "prove the canonicity of the books"
(6) Although the Codices mentioned above and other early manuscripts include the deuterocanon as part of the Old Testament, some contain only some of the books, none of them contain all of the books.
Here it is admitted, though, that three of the most important witnesses did contain Sirach
(7) Only local Church councils approved the deuterocanon's inclusion in the Old Testament; in any case, Christian councils had no authority over deciding the Old Testament canon.
Regarding the first point, the 7th Ecumenical Council in 787 ratified all of the Old Testament canons put forward by all of the various local Councils, all of which included the deuterocanon.
(8) Although the Eastern Orthodox (and not only the Roman Catholic) Church always accepted the deuterocanon, the "Larger Catechism" [of Philaret of Moscow] in 1839 expressly omitted it and that has been "their position" (i.e. the position of the Eastern Orthodox Church) ever since.
The Longer Catechism of Philaret of Moscow is technically a document only of the Russian Orthodox Church, and even there for the benefit of the Metropolitanate of Moscow, and not all of the Eastern Orthodox Church. His Catechism is, however, generally accepted among all Eastern Orthodox. Dr. Geisler misrepresents what is in the Catechism, though. Philaret observes that there is "no notice taken in this enumeration of the books of the Old Testament" (emphasis added), meaning an enumeration of the Hebrew books earlier in the catechism. Philaret directly adds, quoting Athanasius 1,500 years earlier, that the deuterocanonical books "have been appointed of the fathers to be read by proselytes who are preparing for admission into the Church," and he never refers to the books with the derogatory term "apocrypha". Sirach and the rest of the deuterocanon is in every single Eastern Orthodox bible printed to this day, including the Russian Synodal Bible that Philaret himself edited. Sirach is here.
(9) The fact that deuterocanonical books were in Protestant Bibles as late as the 19th century is of no consequence, since they were set off in a separate section.
(10) The fact deuterocanonical books were found among the Dead Sea Scrolls in itself is not conclusive evidence that the books were seen as authoritative.
Regarding whether any of these points are truly theological or not, I am not sure what to say. None of Dr. Geisler's points deal with any theological point that I can see other than whose authority it is to set a canon of Scripture. That of itself might be considered a theological problem. If the book did, in fact, have something in it that some Protestants considered "theologically problematic", it is hard to understand how it could have been bound up and distributed with the non-problematic canonical books for almost three centuries.
BACKGROUND
First, it is true that the Jewish canon at the time around Christ excluded the Book of Sirach. The reason for the exclusion was simple. It was written during the time when the prophetic Word of God was silent; there was no valid prophetic line. This "silent period" lasted from Malachi and Artaxerxes’ time to John the Baptist.
Josephus confirms this; "4. From the time of Artaxerxes to our own day all the events have been recorded, but the accounts are not worthy of the same confidence that we repose in those which preceded them, because there has not been during this time an exact succession of prophets."
Melito confirms this; "prompted by your regard for the word of God, expressed a wish to have some extracts made from the Law and the Prophets concerning the Saviour, and concerning our faith in general, and have desired, moreover, to obtain an accurate account of the Ancient Books, as regards their number and their arrangement, I have striven to the best of my ability to perform this task:."
1 Macc. 9:27, 14:41 confirms this; to wit, no prophet at the time of its writing.
THEOLOGICAL PROBLEMS
Second, to the question whether there is a theological problem with Sirach that prevents its inclusion as inspired (God-breathed) as thus part of Holy Scripture, the answer is yes.
Here are a couple of examples to show that Sirach contradicts Scripture. Translations are from http://www.ccel.org/bible/kjv-apoc/Sirach/.
Sirach 25:24 Of the woman came the beginning of sin, and through her we all die.
Scripture: Man is the origin of sin (Num. 5:6, Num. 16:22, 1 Sam. 2:25). And of course the famous Pauline quote “Wherefore, as by one man sin entered into the world, and death by sin; and so death passed upon all men, for that all have sinned:” (Romans 5:12).
Sirach 33:1 “THOSE WHO FEAR the Lord shall live for their trust is in one who can keep them safe.”
Scripture: Fearing the LORD helps, but that’s not all it takes to live. (Deut. 6:2, 13, 10:12, Jos. 24:14). Indeed, it would take Christ fulfilling the Mosaic Law to live and believing it (Rom. 6:8, Psalm 110:4).
Sirach 41:4 And why art thou against the pleasure of the most High? there is no inquisition in the grave, whether thou have lived ten, or an hundred, or a thousand years.
Scripture: After death comes judgment. There is an inquisition. (Ex. 3:6, Mt. 22:32, Acts 10:42).
CONCLUSION
To conclude, the Hebrews, Christ, and early Christians knew Sirach was uninspired, contradictory, misleading, and thus is excluded from Scripture.
